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- Translating Experience: Clarity from Leadership in the People Industry with Christy Honeycutt (2/2)How can we help recruiters advocate for us in a tough job market? According to people industry veteran Christy Honeycutt, our guest in episode 353, it starts with being kind and translating your experience into something a recruiter can understand. And even more importantly, it takes practice. In part 2 of our discussion with Christy, she translates deep experience in talent acquisition and recruitment that gives us insight into the current job market. You’ll hear more details about the nuances of RPOs (recruitment process outsourcers), the difference between job hugging and job abandonment, and the importance of personal branding and differentiation. Stay until the end when Christy shares her reasons for turning down C-suite positions and how clarity on her long-term goals is carrying her forward into what’s next. Now that you’ve heard someone model it for you, how will you translate your own experience? If you missed part 1 of our discussion with Christy, check out Episode 352 – People First: Systematizing Go-to-Market for Your Role with Christy Honeycutt (1/2). Original Recording Date: 09-30-2025 Topics – A Deeper Look at Recruitment Process Outsourcing (RPO), Translating Your Experience with 3 Wins, Bad Actors and Leadership in the People Industry, Today’s Job Market and Life Outside the C-Suite 2:56 – A Deeper Look at Recruitment Process Outsourcing (RPO) When it comes to RPO (recruitment process outsourcing), is this a one-size-fits-all approach, or does it show up differently depending on what a company needs? In Christy’s experience, most RPO organizations offer services like executive search, but they may offer full RPO, which usually involves hiring more than 500 people per year. Normally an RPO brings a mix of skills to the table. A client may want the RPO to take only talent acquisition or may want to control offer management, but they may want the RPO to take everything (attracting new talent, offer management, coordinating with HR for new employee onboarding). “If a company wants it a certain way, they can stop it at a certain point…. But most RPOs, full RPOs, is attraction to offer accepted and then it tees over to the HR team.” – Christy Honeycutt John has worked for companies where the recruitment or talent acquisition personnel were marked as contractors in the internal global address book but had company e-mail addresses. Would this mean the personnel are contracting directly with a company or working through an RPO? Christy says it could be either scenario. When she managed an RPO earlier in her career, they were most successful when the client encouraged the RPO to brand as the company. Someone might indicate they do recruitment for a specific company on LinkedIn but be an employee of an RPO. Christy tells us how important it is for the RPO to understand an organization’s mission, vision, benefits, and culture because the RPO is often attracting talent and selling people on why they should apply and interview. “When you think about recruitment and talent acquisition, regardless, it’s a lot of marketing because you’ve got a really cool position and you’ve got to find the perfect fit.” – Christy Honeycutt 5:55 – Translating Your Experience with 3 Wins Right now, recruiters and talent acquisition professionals have a distinct challenge. Many resumes look the same because candidates are using AI tools. “What people think is helping set them apart is actually making them look more similar. So now you’ve got recruiters and talent acquisition; they don’t know if these are fake resumes. They don’t know if they’re real. And they’re getting on the call with these people and finding out they are fake; they don’t have any of this requirement.” – Christy Honeycutt Christy shares a little secret about learning recruitment. She gives the example of a recruiter needing to recruit for an executive level role in technology. Recruiters are encouraged to seek out and find the C-players to practice asking them questions, understand nuance, and grasp the terminology. This is a training exercise. Following this process, a recruiter would then have more credibility once they speak to the A-players they actually want to hire. “What I would encourage is if you are a C-player, you’re not going to know it. Just be kind and know that the person you’re talking to has never held a technical role (probably, most likely)…and might not understand half the stuff that you guys do. The acronyms aren’t going to be the same. Just be gracious with them because the more you can help them translate your experience, the better you’re going to be positioned to get you over the line…. They don’t want to talk to 10 people to get 1 hire. They want to talk to 3 people to get a hire…. And remember that the TA, HR, recruiters, whatever you want to call them…there’s a pretty good chance that they want to help you and that they’re doing the job because they like people. And I think they get a bad rap.” – Christy Honeycutt Christy tells us about something called a slate (a group of 3-5 individuals who apply for a job that a recruiter will go and interview). Recruiters are using AI to help filter through applications. “The biggest thing I can tell you is be your own person. Be your own, authentic person. Have your stories of how you’ve shown up and shown out…. I tell everybody for every job that you’ve worked at, you need to have 3 wins…. Figure out…your top things that you accomplished at each role and have that and be ready to speak to it. And then…ask questions. Interview them too…. Make sure it’s a culture fit for you.” – Christy Honeycutt Christy says things like the great resignation and quiet quitting are just behaviors that get repeated over time. Right now, there is a fearful state of job hugging. “We’re job hugging. No one is hugging a job. People are trying to stay employed in the market. That’s all it is.” – Christy Honeycutt Christy says if you are staying somewhere because you have a job and are not happy, figure out how to make yourself happy by determining it is not a fit, understanding your passions, and beginning your exit plan. “Companies are not our families. They are going to let us go. It’s going to come down to the business.” – Christy Honeycutt It’s important to keep the human element in mind if we are seeking a new role (the human element on both sides). Christy tells the story of a senior recruiter who called her about a conversation with a job candidate, and Christy knew the person was burned out, bored, and curious. “High performers are always open minded and curious, but if you fall in that category, figure it out sooner than later so you’re not burning yourself out because then you’re in a very dangerous situation. That job hugging is going to be job abandonment. You’re going to get to boot. It’s not going to be the other way around. It’s just kind of level setting with your psyche.” – Christy Honeycutt 11:28 – Bad Actors and Leadership in the People Industry Going back to recruiters getting practice and experience from interviewing candidates, Nick looks at this from the lens that everyone needs at bats to gain experience. Though it may be batting practice for a recruiter, it is also practice for the candidate. We don’t practice interviewing very often. Christy agrees it is practice on both sides and emphasizes that kindness is key. She’s had multiple conversations with recruiters who didn’t understand why a hiring manager did not want a specific candidate. We might never know all the effort a recruiter put into promoting us with a hiring manager. Some recruiters, however, should not be in their roles. Christy tells us about a time in her career when she was referred to as “The Kraken.” Christy managed a tight team of talent acquisition professionals who respected and loved her as a boss. They knew she had high expectations of her team. Christy’s team members would have to launch programs for global clients within 30-60 days sometimes, for example. “So, my team had to be kind of like special ops because we managed the globe, and it was high pressure.” – Christy Honeycutt As she progressed in her career, Christy would be given individuals who were not performing on other teams. Before managing someone out of the business, Christy always gave people a chance to redeem themselves because until she met the person and they worked for her, she was only hearing one side of the story. Christy recounts being asked to join an RPO to clean it up. She met with each recruiter to understand the key metrics and performance indicators. Christy tells us that for any job opening (or job requisition) a recruiter was carrying at this time, they should be submitting 3-5 candidates for each job, and a manager would expect this within 2 weeks of the job opening. There was a specific recruiter who only submitted 2 candidates per week across 15 job openings, and Christy recounts the performance conversation with this person. “There are some people that are in roles that they shouldn’t be that take advantage and kind of sit back….” – Christy Honeycutt As people gain seniority in talent acquisition and recruitment, sometimes you deal with people’s egos. This is the exception and not the rule. John mentions it would probably be difficult to coast based on one’s reputation in talent acquisition. Based on the metrics for success and open job requisitions, it should be obvious who is doing well and who isn’t. Christy says this goes back to leadership. Maybe these individuals never had a boss who would hold them accountable. “If we go back to managers and leaders, most of them aren’t trained, and a lot of them want to be liked.” – Christy Honeycutt Christy is the daughter of a Marine. This means the mission gets accomplished no matter what with the fewest amount of casualties. It’s her job as the leader of a team to keep them focused on the mission and accomplishing it. Removing someone from the team may be the best option to keep the rest of the team on track in accomplishing a mission. “You’re only as strong as your weakest link, so if your weakest link is not holding themselves accountable and respecting their team, then they’re putting everybody else’s jobs at risk. And unfortunately, there are bad actors in every industry, in every role, in every organization…and we’ve all seen them. They are like cancer. They really hurt retention. They hurt elevation. They are usually the ones taking credit, taking too long at lunch, whatever the case may be…we’ve all seen them…. It all comes down to behaviors.” – Christy Honeycutt Christy thinks leaders want to be liked and are afraid of having a complaint filed against them. For example, people might file a complaint because they were not doing their job and their manager held them accountable for not doing it. “It’s weird to be in the people industry for so long because it’s just behaviors. It’s just humans.” – Christy Honeycutt Before someone shows up for work, we have no idea what may be going on in their life outside work. Christy encourages us to meet one another with more grace. “Those of you out there, if you’re lucky enough to have a job and be employed, do the job. Because there’s a lot of people that don’t that will come in and do a better job than you. Honor yourself, honor your employer, and show up. But unfortunately, there’s bad actors.” – Christy Honeycutt John directs the conversation back to hiring cycles. He has heard it’s beneficial to apply for a job opening quickly and to be in the first wave of candidates but didn’t really think about the why behind it. Christy tells us this varies based on the position, the job requirements, location, salary, and other factors. In fact, recruiters often have to reset unrealistic expectations from hiring managers (i.e. what a specific role salary should be). “If you think about a client and them opening a position, they probably needed that position 30 days before it was ever approved. So, there’s already a ticking time on the recruiter whether that’s fair or not because in the manager’s mind that role opened the second they thought they needed it. Not when they requested it, not when it got approved, but when they realized in their brain, ‘I need this position filled,’ that’s when the clock starts for them. So, it’s an unfair disadvantage for a recruiter.” – Christy Honeycutt Listen to Christy’s description of a best-in-class 4-week process from job opening to making the right candidate an offer. 