💚 Welcome to the weekly newsletter for ambitious leaders staying sharp and staying human in the age of AI.

Every edition is:

📬 If you like this, share it with a fellow leader. It’s a low-lift way to stay connected to the people you care about when your calendar has zero room for 30-minute Zoom catch ups.

Welcome to Part 3 of The Buyer's Seat series, where I am breaking down the counterintuitive influence traps I’ve experienced recently as a buyer, and sharing them with you as a leader (because if you are in leadership, you are always selling).

Recently, I got on a discovery call with a potential partner, and they proceeded to ask me a list of questions.

What are your goals?
What is your timeline?
What is your budget?

The intent behind this is usually to show curiosity. We are taught that good leaders and good sellers are active listeners who ask great questions to uncover pain points.

But sitting on the receiving end, I found myself thinking: Literally anyone could ask me these questions. You could be exceptional at your job or you could be terrible, and the script would sound exactly the same. How am I supposed to know if you're actually any good at what you do?

We do this internally, too. In 1:1s with our managers, cross-functional check-ins, or project kickoffs, we pepper our teammates with questions to gather information, totally unaware of how unbalanced it feels because we aren’t adding insight.

When you only ask questions without sharing your own insights, the conversation feels fundamentally unbalanced.

Psychologists refer to this dynamic through Social Penetration Theory,¹ which is built on the concept of reciprocal disclosure. The science shows that trust is built systematically through a balanced exchange. If one party only extracts information without revealing their own perspective or putting skin in the game, the interaction stops feeling safe. It triggers defensiveness.

When you just ask questions, you are asking the other person to be vulnerable and expose their messy reality, while you sit safely behind your metaphorical clipboard.

In a time when AI can generate a list of the questions, what separates a human leader is the rhythm of the exchange. Your value is in the unique perspective you offer before you ask them. Sharing an insight shows your way of thinking. It deposits a reward before making an ask.

To move from an unbalanced interrogation to a genuine conversation, change up the rhythm and practice the insight-first curiosity:

Offer an insight. Then, ask a question related to that insight.

Here are three ways to apply this rhythm to your conversations this week:

Instead of: "What are your biggest challenges with this launch?"

Try: "In my experience with Q4 rollouts, the biggest bottleneck usually ends up being design bandwidth. Are you seeing that same constraint, or are you worried about something else entirely?"

Instead of: "What is your timeline for this project?"

Try: "Usually, when I see a data migration this complex, it takes at least three weeks just to clean the legacy system. How are you factoring that phase into your timeline?"

Instead of: "What resources do you need?"

Try: "I've noticed that when we launch in a new market, we often underestimate the localization costs by about 20%. How are you thinking about the budget allocation for translation?"

A massive part of influence is finding ways to show you know your stuff in a graceful way.

Anyone can read down a laundry list of generic questions. But to build influence, you have to show people how you think before you ask them to expose how they work.

To recap, we've covered:

These are highly nuanced skills that make influence an art rather than a rigid playbook. Finding your authentic way of practicing them is the work of a leader.

Thanks for coming along for the ride!

Join the community of leaders staying sharp
and saying human in the age of AI.