If you were to write a list of the leadership soft skills to develop, you might think of things like decision-making, communication, delegation, and strategic thinking. And top marks if you did, because they're super important. However, there's one that not many leaders seem to have a firm grasp of, but it can be a bit of a game changer. We're talking about asking better questions.

In this article, we'll get into why the leadership questions you ask matter so much, what better questioning looks like, and why leaders who get good at it grow faster than those who don't.

But first, let’s look at one of the most important things you can glean from your team members.

The Truth, the Whole Truth, and Nothing but the Truth

What percentage of the time do your people tell you the unadulterated truth? It’s probably not 0%, but it's almost certainly not 100%. Instead, they’ll likely tell you a version of the truth, shaped by what they think is safe and adjusted to avoid a response they're afraid of. This is how leaders end up making big decisions without the full picture.

Napoleon Bonaparte, of all people, was acutely aware of this problem. He found that his generals agreed with him simply because he was in charge, and that he essentially had a load of yes-men on his hands.

His solution was to designate an "Idiot General," a trusted senior figure kept out of all battle planning. The Idiot General was then invited to explain why a proposed plan wouldn't work. And because they had no idea whose ideas were whose, there was no reason to hold back.

And while you hopefully aren't planning on taking over half the world, the principle still holds up for leaders today. Because if you want honest input, you have to make it safe to give. And since we wouldn’t recommend advertising on LinkedIn for an Idiot General (which is a HR nightmare waiting to happen), you should make people feel safe with an environment where the truth isn’t something to fear.

Now, let’s look at the right kinds of questions to ask of your team.

What Do You Ask When Things Go Pear-Shaped?

When something goes wrong, many leaders instinctively reach for one of two questions:

1.  "Why did you do that?"
2.  "Who's responsible for this?"

Both are backward-looking and heavy on the blame. As a result, you’re more likely to get a defensive answer rather than an honest one, and a performance of accountability rather than the actual story.

But what happens if you reframe your response with curiosity instead? It might look something like:

"Walk me through your thinking."

"What were you trying to achieve?"

"What would you do differently now?"

These questions help you properly define the problem before charging in to fix it, and a problem well defined is a problem half solved. Which is considerably more useful than throwing your toys out of the pram.

The ripple effect of this simple reframing is significant, too, because when people see that bringing a problem to you results in a curious conversation, they start bringing problems to you earlier. And that, dear leader, is how you stop firefighting and start leading with intention.

Let’s Go Fishing

“Give a man a fish, and you feed him for a day. Teach a man to fish, and you feed him for a lifetime.”

It’s a proverb so old that it’s almost cliché, but it’s genuinely useful in this leadership context.

Because when you give a team member the answer to a question immediately, you solve today's problem. But if you ask them a question that helps them find the answer themselves, you develop their ability to solve tomorrow's problem without you.

It's why "Tell me more" has been one of our go-to questions for over twenty-five years. It doesn't seem like much when you see it written down, but it creates space for people to think out loud. And people who do that develop faster, trust you more, and bring sharper thinking next time.

The Question No Great Leader Skips

The most important leadership question you'll ever ask isn't directed at your team at all. It's directed at yourself. We call it the Magic Question of Leadership, and it goes like this:

"Where and how could I have done better today?"

All great leaders ask it, and the best of the best write the answer down. Why? Because they know that wisdom doesn't come from time served, but from time examined.

Two more questions to really get the gears turning are: “Did I earn my money today?” and “Did I do my very best today?” The answer to the first is usually yes, but if you answer the second one honestly, it might well be a no. But don’t worry, because that brings another, crucial question into the mix:

“So what would, or could, or should I have done differently?”

Which is where the real fun starts. Because knowing how to ask these questions of yourself is one of the very rare exemplary leadership skills that you can embed into your daily routine as a leader.

Final Thoughts

Leadership soft skills like asking questions don't get the headlines they deserve. However, the leaders who master them get more truth, develop more capable people, and grow faster as leaders.

In fact, we’d go so far as saying asking better questions is one of the most underrated leadership skill sets there is. All it takes is curiosity, a willingness to sit with the answer to difficult questions, and the humility to be more interested in what comes back than in proving you already knew it.