Hi everyone, welcome back.
In this week’s Deep Dive: why you keep putting off that conversation with a difficult team member, and exactly what to say when you have it.
First, one quick tip…
QUICK TIP
Before you speak, decide: is this the moment to add something, or the moment to let what you said land?
Why it works: Not every silence needs filling. Sometimes it’s better to let a point sit.
Use it: When you're tempted to speak just to be seen speaking.
🔍 DEEP DIVE
The conversation you keep putting off with a difficult team member
You've got a team member you're avoiding having a conversation with.
Not in an obvious way.
You still have your one-to-ones. You still reply to their messages.
But there's something you should have raised a while ago, and you keep finding reasons not to.
They're late.
They push back on almost everything you ask.
They miss deadlines, then tell you at the last minute.
And the moment you correct them, they get defensive, so you've quietly started correcting less.
If you had to sum it up, you'd probably say something like: "None of these things are huge on their own, but together they're a pattern I can't ignore."
But you just haven't said it to them.
You tell yourself you're being fair. Giving them time. Not turning something small into something big.
I don't think that's fairness.
I think it's delay, and it gets more expensive the longer it goes on.
What's Actually Happening
Your brain is very good at weighing up today and very bad at weighing up next month.
Having the conversation means discomfort now. A tense room. A defensive reaction.
Not having it costs nothing. At least not today.
So your brain picks the option that costs nothing today.
This is called present bias (the tendency to choose what feels easier now over what's better later).
It's why you'll answer twenty emails before you book one thirty-minute conversation.
The problem is, the cost doesn't disappear. It builds.
First, in you.
Resentment creeps in. You notice everything they do.
Your tone gets shorter. You avoid them in ways you think nobody can see.
Second, in your team.
They've noticed. They always notice.
They're watching to see whether the standards apply to everyone, or just to the people who don't push back.
Every week you say nothing, you're answering that for them.
Third, in the behaviour itself.
Nobody has named it, so as far as your team member is concerned, it's fine.
It rarely stays the same. It usually gets worse.
This is such a common pattern.
You'd handle a difficult client or a tough board question without blinking.
But you'll rearrange your whole week to avoid a difficult conversation with someone on your team.
Avoidance is one of the most costly habits in leadership.
You just don't see the cost until much later.
What to Do Instead
1. Build the case before you walk in
Write down three specific examples. What happened, when, and what the impact was.
Not "You're always so negative." That invites an argument.
"You were twenty minutes late to Tuesday's client call, and Sam had to cover the first agenda item." That's a fact.
2. Open with the pattern, not the incident
"I want to talk about something that's been building for a while. None of these things are huge on their own, but together they're a pattern I can't ignore."
Then give your examples.
Then stop talking and let them respond.
3. Hold steady when they get defensive
They probably will. That doesn't mean you've handled it wrongly.
"I'm not asking you to agree with every example. I'm asking you to acknowledge the pattern."
"I can see this is hard to hear. It still needs to change."
"Let's stay on this for now. We can talk about the other things separately."
4. Be clear about what happens next
If you end the conversation with "OK, great, thanks for the chat," nothing will change.
"What I need from here is for you to be on time to client meetings, and to bring concerns to me directly rather than raise them in front of the team."
"Let's check in on this in two weeks."
Then put the check-in in your diary before they leave the room.
You've put this off long enough.
Pick a time this week. Write your three examples tonight.
It won't be comfortable. It doesn't need to be.
It just needs to happen, and you're more than capable of doing it.
ONE CLEAR THOUGHT: A question to help you think more clearly about a work situation
What am I avoiding saying, and why?
How this helps: Avoidance often shows up as over-explaining.
BEFORE YOU GO…
If you’re dealing with ongoing work situations where it’s hard to stay clear, hold your position, or be taken seriously, I offer 1:1 coaching.
My work is practical and focused on real conversations, decisions, and day-to-day leadership moments, not theory or motivation.
Thanks for reading.
Until next time,
Kaley

PS. If you have any questions, just reply to this email. I’d love to hear from you!

