I'm a CEO. How do I get people to really tell me the problems around here?

Dear CEO,

You’re probably not surprised to hear we get this question a lot. If you’re like our clients, you’re a good person with a genuine interest in helping people and your company. You’ve worked hard to get where you are and you have an open door policy. And yet, you still get surprised by what you don’t know in your business.

Do these situations sound familiar?

  • One leader we worked with had intense conflict with a manager in the business. She wasn’t sure exactly how it was influencing the team, but she knew it wasn’t good. The situation got so bad the leader felt forced to take action and asked the person to leave the organization. Once the dust settled, the leader checked in with the team about how they were doing and was surprised to find people relieved. One person even said, “We all knew it was a matter of time - and why did you wait so long?”

  • Another leader shared about an encounter at a company event. Early in the evening, as everyone was enjoying themselves, an employee walked over and asked offhandedly: “What are you going to do about the bottleneck in shipping?” The leader was surprised and started asking more questions only to discover there was a significant problem he had no idea about. His employee looked straight at the confused CEO and said, “I thought you already knew all about this.”

Despite many CEO’s best efforts, receiving accurate information about the state of the company and the status of employee engagement rarely makes it to their offices on its own. This problem spans all kinds of industries and reaches companies of all sizes.


We’ve found, through the best of intentions, information gets filtered as it moves toward you.

Here are some of the reasons we believe information doesn’t always make it to leaders:

  1. There are too many details to share in the time available.
    People pragmatically distill information to deliver updates in a timely fashion. Your team appreciates how much is on your plate, so they give you high-level highlights and move on to the next agenda item.

  2. Positive news is easier to deliver and is better received.
    Everyone likes to be the bearer of good tidings. And when leaders listen on the defensive, employees notice and protect themselves from emotional blows.

  3. Responsible people are expected to bring solutions, not problems.
    Employees fear that raising problems irritates leadership and is seen as weakness. People want to be seen as competent problem-solvers. Bringing less-than perfect situations to the attention off the boss may be perceived as the team member showing they are not competent or able to successfully do the job.

So how can you, dear CEO, find out what’s really happening in your organization?

Let’s first start with the most necessary precondition for success - trust. Ask yourself these questions to poke at the level of trust in your organization:

  • How much do your employees trust you want their feedback and believe they can deliver bad news safely?

  • How much time have you invested time in building honest, two-way relationships with your employees?

  • When have your employees seen you admit weakness or uncertainty, or express the desire to work through problems with your team?

Photo by  A. L.  on  Unsplash

If these question cause you to pause, you’re in the right place. Trust is the oil that can lubricate your organization to run more smoothly and effectively - and get you to know what’s really happening earlier than when the red check engine light goes on!

One of the most effective ways to build trust is through effective conversations with your employees.

Here are two great conversation starters, along with don’ts and do’s to make these explorations successful.

Starter #1 - “What drives you crazy at work?”

Don’t: Do open-problem surgery. Drilling down with Why? can imply blame.  
Do: Listen. Listen. Listen. Then ask open-ended, clarifying questions to explore both the situation and the other person’s thinking, like:

  • How did you find this out?

  • What have you already tried?

  • What do you think we should try?

  • How could we make that happen?

Starter #2 - “How is what I’m doing affecting you, plus and minus, at work?”

Don’t: Explain why you are doing what you’re doing or demand specific examples. You may think you are providing or getting information, yet employees experience this as you being defensive.
Do: Listen. Listen. Listen. Then explore what the other person is experiencing. Get into their reality to get insight into what you can choose to do differently. Once you understand the other person’s experience to their satisfaction, you can ask something like: “Given this situation, if you were me, what would you do differently?”

CEO, this is tough work leading you to some of the most valuable insights you can have. By connecting authentically with your employees, you can build trust, get to know what’s really happening, and uncover problems bubbling beneath the surface.

We hope these tips help you to genuinely understand what employees are experiencing. We’d love to talk with you about how implementation is going.


Chris Hutchinson

As CEO of Trebuchet Group, Chris Hutchinson thrives working with clients and his team to improve organizational clarity, teamwork, and leadership impact.

After years of building Legos® and tree houses around the world, Chris earned his Mechanical Engineering degree and followed that with an MBA. His experiences in the military and the business world taught him great leadership can be learned, and everyone is in some way a leader.

Clients and peers describe him as an inspirational catalyst for positive change. He is the author of Ripple - A Field Manual for Leadership That Works.

Chris and his wife live, garden, and bike in Fort Collins, Colorado, and have four children. He has an unrequited love affair with brownies.