20:45 – Today’s Job Market and Life Outside the C-Suite If we look at this through the lens of the current job market, how much do recruiters need to sell candidates on roles when there are hundreds of applications to sort through for a single job opening? “Tech is like recruitment, like marketing. It’s always the first to go…until they realize…it went, and we need it. So, it’s a boomerang effect with those industries…always has been, always will be.” – Christy Honeycutt Christy tells the story of being at the HR Tech conference with a young lady who was recently laid off from a tech company. This person walked from booth to booth and began networking with people in search of new roles and was able to leverage Christy to get some introductions. She had 5 interviews over the course of the 3-day event. “In the job market today, with recruiters not able to tell if it’s an AI resume or not, with them being overloaded with a vast amount of resumes…the best thing that anybody can do is make sure that your personal brand is on point. Make sure that whatever it is that you’re doing…you’re sharing, you’re engaging your community, and that you’re seen doing it.” – Christy Honeycutt Christy was part of the same tech startup mentioned above and also lost her job. But she had been working on her personal brand before that happened. Christy was speaking at events, sharing with her community, doing podcasts, and doing many go-to-market things on behalf of her employer. Christy’s heart goes out to others in her field who have been out of work for multiple years. Within 3 days of losing her role, Christy was offered 3 different C-suite positions. She turned them all down. “I’ve had that moment where I’ve realized that where I want to go and where I am are 2 different places…. If I put my focus on something, my energy is going to flow in that direction, and I need to make sure that’s the direction I want to go…. Do I want to go be c-suite and kill myself for the next 4 years? …But the reason that gave me confidence is I’m 3 days without a job. I’ve got several job offers. And I realized, they don’t care how I work with them. They just want to work with me, so why don’t I go out on my own?” – Christy Honeycutt, on the internal discussions she’s having after encountering job loss Christy understands she’s in a gifted place only because she put in the work of giving back to her community before she was in a tough spot. Her efforts include things like hosting Inside the C-Suite and doing free mentoring and coaching for others. “It’s because of all the goodwill I’ve done. My community paid it back tenfold. So set yourself apart in whatever it is that you’re doing…. Where we are today is you have to have a differentiator, or you’re going to be sitting on the shelf for 5 years.” – Christy Honeycutt Christy mentioned previously that it’s lonely when someone takes a C-suite role. How did her conversations with executives on Inside the C-Suite together with her experience in talent acquisition and recruitment impact her decision to not take a C-suite role? Christy knows that she doesn’t do anything halfway. If she were to take a C-suite role, she would be working 80 hours per week and traveling nonstop. Christy and her partner want to slow the pace down for their family, take time to travel, and do more purposeful things. She shares a story about Matthew McConaughey wanting to make the shift from romantic comedies to more serous roles to illustrate a shift of priority and focus. “Yeah, it crossed my mind. But it does not align with my long-term goal…. I realized I have a choice. You know, the universe has brought a lot of stuff to me. Is it because it’s meant for me, or is it noise?” – Christy Honeycutt Christy has shown up, given to her community in a visible way, and found her voice. But taking a C-suite role right now is not where she wants to be. Some of the job offers Christy received came from people who had been on her podcast. Christy tells more of the story of being at HR Tech and the reactions people in the industry had to her being on the market. Christy plans to continue conversations with those people about ways they can work together moving forward. “I’m really good at certain things, which you guys have broken down and helped me understand. I repeatedly get asked for those things, and those are the things I like to do. So why not go do that? Why not go be a consultant and do the things that I really like to do for people and not do the things I don’t like to do…? …I can just go do the fun stuff that they need my specialization in.” – Christy Honeycutt Christy wants to stay true to herself and honor the decision to increase bandwidth for her family. Many of the C-level executives Christy speaks to on her podcast love what they do, but they’ve had to learn to put themselves first. “I hear this more often than not. When they first start their organization, it’s business business business. Their health fails. Their family fails. So, the ones that actually made it and recovered through that little spike and actually make it out on the other side very quickly flip to ‘take care of my body (my temple), my soul, my family, then my business. It’s a battle for them.” – Christy Honeycutt At the time of this recording, Christy is thinking of starting her own firm, so she hopes she can take it slow enough to avoid these pitfalls. When we decide to slow the pace and do more of what we enjoy, can reflecting on those 3 wins from each previous job help us be confident that we can still get those wins without running at a hectic pace? Did Christy do this when thinking about what she wanted to do? Christy says she did not think about these for herself even though it would be her coaching to others in need of advice. “What I found interesting is that when you’re looking for an answer, if you actually open your eyes, it’s right there. It plays back to you. It plays back to you in conversations you have with people…. You often say what you need and what you want and where you’re at, but you don’t comprehend it. But if you hear someone you love, that you trust, repeat it back to you…it’s almost like it gives you permission to accept it.” – Christy Honeycutt Sometimes instead of giving people advice, we need to act as a mirror and reflect back what they’ve said. Christy didn’t need a C-level title. She doesn’t need to go do something to prove she can do it. She’s already done it. Christy understood she was ready for something different, even if it’s a little bit scary to consider going out on one’s own. “It’s scary to put yourself out there like that, but if you don’t, you’ll never know. I’d rather try and fail and learn than regret and not know.” – Christy Honeycutt If you want to follow up with Christy on this conversation, you can find here: On LinkedIn On her website On the podcasts she hosts – Inside the C-Suite and StrategicShift Mentioned in the Outro Do you have 3 wins from each job or at least the past several jobs you’ve held? And do you know the stories that go along with these? There are prerequisites that must be met before we can speak to our wins in an interview. It starts with documenting our accomplishments on a regular basis. Consider what the 3 wins are from your accomplishment list. Maybe you have more than 3 or need to use a different set of 3 based on a job to which you’re applying. Consider writing the story that goes with each win. It could be a resume bullet, but think of it as more detailed and something you can share in an interview. This is part of drafting a career narrative like Jason Belk suggested in Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2). We should not only write the draft but gain practice sharing the stories verbally in interviews, possibly conversations with our manager, and maybe even in conversations with industry peers at networking events (if and when appropriate). This is an iterative process! We like looking at conversations with recruiters as opportunities to practice telling our win stories. In the discussion with Christy, we heard about her experience losing a job. In Christy’s case she had been giving to her network long before this happened in a very visible way. Maybe you are doing this in a less visible way. Consider documenting that work, but make the overall intent to help others and impact people positively. It will pay off later when you need help. Christy shared an exercise in finding clarity. She knew a C-suite role would not match the pace that was aligned with what her family wanted. It wasn’t just about personal ambition. Remember to check out Christy’s podcasts, Inside the C-Suite and StrategicShift. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.--------38:58
