The worst first session I ever ran wasn't because the client was difficult. She was smart, articulate, genuinely motivated. The problem was me. I walked in knowing her name, her title (VP of Product at a Series C company), and that she wanted to "become a more strategic leader." That was it. That was everything I had.

So I spent the first twenty minutes doing what should have been done days earlier. What's your team structure? What prompted you to look for a coach? What does your CEO think you need to work on? She answered patiently, but I could feel it. The air going flat. The unspoken question: didn't you prepare for this?

I had prepared. I'd just prepared with the wrong information, because I'd asked the wrong questions.

That was year two. I've rebuilt my intake form probably six times since then. What I use now looks almost nothing like what I started with, and it takes new clients about fifteen minutes to fill out. Here's what I've figured out about what to ask, what to stop asking, and how to use AI to turn those answers into a first session you actually feel ready for.

Why most intake forms ask the wrong things

Most coaching intake forms I've seen (and I've seen a lot, because coaches love sharing templates in peer groups) read like they were designed by someone who's never actually used the answers. They ask for job title, years of experience, reporting structure, what assessments you've taken, your Myers-Briggs type. Demographics. Org chart data. The kind of information that makes you feel like you've done your homework but doesn't actually help you coach anyone.

Here's what I've learned: the facts of someone's situation are the least interesting thing about them. I can learn that you manage twelve people and report to a COO in the first five minutes of conversation. What I can't learn quickly, in a live session where I'm also trying to build trust and read the room, is how you think about what's happening to you. What you've already tried. What you're afraid of. What "better" actually looks like in your specific life, not in the abstract.

The intake form's job is to get me that information. Everything else is filler.

I also stopped asking anything that feels like a corporate onboarding form. No rating scales. No "on a scale of 1-10, how satisfied are you with your current role." People either game those or agonize over them, and neither response tells me much. I want sentences. I want someone's actual words about their actual situation.

The questions that actually tell you something

I'll give you the full template below, but first I want to walk through the thinking behind the questions that matter most. Because copying questions without understanding why they're there is how you end up with another useless form.

What they've already tried. This is the most underrated intake question. When someone tells me they've worked with two coaches before and both "didn't click," that's enormously useful. When someone says they've read every leadership book and listen to three podcasts a week but still feel stuck, that tells me something about the gap between knowing and doing. When someone says "nothing, this is my first time trying anything like this," that tells me something about what it took for them to reach out.

What success actually means, below the surface answer. Everyone says they want to be a better leader. That's the presenting request. I want the one underneath it. So I ask it sideways: "If this coaching worked exactly the way you wanted, what would be different in your day-to-day life six months from now?" People's answers to that question are specific in ways that "what are your goals" never gets. One client wrote: "I'd stop checking Slack at 10 PM and not feel guilty about it." That's a real answer. That's something I can work with.

Who knows they're doing this. This one surprises people, but it reveals a lot. A client who's told their manager, their spouse, and their best friend that they're starting coaching is in a very different place than someone who's keeping it private. Neither is wrong. But the person keeping it private is often carrying shame about needing help, and that's going to show up in our work whether we name it or not. I'd rather know going in.

The relationship with their boss. Not "describe your manager's leadership style." That gets you a LinkedIn-polished answer. I ask: "What's one thing you wish your direct manager understood about you that they don't seem to?" Clients write the most revealing things in response to this. Things they haven't said to anyone.

The full intake form

Here's what I actually send to new clients. I use a shared Google Doc (not a PDF, not a form builder) because I want them to be able to write as much or as little as they want without being constrained by text field limits. Some of my clients write two paragraphs total. Some write two pages. Both are useful.

A few platforms have built-in intake form features that work well if you want something more polished. Simply.Coach, Paperbell, and CoachAccountable all handle this (see my coaching software comparison for details on each), and they keep everything in one place alongside session notes and scheduling. I used Paperbell for about a year before switching back to a simple shared doc, mostly because I wanted full control over the questions and formatting. But if you're starting from scratch and want less manual setup, any of those three are solid.

Here's the template:

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INTAKE FORM TEMPLATE

Before our first session, I'd like to understand a bit about where you are and what you're looking for. There are no right answers and no length requirements. Write as much or as little as feels right. I'll read everything carefully before we meet.

This stays between us. Always.

1. What's happening right now that made you decide to try coaching?

Not the polished version. The real one. What's the thing that's been on your mind?

2. Have you worked with a coach, therapist, or mentor before? What worked and what didn't?

This helps me understand what kind of support has been useful for you and what hasn't. If the answer is "never," that's completely fine too.

3. If this coaching worked exactly the way you hoped, what would be different in your daily life six months from now?

Be as specific as you can. Not "I'd be a better leader." More like "I'd stop dreading Monday mornings" or "I'd actually delegate the thing I keep holding onto."

4. What's the thing you're best at in your work? The thing that, if you're honest, you know you're really good at?

I'm asking because I want to know what you're building from, not just what you're trying to fix.

5. What's one thing you wish your direct manager (or board, or co-founder) understood about you that they don't seem to?

6. Who in your life knows you're doing this? (Partner, manager, friend, nobody yet?)

No judgment either way. I just want to understand the context.

