How to Tell Someone They’re Underperforming Without Totally Crushing Them

Giving constructive feedback is one of the most awkward conversations that we face in the workplace.

There are so many things to consider – timing, delivery, content… the list goes on.

And this task becomes even more daunting when the person we’re giving feedback to is underperforming.

Whether you’re an executive with an employee who’s not meeting expectations, a professional with a colleague who isn’t pulling their weight, or a manager with a difficult boss… none of us are immune to the dreaded feedback conversation.

I hope this little story will help you think about feedback in a different way and inspire you to try something new… whatever that might be for you :)

Early on in my career I was fortunate enough to snag a dream job, doing work that I loved with amazing people. Needless to say, I was beyond thrilled.

Except for one thing.

I had to teach and facilitate large group discussions… but I also had this paralyzing fear of public speaking.

Yes… I had gotten myself into a bit of a pickle.

So right about now, you might be saying to yourself, “But Nayla, why take a job where you have to do something that you really hate doing?”

Great question :)

I took the job because I was TOTALLY passionate about the field that it was in… the very same field that I’m still passionate about today (helping people thrive in the workplace).

So I applied for it and somehow made it through the rigorous interview process… which also involved a bit of facilitation.

And then I had to start facilitating workshops with real participants.


To cut straight to the punchline here… yes, I was the underperforming employee in this scenario.

One of my first debriefs was particularly rocky… filled with awkward silences, lots of stalling, and a healthy dose of self-consciousness on my part.

Good times :)

Now, as I mentioned, the people in that workplace were amazing and they didn’t shy away from those awkward feedback conversations.

Right after the debrief, one of my managers came into my office and with the best of intentions, told me about 20 things I could improve in 5 minutes flat.

I think I mentally checked-out after item #2… already feeling horrified that I hadn’t lived up to my own perfectionist expectations.

He was intuitive enough to notice and check-in with me, but by that point the learning opportunity had been lost… as I stood there staring blankly at him, wondering how weird it would be for me to crawl under the desk and wallow in self-pity for the rest of the afternoon.

A few days later, another manager came to see me.

His demeanor was upbeat, open, and friendly… and he asked if he could talk to me about the workshops.

I was sold… his energy alone had me eager to hear whatever he had to say.

He asked me one simple question… and that 5 minute conversation changed my professional career forever.

He said something like, “Nayla, you know when you’re up there facilitating… we want to see more of you. You know the fun, caring, bright Nayla who we see around the office… that’s who you need to be when you’re up there in front of a group. How can we see more of her when you’re teaching?”

And with that one rhetorical question, he literally… blew… my… mind.

I’d been keenly watching all of the experienced facilitators, taking copious notes on how they did things… and attempting to imitate them to a tee.

So I had most of the workshop content pretty much down pat. It just wasn’t showing through because I needed to bring it to life with… well… ME!

My facilitation skills skyrocketed after that conversation and to this day, I LOVE facilitating and remember that manager with incredible gratitude.

And so, dear readers, this bring me to my tips for giving constructive feedback.

There are so many helpful ones out there, so these are just a handful that you might want to keep in mind as you’re making your way through the wonderful world of life at work.

Tip #1: Check Your Energy

Your energy speaks before you even begin to open your mouth. So take the time to get yourself into the right frame of mind for the discussion.

Tip #2: Pay Attention to Timing

If someone is in an emotional state, they’re not in the right head-space to integrate whatever you have to say. Make sure that you pick the right timing for the discussion.

Tip #3: Three Pieces of Feedback Max

My experience is that people can usually only integrate up to 3 pieces of constructive feedback at a time. So focus on the key things that you want to help the other person improve.

Tip #4: Strike the Right Balance Between Mentoring and Coaching

Know when to tell and when to ask. In my little scenario above, “telling” definitely helped a little… but what I really needed was someone to help me get unstuck by asking the right questions. I work with leaders on this very issue in my Virtual Peer Coaching Circle Program.

Tip #5: Give Positive Reinforcement

This one is a no-brainer and so much has already been written about this. So all I’ll say here is that it’s helpful to share some genuine positive feedback too, especially in those particularly tough cases.

Tip #6: Jedi-Mind-Trick Them

Kidding, of course. Everyone knows that Jedi mind tricks are for storm troopers.

But you can ask them some perhaps unexpected, but helpful questions, like “How do you like to receive feedback?” Even if the other person doesn’t know, they’ll start thinking about it and you’ll get some tips for framing.

And if you really want to take it up a notch, you can do what one of my favourite bosses used to do once a year – go around and ask everyone for feedback on yourself :)

I hope this little anecdote gives you some food for thought.

If you’d like some more, check out my Difficult Conversations Cheat Sheet for actionable strategies to talk about awkward things without losing your nerve.

And, of course, may the force be with you ;)