- People First: Systematizing Go-to-Market for Your Role with Christy Honeycutt (1/2)Go-to-market strategy is something we often associate with a company or its products / services, but what if we could apply go-to-market to our job role? Christy Honeycutt, a talent acquisition veteran and our guest this week in episode 352, has used this mindset as a personal differentiator starting with her first job in the banking industry. We’ll follow Christy as she describes early experience as a people manager, learn why she developed a people first mentality, and recount the events that kickstarted her career in recruitment. This story helps us understand what is required to systematize the work we do and how difficult it can be for things that seem easy. Christy will also educate you on the importance of developing AI competence and the impact of recruitment process outsourcing on job candidate experience. Original Recording Date: 09-30-2025 Topics – Meet Christy Honeycutt, A Go-to-Market Perspective, Beginnings in the Banking Industry, Learning to Systematize and Duplicate Yourself, A People First Approach, Getting into Recruitment 2:10 – Meet Christy Honeycutt Christy Honeycutt has 20 years of talent acquisition experience, go-to-market experience, and some marketing experience sprinkled throughout. Christy is also the host of two different podcasts: On Inside the C-Suite, Christy interviews executive leaders to gain insight from life in these roles. StrategicShift is focused on the future of work, innovation, and AI. 3:17 – A Go-to-Market Perspective How would Christy define talent acquisition and recruitment and the differences between them? Recruitment should be thought about as more active. There is a job open with specific requirements which need to be filled based on time constraints. Talent acquisition is more strategic according to Christy. This would include understanding why a role is vacant, the succession plans, cultural initiatives, and workforce planning. Christy refers to this as “engaging passive pipelines for long-term goals.” Personnel in talent acquisition and recruitment are usually in those roles because they want to help people, but these roles may look slightly different across companies of various sizes and in different industries. How would Christy define go-to-market? We hear this term quite often but are not confident that everyone truly understands what this means. For context, Christy talks about looking at this with a lens across many different departments / internal organizations – marketing, recruitment, and even sales. “Go-to-market is understanding what is the product and who is the end user…. Am I filling a job? Then I’m going to market for that candidate that fits that job. Am I working for a tech company (which I most recently did)? Then, yes, I need to understand what is our product, who is the end user, who is the buyer…and how can I get this to market for them…to see, to use to buy, and to be delighted in? The go-to-market is really kind of a Frankenstein effect in my opinion. It’s really understanding the value and how it translates and then how you can connect the dots…. Go-to-market for me has just kind of been at my core since I was a kid.” – Christy Honeycutt For recruitment, the go-to-market is usually set based on an organization’s vision, mission, values, and culture. Christy uses the example of negotiating with her father (a former Marine) to get what she wanted when she was younger to illustrate that go-to-market can mean understanding how to sell. 7:01 – Beginnings in the Banking Industry Christy was a cheerleader in high school and got a fully paid scholarship to college, but at age 17, she was diagnosed with cancer. As a result of the diagnosis, she was not able to attend college. Christy always wanted to be a mom and did not want to ruin her chance to have children. Christy married her college sweetheart and became a stay-at-home mom of 2 children. She is now heathy, happy, and thankful she was able to have children. Christy’s father owned a nonprofit, and even while she was a stay-at-home mom, Christy was involved in marketing for nonprofits as a result. Christy also was part of the boards of her children’s schools, did volunteer work, and even taught pre-school. After moving to a new state, Christy needed to get a job to support her children. After applying at a bank, she landed a manager job. Within 6 months, the bank branch where she worked was the highest producing in the state of Texas. Christy came up with marketing initiatives to get customers to visit the bank. She gives the example of a yearly Halloween contest. At one point, the bank was robbed, and Christy learned to lead in stressful situations through this experience. She also learned that she has a photographic memory. Christy tells us her career really began in banking and then transitioned into marketing. Listen to the story about one of her clients who was a mortgage broker. Christy had 2 boys in various sports and was wearing herself out between work at the bank and home life. This mortgage broker sent an e-mail to help Christy get interviews for a role at a different bank. Christy tells the story of interviewing in the mortgage division of another bank (Prime Lending) close to Halloween. She was dressed as Lucille Ball for an event at her employer and ended up going to the interview in costume. The people who interviewed Christy loved it, and she was offered the job on the spot. 11:40 – Learning to Systematize and Duplicate Yourself “But the really interesting thing that happened is they said, ‘we want you to hire 3 of you…. What you’re doing is working, so what we’d like you to do is go have a think about how you can multiply that into other branches….’ Can you imagine sitting down and going, ‘what is it that I did today and how did I do it?’ …And, just really creating a job description, a profile, how they’re going to be successful…and then find the people and train the people? So that was my very first…experience with recruitment.” – Christy Honeycutt After removing the shock of being told to multiply herself, Christy began a process that she would repeat over and over in her career – thinking outside the box to create something special that she could automate or systematize. At that first bank, Christy managed people but had no prior training as a manager. How did she figure out how to manage people, and then how did that translate to the role in which she was asked to create job descriptions and multiply herself? We’ve heard from some guests that most first-time managers do not get training. Christy echoes this sentiment. Large banks will train you on laws and procedures, but Christy tells us she had to train herself on the people side. Mainly, she needed to learn how to manage the people, their schedules, and learn how to encourage them. Despite being the boss, Christy was still friends with the people who worked there. In being asked to multiply herself, Christy had to systematize the job she was already doing. She tells us it was a daunting task. “When you’re really good at things, what I’ve found is they seem natural to you, and they are not that hard.” – Christy Honeycutt When asked to duplicate herself, Christy downplayed her contributions a little bit. She advises all of us to step back and really think about the work we have done because we might not immediately recognize it and may downplay it in a similar way. As humans, we might at first feel like it is bragging to share the factual things we have done. Christy had to think about what she did, simplify it, and figure out how to translate that to the people she needed to hire. Christy was working for the mortgage division at a bank, and they needed to get more loans. She first sought to understand the sentiment of the bank’s customer base and if they had any needs. Step 1 was hosting a customer appreciation event. The customer appreciation event generated direct feedback on the bank’s processes and product offerings. Next, Christy sought to understand the bank’s target market, which was real estate agents. She thought about how to get real estate agents to use this specific mortgage broker. New real estate agents need help with marketing, so Christy got certified and began teaching marketing classes to real estate agents. All of the agents would eventually begin using the bank. “It’s just kind of understanding what’s in it for someone else…. I just…went step by step by step and built the framework….” – Christy Honeycutt The framework Christy mentions above outlined where the opportunities were for the bank (i.e. who might need their services), allowed for dividing up the work across divisions, and provided insight into the key performance indicators (KPIs) for measuring success. In many ways, Christy acted as a liaison between the bank, the real estate agents, and end customers. When seeking to hire people to do the work, Christy looked for empathetic people who were interested in helping others. Another avenue for the bank to increase the number of loans was working with first-time home buyers who might have poor credit. This would help real estate agents who needed home buyers. The bank started doing credit repair seminars to generate new leads. “I was bringing in buyers, delighting previous buyers, and then also going after the vendors that would help participate. Honestly, that model…has kind of been my two step my whole career.” – Christy Honeycutt Nick thinks Christy’s process is actually a three-step with the third being supplementing the above with the type of education which will both Christy and the audience she seeks to serve. Nick thinks this pattern will probably be repeated somewhere in her story as well. Christy says it actually does repeat. She recounts getting an AI-focused certification when this technology wave started catching on. “In the next 12-18 months, over 80% of all organizations globally will have adopted AI if they haven’t already. So, if you’re looking for a job, and you don’t understand the basics…AI has a lot of different names. I want you guys to think about that. That’s usually marketing.” – Christy Honeycutt Christy tells us AI agents are mostly marketing and an attempt to make things more consumable and understandable rather than some flashy new invention. Christy recounts talking to executive leaders who have mentioned having AI in one’s toolkit even as a kid is important to be relevant in the future workforce. All of us need to have more than a bare minimum exposure to ChatGPT, for example. We need to play, create, and tinker with AI tooling to develop a point of view that is uniquely ours. Christy feels AI will take jobs but that they will be lower-level things that we probably wanted automated anyway. She gives the example of a communications outage impacting airports in Dallas / Fort Worth and the decision to go get information from an AI agent on the company website rather than call the help desk. For any job you go into, expect to get questions around AI. Christy mentions a recent visit to the HR Tech conference. Every booth was promoting some kind of AI, and Christy shared with executives at the conference that buyers don’t fully understand the difference between products because “everyone is saying the same thing.” Christy reminds us there are ways to get low cost or even free education on the topic of AI so we can develop competence and a point of view. Nick shares his perspective on what he calls the “double check mark,” which is looking to educate yourself or build skills in an area that can help you both at your current employer but also make you marketable and relevant in the greater job market. Something that only helps you with your current role isn’t quite as attractive as something that can help you later as well. Ideally, you span into both categories, but it is not always possible. Christy mentions this is a very tech answer and gives the example of making a suggestion to an executive leader while advising for a tech startup. She only brought suggestions that would be attractive to / helpful to many customers (not just a single customer). When Christy did research on what was impacting customer sentiment and spoke about understanding product market fit, was that all natural at the time she did it while working at the bank? Christy says it was natural at the time. As a single mom, she needed to be scrappy. “It’s funny because as I sit back and I think…I realize everything was kind of predestined. And at the moment it just felt like I was reacting and I was doing it, but…as I do my own reflection, I’m realizing that these cycles I’ve been on have always been for a reason, guiding me to where I’m at.” – Christy Honeycutt Reflection is one way to uncover our strengths, and Christy reminds us that just because something is easy for us does not disqualify it from being a strength. John mentions that performing a skill really well is different than being able to teach other people how to do it. When something comes easily to you, it might be difficult to know how to teach someone else to do it. But it sounds like Christy had to learn how to systematize the things she did so she could train others (i.e. it was not natural). Christy says it definitely was not natural. She remembers how she felt when asked to duplicate herself. It seemed like a crazy request at the time. One thing that really helped Christy through this process was looking at job descriptions for roles similar to hers at other companies and analyzing both similarities and differences. “Everything is a learning lesson. I don’t regret any place I’ve ever worked. I don’t regret any situation I’ve ever had because it was all opportunity for me to learn how to manage through a situation (good, bad, or indifferent) and reflect on it and how I would do it differently.” – Christy Honeycutt Christy mentioned earlier that no one learns how to be a manager. She is a forthcoming author and was recently signed with Postal Publishing House, and the book will be about leadership. In the book Christy talks about how no one is trained to be a leader and how people often just kind of fall into it. She feels it is a big gap. Even as people get up to the director level and maybe even the VP level, they are still learning. “No one sits you down and says, ‘hey, these really crazy things are going to happen, and you’re going to have to respond to these humans in a particular way. And by the way, you’re human, and you might have a really bad response to what you have to respond to….’ There’s lots of things that you deal with that I don’t think anyone could prepare you to deal with. And so, you learn on the job.” – Christy Honeycutt Did the need to create job descriptions and hire people to multiply herself make Christy enjoy management more or question whether she wanted to keep doing it? Christy tells us she questioned whether she wanted to keep doing it. Her responsibilities ended up expanding well beyond the go-to-market work she was doing, and things became more complex. Christy went from being in charge of 1 person to being in charge of 4 people trying to do everything using her methodology but with their own flair. “Frankly, I got kind of bored because I created something, I duplicated myself, multiplied myself…. Ok, I’m ready for the next thing. I can do this, and I’m ready for the next thing…. I’m constantly curious, and I always need something more just to kind of keep my attention. There’s a lot of people in the industry I think are that way, especially in tech…. And those are the people that employers are looking for. They are looking for the curious people. They are looking for the open-minded individuals that want to adapt and want to learn and do more because those are the ones that have the longevity.” – Christy Honeycutt Once we master things as technical people, we often want to move onto what is next (something new to learn, a new certification to chase, etc.). 26:23 – A People First Approach Did Christy’s background in cheerleading help her in marketing? Actually, yes. Christy gives the illustration of high school cheerleading and pep squads. These are made up of people who love community and love to empower and cheer on other people. Christy reminds us that cheerleading is a sport. For those in cheer or pep squad, it’s not about wearing cute outfits. There is a commonality among the people who participate: an enjoyment of collaboration, a desire to win, and a belief that there is power in the energy they are giving. Christy likes to look at things from an energy lens. “In every industry you’ve got really good players, and you’ve got bad actors. So not all recruiters, not all talent acquisition people are really kindhearted, love what they are doing, and in it for you…. But the majority of the people in the HR and TA (talent acquisition) space generally joined that type of work because they love people, and they are fearful right now because they think AI is taking their job. And some of them it probably will, but you’re never going to get away from the EI and the EQ piece that is required in the age of AI. We need to be more human now than ever.” – Christy Honeycutt Some people in these roles may hate their job. Some may love you as a candidate but be unable to get anything through. At what point did Christy realize that for her it was more about the people? “It’s always been about the people for me. Everything I do has been about people. I’m people first just in everything I do.” – Christy Honeycutt After getting the job where she needed to duplicate herself, Christy wanted to talk to all of the company’s customers as her first task. Christy mentions the concept of go-to-market is the same regardless of the company where we work. “Your customers are your biggest resource because they will either be the loudest complainers or your biggest fans.” – Christy Honeycutt Customers with a positive sentiment toward a company (or its products and services) can offer free insight on how to serve them better. This may come in the form of suggestions for new features and capabilities or advice on overall direction, for example, and provides a perspective that a vendor cannot otherwise see. Christy has been told she is too “client advocate friendly.” When selling a product or service to a customer, if users don’t adopt it, you are only as good as the contract. Christy calls this being a one trick pony. On the other hand, we can sell a product or service and care enough to check in with customers and make pivots to make the product or service more valuable. This creates what Christy refers to as a “client for life.” “And that’s, I think, where my specialty comes from is the human side, the people side. It’s just always remembering what’s in it for somebody else. Because we all have exchanges every day. What’s in it for the other person?” – Christy Honeycutt Christy makes a hypothesis that we do this podcast to help people and because we care, and at some point in our career we probably needed what we are giving. What would you have said is the reason for the podcast based on being a listener? “People are my thing. I get the heart. I get the energy, and I think at the end of the day, we all put our shoes on the same way.” – Christy Honeycutt Christy really enjoys hosting Inside the C-Suite because it demystifies what it is like to be an executive leader. “It’s understanding how you navigate and how your priorities change…what’s now, what’s next, what’s urgent always evolves as you grow in your career.” – Christy Honeycutt 31:52 – Getting into Recruitment How did Christy end up getting into talent acquisition and recruitment? Even with her hectic travel schedule hosting events for her employer, Christy never missed a little league baseball game in which her kids were playing. At a specific game, someone asked Christy what she did for a living and if she had ever thought about working in recruitment. The person who made the suggestion helped Christy see the similarities between recruitment and marketing. “Client needs a certain thing, and you go find the certain thing. And however you find it, you find it. That’s a lot like marketing. Exactly.” – Christy Honeycutt, describing an exchange with someone who encouraged her to pursue work as a recruiter Christy went to an interview for a recruiting role and got the job on the spot. The company was bought out by Kenexa(CEO was Rudy Karsan) which was later acquired by IBM (or “big blue” as Christy calls them). Christy did recruitment process outsourcing for this company (or RPO for short) and specialized in this area for many years. She led this at IBM and later at Korn Ferry. She tells us there are so many layers to recruiting that people don’t know. Staffing agencies, for example, often get a bad reputation. These agencies are predominantly focused on high-volume hourly roles or other short-term positions. Quality and candidate experience are not always the best. These recruiters have to move quickly because a successful placement is how they get paid. “And when you do that really, really well the clients think that you’re their internal recruiter…. I think over my career, not me directly but within my teams, I’ve probably placed around 30,000 individuals.” – Christy Honeycutt, on specializing in RPO Listen to Christy talk through an example of mapping through the workforce strategy for a client that wanted to outsource global recruitment on a tight timeline. She emphasizes that when we work with a recruiter, that recruiter might not work for the company where we are interviewing. “When an RPO does a good job, not only does the candidate think that they’re an internal recruiter, but the clients think they are an internal recruiter.” – Christy Honeycutt Christy talks about making a move from being a liaison manager for a client (focused on the client’s technology sales and marketing) to managing an internal team. The client thought she was their employee. Don’t miss the part where Christy mentions she wanted to take a role as a recruiter so she could understand how to be a better manager. “While your…audience is out there looking for jobs, just be mindful that…TA, recruitment, HR…depending on the size of the organization…you may be talking to an agency. You may be talking to an RPO. You may be talking to an internal recruiter. You can ask them. They don’t have to tell you.” – Christy Honeycutt Another challenge for the job seekers out there is the amount of fraud happening. On average, every US citizen has 7 points of fraud directed at them per day. Christy mentions getting multiple text messages from companies claiming to be Randstad, Robert Half, or some other firm about jobs. It’s all fraud. Don’t fall for it! When Christy worked for Korn Ferry and another tech startup, as part of the go-to-market strategy, she created a candidate application analysis tool which informed clients about the candidate’s experience. Some clients didn’t realize, for example, that their site was down and was preventing people from even applying. This tool also informed clients about how they showed up on sites like Glassdoor and what the biggest complaints are. The lowest scores 9 out of 10 times for a company are for leadership. Keep in mind rankings on Glassdoor are from job candidates and people who have worked at a specific company, and most do not take time to write glowing reviews of an employer. “We have to give the employers the benefit of the doubt. So when you know where the sources are coming from and you’re honest with yourself on when you give feedback and how you give feedback…until we can all step up as humans and start giving 2-3 good feedbacks a day, we’re never going to balance out the negative.” – Christy Honeycutt Mentioned in the Outro Christy did a great job emphasizing that we understand what is it for the other people we work with (incentives, metrics, what success looks like for them), and that was part of executing a successful go-to-market strategy in banking and other areas. Here’s how Nick thinks a go-to-market might look for someone working internal IT: Understand the technology landscape at your company (hardware, software, cloud services and subscriptions – the overall vendor landscape) Understand the end user base you support and the capabilities you are providing to them. Think also about the value being delivered through these capabilities to both internal users and external users if applicable. Think about the capabilities you provide like products. Can your products be enhanced based on end user needs and feedback, and are we willing to take the feedback? Christy modeled the importance of understanding customer sentiment that can help us here. Will an enhancement save time, decrease cost, decrease risk, or increase revenue? These are important impact metrics to understand (and document). If you change a hardware / software vendor (i.e. a tooling change), will it disrupt your customer base, or can you still provide the same capabilities? Make sure you understand this! Is there a new capability you could provide that delivers more capability? That’s part of the go-to-market. Are there members of the end user base who need education to get more value from the services and capabilities you’re offering? Don’t forget to check out the podcasts Christy hosts –Inside the C-Suite and StrategicShift. Nick feels podcasts such as Inside the C-Suite are great sources to gain perspective on how executive leaders operate. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.--------43:25
