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The usefulness of being mildly annoying.

The person asking where the number came from is rarely the most beloved person in the meeting. They are often the reason the meeting survives contact with reality.

2026-03-17 · 6 min

I have become professionally useful in part because I am willing to be mildly annoying.

There are more elegant ways to say this. Curious. Rigorous. Systems-minded. Detail-oriented, if you want to make everyone sad.

Mildly annoying is more accurate.

I am the person who asks where the number came from. I want to know what changed between last month's deck and this month's deck. I want to know why the source field says "Web" if the lead came from a partner email that forwarded a PDF to someone who typed the URL manually in an airport. I want to know whether sales agrees with the definition before marketing starts celebrating the chart.

This does not always make me fun at the beginning of a meeting.

It sometimes makes me useful by the end.

Companies run on claims. The campaign worked. The market wants this. The pipeline is healthy. The message is landing. The team is aligned. The forecast is solid. The launch is on track.

Some of those claims are true. Some are seasonal decorations.

The hard part is figuring out which is which before the business makes a decision with real money attached.

That is where annoyance becomes a service.

A good question can save weeks of decorative labor. A bad definition can infect a quarter. A soft metric can get promoted until it starts wearing a blazer. A vague owner can turn a simple handoff into a small municipal failure.

I have learned to respect the boring question.

What do we mean by qualified?

Who owns follow-up?

When does this become sales' problem?

Where does the source value get set?

What happens if the buyer does the weird thing buyers always do?

Why do we believe this?

That last one is the troublemaker.

Why do we believe this?

It is a simple sentence with a tiny crowbar inside it. Sometimes the answer is strong. There is customer evidence, clean data, direct feedback, repeatable behavior. Great. Move faster.

Sometimes the answer is thinner. A loud anecdote. A board member's memory. A salesperson's heroic story about one account. A competitor's homepage. A number that came from a dashboard nobody trusts but everyone keeps screenshotting because the colors are nice.

The job is not to be cynical. Cynicism is lazy. Cynicism gets to feel smart without building anything.

The job is to keep the work attached to reality.

That requires tact, because nobody likes being cross-examined by a man who appears to have developed romantic feelings for source hygiene. The tone matters. The timing matters. The level of force matters. You can ask a necessary question in a way that makes people want to help you, or in a way that makes them imagine your chair empty.

I have done both.

Age helps. So does being wrong enough times to respect other people's instincts. The goal is not to win the room by proving the number is bad. The goal is to make the room safer for the truth.

That sounds soft until you have seen the cost of the alternative.

Bad truth handling is expensive. It creates campaigns nobody needed, dashboards nobody trusts, handoffs nobody owns, forecasts nobody believes, and strategies that survive only because nobody wants to be rude to the slide.

A business can absorb a lot of uncomfortable questions. It has a harder time absorbing comfortable fiction.

So I will keep asking.

Carefully, I hope. With better timing than I had 10 years ago. With enough humor to make the medicine go down. With enough humility to remember that the person closest to the problem usually knows something the dashboard does not.

But still asking.

Because the number came from somewhere. The system did something. The buyer behaved some way. The handoff worked or it did not.

Reality is annoyingly specific.

I try to meet it there.