The Difficult Conversation That Wasn't (And What It Taught Me About Manager Assumptions)
Have you ever avoided a difficult conversation at work because you convinced yourself it was going to be a battle?
Of course you have. We all have.
But here's the thing. What makes a conversation difficult isn't usually the conversation itself.
It's what we assume is going to happen before we even open our mouths — what I call the Assumption Escalation Loop.
The Difficult Conversation I Was Dreading (And Why)
I was a new area manager at Greggs. Only about six months in.
And I had this shop manager. Let's call her Jane.
Jane had been there 25 years. Started part-time, worked her way up to shop manager over the years.
Lovely person. Everyone liked her.
But the brand was growing. The shop was getting busier. Standards were getting tighter.
And from my view? She was out of her depth.
My operations manager had already painted the picture for me.
"She's a lovely lady, Jon. But she's struggling. The figures don't lie."
I picked up those assumptions. I went in believing it was going to be difficult.
I assumed she'd be defensive. That she wouldn't agree with my points. That she'd fight to defend herself.
So I put it off.
Didn't have time. Didn't have the appropriate time. She wasn't at work. We've got a launch coming up, it's not appropriate.
We're very good at giving ourselves reasons why we wait, aren't we?
When I Finally Had the Conversation
Eventually, I couldn't put it off anymore.
We sat down. Cup of tea.
I started with, "How's it going? How are you finding it?"
She gave me the usual reply. "Everything's okay."
But I dug a little deeper. I asked how she was. Not just about work. About her.
And this conversation developed to the point where you learn a lot about your people.
The trials they're going through. The stress. Very external to the work.
You get to a point where you think, "I'm amazed you get up at four in the morning and come to work after you've looked after your poorly mother."
So I said to her, "You know, there's options."
She looked at me.
And tears started to roll down her face.
"What are the options?"
So I went through them.
She could go part-time. She could step down a level, though financially that would have an impact.
More tears.
And then she said something I will never forget.
"I didn't know there were options."
"I thought the only option was to carry on battling through. Probably hating every day of coming to work. The job I'd done for 20-odd years. Or to leave."
It wasn't a battle.
It was a relief.
She was looking for alternatives. She needed space. She needed time.
For her, it was relief. And the pressure just came off.
What Actually Happened
She stepped down. Became a sandwich maker.
And she was fast. One of the best.
She moved to a bigger shop in the town, became a key trainer, found her niche.
I visited about 10 years later. She was still there. Part-time. Much happier.
Her mother had passed away by then. The pressure had come off.
What it taught me: Don't rush to conclusions when you haven't even asked the questions.
Why Managers Avoid Difficult Conversations at Work
That shop manager? She's every "difficult" conversation you're avoiding.
Research shows 71% of leaders report increased stress from their roles, with 40% of those stressed leaders considering quitting.
Why?
Because they're carrying conversations they haven't had. Problems they haven't addressed. Issues they're working around instead of working through.
And here's what research shows: Silence doesn't protect relationships. It slowly strains them — something I describe as the Silence Spiral.
When leaders don't address issues directly, teams fill in the gaps themselves.
People start guessing instead of asking. Frustration replaces clarity. Engagement fades quietly.
But here's what I learned from that conversation all those years ago.
The conversation isn't difficult because of the other person. It's difficult because of your assumptions.
What Makes Workplace Conversations Actually Difficult
The conversation is only difficult because you've convinced yourself it will be.
You've already painted a picture in your head. And that picture is causing the dread.
My operations manager said, "She's struggling. The figures don't lie."
I picked up those assumptions. I went in believing, "This is going to be a battle."
Reality? It was a relief.
Here's the trap.
Maybe they're not "resistant to change." Maybe they just haven't changed quickly enough according to your timeline.
Maybe they're not "defensive." Maybe they just don't feel heard.
So before you have the conversation, ask yourself: What assumptions have I made?
Write them down. Challenge them.
Ask yourself, "Is this fact, or is this just what I think?"
Because assumptions are one-sided. They're just your reality — part of the Assumption Escalation Loop.
The Person Already Knows They're Struggling
Often with these difficult conversations you think you need to have... the individual already knows.
She knew she was struggling. She knew it was too much.
She was just looking for options.
I assumed I'd have to prove to her that she couldn't run the shop anymore. I assumed she'd defend her position.
Reality? She was drowning and knew it.
Most of the time, the person you're about to have a "difficult conversation" with already knows they're struggling.
They're not blind. They're not stupid. They're not in denial.
