Better Questions Lead to Better Business Decisions

Most leaders are paid to have answers.

• What should we do?

• Why is this happening?

• How do we fix it?

• Who should own it?

• What’s the plan?

In reality, sometimes the most valuable thing a leader can do is stop answering obvious questions and start asking better ones.

Critical thinking gets a lot of attention in leadership conversations, but it doesn't have to mean complicated frameworks or hours spent analyzing spreadsheets. At its simplest, critical thinking means slowing down enough to understand a problem before deciding what to do about it.

One of the easiest ways to do that is by asking better questions.

Fast-moving organizations are very good at jumping from problem to solution.

• Revenue is down → let's increase advertising.

• Employees are overwhelmed → let's hire someone.

• Meetings are inefficient → let's have fewer meetings.

Sometimes those are exactly the right answers, but those “obvious” answers solve the wrong problem.

The Question Behind the Question

I have a tendency to move quickly—one of the benefits of working at a smaller organization is the ability to be nimble and unencumbered by layers of bureacracy. However, one of the biggest operational mistakes I see is accepting the first (or most obvious) explanation for a problem as if it were a fact.

For example, how do you respond when someone says: "Our team isn't communicating"?

It is tempting to jump to a solution, but pausing can give you time to ask—what does that actually mean? Are people not talking to each other? Are they talking but not sharing the right information? Do they know who needs to be involved? Are decisions being made without people knowing? Do people know who the decision maker is? Are priorities changing so frequently that communication can't keep up?

Each of those are very different problems, which require different solutions.

Good operations work isn't just about implementing systems—it is about figuring out what is actually happening before deciding what to change.

Five Questions Every Leader Should Ask More Often

1. What are we assuming is true?

Every organization operates on assumptions. Some are documented, but most are not. I have worked with many different companies in different industries—every time I enter a new organization with fresh eyes and start asking questions, I hear some combination of the following:

"We've always done it this way."

"That's just how our industry works."

"We need another person."

"Leadership needs to approve everything."

"We can't afford to fix that right now."

Maybe those statements are true. But what if they aren’t?

Assumptions can start to look like facts simply because they have been repeated enough times.

Try this:

When you are discussing a significant problem, ask:

• What are we assuming?

• What evidence do we have?

• What would change our minds?

• When was the last time we tested this assumption?

• Are we solving a current problem or responding to something that used to be true?

You don't need to challenge every assumption in your organization, but you may be surprised if you challenge the ones that are driving expensive decisions.

2. What else could be causing this?

Leaders often fall in love with the first explanation. Once we have decided what the problem is, we start looking for evidence that proves we are right.

Instead, deliberately generate a few alternative explanations.

For example—Problem: Employees aren't completing projects on time.

Possible explanations:

• Employees aren't prioritizing effectively.

• There are too many projects.

• Priorities keep changing.

• Ownership is not clearly defined.

• The deadline was aspirational and not based in reality.

• Employees are waiting on decisions from leadership.

• The process itself is inefficient.

• The team doesn't have the necessary information or tools.

Notice how many of those problems have nothing to do with employee performance.

Before you put someone on a performance plan, add another meeting, or hire another person, make sure you've identified the actual constraint.

Try this:

When you think you have identified the cause of a problem, force yourself to come up with three other possible explanations.

You don't have to believe them, but you should at least consider them.

3. What am I not hearing?

Good questions aren't just about speaking—they are mostly about listening.

People often do not tell the CEO, Executive Director, or department head what they actually think or know. Sometimes they are worried about being perceived as difficult. Or they assume leadership already knows. Or they don’t want to repeat what they’ve already said. Or they believe speaking up won’t make a difference.

Try this:

Instead of: "Why didn't your team follow the process?"

Ask open-ended questions, such as:

• "Walk me through what happened."

• "Where did the process break down?"

• "What made this difficult?"

• "What would you change?"

• "What am I missing?"

Then, resist the urge to immediately explain why the current process exists.

Ask questions with the goal of learning.

4. What if we're wrong?

This is one of the hardest questions for leaders to ask, especially when they've already invested time, money, reputation, or political capital in a decision.

Remember that changing your mind isn't necessarily a sign that the original decision was bad—sometimes it is a sign that you learned something.

Strong leaders should be willing to hold their hypotheses loosely and reconsider initial conclusions without becoming defensive.

Try this before a major decision:

Ask the team:

• What could make this fail?

• What are we overlooking?

• What would someone who disagrees with us say?

• What information would change our decision?

• If we had to argue against our current plan, what would we say?

You don't need consensus, but you need enough intellectual honesty to identify the weaknesses in your thinking.

5. Do we actually need to decide this today?

Not every problem needs an immediate solution.

This is particularly difficult for high-performing leaders because action often feels productive. Sometimes moving quickly is best, but sometimes we move quickly because sitting with uncertainty is uncomfortable.

There is value in giving complicated problems time to develop, and in distinguishing between urgency and importance.

Try this:

When you are about to make a significant decision, ask:

• What happens if we wait 24 hours?

• What happens if we wait a week?

• What information are we missing?

• Is there a decision we actually need to make right now?

• Can we make a smaller decision that gives us more information?

Sometimes the best next step isn't a decision, but another question.

Better Questions Are an Operations Tool

Asking better questions isn't just a leadership skill—it is an operational skill.

When you are trying to improve an organization, you need to understand how work actually happens—not how the organizational chart says it happens, how the policy manual says it happens, or how someone remembers it happening two years ago.

Discovery requires curiosity and resisting the temptation to immediately fix things.

A good operations leader might walk into a situation and ask:

• Where is work getting stuck?

• Who is waiting on whom?

• Where are decisions being delayed?

• What gets done manually that shouldn't?

• Where do people have to ask for permission unnecessarily?

• What information isn't getting to the people who need it?

• Where are we creating work because of another process?

• What problem are we trying to solve?

• What would happen if we did nothing?

Try a "Better Questions" Meeting

Consider trying this a simple exercise with your leadership team—identify one problem your organization is currently trying to solve. Before anyone proposes a solution, spend 15 minutes asking questions.

No fixing.

No defending.

No explaining.

Just questions.

Start with:

• What do we actually know?

• What are we assuming?

• What don't we know?

• What are three possible causes?

• Who experiences this problem differently than we do?

• What would we see if our current explanation were wrong?

• What have we already tried?

• What happened?

• What haven't we tried?

• What would happen if we did nothing?

Then—and only then—start talking about solutions.

You may discover that the problem you walked into the room trying to solve isn't actually the problem that needs solving.

The Goal Isn't More Questions

Of course, asking questions isn't automatically a good thing.

You can also create a completely dysfunctional organization by questioning everything and deciding nothing.

The goal isn't to turn every meeting into an interrogation, but to create enough space between "We have a problem" and "Here is what we're going to do" to make sure you're solving the right problem.

Good questions help leaders:

• Challenge assumptions.

• Find the root of a problem.

• Surface information people aren't volunteering.

• Avoid groupthink.

• Identify unintended consequences.

• Make better decisions.

• Build stronger teams.

• Find opportunities that weren't obvious at first.