7 Questions Great Leaders Ask Regularly

A wise man never stops asking questions, and that goes double for entrepreneurs. To lead your team effectively, you should constantly be asking questions: about the health of your business, the satisfaction of your customers, and the wellbeing of your employees.

To keep your finger on the pulse of what’s really going on inside your company’s walls, ask your team these seven questions on a regular basis.

1. What do you need from me?

It’s perhaps the most important thing a boss can give her team members: her support. When your employees know you’ve got their back, they’re more empowered to make smart decisions and take action to solve problems.

If you’ve properly empowered your team, they often won’t need anything at all from you. Simply checking in and being available goes a long way toward the “we’re all in this together” mentality that keeps morale strong.

Most importantly, if one of your employees does enlist your help, follow through! Or, direct them to the appropriate channel where they can get the help they need.

2. Can you help with this?

Secondary to offering your help is to actively ask for it. Enlisting your team to assist with tasks is important for two key reasons.

Number one, delegation is essential to your success in business. No great entrepreneur got to where he is by doing it all, and you need to conserve your time and energy for the tasks that absolutely require the CEO’s touch.

And number two, to develop your team. Employees can’t grow if they’re never pushed beyond their current box. Help them explore new career avenues and develop new skills by giving them an active hand in projects that matter (and read more about employee development in this post).

3. Why is that?

All too often, the boss gets a status update from her team and that’s as far as it goes. Understanding what’s happening means little if you don’t understand why.

This is especially significant when you’re confronted with challenges—a supplier misses a deadline, a client drops you, and so on. Understanding all of the links in the chain will help you correct the issue or prevent it in the future.

Asking why also helps your staffers flex their critical thinking muscles. I once had a boss who told me she’d always trust my decisions—even if she didn’t agree—as long as I could back them up with clear reasoning. Now that’s empowering!

4. How can we do better?

This one is not only for your team, but for the customers who keep you in business.

The smart entrepreneur is constantly looking for ways to improve, even when the going’s good. That’s how you stay ahead of the competition and win lifelong customers.

Involving your team in the feedback process can help reveal blind spots in your business model, while asking customers for their input makes them feel valued.

5. What do you think?

It’s a common maxim to surround yourself with people who are smarter than you. You’ve worked hard to build a solid team, so lean on them for their advice.

Whether it’s a decision about your new product line or how to deal with a demanding client, asking for the input of your inferiors shows them that their input matters. While the final call may be yours to make, letting others do some of the legwork helps minimize decision fatigue on your part.

6. What did we learn?

We’ve talked often about failures on this blog and how they’re a critical step on the path to success. The reason? Because failures force you to learn.

When you lose it can be tough to see the silver lining, but asking this simple question can help. If it’s a departmental failure, hold a debriefing session to weigh the takeaways. If an individual team member made a blunder, help them to identify the error that got them in a bind.

7. How are you?

Even for the best boss, it’s possible to get so focused on business that we lose sight of the bigger picture: our people. If your employees aren’t in a good place mentally, emotionally or otherwise, their work will suffer, plain and simple.

Happy employees are good for business, and these three small words demonstrate that you see them as more than just an expendable resource.

Asking the right questions makes the difference between simply being a manager of people and being a true leader. As one of my favorite business quotes goes:

“The difference between managers and leaders is fundamental. The manager administers; the leader innovates. The manager maintains; the leader develops. The manager relies on systems; the leader relies on people. The manager counts on control; the leader counts on trust. The manager does things right; the leader does the right thing.” -Warren Bennis, Forbes Magazine

What are the most insightful questions you ask in your business?

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