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 will 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)

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