Good leaders ask good questions

A common myth is that leaders make all important decisions.

This assumes leaders should own decision making instead of focusing on what’s more important: the decision making process.

The reality is that the best leaders I know are the ones that provide clear direction, hire the best people around them, and do an amazing job of learning and coaching through asking the right questions. It shines less of a light on them, that’s intentional. Good leaders are good at standing behind the scenes holding the light for their team, not in front of them blocking their view.

Asking good questions comes from a place of genuine curiosity and a desire to learn. It’s better for leaders, their teams, and the culture they build.

Better for them because it enables them to leverage the experience and expertise of the teams they're working with. Leadership is a continuous act of learning. The best leaders are lifelong learners who have genuine curiosity to solve complex problems empathy to understand the pain and joy of their team, and have the focus and discipline to truly execute.

Understanding more from those with far more experience on the ground is a prerequisite to making good decisions. If you’re hiring people smarter than you in different areas of the business, why wouldn’t you focus on learning the best from them?

Asking good questions is also better for the team. Nothing is more frustrating than leaders who don’t understand or leverage their team’s experience or don’t have the desire to consider different viewpoints into their decision making process. Asking questions is also a much better way to develop teams. We learn this early in our lives, the more others solve your problems for you the less you learn problem solving skills yourself.

Many leaders take this advice halfway but never actually apply it. They ask questions with an outcome in mind. Instead of leveraging their team’s experience and helping them think deeper, they force their team to decipher what they actually want. Understanding what good questions are is important. Not all questions are created equal.

Asking questions is also better for the culture you’re building around you as a leader. Building a culture of genuine curiosity and growth mindset is difficult. The best way to build that culture is to model it yourself.

Good questions

There is no shortcut to learning how to ask good questions or a checklist definition of what a good question is. However, there are some characteristics that might help you and your team, as a leader, spot good questions and sometimes more importantly, spot bad ones early on.

Three key characteristics of good questions, to me, are:

Good questions come from a place of a genuine desire to learn and grow. Leaders that ask good questions don’t have a predetermined agenda of what the right answer is and have no pre-judgement on the answers they will receive. Leaders that ask good questions have a genuine desire to learn from their team and ask because they genuinely either don’t understand or would like to understand the topic of discussion.
Good questions are smart. They push the boundaries of thinking for teams. They are different from clarifying questions where you’re simply trying to understand a term mentioned, a basic fact discussed, or a thought shared. Good questions are obvious in retrospect but not always obvious before they're asked. They push the boundaries of a team’s thinking and help them consider a deeper view of a topic or think through it from a different angle.
Good questions assume expert knowledge of the person on the receiving end, they’re not designed to question them. They are designed to help you, the person asking, to understand. Smart teams can quickly sense it when questions are designed to question their expertise instead of learning from their expertise.

How do you ask better questions

The how, in these types of situations, is almost as important as the questions themselves.

The environment you create to share questions, the way you ask these questions, and the expectations you set around them make all the difference.

Here are a few things that will help:

Build an environment of trust: at the foundation of any conversation with your team is the trust you build with them as a leader. Almost all work-related progress comes from a foundation of trust. Have you actually trusted the expertise of your team? Do you understand what your team members are good at? What are they better than you at? Do they trust your questions are coming from a place of curiosity?
Set clear principles, not guidelines, so trust is codified: guidelines are generally designed to help people follow guardrails, principles are designed to help people set up the guardrails themselves. Codifying your principles is one of the most valuable ways for you to build trust with your team, ensure you’re operating off the same manual, and having a clear set of expectations to evaluate on. They’re like the constitution, broad enough to give teams space yet specific enough to codify what you care about.
Listen: practice active listening, give space and leave your questions to the end. If you’re like me, you’re often excited to jump in with questions, thoughts, and opinions mid-way through a presentation. Taking notes through a conversation with your questions can help enable your team to have the space to share. This separates the “question asking” segment from the “content sharing” segment of a conversation. The only exception is a clarifying question that is required in the middle of a presentation to help understand the rest of it. Those questions often start with “sorry to interrupt, but what did you mean when you said X”.
When your questions aren’t answered, assume it’s you not them. When trust is the foundation of this conversation, you have to assume your team knows what they’re talking about. With that assumption in mind, put the burden of clarifying your questions, asking them in different ways, and digging deeper on you, not your team. If you feel like they haven’t answered, it’s you not having asked this right or needing to dig a bit deeper vs. them not having the expertise.
Build mechanisms for feedback. Nobody is perfect. This includes you! Leave room for feedback during every conversation to better understand if your questions were truly good. Most of the time, this can come best from anonymous sources. Google Forms, for example, is a great way of collecting that feedback.
Empower the team to make the final call. Set expectations on who’s making what call before you go into these conversations. RAPID is one way of doing this but there are plenty of other frameworks like it that your organization might already be using.
Never ever “told you so” to your team. Your team, just like you, will get a decision wrong at times. If the decision is reversible, it’s almost best to let them go through a path even knowing it might result in suboptimal results. When they inevitably get a decision wrong, never ever “told you so” to your team even if you had a hunch or knew that direction wouldn’t work. Don’t let them go blindly to it. Share your thoughts, ask better questions, and show your disagreement. If they end up going there anyway, however, support their ability to take risks instead of judging their willingness to disagree with you. At one point, what you knew would fail might actually be an opportunity.

Good luck!

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Special thanks to Lily and David for keeping me accountable on writing this post and to Nick for sharing thoughts on Twitter that inspired a portion of this. As always, also to Dima for reading an early version of it.