- A Special Announcement – Changing Our Release ScheduleOriginal Recording Date: 11/2/2025 Expect a Change Moving Forward – The Schedule Hi everyone – thank you for being a listener. This is a brief reminder that episodes from this point forward will be releasing every 2 weeks for the time being. Life circumstances have demanded we make this change to keep producing the show. Don’t expect any changes to our content. We remain committed to serving the technology professional and helping them accelerate career progression, increase job satisfaction, and be more effective in their existing role. Thanks for coming along with us on the journey, and it will continue. Expect to hear from us every 2 weeks from this point. See you next week for another action-packed episode! If you have ideas for a topic we should explore or a guest we need to have on the show, feel free to contact us via any of the channels below. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.--------0:52
- Opt In: A CEO’s Take on Becoming AI Native with Milin Desai (3/3)What does it mean to become AI native? It’s not about using every AI tool on the market. For Milin Desai, the CEO of Sentry, it’s about becoming familiar with the tools and opting in to use the capabilities that deliver practical value. This mindset was born while Milin was the general manager of a business unit at a software company. In this role, he had to manage a profit and loss statement, learning the art of constrained resource planning and organizational adaptability. In episode 351, our final installment of the conversation, listen as Milin describes both the gravity and different intensity of the CEO’s role compared to past roles. You’ll get insight into the strategy behind enabling an entire organization to shift and become AI native, how this translates into value for customers and employees, and how the individual contributor can be a better contextual communicator when speaking to busy leaders. Stick with us until the end to understand how a set of first principles can guide our career progression if we choose to actively participate in it. Original Recording Date: 09-29-2025 Milin Desai is currently the CEO of Sentry. If you missed parts 1 and 2 of our discussion with Milin, check out Episode 349 – Expand Your Curiosity: Build, Own, and Maintain Relevance with Milin Desai (1/3) and Episode 350 – Scope and Upside: The Importance of Contextual Communication with Milin Desai (2/3). Topics – Contrasting the Role of General Manager with CEO, Embrace Practicality with New Technology, Junior Personnel and a Return to First Principles, Shifting Organizational Focus to Becoming AI Native, Contextual Communication to Leaders and Parting Thoughts 2:41 – Contrasting the Role of General Manager with CEO General managers usually own a profit and loss statement (or PNL statement). How was this different than the things Milin had previously gone through? Milin says you do have to prepare yourself for it, and his experience as part of product teams was very helpful to gain familiarity with many of the elements of the general manager role (i.e. revenue protections, investing resources in specific efforts, etc.). Things get very interesting when you are managing PNL in a constrained environment. Milin gives some insight into annual planning and the behaviors he has observed during these times. “Very rarely do people come back and say, ‘I’ve got the same org. I’m going to reshape the org, move things around, and I’m going to do these new things with the same number of people.’ I think most leaders are not very good with that philosophy.” – Milin Desai In this role Milin tells us he learned how to do planning with specific constraints in mind (i.e. stress testing as if no resources / extra people could be added), and this idea of keeping teams lean taught him about the adaptability of an organization. “I really think every organization should do that, and then, you always have the ability to go add more people…. Structurally say, ‘is this how we still want to operate?’ And we rarely do that…. I knew the numbers, the resources, and everything else. We did a lot of planning. But what I learned I needed to get better at is this constrained planning…” – Milin Desai Milin loved working as a general manager and thinking through how to optimize even if the organization didn’t get everything it wanted. “What is the hardest thing to do? To say no. What is the hardest thing for a product manager to do? Shut down a feature. What is the hardest thing for a VP of engineering to do? To shut down a product…. I’m lucky enough to have a leadership team that…thinks along those lines. We are unconstrained, but we kind of try to make sure…let’s put some artificial constraints and see what we would do different.” – Milin Desai Nick mentions this is analogous to the employee who is no longer a fit and having to say no to that person moving on with the company. What is the contrast between being a general manager of a business unit and being the CEO of an entire organization? Milin remembers some of the conversations when he was considering becoming a CEO. “Milin, are you sure you want to do this? And it was not a capability question. It was, ‘do you understand what you are signing up for?’ …It is very different. You are responsible for everything. There is no other person. There is no other excuse. There is no other system I can blame. Something goes wrong at Sentry…I am it. And I have to go to sleep every day thinking about it. I wake up every day thinking about it.” – Milin Desai, quoting a question from former boss John Martin and speaking to the contrast of being CEO compared to general manager You have to know you want to be CEO. Many people think they want to do it until they are doing it and realize how difficult it is. Milin admits being CEO has been difficult, but having a great team has been very helpful. Before taking the role, Milin spoke to his wife about it. He describes the role as “a very different intensity.” Three months into Milin being CEO of Sentry, COVID showed up. That is a challenge he never would have expected. “It’s very different to be a GM versus being a CEO. You’re using your same skills, but it’s a completely different magnitude of responsibility and impact.” – Milin Desai As a general manager of a business unit, Milin could change the trajectory of his business unit. As CEO, mistakes are much more costly. But you cannot do it in fear. In fact, for Milin, the larger impact of his role is exciting. The right partners and team around you as CEO are very important as are taking and applying lessons you previously learned. Milin continues to push himself to improve over time even after reaching the CEO level. 9:22 – Embrace Practicality with New Technology John cites technology waves like virtualization, cloud, mobile, and generative AI. With generative AI, many of us get value from it. But many people are unconvinced of the value and are even fearful it will turn into something like Skynet (a reference from the movie Terminator 2). How does Milin approach people with this mindset? Milin is practical with his approach to technology. “The unconstrained view of what AI could do…we have seen it in movies already. So, I think the unconstrained aspect of this is what we can imagine or maybe even worse…. You can almost think about that and worry and not participate and be on the other side if that happens…. Or, just practically, on a day-to-day basis, figure out what aspects you want to opt in. So, I’m more in that camp…. On the AI front, just think about how it could practically help you on a day-to-day basis versus trying to worry too much about all the aspects, some of which you absolutely don’t even control…. I think it will bring productivity in ways that we don’t even know.” – Milin Desai For example, Milin doesn’t have a voice assistant, didn’t find them useful, and did not opt in. If you’re worried about supporting a bigger cause, Milin tells us that bigger cause is going to happen irrespective of us supporting it. Instead, we should think about how to practically use AI tools and become an active voice in it. Milin tells us his wife just started using ChatGPT and loves it. He asked her the value question on whether it was worth paying for it vs. staying on the free tier after she talked about how much it helped. She agreed that it was worth the money. Milin cites the potential for productivity gains we don’t even know or understand yet. For example, imagine a robot doing laundry for you so you can do something else. Milin thinks there will be some significant value points with robotics and AI. He’s excited at the potential for optimizing daily tasks that this could bring. “Just be practical in how you’re using it and how it will bring value to your life, and the ones that you don’t find valuable, don’t do it. I don’t try every AI tool…. But the things I care about, I lean in.” – Milin Desai We don’t control the unconstrained and should not worry about it according to Milin, but we can be a positive participant in this (AI) by participating in communities that serve the greater good in this area. Milin says the idea of an AI bubble bursting will be determined over time, but transformation is happening. There are business use cases in vertical industries for AI (i.e. for medical transcribing). It’s not just people doing personal research at home, for example. The intersection of AI and robots will be an exceptional thing. We have to figure out our place in all of this, which is a harder question. “I fundamentally believe you will still need engineers. You will still need certain things. But certain functions are getting automated…. You’re going to have to figure out where is the new value being created and how…you participate in the new value system.” – Milin Desai This comes back to curiosity, asking good questions, listening, watching for where things are moving, etc. We can apply those same principles to the field of AI. Milin tells us almost every company out there is willing to let you explore and learn when it comes to AI (which means. At Sentry, people are encouraged to use the tools they want to become “AI native.” “Leverage that. Lean into it. Don’t shy away from it.” – Milin Desai, on utilizing your job role and resources to learn AI tooling