How To Deliver Bad News To Your Boss

I’m not gonna lie. Moments like these will never be among the most pleasant experiences of your professional life. Your boss may well spit the dummy and its very unlikely they will thank you graciously for bringing this to their attention.

But it is possible to deliver bad news to your boss with some degree of aplomb – without dissolving into a pool of weeping, caterwauling sludge. Don’t laugh. I have done this.

So the next time you’re the bearer of bad news, put your big girl or big boy pants on and do the following:

1. Front up, fess up and don’t fall prey to procrastination. I’ve spoken about this before here, but it bears repeating. If you wanna put your head in the sand and make like an ostrich, this is your cue to do the opposite.

[Tweet “If you wanna put your head in the sand and make like an ostrich, this is your cue to do the opposite.”]

Delaying the inevitable merely delays the torture. And lemme tell you – it will be less pretty if they find out from someone else.

BUT.

2. Do take some time to plan your communication and your potential solutions to ‘said pickle’.

Make sure you’ve put some thought into the following:

– What exactly is the problem? Get it crisp, concise. Outline the impacts and implications. Positioning the problem concisely and effectively helps you frame-up the conversation.

– When is the best time to deliver this? Grabbing her as she’s about to go into a high-stress customer meeting, or just before the Board meeting, or even as she dashes out the door to the airport might not be the best timing. Giving thought to time of day and place might seem like an obvious thing, but it’s often overlooked.

– Considering how you can give them a ‘pre-warning’ or heads-up might be a clever approach. One of my most talented team members in Executive Search would give me a heads up via a short email. From this, I was able to glean it wasn’t great news, which helped me prepare myself. It meant I wasn’t blindsided and could be more emotionally ready to receive the bad news.

3. Choose your timing and method of communication. See here for a clever short video on choosing the comms that your customer (or in this case boss) prefers.

4. Fall on your sword. Take accountability. Accepting responsibility is a crucial part of the equation.

5. Prepare and discuss. Potential solutions, the implications of each, the risks, the benefits and next steps. And always aim for at least three possible solutions. In their book, Decisive, Chip Heath and Dan Heath state that widening your options beyond binary decisions improves decision-making.

At the very least, outline key learnings.

6. You’re a boss. Put yourself in their shoes and ask, “if one of my direct reports had to tell me some bad news, how would I want them to approach and handle it?” This will offer up some ideas.

7. Put it in perspective. This one is more for you to remember when you are contemplating running off to Costa Rica to join a commune in the jungle. I know there have been professional occurrences in my life which at the time I thought would be my career death knell (I am prone to being slightly drama-queenish). Looking back now, they’re kinda “meh” moments.

As Winston said –

“If you are going through hell. Keep going.”