They just don't know what the options are.
I think people often don't know what the options are. Their assumption is: they do the job they're employed to do, or they have to leave.
And if you, as a line manager, believe that to be true of your people, you're missing a big trick.
So go into the conversation asking, "What do you need?"
Not "Here's what I need you to do."
Why Waiting Doesn't Make Difficult Conversations Easier
Waiting rarely makes things better.
And we're very good at giving ourselves reasons why we waited.
Didn't have time. They weren't at work. We've got a launch coming up.
We're great at finding excuses if we don't really want to do it.
I've seen shop managers let staff always do the job they like doing. Because if they don't, the staff member is awkward, painful, causes disruption.
Other staff see it. They start doing the same thing. "This is my job. I don't do that job."
The shop becomes entrenched.
So the manager covers it themselves.
Rather than addressing the issue, they smooth it over — what I call the Smooth Trap — and it becomes a full-blown problem.
You might believe you don't have enough time to have these conversations. But they probably save you a lot of time.
Block the time. Have the conversation. Don't answer your phone. Don't leave the meeting.
And remember: If you don't block enough time, the individual feels that you're rushing.
Particularly if they're going to talk about really personal stuff — things that are important to them — you've got to be respectful enough to give them that time.
What to Do This Week
If you're avoiding a difficult conversation right now, if you've convinced yourself it's going to be a battle... here's what I want you to remember.
First: Your assumptions are making it difficult
Write down what you're assuming. Challenge it. Ask yourself, "Is this fact, or just what I think?"
Second: The person already knows
You're not telling them anything new. You're offering options.
Go in asking, "What do you need?" Not "Here's what I need you to do."
Third: Waiting makes it worse
Block the time. Have the conversation. Don't smooth it over.
That shop manager I sat down with all those years ago? She didn't need me to tell her she was struggling.
What she needed was for someone to say, "You know, there's options."
And when I did, the pressure came off. Not just for her. For me, too.
Because I realised the conversation was never going to be as difficult as I'd made it in my head.
If you're avoiding a conversation right now because you've convinced yourself it'll be difficult, join The Empowered Leader's Circle.
We break down the EI, the NLP, the frameworks that help you have these conversations without the dread.
Free. Practical. Full of managers going through exactly what you're going through.
Jon Manning
Former Retail Operations Manager | Author of Emotional Intelligence Unleashed
Frequently Asked Questions
Why do managers avoid difficult conversations?
Managers avoid difficult conversations because they've already convinced themselves it will be a battle. They assume the person will be defensive, resistant, or upset. But most of the time, the person already knows they're struggling — they just don't know what the options are. The conversation isn't difficult because of the other person. It's difficult because of your assumptions.
How do you prepare for a difficult conversation with an employee?
Before having the conversation, write down your assumptions and challenge them. Ask yourself: "Is this fact, or just what I think?" Then go into the conversation asking "What do you need?" rather than "Here's what I need you to do." Block enough time so the person doesn't feel rushed, and don't answer your phone or leave the meeting.
What if an employee is struggling but won't admit it?
Often the employee already knows they're struggling — they're not blind or in denial. They just don't know what the options are. Many people assume their only choices are to do the job they're employed to do or to leave. As a manager, your job is to present options they may not know exist: part-time, different roles, alternative responsibilities.
Does waiting to have a difficult conversation make it easier?
Waiting rarely makes things better. While you're avoiding the conversation, the situation worsens, other team members notice and start behaving similarly, and you end up smoothing over problems that become full-blown issues. The time you "save" by avoiding the conversation costs you more time managing around the unaddressed problem.
How do you know if your assumptions about an employee are wrong?
Your assumptions are one-sided — they're just your reality. Before the conversation, distinguish between facts and interpretations. "The figures show performance is down" is a fact. "They're resistant to change" or "they'll be defensive" are assumptions. Challenge every assumption by asking: "Is this fact, or just what I think?"
What stops managers from having difficult conversations sooner?
Managers create their own obstacles by convincing themselves they don't have time, the timing isn't right, or there's a launch coming up. But these are excuses driven by dread, not reality. The conversation you're avoiding probably takes less time than managing around the problem for weeks.
How long should you allow for a difficult conversation with an employee?
Block enough time so the person doesn't feel rushed - at least 30-45 minutes. If they're going to talk about personal situations affecting their work, they need to feel you're genuinely listening, not watching the clock. Don't answer your phone or leave the meeting. Respect their time by giving them yours.