and the value it can provide 15:07 – Junior Personnel and a Return to First Principles Nick wonders how junior technology personnel can develop the expertise of someone who is more senior when the senior folks developed their expertise before AI existed? Can giving a junior employee AI tooling help them gain that same level of expertise? Milin says this is about getting more “at bats.” Someone could read all about running a company or working with top leaders, but until they have done it, they cannot really understand what it is like. For senior personnel, using AI tools will remove some of the tedious tasks and be more of an accelerant. Junior personnel do need to become AI native, but in addition to this, Milin recommends spending your time thinking through failure modes and other fundamentals. “If something breaks, will I be able to debug it? What are the failure modes for a user that is accessing the system? At what point in time will we have to look at scale aspects of the system…both just scaling versus architecturally? And then you start asking those questions and putting those pieces as learning building blocks…. I think you have to think again at first level principles, system level thinking.” – Milin Desai In addition to the above questions, think about the following: Is the user’s experience intact? Does good design documentation exist? Milin says these “first principles of system thinking” develop from writing, deep thinking, thinking through things from a user’s perspective, considering failure and scaling modes, etc. “And so you build those habits, even as a young engineer…. When you get to a point, you will start asking the right questions, and AI or no AI, you’re going to be successful and valued because you’re thinking in first principles. You have to develop that, but you can develop that with AI and with the folks around you.” – Milin Desai 17:47 – Shifting Organizational Focus to Becoming AI Native With Milin’s view on AI as not pure hype, how are organizations reorganizing priorities around how products get developed, tested, and shipped? Milin tells us over 150,000 organizations use Sentry from the smallest startups to the largest organizations. The customer base scale is massive, and the feedback is constant, fast, and iterative. “We have basically told the entire company, ‘You must become AI native….’ The number one thing we did was we unconstrained everyone to say, ‘go figure out how to become AI native.’ Whether you’re at Sentry or otherwise, this is a skill you are going to need. So, participate in it.” – Milin Desai Milin says employees were encouraged to initially choose the tools necessary to become AI native, and corporate constraints would come into play a little bit later after personnel had built a skill base. The Sentry team also had a set of people building AI-specific capabilities, but the intention was not to have a single, centralized AI team. “There is a set of people who are experts at fine-tuning…the models and how everything works. But, if you want to be the company of the future, it’s not an AI team. It’s everything in terms of what you’re building has a perspective of participating in an AI native world. It cannot be that…30% of the team that is working on AI stuff, and the others are not….” – Milin Desai AI is a tailwind for Sentry according to Milin. It was a goal to take some of the things the team was already doing (i.e. products they were building) and look for ways to make those products AI native. Milin spoke to some of the work new graduates at Sentry did to build session replay summarization. This was their chance to take a project from 0 to 1. Having an AI-themed “hack week” inside the company created a new energy and air of excitement. “And so where are we right now? We basically are like, ‘what does it mean for Sentry to exploit all the opportunity it is in software?’ …It’s not constrained to a team. It’s organization wide…. Pretty much across the board, every team is going to look at what they do and say, ‘Is it a version that brings the experience forward because we now have LLMs and AI and all this new tech?’ That’s the question you have to answer.” – Milin Desai The individual teams also have to think about where the experience in their product gets enhanced with these new technologies. It might be in the front end, back end, or something invisible to the user entirely. Milin also mentions there is an internal team that owns building the core AI and infrastructure elements separate and apart from their product enhancement focus. While everyone is moving in the same direction now, this shift Milin describes came in phases. It was introduced with a little guidance and happened over a period of 3-4 months. “But you have to bring people along for the ride versus… ‘here’s what you’re going to do.’ That doesn’t work.” – Milin Desai John says at first these steps sound like ways to modernize an organization, but in this case, it’s more to keep up with current trends and new ways to provide value. Milin says it is to stay relevant. “It’s to stay relevant. That’s why I made the statement – with or without Sentry, every employee has to become AI native…. What we did was let folks opt in into kind of new areas of the product, and now everybody’s opting in.” – Milin Desai Milin says they did not need to do unnatural things to leverage AI as a tailwind. If you are in a situation where a new trend like AI has come out of nowhere to impact what you do or threaten your relevance, it might require a pause and reset. John speaks to the technology adoption lifecycle. There are bleeding edge use cases that apply to only the innovators. Next comes the use cases for innovators and early adopters. John says we can be the late majority to some of the things happening and gives the example of e-mail summaries from AI being an extremely useful of a late majority feature. We can opt into late majority features without opting into everything or opting into the worst possible outcomes of using AI. Milin gives the example of Sentry shipping a grouping feature powered by AI that resulted in big efficiency increases for customers. Most people would not know it’s powered by AI, and it was one of the first capabilities they shipped after implementing some of the internal changes Milin described earlier. Milin says our attention spans are getting shorter and shorter, and some of the capabilities AI can bring are going to help with this. 25:35 – Contextual Communication to Leaders and Parting Thoughts We spoke about the importance of contextual communication from management down to employees at lower levels and even about how important this is when using generative AI tools. Where Nick sees a lot of people struggle is when they are an individual contributor trying to be a contextual communicator upward to leaders. How can we do this well when working with busy leaders in a world where attention spans are getting shorter? Milin says we don’t really think about this. We don’t think about the potential for running into a senior leader at a company and what we would do if they asked us a question. “What tends to happen is you run into somebody who is maybe 1 or 2 levels of ownership higher than you. They ask you a question. You are deep in the weeds of solving a problem, and so you’re so lost in that problem that when you speak to that person…you may miss an opportunity to talk about why you’re solving that problem…. Always remember and always ask early on in your career…why are we doing this? How does this help? Who does it help? Just knowing that and starting to believe in that is helpful.” – Milin Desai Milin says he’s had 1-1s with people who have told him something isn’t going to work. He would prefer them to speak up and question why something is being built if it’s not going to work based on those questions above. “What is the job of somebody two levels up? They are just asking the right questions. What do you think? Is it going to solve the problem?” – Milin Desai Knowing the fundamentals as Milin outlined above (why, how / who something helps) allows you to have a conversation with a leader on the topic, and you can bring a point of view. It helps with what he calls “asynchronous communication” where you end up getting those unexpected questions about how things are going. “Just always ask this – ‘why am I doing this? Who am I doing it for? And then as a result you’ll know the value, you’ll know the persona, and how does it fit in. Those questions then contextualize everything. It doesn’t matter level 1 or level N at that point in time.” – Milin Desai Milin hopes listeners can parse out the value from this conversation. "Just come back to first principles of all the things we talked about. Be insanely curious. Be insanely active. Participate. And then everything kind of flows from there…. At the end of the day, we are only as good as the people around us. And whether you’re a manager listening, you’re an IC…remember, it’s about the humans…. Those people can only help you if you want to be helped. So, you need to take charge and ask and drive the conversation. And there will be a point where you may not be satisfied. We all are impatient. We all want to reach the summit on the very next day. Sometimes it takes time, so you have to understand what level of patience you have. But you own your path, your narrative, your direction…and you need to make sure that you get the most of an organization. I think people tend to forget that. Organizations sometimes get busy. I am not making excuses for people like me and others, but what I am trying to get at is I didn’t get here by waiting for people to give me what I believe was mine…. I actively participated in that conversation. Of course, I then had great mentors who then helped me with it. It did not come right away. I had to wait, be patient. But I’ll tell you, for the most part if you work hard, you’re an active contributor, you’re curious, you have good people you’re working for…things come along. And that formula is going to work. " – Milin Desai We cannot assume an organization is going to do wonders but should be active in the story. Milin is living proof of this. To follow up with Milin on this conversation: Follow him on X – @virtualmilin Follow Milin on LinkedIn Follow what is happening with Sentry: Sentry Blog Mentioned in the Outro There are layers of opting in throughout this discussion: Opting in to use and learn about AI tools is one aspect, and opting in to leverage the tools for the use cases that provide value is another. Milin had to opt in when he moved into the CEO role, and he has created an environment at Sentry that has enabled people within his organization to opt in for leveraging AI to provide more value to customers. Remember those 3 questions Milin mentioned: Why are we doing this? How does it help? Who does it help? Due to life circumstances, our show is moving from a weekly release to releasing every 2 weeks for the time being. We want to make it on a schedule that is sustainable and at the quality we want. When you don’t see a release next Tuesday, it’s because of this change. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.--------35:38