7. How do you typically handle feedback that's hard to hear?

Again, honest answer. Not the interview answer. Do you get quiet? Defensive? Do you process it later on a walk? Do you argue first and agree three days later?

8. What's a pattern you keep repeating that you'd like to interrupt?

Could be at work, could be broader. Could be "I say yes to everything" or "I avoid hard conversations until they become crises."

9. Is there anything happening in your life outside of work that's relevant for me to know?

You decide what's relevant. I won't push, but I also won't pretend work exists in a vacuum.

10. What would make you fire me?

Seriously. What would make this not work for you? Knowing this upfront helps me be a better coach for you specifically.

11. Anything else you want me to know before we start?

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That's it. Eleven questions. Takes most people fifteen to twenty minutes. The magic isn't in any single question. It's in the cumulative effect of being asked things that feel like a person is actually curious about them, not processing them.

Turning the answers into a first-session prep brief

I used to spend forty-five minutes on pre-session prep for a new client. Reading and rereading their intake responses, making notes, trying to figure out where to start, second-guessing my instincts. It was thorough. It was also unsustainable when I had three new clients starting in the same week.

Now I spend about twelve minutes. Here's the workflow.

I copy the client's intake responses (with their name removed, because I'm not putting identifying details into any external tool) and paste them into a prompt I've built over time. I run it through Margaret, make a few edits based on my own gut read, and I'm done. I've got a one-page prep brief that tells me where to start, what to listen for, and what to leave alone.

Here's the actual prompt:

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AI PRE-SESSION BRIEF PROMPT

Paste this into your AI tool along with the client's anonymized intake responses.

Prompt
You are helping an executive coach prepare for a first session with a new client. Below are the client's intake form responses. Based on these responses, generate a first-session prep brief with the following structure:

THREE THEMES TO EXPLORE
Identify the three most significant themes or tensions in these responses. Not surface-level topics — look for the underlying dynamics. What's pulling against what? Where is there energy, contradiction, or something left unsaid?

OPENING QUESTIONS (RANKED BY LIKELY IMPACT)
Suggest 2-3 opening questions for the first session, ranked by which is most likely to create immediate depth and trust. These should feel like questions a thoughtful human would ask — not diagnostic, not clinical. The kind of question that makes someone pause and think.

ONE THING TO HOLD LIGHTLY
Identify one element in the responses that seems important but shouldn't be pushed on in session one. Something that probably needs trust to develop before it can be explored directly. Name it and explain briefly why it's worth waiting on.

STARTING POSTURE NOTE
Based on the tone, word choice, and content of these responses, write one paragraph about what kind of energy this client probably needs in the first session. Are they someone who needs warmth and safety first? Someone who'll respect directness and lose patience with soft openings? Someone who's intellectualizing and needs to be gently brought into their body? Describe the posture, not a strategy.

Keep the entire brief under 500 words. Use plain language. No coaching jargon.

CLIENT INTAKE RESPONSES:
[Paste responses here]

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The output is never perfect. Margaret tends to over-index on whatever the client wrote the most about, which isn't always the most important thing. Sometimes the most important thing is the question they barely answered. I always cross-reference the AI brief with my own reading of the responses, and I'll often swap out one of the suggested opening questions for something that occurred to me during my walk that morning.

But as a starting point, it saves me from staring at a document for thirty minutes trying to organize my own thoughts. It gives me a scaffold. I bring the judgment.

When the intake responses are thin

Sometimes a client fills out the intake form in what appears to be ninety seconds. Three-word answers. "Fine." "Not sure." "Nothing comes to mind."

I used to worry about this. I'd wonder if they weren't invested, or if my questions were bad, or if this was going to be a difficult engagement.

Now I see it differently. A client who gives you almost nothing on an intake form is already telling you something about how they move through the world. Maybe they don't trust written communication. Maybe they're testing to see if you'll push. Maybe they process verbally and a form feels like homework. Maybe they're guarded because the last time they were vulnerable in a professional context, it went badly.

That tells you something useful. Some of my best coaching relationships started with nearly blank intake forms and clients who opened up twenty minutes into the first session when they realized I wasn't going to stick to a script.

What I do with thin responses: I still run them through the prompt, but I add a line at the top. "Note: responses are very brief. Focus your analysis on what might be implied by the brevity itself, and weight the starting posture note heavily." Margaret handles this surprisingly well. The brief comes back shorter, more tentative, and usually includes a useful observation about the client's possible communication style.

Then I adjust my first session accordingly. I plan fewer questions. I leave more silence. I let the intake form come up naturally ("I noticed you kept your answers pretty short on the form, which is totally fine, I'm curious whether writing things down just isn't your thing or if something about the questions didn't land").

What I'm still changing

I've rewritten question eight four times this year. The pattern-interruption question. I want it specific enough that people give me something real, but open enough that it doesn't funnel them toward what they think I want to hear. Still not there.

The intake form isn't a finished product. The questions evolve. The AI prompt gets refined. But the function stays the same: walk into that first session already thinking about this person. Not their title. Not their org chart. Them.

I've got an intake sitting in my inbox from last night. Eleven questions. Probably took her fifteen minutes. It'll take me twelve to turn it into a prep brief. And tomorrow I'll be ready instead of catching up.