The First Yes Session

A focused working session to define the first thing a buyer can actually say yes to - before a proposal is ever needed.


Most founders don’t have a pipeline problem. They have a starting point problem.

Your network already finds you interesting. These are people who know your work, have seen what you’ve done, or have been referred to you. Conversations happen. There’s engagement, questions, and a genuine sense that something could happen.

But then nothing does.

Things drift into “let’s stay in touch.” Not because the need isn’t there, but because there isn’t a clear way to begin. The conversation doesn’t land on something concrete enough for the other person to say yes to.

So you compensate in the only way that makes sense. You explain more, add context, reshape the idea to fit the situation. Over time, every conversation becomes slightly different, and every deal starts from scratch.

From your side, it can feel like a positioning or pipeline issue. From the buyer’s side, it’s simpler: they don’t know what they’re actually being asked to commit to.

That’s the gap this session is designed to close.

What It Is

This is a 90-120 minute working session. We focus on one question: What is the first thing someone in your network could realistically say yes to right now?

It’s not a brainstorm and it’s not a strategy exercise. We don’t explore broad options or redesign your entire positioning. We work with what’s already happening in your business and bring it into a more usable form.

The session is grounded in a few very concrete inputs:

  • Recent conversations that didn’t move forward
  • People in your network who have shown interest
  • The situations where your work has already been relevant

The goal is to take that existing signal and shape it into something specific enough to act on.

The Problems This Solves

Most founders who come into this session are not starting from zero. They’re already in motion, but something isn’t quite clicking.

The patterns usually sound familiar:

  • Conversations go well, but don’t turn into anything concrete
  • The starting point changes depending on who you’re speaking to
  • You end up explaining their work from scratch each time
  • Proposals take time to write, but don’t consistently land

On the surface, this looks like a sales or messaging issue. In practice, it’s usually a lack of a clear entry point.

When there isn’t a defined way to start, everything downstream becomes heavier than it needs to be.

What You’ll Leave With

By the end of the session, you will have:

  • 2-3 candidate first offers: Each scoped tightly enough to describe in one sentence.
  • One recommended starting point: A clear decision on what to lead with, and why.
  • A usable message: Language that fits how you already speak, but lands more clearly.
  • A short go-to-market plan: With a specific list of people in your network you can reach out to, and a clear way how to approach them.

You’ll receive a written summary within 24 hours so you don’t have to reconstruct anything yourself.

The change is not dramatic, but it’s noticeable.

Instead of conversations ending with an open loop, they tend to move toward a defined next step. The interaction becomes simpler for both sides. You’re no longer asking the other person to figure out how to work with you.

You’re offering them a place to start.

What This Is Not

This session is intentionally narrow. It’s focused on one decision and the immediate implications of that decision. We’re not:

  • Redesigning your entire positioning or brand messaging.
  • Creating a full service catalog or client purchase path.
  • Mapping your full go-to-market approach.
  • Optimizing pricing or delivery.
  • Generating leads or traffic.

Those things become more useful once there is a clear starting point in place.

Who It’s For

This tends to work best for founders who are already active, but feel a bit stuck in the middle.

Typically:

  • You run a tech-enabled consultancy (bonus points if you're focus on digital transformation, AI adoption, data & analytics, cloud & infrastructure consulting, cybersecurity & risk management, or sustainability tech).
  • You’re already having conversations with potential clients.
  • There is interest, but it doesn’t consistently convert.
  • You feel like you’re re-explaining your work more than you should.
  • You don’t have a clear “start here” offer you can rely on.

It’s less useful if you’re not yet selling, or if you’re looking for a broad strategic exploration rather than a concrete output.

How It Works

1. Book your session: You’ll be taken to a page where you can choose a time and complete payment in one step. This secures your spot.

2. Share a bit of context (5 minutes): Right after booking, you’ll receive a short intake form. It’s 5 questions focused on your current situation and a recent conversation that didn’t move forward.

3. Session (90–120 minutes): We meet and work through your actual context. The goal is to define 2–3 possible starting points and decide which one you should lead with.

4. Follow-up (within 24 hours): You’ll receive a written summary with your recommended first offer, how to describe it, and a short plan for testing it in your network.

5. Optional check-in: A short follow-up call a couple of weeks later to review what’s moved, what hasn’t, and whether anything needs adjusting.

Pricing

The First Yes Session is $600, credited 100% toward any follow-on work.

If you decide to continue into a pilot or a longer engagement, the session effectively becomes part of that. If not, you still leave with something complete and usable.

Because each session is delivered personally, we only schedule five founders per quarter.

A Recent Example

I spoke with a founder recently who had a strong background in AI and product. The conversations he was having were good. People were engaged, and there was clear interest.

But nothing was turning into actual work.

He initially thought the issue was around ICP or how he was presenting himself online. Once we looked more closely, the pattern was different. There simply wasn’t a clear way for someone to start working with him.

During the session, we mapped his network, identified the situations where his experience was most directly relevant, and shaped one starting point that could be described and accepted within a single conversation.

The following week, a conversation that had been sitting at “let’s stay in touch” for a couple of months moved forward into a scoped engagement.

That’s the kind of shift this session is designed to create.

Ready To Become Easier To Choose?

Book your session below. You’ll be taken to a page where you can choose a time and complete payment in one step. This secures your spot.

Book your First Yes Session

(Founder-led firms under $1M revenue · 5 sessions per quarter)