A few weeks ago a member of our leadership team asked me a simple question: can our staff accept tips?
Simple question. It has a simple answer, and I could have sent it back in one line before lunch. Instead I spent an afternoon on it, and what came back wasn't a yes or no. It was a structure —
three separate pools for the store, tours, and events teams rather than one combined pot, shares split by hours worked inside each pool, and managers excluded from receiving any share at all.
But the part that actually mattered was buried in item four, and nobody had asked about it: on the events side, we hadn't decided whether gratuity is a voluntary tip or a mandatory service charge.
Those are two different things. They're taxed differently. They're treated differently under the law. They change what you can put on a contract. And we were about to build a payout structure on top of a question that had never been answered, which meant we'd have answered it by accident, in whichever direction the first event contract happened to go.
Nobody asked me that question. The question I got was "can our staff accept tips."
The presenting problem is never the whole problem
Every principal, every client, every founder hands you a presenting problem. It's real. They're not hiding anything. But it's been sanded down into something answerable — a yes/no, a deliverable, a task — because that's what people do when they're busy and they need one thing off the list.
Your value is not answering the presenting problem faster than their team would have. Anyone can do that, and a search engine can do most of it. Your value is the twenty minutes where you look one layer down and find the thing that's going to cause a problem in November.
A partial translation guide, offered without warranty:
What they say | What's often underneath |
"We have a communication problem." | Nobody knows who decides. |
"We need better project management." | We said yes to more work than we staffed. |
"The team isn't aligned." | Leadership has two answers to one question and won't pick. |
"We need a tool for this." | We have a process nobody follows, and we're hoping software will do the enforcing so no manager has to. |
"Can you build us a dashboard?" Someone upstream asked a question we couldn't answer and it was embarrassing.
What they say | What's often underneath |
"We need to hire someone for this." | The work has never been scoped, and hiring feels like progress. |
"Can our staff accept tips?" | We have an undecided policy question with tax consequences. |
The intake: Three Whys and a What-If
Four questions. Ask them before you've priced anything or promised anything. 1. Why this problem? Of all the things on fire, why did this one make the list?
2. Why now? What changed in the last 90 days? Something always changed — a board meeting, a departure, a number that came in ugly, a new role that just got filled. The trigger tells you more than the brief does.
3. Why me? Why isn't someone internal doing this? The answer is one of four things: no capacity, no capability, no credibility, or no appetite for the blowback. Those are four completely different engagements, and the last one means you've been hired as a lightning rod. Know that going in.
4. What happens if we do nothing for six months? If the honest answer is "not much," you have a nice-to-have and a small budget no matter what you've been told. If the room goes quiet, you've found the real urgency — and the real number.
Then comes the hard part: saying it
Finding the second problem is analysis. Naming it is politics. You're about to tell a senior person that the question they asked wasn't the important one, and depending on the week you may have known them for eleven days.
Three moves that keep you employed:
Return it as a hypothesis, not a verdict. "Here's what I'm seeing — tell me where I've got it wrong" beats "here's the real problem." You're not softening. You're leaving a door open for them to agree without conceding anything.
Attribute it to the system, not the person. "This decision doesn't have a clear owner" is a structural observation. "Dana and Marcus both think they own it" is gossip with a slide attached.
Bring the fix with the finding. Don't hand someone a new problem and walk away. In the tip case, the message ended with an offer: pick the direction, and I'll draft the one-page written policy for each team. A problem plus a next step is help. A problem by itself is a complaint.
One thing to try this week: Take the last simple request you got. Write down the answer they wanted. Then write down the question they didn't ask. If nothing comes to mind, you answered it too fast.
Reply and tell me what you were asked for this week. I'll tell you what I think you were actually being asked.
— Michael J Washington, Ocean Stride Advisory