Private Diagnostic

What Are You Trying to Solve?

Even if we never work together, I hope answering these questions brings you some clarity. This diagnostic helps me understand the problem, you, what you've built, what's at stake, and the resources you have, so we can both see whether Private Advisory is the right fit.

01Private Diagnostic

Estimated time: 15 to 20 minutes

Your responses are sent directly to Gregg for private review. Answer what is relevant and leave anything that does not apply blank. They are not stored on this site or added to a mailing list.

Section 1

The Problem

1. What are you trying to solve?2. What do you think the real problem is, underneath what's visible?3. What have you already tried, and what did you learn from it?4. If this stays unresolved, what do you think will happen?

Section 2

The Stakes

1. Why does this matter now?2. Who else is affected if you get this right, or wrong?3. What has this been costing you personally?4. What worries you most about how this could go if it's mishandled?5. A year from now, what would a really good outcome look like?

Section 3

The Build

1. What are you building, leading, protecting, repairing, or trying to grow into something more?2. What stage is it in now?3. What scale have you reached, in this work or elsewhere in your career?4. Where are you trying to go, and how quickly do you want or need to get there?

Section 4

The Person

1. Tell me about your role in this. What position do you hold, formally or informally?2. What do people come to you for?3. What do they come to you for that you wish they didn't?4. What education, formation, or life experience has shaped your thinking most?5. What's your age range?6. What's your family situation, if it's relevant here?7. Do you have children or others who depend on you? If so, how are they affected by what you're deciding?

Section 5

The Resources

1. What financial resources, assets, revenue, or access to capital could you put toward solving this?2. Who do you have around you? Think team members, partners, advisors, employees, family, board members, or trusted operators.3. What network, influence, reputation, audience, relationships, or credibility can you bring to this?4. Are there materials that would help me understand your situation, like a website, deck, business plan, financial model, legal documents, or media coverage?

Section 6

The Fit

1. Think about the mentors, teachers, or advisors you've had. How do you usually respond when someone challenges your assumptions or sees something you've missed?2. What made you reach out?3. How did you hear about me?

Before You Send

Review and next steps

Private Advisory is a significant investment of time and resources, on both sides. If we move forward, we'll talk through scope and terms before anything begins.

I normally review submissions within two to three business days. Sending this diagnostic is an inquiry, not an acceptance of a Private Advisory engagement. Review your responses, then add your contact details so Gregg can reply directly.

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