COACHING & DEVELOPMENT · 4 min read

I have conducted many first coaching sessions. Enough to know that the questions you ask in the first hour set the entire tone for what follows. And that most of the questions coaches are trained to ask in intake sessions are the wrong ones.

The typical intake approach goes something like: 'What are your goals? What does success look like for you? What obstacles are in your way?' These are not bad questions. They are just surface-level, producing surface-level answers. You get the version of the situation that the client has already told themselves. You do not get the thing underneath.

Over time, I have narrowed my first-session approach down to three questions that consistently produce something actually useful. I am sharing them here not because I think you should all become coaches, but because they are useful in any performance conversation (e.g., with a direct report, a peer, or even yourself).

Question 1: What are you tolerating?

Not 'what are your challenges?' Not 'what is getting in the way?' Those questions are easy to deflect with professional-sounding answers about workload and competing priorities.

'What are you tolerating?' is different. It asks about the situation as it currently exists — not the aspirational state, not the narrative the client has constructed about why things are this way, but the actual reality they are living in and have, consciously or not, decided is acceptable.

The answers to this question are almost always where the real work is. Tolerating a reporting relationship that does not work. Tolerating the feedback they have received and not acting on it. Tolerating a version of their own leadership behavior that they know is costing them something.

'What are you tolerating?' consistently surfaces the thing that 'what are your challenges?' never reaches.

There is also something useful about the word 'tolerating' specifically. It implies agency. The client is not a victim of the situation. They are, at least in part, choosing to coexist with it. That framing tends to produce more useful conversation than 'what problems do you have?', which invites a passive stance.

Question 2: What would you do if you were not worried about how it would land?

Most leaders I work with already know what they need to do. They know which conversation they have been avoiding. They know which decision they have been postponing. They know which structural problem on their team they have been managing around instead of addressing.

They are not doing those things because they are worried about the reaction from a team member, from their own leadership, or from the part of themselves that values being liked or avoiding discomfort.

This question externalizes the constraint. It separates what the person believes is the right action from what they are allowing themselves to do, given the relational or organizational risks. Once those two things are separated, the conversation can actually address them both, instead of just spinning around the presenting constraint.

The follow-up question, when the client names something: 'What specifically are you afraid will happen if you do that?' is where the session usually goes to a genuinely useful place.

Question 3: What story are you telling yourself about this?

Every leader I have ever worked with has a narrative about their situation. Some of those narratives are accurate. Many of them are partially accurate, constructed over time from a mix of real data and interpretation, and now function as filters limiting how the person sees the situation.

'What story are you telling yourself about this?' asks the client to step back and look at their own framing, not to invalidate it, but to examine it. Is the story that a team member is underperforming, or is the story that the leader has not yet found the right way to develop them? Is the story that the organization does not value their work, or that they have not yet created the conditions for the work to be visible?

I use the word 'story' very specifically. It is not 'what are your assumptions?' (too clinical). It is not 'what do you believe?' (too close to attacking their identity). 'Story' is neutral enough to invite examination without triggering defensiveness.

Why these three questions work

Each one targets a different layer of the same problem. 'What are you tolerating?' surfaces the reality as it actually exists. 'What would you do if you were not worried about how it would land?' separates desire from constraint. 'What story are you telling yourself about this?' examines the interpretive frame.

Together, they map the gap between where someone is and where they could be, ensuring the client stays in the driver's seat. That is what good coaching actually is: not advice, not direction, but structured inquiry that helps a person see their own situation more clearly than they could on their own.

Interested in coaching that asks the right questions? Book a free discovery call to see what a session actually looks and feels like.