- Scope and Upside: The Importance of Contextual Communication with Milin Desai (2/3)When we use a generative AI tool, providing more context can often lead to better output. What if we could apply this to our communication with other humans? Milin Desai, the CEO of Sentry, says contextualizing communication will change the way you operate. This week in episode 350, we’ll follow Milin’s story of changing companies and pursuing different levels of leadership. Listen closely to learn about the importance and impact of active listening, how practice with written communication can help us develop a clearer narrative, the skills needed in higher levels of leadership, and how we can evaluate new opportunities through the lens of scope and upside. Original Recording Date: 09-29-2025 Milin Desai is currently the CEO of Sentry. If you missed part 1 of our discussion with Milin, check out Episode 349 – Expand Your Curiosity: Build, Own, and Maintain Relevance with Milin Desai (1/3). Topics – Customer Discovery and Active Listening, Contextual Communication and Iterating on a Narrative, Scope and Upside, Necessary Skills at Different Leadership Levels, Enabling Active Participation 2:49 – Customer Discovery and Active Listening What Milin said without stating it explicitly was that we need to do a better job of asking people more questions to understand where they are coming from and what they care about. This is what Nick refers to as doing discovery, and it applies to the person working a ticket in IT just as much as the product leader or sales engineer working with a customer. “AI is best when given the best context, so contextualize every conversation. And if you contextualize every conversation, it will change how you operate.” – Milin Desai Milin gives the example of a support technician doing the work to close a ticket for someone but then taking a proactive step to let the submitter know there are other related issues you could help resolve. He classifies this as the “extra step” that some people just do without being asked. Very few people are self-aware and like to rate themselves as the best at different things. “That self-assessment is super important…. That extra juice that people are looking for is that contextualization, that personalization, that dot connecting…that is what will change you. And that comes with being curious, asking the questions, listening…active listening.” – Milin Desai Milin says active listening is difficult for him, but it’s something he has become better at over time. John says sometimes the question a person asks is not the question that person wants the answer to. It’s not up to us to just answer the question that was asked. It’s up to us to go the extra mile and ask questions to get more of the context. Milin shares an anecdote for people in customer-facing roles. Validation that a product pitch is resonating with a customer comes from active listening and questions. But there’s even more. “But you forgot to ask a simple question…in the next six months, if you had a dollar to spend, would you spend it on this? We forget to ask the most important question. If I’m going to build it, will you use it? Will you buy it?” – Milin Desai Without asking the above questions, product teams may relay that feedback from a customer was nothing but positive and not understand why product activation numbers are low. We need to figure out why a customer would use a product or feature rather than assuming they will use it when it is pitched / suggested to them. Be intentional about understanding the customer’s priority as well. “The same principles apply to development and everything else in our lives too. If you only had an hour a day, what would you do with it? Start thinking that way, and it makes things very, very simple.” – Milin Desai Nick says we could also ask about priority when pitching an internal project idea to management. Would someone approve the project in the next six months? John suggests asking how far out in someone’s priority list a project would be. What if your project idea or the product you are pitching is not on someone’s priority list? Should you just stop there? At this point with time left in a meeting you have options. Asking to tell someone what you are building is a mistake, and so is just ending the meeting. “What if you spend the next 5 minutes asking, ‘what is the most important things you’re thinking through?’ Because yes, it may not be the current thing you are doing, but again, coming back to knowing what other people in the company are doing, it could be connected to another initiative, another project, another product that the team is building. So, coming back to the same curiosity we talked about, and knowing what’s happening around you, you may find something. Or you may just learn…. But you came ahead as a high IQ individual who is saving them time, who cares about them more than they care about selling a product.” – Milin Desai It’s important that we learn to pause in this way to gain understanding. Asking someone what they feel is important or what their priorities are after they’ve said something is not a priority is an acknowledgement that what you brought them isn’t relevant. Learning more about the priorities of your audience may bring about an opportunity for a different group / team if you’re plugged into what is happening in other parts of your organization. One option is nothing comes of it, and you learn something. Nick says once we learn what someone thinks is important, we might get a much better idea than what we originally came to the meeting with. 9:00 – Contextual Communication and Iterating on a Narrative John says this goes back to empathizing with the customer and living in their shoes. Part of this job is to collect customer priorities and report it back to your organization. This information might indicate a product a company is building does not solve the right customer problems or doesn’t align with customer priority. From a career perspective, people might think they need to do all of this alone – get on the customer calls, understand what customers want, and synthesize it to relay to other teams. When Milin was a product manager, he started pulling in other team members to be on customer calls with him. This began when Milin was at Riverbed, but Milin tells us he leveraged it much more during his time at VMware. “The interpretation of that conversation can be very different…. After that call is finished, you ask for their interpretation. Did they have happy ears? Did you have happy ears? But more importantly you as a team get on the same page about the opportunity.” – Milin Desai Milin is speaking about promoting collaboration between product managers and engineering teams by ensuring the engineering team members have access to the same set of information. Getting them to hear information straight from a customer helps promote alignment better than receiving feedback only via the product manager who spoke to the customer. Being part of the live conversation is also better than only having access to the recording. Letting other members of your team that you work closely with participate along with you is extremely important according to Milin. You don’t need to do it alone. “So, I think that participation is really important, and the second most important thing in any career progression, anything from non-tech or tech, is communication…contextual communication…. Talking to a VP versus an EVP versus a CRO…everyone is different. We as humans don’t spend enough time on contextual communication in our personal or professional lives. And I would say the single biggest thing I see people make a mistake on is not invest in communication, written form communication….” – Milin Desai If communicating to an engineering team, have them feel they were in that conversation. Give them a synthesis of the problems you talked about and what happened as a result. Storytelling and communication are important to provide your perspective on what happened to others. We can write our thoughts down and then iterate on them. When the thoughts are fully formed, we can share them with a group. Spend time writing down your thoughts, and contextualize them for the audience with which you are sharing them. When we write down our thoughts in draft form, Milin says it should feel natural and not take a lot of time. The story arc can be cleaned up as a next pass / next iteration. John mentions there is a difference between a transient idea and something you take the time to articulate through writing. The latter is something you can understand and have a conversation with others about. John talks about writing as something that enables fully formed thoughts and the evolution of those thoughts. Milin had the opportunity to work for Marin Casado (founder Nicira), and Martin encouraged people to write things down because “you don’t think in PowerPoints.” Milin has developed a habit of writing over time. When he gets an idea, even if it is sitting on a train, he might write it down and save it in his e-mail drafts folder to get it out of his head. Milin will then come back to it later (a day, a week, etc.) to refine it and then share with a larger audience. Martin Casado also encouraged people to think like a story. “The art of storytelling allows you to bring a point of view to the world.” – Milin Desai Nick says this idea of writing, letting it sit for a time, and coming back to refine what you wrote sounds like a great way to prepare for scenario-based interviews. Milin shares some of the feedback he gives people who have completed an internship at Sentry. “Make sure you have a narrative around this. If you choose not to come back to Sentry for a full-time job, when somebody asks you what you did, you have a compelling narrative around what happened and what you learned…. You’re absolutely right. You need to own the narrative and drive it. But you need to find that balance between too much, too little, too boasty, or not telling enough about yourself.” – Milin Desai As we develop a narrative, the brevity and depth might change as we change roles. In Milin’s case, he moved to product management but then began to move into leadership positions. How did he see his narrative change in depth and brevity over time? Milin says it has been the hardest thing. Written form communication is hard. We should be self-aware and self-critical but not let these things affect our confidence. “I just want to make sure everybody understands when I keep saying these things, it’s not about breaking your confidence. It’s knowing who you are and then improving on it.” – Milin Desai Milin tells us he is either very verbose or very succinct, and writing / narrating a full story has taken time to improve. Milin is very good with story arcs, but it’s writing the entire story which is the hard part. “That’s been my strength. I can get you to understand the core, the why, very quickly. But then when I have to make it medium form or long form, I continue to struggle in that. That’s been work in progress.” – Milin Desai This is the contextual communication piece of things. Milin talks about his experience doing all-hands calls as a general manager or as a CEO. Giving too much information in these cases will lose the audience. Most of the time you have to find a middle ground between too much and too little information. Milin says the question-and-answer section of these all-hands calls tells you where the gaps are. He would fill in the gaps either using offline mechanisms or a smaller set of meetings to address these questions. Milin also said it took him a while to get to this point. “And it takes practice to take 3 pages and make it 1 page and make it relevant. It’s really art.” – Milin Desai Maybe AI tools can help here, practice certainly helps, and knowing your audience helps. Knowing your audience is part of contextual communication. Milin says he’s done a lot of iteration and practice to develop these skills. 