How to start giving difficult feedback (when you haven’t been doing it regularly)

Delivering negative feedback is hard — especially when you’re seen as a “the positive person” on your team. Here’s how to start doing it more regularly.


“I need to right the ship.” A member of The Watercooler, our online leadership community, admitted this a few months ago. He shared how he’d long delayed giving critical feedback, and it was causing team chemistry problems.

“I think it will seem out of character for me to go from ‘positive nice guy image’ to ‘critical feedback,’ so I’m trying to think of best approach,” he revealed.

His admission prompted a wonderful discussion in The Watercooler: How do you start giving difficult feedback, especially when you haven’t been doing so regularly? Here’s what other Watercooler members recommended…

Ask for permission.

Set aside time to have a discussion, instead of just dropping the feedback on the person unsuspectingly. Everyone processes news differently, and you don’t want to bombard someone in the middle of their work day. You could say, for instance, “Have a moment to chat about some feedback I have about the last client meeting?”

That being said, still do it right away.

There’s never an ideal time to give feedback. One Watercooler member remarked how “I don’t wait to give feedback, I give it as soon as possible. This removes any stress worrying about it. Additionally, the details are fresh in everyones mind and it’s relevant and topical vs. after the fact.”

Give yourself small “feedback” goals.

Challenge yourself to find three things every day on which you could give feedback. This helps train your mind to see everything as a opportunity to give feedback, instead of dismissing your own observations.

Explain “the why.”

Share context of why you’ve decided to start giving more feedback. Are you motivated to become a better leader? Were you inspired by a recent book you read? Providing background about why you want to start giving more honest feedback will help employees see the big picture.

Acknowledge your own mistakes.

When you admit how you yourself were wrong, you help create a safe environment for people to make mistakes, learn and grow from them. It also shows that just because you’re the boss, you’re not infallible to critical feedback, yourself.

Invite critical feedback about yourself.

Feedback is not a mandate — it’s a conversation. You should actively ask specific questions about yourself to get critical feedback on your own performance and management style. It’s the only way for a team to grow together. If feedback is only one-way, your team will never progress as much as it could or should.

Use a framework.

In his piece Negative Feedback Antipatterns, Charles-Axel Dein suggests four ways you can deliver difficult feedback:

  • Observation of a fact: A fact is rarely controversial, so it’s a great way to start a conversation.
  • Feeling: Express your feelings and your story. Clarify that it’s your story.
  • Need: State what you value, or the kind of impact you’d like to see.
  • Request: Explain what concrete action the person who’s receiving the feedback would need to take. Be objective.

I’ve also written some recommendations on a framework for giving difficult feedback here.

Anytime you feel intimidated by giving critical feedback, remind yourself that this is in the best interest of your team. Being a good leader requires hard and uncomfortable conversations, and as unnatural or painful as it might seem, you’re doing the right thing by telling the truth.






P.S.: If you enjoyed this piece, please feel free to share + give it 👏 so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

Written by Claire Lew

CEO of Know Your Team. My mission in life is to help people become happier at work.

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