When someone brings me a problem, I always ask what they would do or suggest. I want to hear what they say before I give them my answer.

“What would you do?”

Their response tells me how they’re seeing the situation. If they’re thinking about it the right way, I guide them and encourage them to move forward. If they’re missing something, I help them see how I’m looking at it, then challenge them to take the next step.

That’s the approach I come back to: ask, guide, and encourage them to move it forward.

There’s a decision to make today. There’s also an opportunity to help someone become more confident and thoughtful about the next one.

01 / Ask what they would suggest

It’s easy to give someone an answer, especially when you’ve dealt with a similar situation before. But I want to understand their thinking first.

They might already have a good recommendation and just need encouragement. Or they might be focused on one part of the problem without seeing what it means for the client, the budget, or another team.

Those are different conversations. Asking for their suggestion helps you work out which conversation you need to have.

A useful follow-up is, “What’s making you lean that way?” It gives them room to explain. It also gives you a chance to learn something you may not know about the situation.

This shouldn’t become a rule that people can’t bring you a problem unless they already have the solution. Sometimes they’re dealing with something unfamiliar. Sometimes something needs attention immediately. They still need to know they can come to you.

02 / Help them see more of the situation

Consider a project lead who wants to bring in a freelancer because the team is struggling to meet a deadline. That could be the right call. There may simply be more work than the team can do.

But imagine the scope is still changing. Before adding someone, it’s worth understanding whether more capacity will help—or whether the team needs a clear decision about what it’s delivering.

In that example, I’d want the conversation to cover three things:

  • What are we committed to delivering?
  • What’s actually keeping the work from moving?
  • What would another person be able to start and finish?

Those questions make the choice more concrete. The answer might still be to bring in the freelancer. It might be to confirm the essential deliverables with the client first, then decide what help is needed.

The important part is explaining what you’re seeing and why it matters. Simply saying “yes” or “no” leaves much of that thinking with you.

And you have to be open to their perspective, too. They may have information that changes your recommendation. The conversation should make the decision better.

03 / Encourage them to move forward

Once the direction makes sense, help them act on it. Be clear about what they can decide and when they need to bring you back into the conversation.

That might sound like: “Go ahead within the agreed budget. If it changes what we’ve promised the client, let’s talk before we commit.”

Now they have a next step and understand the boundary. They can move without checking every small decision.

Give them the perspective they need—and the room to use it.

There are times when a leader needs to make the call directly. An urgent issue, an unfamiliar risk, or a commitment beyond someone’s authority may need your decision. You can explain the reasoning afterward.

The amount of guidance should fit the person and the situation. Someone doing this for the first time may need you alongside them. Someone who understands the work may just need to hear, “That makes sense. Go ahead.”

The same question matters when AI is involved

AI can help someone organize a proposal or explore different options. But a polished recommendation still needs someone who understands why it makes sense for the actual situation.

“What would you suggest?” remains a useful starting point. So does asking what they checked and what they’re unsure about.

The goal is to keep people involved in the thinking as the tools change. They need to understand the recommendation well enough to act on it, explain it, and recognize when the circumstances have changed.

That brings me back to the original conversation. Hear what they would do. Help them see what they may be missing. When their thinking is sound, encourage them to move forward.

Help them make this decision in a way they can carry into the next one.

A Field Note by Devin Fisher.

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