17:57 – Scope and Upside Regarding Milin’s transition away from Riverbed… Milin says he really enjoyed his time at Riverbed but had hit a wall. In aggregate from a dollars and cents perspective, making the move to VMware was a step down. Six months after making the move, Riverbed stock doubled and split. “But I had zero regret, and this is super important. Why did I move? I moved because I had wanted to spread my wings more, and it looked like the organization that I loved could not make that happen. So, I had to do something about it. I waited, and then I moved on…. I had to take a step down to make that step up. I got lucky…good choice, great people, great mentors at VMware…. I had reached a point where I needed to spread my wings, and that opportunity was not showing up. So, I made the call.” – Milin Desai Everyone has their own reasons for leaving a company. Milin would first encourage us to be patient and not make abrupt decisions. We should seek to leave a company better than when we joined it. When Milin made the decision to leave Riverbed, people immediately thought it was because something was wrong. Nothing was wrong with the company. Milin needed to spread his wings. “Career trajectory does not always have to be a step up. It can be sideways or…down. You look at the opportunity…. I looked at scope, upside, and then I believed that if the scope and upside would work out, things would work out for me. And they did.” – Milin Desai Milin had the opportunity to go and focus on networking at VMware at a time when this was an emerging area of focus within the company. It was a chance to build upon his existing expertise. Milin talks a little bit about his first manager at VMware (Ushan) and how that person’s support accelerated his progression within the company. When the time came, this manager supported Milin taking on a different role within the company. “It’s crazy. I’m telling you…people make people.” – Milin Desai, on having great managers Milin would encourage listeners to optimize for scope and upside, even if you need to take a small detour. In Milin’s case, he did not know many people at VMware when he made the move from Riverbed. It was a risk he took based on the scope of the role he would be in, and it worked out. 21:20 – Necessary Skills at Different Leadership Levels John asks Milin about the difference in skills for each of the roles he has held from individual contributor to first-line manager and upward. John says getting to the next management level does not mean all the skills you had to that point are going to help you (i.e. new skills may be required). “The first thing I am going to tell you is that management is hard. You should know you want it because it’s more than you…. I want everybody kind of walking into that role to realize that it’s a lot of work, and it will never get easy.” – Milin Desai A manager has team members working for them, but there is an additional burden that requires translation of the greater organization’s expectations to your team. Milin says the skills you need as a manager are not something you can take a class to gain but rather something you learn over time. We can also learn from the great managers we’ve had. Milin knew what great managers looked like. They let him be himself, allowed him to take initiative, had high expectations, and they gave him context. Milin found it easy to manage people who were like him, but his biggest lesson was adjusting to the different ways in which people on the team operate and bring value. It was important to create a forum to enable all types of people to succeed. John says we learn how we as individuals are managed well (because it is modeled for us) but not necessarily how to best manage people who need to be managed differently (i.e. needing different types of guidance / structure / guardrails, etc.). Milin continues to struggle with this. Milin likes to be pointed in a direction by a manager, and he can do the rest. Milin would come to a manager with problems when needed, but he will figure out how to get what he wants from a manager. Milin reminds us of the time he was asked to go find a new role and how much it changed him. Learning how to manage people different than you is a skill that takes time to acquire. “There’s a point in time when it’s not about you or what you bring to a team. It’s about who you can hire….” – Milin Desai, on an aspect of rising to more senior leadership levels When Milin was moving up to senior vice president, it became more about whether he could bring in exceptional senior talent. This kind of caught him by surprise, but Milin knew he could go and figure out how to do it well even though it might not have come naturally to him. This was a new aspect of leadership after he had gained experience running a business unit and making it profitable. “If you bring in the right people, you automatically become potentially a great manager because they unburden you. They understand you really well.” – Milin Desai Milin says we should be willing to bring in people who are smarter than us, and we should be ok with that. He’s never had an issue with it, but some people do. Hiring the right people is a form of leaving an organization in a better state than you found it. Moving on from people is also something you learn as you move up. Milin calls this active management. “There’s a point in time where a person could be doing everything they are supposed to be doing. They have been with the organization, but the organization has shifted…. And this person is not able to adapt to it. It’s the company transitioning at that point. It’s not the person. And the ability for you to quickly recognize that for this phase of the journey…somebody you had loved before is not going to work out is probably one of the hardest things you will do as a people leader.” – Milin Desai When John was at Google, they talked about rearchitecting a product when the user base increases by a factor of ten. Similarly, the people organization has to be rearchitected. “There is a journey of an organization. It is a living, breathing thing, and it goes through its own phases. And through that phase, there are some people who grow through every phase and continue to be part of the organization…. There is a time when somebody who was a perfect fit no longer is a fit…. To identify that and to make that person successful in a different role in the company or something else…those were the things I had to…learn at these different levels. It’s hard.” – Milin Desai Some employees may only be part of 1 or a couple of phases of an organization’s growth / change. Milin gives the example of people later in their careers who are very self-aware. They might understand that the most enjoyment for them is found when they work in startups that have between $10 million and $100 million in annual recurring revenue, for example. Milin shares the example of bringing in someone to work with him who helped build a specific team and then others who helped scale the team and greater organization. Other senior leaders taught Milin that bringing in the right kind of senior talent would free up some of his bandwidth to be spent in other areas. Milin says he has luckily not needed to let people go because a business was not profitable. “Through that journey, the thing that has inherently worked, continues to work, is writing down my intention for the org, for the team, for the company…what we will bring to the table and keeping that written and clean 24 by 7. It doesn’t become stale…. That has been the consistent point of help besides having great people to work for.” – Milin Desai According to Milin, someone can write an 18-month strategy, but they should go and clean it up every 3 months. 29:55 – Enabling Active Participation Nick says by maintaining clarity on all of these things, it cascades to help leaders like Milin understand what the roles and job requirements within the organization should be, even if they are not formally changed. Milin says having it written down helps with everything. “It’s super hard to cascade a point of view or a vision. You have to repeat it multiple times, in multiple forums, and everything else. But if that itself is stale…it becomes really hard. So, I still to this day tell everyone, ‘give me a one-pager of where you’re taking the team for the next 3-6 months. If you don’t have that, how will you be effective?’” – Milin Desai The one-pager Milin mentioned is different than a feature or function to be built. It’s more about outlining the set of problems a team will solve in the short term (i.e. next 6 months) and then coming up with the measurements of how to do it within that specific time frame. He suggests highlighting the longer-term problems the team wants to solve as well. These things are written down and get revisited regularly by the team (maybe every 3 months) to determine if they are still relevant. Milin calls this “active participation.” “Are these still relevant? I want you all to think about it. Active participation, right? Now they get a point of view on the 3 things next six months we agree and the 4 things long term maybe we need to change or something like that. So that allows for active participation. I would say that’s another great thing I learned as my roles started getting bigger and the scope started getting bigger.” – Milin Desai Mentioned in the Outro Contextual communication has many layers to it. We can share context verbally with others but also gain it from them in the way we ask questions. We can also provide context to others through writing. Milin has done this for a long time. He will write a draft and iterate on it regularly to keep it fresh and clear. Duncan Epping uses writing to learn Episode 303 – Write to Learn and Learn to Present with Duncan Epping (1/2) Jason Belk emphasized developing his narrative through writing before talking about it Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.--------35:01
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About Nerd Journey: Career Advice for the Technology Professional
Are you a technology professional unsatisfied with your current role? Looking for a resource to help understand changing job functions, changing organizations, or gaining recognition and progression? The Nerd Journey podcast helps explore alternative roles, increase job satisfaction, and accelerate career progression. Each week, we uncover patterns of technical career progression by dissecting careers of guests and discussing different job roles they’ve held, or discussing relevant career topics. We’ve interviewed people in IT operations, sales engineering, technical marketing, product management, people management, network engineering, cybersecurity, software development, entrepreneurs, and more. We also discuss improving job satisfaction and accelerating career growth. We are John White and Nick Korte, two technologists with experience in IT operations and sales engineering who started this podcast in 2018. We release on Tuesdays, and can be found at https://nerd-journey.com.
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