A few years into my coaching practice, I got an inquiry that looked perfect on paper. Established company. Real budget. A leadership team that knew what they wanted — or so it seemed.
We had three calls before I signed anything. Each time, the scope shifted slightly. Not dramatically — just enough to notice. The success criteria changed depending on who was in the room. HR wanted culture. The CEO wanted performance. The team lead wanted someone to finally say out loud what everyone already knew.
My gut said yes. My head said: whose project is this, exactly?
So I stopped the process. Asked for one more call, just to get aligned on what a good outcome would look like six months in. Some people push back when you do that. This team didn’t. We spent 90 minutes making the unspoken stuff spoken. Rebuilt the brief together. Then I said yes.
The project ran for four months. It worked. Not because everything went smoothly, but because we’d agreed early on what “working” actually meant.
That experience gave me a filter I now use before every project, collaboration, or career decision. Four questions. Simple, but they cut through almost anything.
“My gut said yes. My head said: whose project is this, exactly? That tension was the signal, not noise.”
Before I say yes, I ask:
1. Do I give value? 2. Do I learn something? 3. Do I earn enough? 4. Does this point somewhere worth going?
You don’t need a yes to all four. But you need at least one that truly counts. And if all four are a no — you already have your answer.
That fourth question is intentionally open-ended. Worth going — not just for me. The “and others” is built into it, and honestly, it’s the one I think about most.
I’ve worked with enough leaders to see the pattern: optimize only for yourself, and six months in, the role feels hollow. The people I respect most — whether they’re running a team of five or a division of five hundred — don’t just ask where is this taking me? They ask what am I part of building?
That shift changes everything. It turns a job into a contribution. A project into something worth finishing. And it’s often the question that separates leaders who stay energized from those who quietly check out while still showing up.
This works whether you’re a leader evaluating your next initiative, or someone weighing a career move. The question underneath is always the same: Is this worth my yes?
A yes from clarity is worth ten yeses from momentum or obligation.
Your turn.
Think of a decision you’re sitting on right now: A project, a role, a collaboration. Run it through the four questions. Which one gives you the most resistance? That’s usually where the real answer lives.
