What being a CEO has taught me about delivering bad news

Boris is the wise ol’ CEO of TNW who writes a weekly column on everything about being an entrepreneur in tech — from managing stress to embracing awkwardness. You can get his musings straight to your inbox by signing up for his newsletter!

I recently had to deliver some bad news to a group of people. Delivering bad news is part of the job, and I don’t want to complain about it. I don’t take pleasure in it (on the contrary), but I also want to do it right. Kind of like a doctor who might need to do something that’ll  hurt the patient in order to make them better. 

I think you can handle a crisis, or bad news, in a good or bad way, and I’m happy if I can make the best of a bad situation. There’s a weird contradiction in there, but such is life.

I’ve learned a few lessons through the years in delivering bad news, and I thought I’d share those with you.

Announce, explain, repeat

When we do a presentation at TNW, we try to start with the actual announcement. Get it out as soon as possible, and don’t build up to it. Then explain what and why, and then repeat the announcement and come to a conclusion. 

I’ve often felt the need to first explain the why and how and then come to a conclusion with the announcement. That’s a mistake I’ve made too many times. People feel you’re working towards the actual announcement and want you to just spit it out — so don’t keep them waiting. Start with your announcement, then explain, then repeat the conclusion.

Be honest, and don’t sugarcoat

I’m a persuasive motherfucker and tend to bullshit my way out of a lot of things. My natural inclination is to sugarcoat everything. But even though I think I’m good at that, I’m not. People read through bullshit, and appreciate honesty a lot more than a shit-sandwich (bad news packed in between good news). Be honest, and start with the truth. 

Make sure to provide ample evidence, data, and background on request along with your bad news. The more data you have to back up your announcement, the better. But be careful not to overload your audience.

If the news is essential, people will need some time to digest and understand what you’re saying. If you throw too much data at them, you’ll lose your audience. But… it’s great to have the data ready so that if there’s a request for more data, you can show it.

Sooner is better than later

It’s essential to think about how you’re going to deliver the news, who to tell first, to make an action plan, etc. But it’s also imperative to give people the news as soon as possible. 

I’d rather be fast, and stutter and give an unpolished story,  and show that I wasted no time in sharing my news, rather than wasting time on crafting a super polished story.

Be personal, without hiding behind it

If I’m genuinely emotional, I don’t mind showing that. I think some people notice I get flustered and my voice breaks a bit when I’m delivering bad news. I’m human, I have feelings, and I’m sensitive. I’m not ashamed to show that. But I would never make the mistake of saying to someone who is about to lose their job “yeah, I feel awful too.” 

Emotions are not a currency you can use as a tool, and if people see you do that, it will come over as an insult. Be honest, as well as sincere.

Time to digest

I’ve said it before, but it is worth it to emphasize: By the time you deliver bad news, you’ve already had time to understand it, consider the consequences, and then think about the wording. You might have had time to sleep on it. Your audience will have a lot less time to process it. 

They’re listening, processing, digesting, and calculating what this means while listening to you deliver the news for the first time. You had a few hours or days as a head start. So remember to give your audience some time. Make the extra effort of explaining things twice, or three times. Give people the option to reach out to you directly to discuss things.

Conclusion

Life is full of surprises, and not all of them are positive. I think there’s honor in being able to deliver bad news thoroughly and constructively. Dealing with the good news is easy; delivering bad news takes skills. Hone those skills, and then hope you’ll need them as little as possible. 

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