The questions that matter

Photo by Evan Dennis on Unsplash

In my experience, the best leaders ask the questions that matter. And the questions that matter are the key to driving the organization forward.

As the founder or leader, you’re in a unique position with a wider, more all-encompassing perspective. You can see the vision of where you need to be in 3 years and in 5 years, the reality of your bank balance and fundraising, and the sense of the morale of the organization. You’re the only one with all this information floating in front of you as you chart a path forward.

What do you do with that?

The best leaders use their unique position not only to make objective observations on the state of the business, but to determine the right questions to ask the team. They use these questions to guide the organization towards the most important goals.

Imagine a product team that has spent the last few weeks designing a feature. They’re excited to present it to you. It’s a great feature — but based on where things stand, it’s not the highest priority. While you know that, you have to communicate it in a way that’s productive.

This is where you ask the questions that matter. By asking the right questions, you won’t just tell people what you see; you’ll help them see it, too. You’ll keep them on track while keeping them motivated.

A few of the questions that matter, in this example:

  • Is this the most important feature we need in our product to achieve our goals for the next 6 months?
  • And if not, why were we spending time on it?
  • Where was the gap in the communication that let these resources get get spent on this?
  • Is there a faster way to get this live (that may involve manual intervention) in order to get it out there?
  • Is there a more cost-efficient/scalable/robust solution?

Instead of command and control, questions help the team think for themselves. It’s the Socratic method for effective orgs. The caveat is that in an emergency or a time crunch, being directive is fine. It may be needed. But organizations that always rely on one person to make decisions end up paralyzed and ineffective.

I once worked with a senior leader who did exactly this. If someone came to her saying a deadline “could not” be met, she’d find the right people and ask the questions that mattered. By doing that, she’d help people figure out how to circumvent the bottleneck. She ensured that the things that moved the company forward, moved forward. It was amazing to see how “impossible” things, once she’d pinpointed the right questions, got done.

The same is true for investors. I find the best investors ask founders questions that make them think about the world differently, change the lens, expand the set of options in front of them with an interesting re-frame.

Asking the right questions indicates a level of thought, knowledge, and facility with the world you are dealing with. A leader asking the right questions can help an organization come up with creative solutions, hit their goals, expand their view of the world, grow to become more self-sufficient, and by doing so, move the organization toward that long-term vision.