The 5-question founder diagnostic I use on every intro call.

What would have to be true for you to walk away from this in the next 12 months?

Most founders have never asked themselves this. They've spent years answering "what would have to be true to win." They've never spent 30 seconds answering "what would have to be true to walk away." If you can't answer this in concrete terms — a specific revenue threshold, a specific co-founder dynamic, a specific market signal — you're not actually running the business. The business is running you.

What I'm listening for: specifics, not platitudes. "If we're not at $X ARR by month Y" beats "if it stops being fun." The first one is a CEO. The second one is a passenger.

Who on your team would you fire today if it weren't socially expensive?

This question is unkind on purpose. The answer reveals whether you're operating the company or protecting your social standing inside it. Most founders have a name in their head before I finish the question. The good ones say the name. The bad ones tell me how complicated it is.

What I'm listening for: hesitation. Long pauses here usually mean the person on your team is also a friend, a co-founder, an investor's preferred hire, or a relative. All of those are real reasons it's hard. None of them are reasons it shouldn't happen. Fractional CEOs and turnaround advisors get hired largely to make this call when the founder can't.

What's the thing you'd never say in an investor update — and why?

This is the question most founders can't answer honestly. The ones who can are dramatically more coachable than the ones who can't.

Every founder has a thing they're hiding. Burn rate that's worse than the deck shows. A customer concentration that scares them at night. A co-founder who's checked out. A pricing strategy they know is wrong but haven't fixed because changing it would require a hard conversation. Everyone has the thing.

The founders who can name the thing — to a stranger, on a 30-minute call — are the ones who are going to fix it. The founders who insist there is no thing are the ones who'll still be insisting six months later, while the thing eats their company.

What I'm listening for: honesty. I don't need to know the thing. I just need to know that you know.

If you had to cut your team in half this quarter, who's on which side of the line?

This is a thought experiment, not a plan. But it's the fastest way to surface who's load-bearing and who's load-passing. Most founders get to the answer in under 30 seconds. The names come out fast.

What's interesting isn't the answer — it's the gap between the answer and what the org chart says. If your "above the line" list is mostly individual contributors and your "below the line" list has a couple VPs, you're carrying expensive seat-warmers. You already know it. Now we both know it.

What I'm listening for: specificity, again. And whether the founder is willing to put their co-founder on either side of the line. (Most won't. The ones who will are different operators.)

What does the next 12 months look like if I help you, and what does it look like if you do nothing?

Last question, and it sounds like a trick. It isn't.

I'm trying to find out whether the founder has a real model of what an advisor changes. If "do nothing" looks identical to "Tejune helps me," then I shouldn't be helping — I'd just be expensive moral support. If "Tejune helps me" looks identical to "any competent advisor helps me," then I'm probably not the right person — I'm not a generalist and I'd refer them elsewhere.

The right answer is specific: "With your help in the chair on the X conversation and the Y deal, we add Z dollars / save Q quarters / avoid M mistake." If the founder can articulate that, we're already 60% of the way to a productive engagement.

What I'm listening for: a clear delta. Not a wish list.