As CEO and founder, there are inevitably times when I have to deliver bad news to the team. I don’t think it ever gets easier, but thanks to some candid feedback I’ve received over the years, I’ve discovered how to relay the information in a factual, but understanding way.

This is something I’ve actually become reasonably good at - perhaps because my style is to be upfront, direct, and honest.

Being honest about the bad and the ugly

Bad news is often preceded by hard decisions. As obvious as it might sound, the first step is to make the decision. It’s something I learned early on that comes with the territory of being CEO.

Then comes the communication part. It’s like ripping off a bandage - sometimes you just have to do it. I’ve found it most effective to be direct in giving people all the information they need and then explain my reasoning for how I arrived at the conclusion.

Sooner is always better than later. And with empathy is always better than without.

In business, the buck has to stop somewhere, and at Geckoboard, it stops with me. I’m happy for that to be the case. I think most of the team knows that I don’t see myself as superhuman or something that I’m not. I try to be honest and straightforward in all my communication. I think that makes it easier when it comes time to breaking bad news because people know there’s no BS.

I have to be real - that means showing emotion

In the past when I was communicating bad news, I had a tendency to try to protect people a little bit. I wouldn’t necessarily give all the gory details or explain the full backstory. Part of that was not sharing that I found it difficult to make the decision.

Someone gave me specific feedback about this approach three years ago. I would present the difficult news and tell the team it was going to be okay, but some people thought perhaps I was being cavalier or emotionless. When in reality I was trying to shield them and protect myself from a lot of the hurt and turmoil that comes along with difficult decisions.

I learned that being completely honest with people by saying “Hey, this is difficult for me too, it’s hurtful, and I’m sorry” - resonated with the team and helped to soften the news a bit. I needed to communicate with empathy.

How my communication improved with empathy

One of the best ways I’ve found to improve my communication (or really any aspect of being CEO) is to surround myself with people who are willing to give honest feedback and criticism.


Starting out, I thought I had some level of empathy. I set up the organization from a people-first perspective. Having a pleasant and enjoyable work environment was one of the founding principles of Geckoboard.

And then I received some really great feedback.

Someone was leaving the organization and I had to share the news with the rest of the team. It was going to be a shock to a lot of people. After discussing this with the leadership team, one person very directly said to me, “Look, here’s what people are going to be thinking when you communicate this. You need to be able to address these concerns if people are going to see beyond ‘oh sh*t, this is going to impact me’ to ‘okay, there is a future for me here.’”

That was really eye-opening for me. What was actually going on in people’s heads was “Oh no! What happens now? How is this impacting me? Am I safe? Is my future uncertain?”

In my mind, those concerns weren’t an issue. I knew everyone was safe and secure. I only wanted to talk about the fact that this person was leaving, since no other areas were changing.

Going into this situation I was thinking, “This is a big change and I acknowledge that. It’s going to impact all of your lives, I’m not going to sugar-coat it.” Which was great, but a little brutal.

But this person on the leadership team reframed the situation from everyone else’s point of view. “That’s not what they’re thinking. They’re thinking about themselves and the impact this will have on them.”

It was completely obvious! But it was certainly a lightbulb moment for me. I was trying to be direct and honest with people. I didn’t want people to feel like I had hidden anything from them. And that includes the fact that “yes, there is some uncertainty here and we’re going to sort through it.”

What I ended up saying (and felt was much more effective) was along the lines of “I know you’re feeling this is going to impact you negatively. I want to reassure you that it’s not. We’re going to come out of this stronger than we were before.”

It was a very different kind of emphasis. I had to cultivate empathy in its purest form - stepping into someone else’s shoes and seeing the situation from their vantage point.

I learned to embrace people's differences

We’re all different. As people, we respond differently to different things. What I personally would have appreciated was someone just being direct and giving me the facts. I don’t necessarily respond well to reassurances.

But not everyone works like that. Not everyone wants all the gory details. Sometimes they just want to know “It’s okay. You’re safe.” While I thought I was exhibiting empathy, I was actually just exhibiting empathy for the type of person I am and not necessarily for other people.

That was a big lesson - one of many - that I’ve learned about empathy. And it has significantly improved the way I communicate with the team, especially when there’s difficult or bad news involved.