Asking better questions

08 May 2026 in Power Skills

There's nothing more terrifying than getting a "Hey, quick question. Are we on track to launch by X?".

It's not the question itself that's terrifying. It's everything you don't know when you hear it:

What do they know that I don't?
Why do they care right now?
What happens if I give the wrong answer?

That ambiguity is what drives anxiety.

There are multiple ways to answer the question, each giving the asker more visibility into your thinking (and more confidence in your answer):

"I think so"
"Yes, we're on track"
"Yes, we're on track. I reviewed the remaining work items and there are approximately 3 weeks of work left, which will give us 2 weeks of testing."
"Yes, we're on track. I reviewed the remaining work items and there are approximately 3 weeks of work left, which will give us 2 weeks of testing. Is there a particular reason you're asking?"

The first three items make your thinking more visible. But the fourth item digs in to the question behind the question. It's unlikely that they've spontaneously taken interest in the project this morning. What changed that made them ask this now?

Sometimes it's as simple as "I'm meeting Customer Z and wanted to let them know when the change is coming". Other times it's "I was chatting to the marketing team and they want to run a campaign around the new features and wondered when it was releasing". And sometimes it's "The last 3 releases have been delayed by a couple of weeks and I wanted to make sure that we're not underestimating the amount of work. Every time we miss a deadline I look bad."

Ambiguity drives anxiety. Context removes it.

Provide the Why

Now that you know what it's like to be on the receiving end of this type of question, how can you reduce the anxiety for teams that you work with? One sentence of additional context is all it takes to remove that ambiguity.

Bad: When will your proposal be finished?
Good: When will your proposal be finished? I won't be able to review if it's Thursday or Friday as I'm travelling, so you'll need to wait an additional week. If it's done by Wednesday I'll carve out time.

You can also lead with the reason you're asking:

Bad: Did we document feature X?
Good: I have partner Y trying to integrate feature X. Do we have any public docs that I can send to them? If not, can you hop on a call to help them out?

Make sure that the context you add is useful, not something that will drive additional anxiety:

Bad: Are we shipping X this week?
Worse: Are we shipping X this week? Sales is asking
Good: I was talking to one of the sales engineers and they mentioned that feature X would help on one of their deals. Is it still shipping this week?

“Sales is asking” adds pressure, but not clarity. It makes the question feel more urgent without making it easier to answer.

Ask the Question Behind the Question

When you're asking a question, make sure to add enough context that the person knows why you're asking.

Context doesn't just give people more information, it changes the shape of the question. Here's what it looks like in practice:

Question: Are we shipping X this week?
Answer: Yes

Let's try that again with the longer question:

Question: I was talking to one of the sales engineers and they mentioned that feature X would help on one of their deals. Is it still shipping this week?
Answer: Yes. Which engineer was it? I can give them early access and some internal docs that I've been writing if they want to try it themselves before we officially ship.

The person being asked has the full picture and can give a better answer.

In practice, adding context tends to do one of three things:

It changes the urgency
It changes the format of the answer
It changes the definition of done

In the first example (when), the additional context changes the urgency of the question.
In the second example (did), the additional context changes the format of the answer from a yes/no to a link.
In the third example (shipping), the additional context changes the definition of done.

If your context doesn’t change one of those three things, it’s probably not useful to the person you're asking.

If you’re being asked a question and they don’t provide context, answer directly, then gently ask what prompted it: "Great question! The answer is X. I'm curious to know what made you ask."