How to Give Difficult Feedback to Your Boss (Even When You’re Scared)

To Ensure Your Upward Feedback is Received Well, Start with Connection and Intention

You have some difficult feedback for your boss, but you’re not quite sure they’re ready to hear it. It might feel safer to stay silent. After all, they can’t shoot the messenger if there’s no message.

But if you stay silent, the problematic behavior will only continue, or even get worse.

If you want to get better at giving upward feedback start with these six steps.

1. Ground yourself in connection and intention.
2. Set up a time to talk in a private place.
3. Be objective and specific.
4. Ask for their perspective.
5. Probe for opportunities to help.
6. Schedule the finish.

6 Steps to Get Better at Difficult, Upward Feedback

Your boss is an imperfect human, doing the best they can. Just like you. They don’t brush their teeth in the morning dreaming up ways to be more difficult and frustrating to you and the rest of the team.

Maybe they’re unaware of the impact of their behavior. Or perhaps they’ve had a bad role model or two. Or, it could be they’ve not received the leadership training or 360 feedback they need to improve.

Start with the benefit of the doubt that this can and will work, be the leader you want your boss to be, and make a plan to get better at giving difficult feedback.

1. Ground yourself in connection and intention.

For years, we’ve been asking this critical question in our leadership development programs:

If you knew someone truly cared about you, your career, and the success of the team, would you want to hear difficult feedback, even if it was hard to hear?

Every single time, every hand in the room goes up.

Every person with that raised hand is somebody’s boss.

Of course, we’re not naive. We’ve both been there and heard the stories. We’ve both experienced the wrath of a toxic boss responding poorly to difficult feedback and have heard from many of you about the times it didn’t go well.

But we also know this.

If you start your difficult feedback with genuine human connection and a good intention, your chances of getting through improve exponentially.

Try something like this:

“I really care about you and the success of this team. I have an observation (or idea) that I think could really improve ________ (insert desired outcome here, e.g. productivity, the customer experience, revenue, morale.) Would you be open to talking about it?”

2. Set up a time to talk in a private place.

Most of the time when difficult feedback goes wonky, the timing or location is off. The easiest way to ensure your feedback will be met with defensiveness is to share it in front of others. Or, to give it from a place of anger or frustration.

Setting up a time and place to talk in private gives you a chance to think through your approach and makes it easier to have a focused conversation. The privacy signals your genuine concern for your boss and conveys respect for them and their position.

3. Be objective and specific.

When hearing difficult feedback, nothing is more frustrating them vague feedback with no examples.

“Everyone is feeling frustrated by your angry, terse attitude,” would be difficult for anyone to hear.

“In yesterday’s meeting, I noticed you raised your voice and cut off both Jon and Kathy when they were sharing their ideas. And after that, no one spoke up again,” is an easier starting point.

Note: If you’re familiar with our I.N.S.P.I.R.E. method for tough conversations, these are the N (Notice) and S (Support) steps.

4. Ask for their perspective (and really listen.)

“I know it’s been a challenging few weeks, how are you feeling? What’s going on for you?”

Or you can even take a “reflect to connect” approach. “You seem really frustrated with our team right now. Am I right? What’s weighing on you the most?”

5. Probe for opportunities to help.

Next, try an open-ended question that offers your support.

“I’d love to help our meetings go more smoothly. How can I best support you?”

“What do you think we can do differently to reduce frustration?”

Note: This might feel frustrating at first. You might be thinking, “Hey, they’re the one with the problem!”

But chances are, this gentle, empathetic approach will help get underneath the root causes of their behaviors. And you might even get an, “Hey, it’s not you, it’s me. Here’s what I can do differently.”

6. Schedule the finish.

If you’re familiar with our 6 concepts you can’t lead without, you know we’re big believers in “scheduling the finish.”

And, we always recommend that you close an I.N.S.P.I.R.E. feedback conversation with a direct report by scheduling time to talk about the behavior again.

You can do this with your manager too (depending on their receptivity to the earlier steps).

“It sounds like we all have some things we can do to reduce the frustration around here, and I think we have a good path forward. Do you want to chat again after our next team meeting?”

Giving difficult feedback to your boss is rarely easy. But, practice builds confidence. And the best way to work for a better boss is to help them grow.