Have you ever left a one-on-one meeting knowing deep down you should have said something—but didn’t?
Maybe the report was late again. Maybe the presentation missed the mark. Or maybe someone on your team keeps dominating conversations and you’re tired of watching others shut down. You tell yourself you’ll address it next time. Next time turns into next month. And nothing changes.
If that stings a little, you’re not alone. In fact, you’re in very good company—even at the highest levels of some of the world’s most successful companies.
The One Leadership Skill Almost Everyone Struggles With
After two decades of managing people and now overseeing leadership development for over 150,000 employees worldwide, one pattern stands out clearer than anything else: the single hardest thing for leaders at every level is delivering clear, honest, constructive feedback.
Not the praise part. We’re pretty good at that. It’s the “here’s where you’re falling short and what needs to change” conversation that makes even seasoned managers break into a cold sweat.
Why? Because most of us desperately want to be liked.
Being liked feels safe. It feels warm. It keeps the peace at the holiday party and makes Slack threads full of heart emojis. Being respected, though? That sometimes requires being the bearer of uncomfortable truth. And that’s where so many of us freeze.
Nice Isn’t the Same as Respected (And Teams Know the Difference)
Here’s the quiet tragedy I’ve watched play out hundreds of times: a well-meaning manager avoids the tough conversation because they don’t want to hurt feelings. The employee keeps repeating the same mistake. The team quietly resents both the manager and the person who “gets away with it.” Performance stays mediocre. And eventually someone great leaves because they weren’t getting the coaching they needed to grow.
Everyone loses.
In my experience, people would rather hear hard truth from someone they trust than soft lies from someone they like. They might not enjoy the moment, but they’ll thank you later—often years later—when they look back and realize that feedback was the turning point in their career.
“Being nice is great. Being liked feels good in the moment. But the name of the game is respect. If you’re not delivering the feedback people need, you won’t have the respect required to truly lead.”
– A chief learning officer at one of the largest tech companies in the world
Where Most Managers Go Wrong (Even When They Think They’re Helping)
Let’s be honest—most of us think we’re already giving feedback. We drop the occasional “I think you could have…” or “Next time maybe try…” and convince ourselves we’ve done our job.
That’s not feedback. That’s a suggestion wearing a feedback costume.
Real feedback is specific, timely, and crystal clear about impact. It separates the behavior from the person. And most importantly—it actually lands.
- “The deck was fine” → vague and useless
- “The deck had 47 slides for a 15-minute presentation, which meant the core message got lost and the exec team left confused about our recommendation” → specific, observable, impact-focused
See the difference? One feels polite. The other feels useful.
The Sports Psychology Secret Elite Performers Already Know
Think about the best athletes on the planet. They don’t get better by hearing “nice try” after every game. They get better because their coaches dissect every minute of footage—celebrating what worked and ruthlessly examining what didn’t.
Win or lose, the debrief happens. Every single time.
Tom Brady didn’t become Tom Brady by surrounding himself with yes-men. Olympic gymnasts don’t stick the landing because their coaches only pointed out the pretty parts. Greatness requires relentless, specific, caring feedback.
And yet in most workplaces we treat feedback like a rare solar eclipse—something we schedule twice a year and hope goes okay.
No wonder performance feels stuck.
Why First-Time Managers (and Former Peers) Struggle the Most
If you’ve ever been promoted over people who used to be your equals, raise your hand. Now keep it up if you found yourself softening feedback because you didn’t want to “ruin the vibe.”
Yeah. Thought so.
Suddenly you’re supposed to hold your former work spouse accountable and it feels… weird. Personal. Almost like betrayal.
Here’s what I’ve learned after watching this scenario hundreds of times: the relationship doesn’t break because you give honest feedback. It breaks when you don’t—and resentment slowly builds instead.
People can handle hard truth wrapped in respect. What they can’t handle is wondering where they stand.
A Simple Framework That Makes Tough Feedback Feel Human
Over the years I’ve stolen the best ideas from sports psychologists, executive coaches, and the rare managers who seem to give feedback effortlessly. Here’s the formula that actually works:
- Start with care – “I want you to crush it here, which is why I need to share something.”
- Name the behavior, not the person – “When the client asks a question and you answer for five minutes without checking if you’re on track…”
- Explain the impact – “…they disengage, and we risk losing credibility.”
- Ask for their perspective – “How did that meeting feel from your side?”
- Co-create the fix – “What could we try next time to keep them engaged?”
Five steps. Takes ninety seconds when done smoothly. Changes everything.
And yes, your heart will still race the first twenty times. That’s normal. Courage isn’t the absence of fear—it’s doing it anyway.
The Surprising Payoff Even Skeptical Managers Discover
I’ll never forget the engineering lead who came to me after a training session convinced this “radical candor stuff” was corporate nonsense. Six months later he pulled me aside: “I started having the hard conversations. My team’s velocity is up 40%. And two people told me they finally feel like they have a real manager.”
That’s the paradox: the moment you stop prioritizing being liked and start prioritizing people’s growth, something magical happens—they actually end up liking you more. Not because you’re easy. Because you care enough to be honest.
Respect compounds. Trust deepens. Performance soars.
Your Challenge This Week
Think of one piece of feedback you’ve been avoiding. Maybe it’s small. Maybe it’s been eating at you for months.
Schedule the conversation. Use the framework. Be kind, be clear, be brave.
You’ll probably survive. Your team definitely will—and they’ll be better for it.
Because great leaders aren’t the ones everyone likes.
They’re the ones everyone grows under.
