Management Let them sleep on it

Don’t Yolo Hard Conversations

On the list of leadership merit badges, “Successfully deliver hard news” is one the hardest badges to acquire. It’s not just that you have news, it’s hard news. It’s an honest something the human sitting across from you does not want to hear. Not only do you need to deliver it, but you need to successfully deliver it.

There are endless ways to screw this up. This is why it’s a merit badge. Once you learn how to successfully deliver hard news, you will never forget. The experience is hard-earned.

Bad news, I’m not going to give you a complete strategy, these are simple tips. Starting with:

  • Write down what you are going to say. Don’t yolo hard conversations.
  • Share that writing with another neutral human who you know will give you critical feedback. They will find flaws and optimizations that you have not seen.
  • Sleep on the conversation that you’ve written down and vetted with the neutral humans. Your background processing skills are strong.

The final tip is the most important. You can fail to write down your thoughts, you can not share your thoughts with a neutral human, and you can fully yolo the delivery, but the final bullet you skipped is my simple tip: let them sleep on it.

The moment that a human being hears hard news they stop listening. It’s a normal and healthy fight or flight instinct. Right or wrong, the human on the receiving end of this news feels attacked and when you’re attacked you run because who wants to be attacked?

They hear you, they are recording the conversation, but they are not listening because their mind is telling them to run for it. Their first reaction, the first words tell you, are not how they feel. They need to let their guard down, and that only comes with time.

Successfully delivering hard news means honestly and compassionately delivering the news. It’s quietly listening to their reaction, hearing each word, but understanding what they feel won’t be known until they’ve taking their time to hear you.

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4 Responses

  1. Yongsheng 3 months ago

    Right on time. We just gave all eng managers a training on having hard conversations. This is super helpful.

  2. GretchenA 3 months ago

    Key point – don’t just write it down. Practice delivering it with a neutral human. Until you’ve actually felt the words leave your mouth, you don’t know how _you_ will respond in the moment. You need to be 100% ok with what you are delivering, so you can be actively listening to the person in front of you. You can only do that if you’ve actually delivered the news at least once.

  3. Julie 2 months ago

    Right on time. Transitioning jobs and love my current boss too much to screw up saying “I’m leaving, but not because I’m not thankful to you” the right way.