If you want to run a team made of actual humans and not robots, you need to build a backbone for awkward conversations.
No more sugar coating. No more staying up at midnight fixing work because you couldn’t be bothered telling someone they missed the mark. No more hoping your Virtual Assistant or LinkedVA team member magically reads your mind.
Most leaders won’t admit it, but here’s the truth. They’re not bad at leading. They’re just bad at giving feedback. Or terrified of it. And that fear quietly destroys standards, culture, and team performance long before anyone notices what’s going on.
The good news is that it’s normal to feel awkward. I’d actually be more worried if you enjoyed it. But avoiding difficult conversations at work doesn’t make you kind. It makes things worse for everyone.
So let’s fix it.
Why Leaders Find This So Hard
Most founders hate conflict. You don’t want to be the bad guy. You don’t want to hurt someone’s feelings. And honestly, some days you’re just too bloody tired.
When a piece of work lands on your desk and it’s… average, the temptation is real. You sigh, mutter something under your breath, and redo it yourself.
I’ve done it more times than I can count. Every manager I coach does it too. Especially when they’re working with a Virtual Assistant and expecting mind-reading instead of giving real direction.
But here’s the problem. Every time you fix something in silence, you train your staff not to care about getting it right. You teach them that near enough is good enough because you’ll swoop in and tidy it up anyway.
Meanwhile, the good people quietly lose motivation because nothing they do seems to matter. That’s how A players become B players. Or leave entirely.
A Real Example From My Own Team
Last week I had to give feedback to one of my best team members. She’s brilliant and cares deeply. Sometimes too deeply. A client raised an issue and she rushed in to solve it without pausing to understand the real problem.
She meant well, but her quick fix made things worse. Now I could have done what most founders do. Redo it, complain to a mate, and quietly move her to the mental list of people I “can’t trust”.
Or, I could have the uncomfortable chat.
So I jumped on a call. I told her what she did well, where it missed, and what to do next time. Ten minutes. No drama. She walked away clearer, and I walked away not feeling like a martyr.
That’s all feedback is. Clarity delivered kindly. Not a character assassination.
The Two Ways Leaders Screw This Up
Most managers fall into one of these traps.
1. They say nothing
Standards slip. Work gets sloppier. Good people leave because they’re sick of carrying the load.
2. They wait too long and blow up
By the time they finally speak up, they’re frustrated, emotional, and the person on the receiving end has no idea what hit them. Now the vibe is weird for weeks.
Both approaches are expensive. Both train your team to tiptoe around you or stop trying altogether. Staff accountability requires consistency, not chaos.
How to Actually Have Hard Conversations Well
This is the approach I use now. It works with offshore teams, onshore teams, and everyone in between.
1. Address it fast
Don’t sit on it for weeks. Don’t wait for a performance review. Talk about it as soon as you see it.
2. Stay calm and factual
Take a walk first if you’re fuming. Stick to the facts. You don’t need to defend yourself. You just need to be clear.
3. Use the Good, Missed, Better model
It’s simple.
Good: Here’s what you did well.
Missed: Here’s where it went wrong.
Better: Here’s how to do it next time.
No awkward compliment sandwiches. Just clean honesty.
4. Make it training, not a takedown
Don’t just say, “This is wrong.” Say why, and show what you actually want. That’s how adults learn. And this is where delegation systems become powerful. When people know what good looks like, they can hit it more often.
5. Act normal afterwards
This is a big one. Don’t treat them like a wounded toddler. Say the thing, then move on. That’s how you keep trust.
The Kindness No One Talks About
The biggest kindness you can give someone who is underperforming is clarity. Protecting their feelings while letting their work decline is not kindness. It’s cruelty dressed up as niceness. Because it eventually costs them the job.
Some people will take the feedback and grow. Others won’t. When they don’t, you have a decision to make. Keep them and quietly suffer, or accept they’re not a fit and move on. Keeping the wrong person is your responsibility, not theirs.
If you want a business where people pull their weight, you need to get brave about the awkward bits. Hard conversations won’t always feel good. But do you know what feels worse? Spending months cleaning up silent messes because you didn’t speak up.
Say the thing. Say it clearly. Then get back to building the business you actually want to run.
