Leading by Question

As a founder, your leadership must evolve from being the one to effectively decide and do everything to creating a company that can effectively decide and do everything. One of the skills you must master along the way is leading by question.

When you start a company, there are more than enough questions to go around. The last thing your company needs is for you to add to the pile. You and the company survive by solving problems and answering questions as quickly as possible.

The more effective you are at solving problems and answering questions quickly, the faster you grow and the more successful you become.

Soon, strapped for time, you start letting go of the doing. You decide what needs to be done and assign others to do it, and the company continues to grow.

Then, one day you realize you don’t have time to make all the decisions, and you start delegating some of the more trivial decisions to your managers.

The next step in your leadership evolution is to assemble a team that together can take on increasingly important and substantive decisions.

But leading a decision-making team is an entirely different ballgame. Many of the skills that brought you success in the early days, like decisiveness, instinct, and anecdote, will prevent you from leading at this level.

If your team gets together to watch you make all the decisions, what is the point of having the team come together? There isn’t one. 

If you are trying to teach your leaders to make gut-level decisions as you did, it’s not going to work. There are many reasons for this, but mainly they don’t have all the information from the sources you did. And they can’t. No one can. If you could, you would still be doing it. Further, they don’t have the experience or perspective that you did and still do today. Sure they can get closer, but it’s never going to be quite enough.

If you are trying to get your team to move quickly and change every time you hear about a new customer problem or potential opportunity, they will get it wrong a lot. And now that there are so many people involved in executing those decisions, the cost of getting it wrong is a lot higher than it used to be.

A better way

There is a better way to lead. You need to start leading by asking questions. This is going to be completely new territory for you and your team. You all got to where you are today, but your team brings issues and maybe an idea or opinion, then sitting back and watching you make the decision.

You will have to lead them to the point where they can make significant decisions without you. 

Think about that for a moment. Think about the freedom of knowing you could step back or even step out, and the company would still continue to move forward. Think about how much time you could spend on doing whatever it is that you love, inventing, spending time with your family, traveling, playing golf, entertaining top clients. All of these things will become available to you if you learn to lead by question.

How to lead by question

So what do I mean by leading by question? I mean exactly that. You start replacing decisions with questions. When Mark, your head of sales, comes to you and asks if they can offer a 5% discount on a big project, rather than answering, respond with a question or set of questions.

• What is our expected profitability on that project?
• What would happen if we don’t give the discount?
• How likely do you think it is to result in future work?
• What would Hannah in accounting say if you asked her?
• If you were in my position, would you authorize the discount?

If you ask the right questions, Mark will start learning how to make the right decision himself. You will empower him to take responsibility for understanding what factors are important and who to involve in the decision-making process.

If you ask the right questions, leaders will start learning how to make the right decision themselves. You will empower them to take responsibility for understanding what factors are important in the decision-making process. Share on X

It’s not easy. It can be downright agonizing, and the answer may be blindingly obvious to you. It would be so easy to rattle off a yes or no with a quick explanation and send Mark on his way. But in doing so, you will limit his effectiveness, capping your company’s growth and trapping yourself inside of your own business.

This isn’t only a change for you

Now, keep in mind, this isn’t just a change for you. It is also a significant change for your leaders. They had it easy. They could just lay all the difficult decisions on your desk and walk away with an answer. They probably are hard workers, but that is not hard work.

It is your job to break the cycle. It is your job to resist the urge to give answers. It is your job to ask the right questions to teach them to think the right way.

This reality is especially true in meetings. When I first start working with a team, I will ask the team a question and watch every team member turn and look at the leader and wait for him or her to make a decision. It feels natural and right for the team, but it is crippling their effectiveness.

As we work together, I’ll encourage the leader to respond in these situations with questions, followed by silence. A brutal, seemingly endless silence. However, if you stick with it, one of your leaders will speak up and offer a solution. And if you keep it up for a few weeks or months, you will reprogram the team’s habits.

By the end of our time working together, when I ask a team a question, I’ll get answers from all over the room, and then someone else will chime in, and they’ll all make a decision and move forward, all within a matter of seconds and without the leader saying a word. That’s when I know they are ready to scale.

The first step

Here’s the first step toward leading by question. In your next meeting, when it is time to make a decision and all heads turn toward you, do not answer. Instead, if your team hasn’t asked all the right questions, then start asking. If they have and you feel the answer is clear, ask this question. 

“What do you think we should do?” Then wait. Don’t say a word.

Once someone speaks up, ask, “Does everyone agree?”

If someone disagrees, ask, “Why not?”

If everyone agrees, thank and affirm the brave soul who spoke up, and move on to the next topic.

Do this a few times, and without ever addressing it directly, you’ll see a remarkable change in your team. And after that will come a remarkable change in the demands on your schedule.

Try it out, and let me know how it goes!