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.