Four Questions Every Leader Should Steal

Most teams run on advice. The best leaders run on questions.

👋 Hi, I’m Jeff. I write weekly about lessons I’ve learned leading product teams and working to lead well in chaotic environments, drawing on 25+ years of building.

1:1 exec coaching: I work with a small number of senior product leaders one-on-one as a coach. These are typically six-month engagements. If that’s you or someone you know, let’s talk.

⏱ Read time: 3 minutes

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I’d just wrapped an 11 a.m. Headspace product review from my home office. I signed off the 17-person Zoom and walked into my kitchen to refill my coffee and process where I could have been better in that meeting. I wasn’t very happy either.

I’d done the thing I’d sometimes do. I’d asked a question in a group setting that was too long, and too complex. It didn’t really move the conversation forward. I was pretty bummed too. In that type of review setting, you don’t get those moments back.

When I think back to leading reviews and meetings, or even one-on-ones, I can see now how at times I’d missed asking better, more useful questions.

This year I’ve spent time in coaching training with a cohort working toward ICF certification. Many of these sessions include live demonstrations led by instructors who are skilled, 20-year coaching veterans. Often the training unfolds with a group of us with our video cameras off, watching someone in the class get coached by one of these expert coaches in real time.

I’ve seen people who have been struggling with a hard problem suddenly see things differently, with new ideas and attitudes. In class debriefs, our group notices how much progress can be made in just ten or fifteen minutes. Just by asking short, powerful questions and listening intentionally.

The learnings made me think back to questions I’d asked or seen asked that could have been better. So I wanted to share some of what I’d learned here. Getting a chance to watch skilled coaches work reminded me that one of the simplest ways to be a more effective leader and help a team is simply to ask shorter questions, and then listen closely.

Most teams tend to run on advice, and advice can be useful. Sometimes your teammate or direct report needs a direct answer or an informed recommendation that comes from your experience.

But advice by itself creates risk. When I give you advice, my context is not the same as your context. So, if you apply my answer as is to your situation, your result will likely be different.

A powerful question works differently. A good question invites the other person to do their own thinking with a useful cue. That can lead to an insight that’s more relevant to them and better connected to the reality they’re navigating. It may also spur creativity you might have otherwise missed.

Questions also allow for greater ownership vs advice alone. People are notoriously more likely to act on an insight they reached themselves vs one that is just stated with them in the room.

The good news is you don’t need coaching training to start using more powerful questions. The best ones tend to share three simple qualities you can try:

1. They are short. The fewer words you use, the better.

2. They are open. They invite a deeper answer versus either/or/yes/no.

3. They are followed by deep listening. This is different from listening while composing your next response in your head. It’s about paying close attention to the person’s answer. Plus, what does their face tell you? What’s the vibe in the room?

Here are four specific questions I’ve learned about and found interesting and useful:

What do you really want? A coach in my cohort called this one out: “The Spice Girls were onto something.” Most people have rarely been asked this question straight away. It can hit hard, in a good way.

What’s the conversation you’re avoiding? This one can surface the issue underneath the issue.

If you fully trusted your read, what would you do? This can help someone move past overthinking and just let it rip.

How are you complicit in creating the conditions you say you don’t want? This question comes from Jerry Colonna, and it may be my favorite. I’ve used this on myself. It hits me like a brick every time.

Try a small experiment this week.

Ask one of these questions, or answer one yourself. Then really listen for what’s being said. You’ll be surprised by what a good question, paired with real listening, can unlock.

Let me know how it goes.