Want to Be a Better Leader? Ask These 2 Scary Questions

boss and employee smiling and facing one another having a conversation

What if there were two questions you could ask your team that hold the key to helping them be more productive?

And they would also help you be a better boss and deliver better business results.

Would you ask them?

I was introduced to these questions a year ago by Strategic Coach, which helps entrepreneurs be more successful.

But did I run back to my office and ask my team these two questions?


Not right away because I was scared of what I might find out about myself.

The first question is:

“What’s frustrating you about our business and the way we’re doing it right now?”

The second one is:

“What’s exciting you about our business and what we’re doing?”

When you’re the boss or person in charge, asking these questions can feel very personal.

What if the frustrations are all about you? What if they can’t think of anything they’re excited about? What if they feel they can’t answer honestly.

But those are all excuses.

After asking my team, what I’ve learned is groundbreaking and will change the way I run my business – for the better. And it will take our team productivity up several notches.

Even if it was scary. For me and for them.

Also read: Six Things My Dog Taught Me About Leadership

Create the conditions for successful feedback

Whether you’ve been a good boss or bad boss, this is an opportunity to open up lines of communication in a more powerful way.

It’s all in how you go about it, so start by creating a safe space for both you and your team to have the conversation.

Here are a few ground rules:

Come in with the right mindset

Enter the conversation willing to learn how you could be better. Avoid conversation killers like being defensive or debating every point.

You need to be okay with whatever they say and demonstrate that in your reactions. Otherwise, you won’t get much useful feedback in the future.

Choose a quiet time

To get the best results, choose a time when things are relatively quiet and you can have an open-ended one-on-one conversation.


Once you pose the first question, sit back and listen. Don’t think about other things, and don’t interrupt. When there’s a pause, ask if there’s anything else.

Be willing to make changes

When you ask about frustrations, it’s important that you’re prepared to take action to address the things you can and want to change.

If you’re not willing to take action on things that will help your team be more productive, then don’t bother asking these questions. It will backfire.

The changes you choose to make should be guided by making a positive difference without changing who you are fundamentally. You’re not committed to doing every single thing that people bring up.

Also read: 5 Ways to Lead by Example

Be prepared to troubleshoot

If your team member starts to whine and complain, keep your cool and guide them back to a constructive place.

You can get their help in focusing on the most important frustrations by saying something like, “Thanks for sharing your thoughts with me – you’ve clearly given this a lot of thought. Are there one or two that you care most about?”

Or, shift the focus to things that are in your sphere of influence by saying something like, “Thanks for sharing that. I can see what you mean, and I even share some of those frustrations. I’d like to focus on the ones that I can do something about.”

Say “thank you”. Then take actions that make sense.

Answers from my team

When I asked my team members about their frustrations, here are some of the things they said:

  • “There are times I need your input, but you’re hard to reach.”
  • “You’re always so busy – I feel bad interrupting you.”
  • “I feel like I’m not in the loop on the latest developments.”
  • “The changing nature of priorities is limiting what I can contribute.”
  • “It’s hard to figure out which projects are the priorities – everything seems equally important.”

Wow. I learned a lot about myself and how that’s reflected in the way I run the business.

I do struggle to prioritize because I want everything to be done right now.

I am always busy and traveling, so you can’t help but interrupt me.

I love new ideas and can’t resist chasing them.

However, I was pleased that they all felt comfortable to tell me the truth. These are areas I’ve wanted to improve in and they’ve now taken on greater urgency.

Actions I’ve chosen to take

  • Return my team members’ emails first.
  • Have a regular catch up session with each individual.
  • Set out priorities more clearly.
  • Create a decision making filter so we can assess new projects as they come up.
  • Enlist a team member to manage me so I don’t derail our plans with new “shiny objects”.

When I asked the second question about what they’re excited about, each team member had a different answer.

When you know what excites people and motivates them, you can help them get more of it. And that will help the whole team become more productive.

What will you do?

Asking these questions and getting feedback from your team can be scary.

But you know what? They’re already thinking these things. So you may as well benefit from knowing how you can help them do more and be better.

Want More Guidance on Leadership?
Watch this Webinar: “Leadership Secrets Every Superboss Should Know”

About the Author

May Busch is a sought-after executive coach, speaker, advisor, author, and former COO of Morgan Stanley Europe. Her passion is helping people succeed in their career and life – to be better, do more, and make the difference they are meant to make. Find her on MayBusch.com and follow her on Twitter at @maybusch