We’ve had the same conversation about a dozen times in the past month.
Different companies, different industries, but the same frustrated HR director or senior leader telling us: “Our managers just won’t have the tough conversations and hold their people to account.”
It’s unlikely that anyone wakes up excited to tell someone their presentation was confusing or that their attitude is bringing down the team. But here’s what we’re seeing everywhere – managers who genuinely care about their people are tying themselves in knots trying to avoid any conversation that might feel uncomfortable.
The result? The stuff that actually matters gets pushed aside while everyone pretends everything’s fine.
It’s not what you think
Most organisations throw another communication workshop at the problem. “Here’s how to give feedback! Use this model! Use that model” But honestly, if it were just about having the right framework, we’d have solved this years ago.
The real issue isn’t that managers don’t know how to have these conversations. It’s that they’re terrified of them.
One team leader we spoke to recently told us she’d been putting off a conversation with one of her direct reports for three months. Three months! Not because she didn’t care. Far from it – she was losing sleep over it. But because she kept imagining all the ways it could go wrong.
“What if he gets defensive? What if it damages our relationship? What if I’m wrong?”
Sound familiar?
The conversations we’re not having
We’re not talking about formal disciplinary meetings here. We’re talking about the everyday leadership moments that actually shape your culture and avoid formal disciplinaries further down the line:
When someone’s constantly interrupting in meetings but nobody says anything. When the work quality is slipping but you keep making excuses for them. When there’s obvious tension between team members that everyone can feel but nobody wants to name.
These are the moments where real leadership happens. Or doesn’t.
What actually works
After working with hundreds of managers, we’ve found three things that make the difference. And none of them involve memorising scripts.
Make it expected, not exceptional
Write down the expected behaviours – of all staff and of leaders. Create a behavioural framework and/or a leadership framework. Include ideal behaviours and ideal language if you need to. Don’t leave room for interpretation.
Also, stop treating direct feedback like it’s some special occasion. Build it into how you operate. In one of our client companies, managers start every quarter by asking their teams: “What’s one thing I should start, stop, or continue doing?” And they expect the same honesty back. As Kim Scott says, you should solicit feedback before you give feedback.
One CEO we work with has a simple rule: if you’re talking about someone’s performance with anyone other than that person, you need to have a conversation with them within 24 hours.
Game changer.
Help them get out of their own heads
Most managers are stuck in stories they’re telling themselves about conflict. “Good leaders don’t upset people.” “If I’m direct, they’ll think I don’t like them.”
We spend time helping managers question these beliefs. Usually through coaching, sometimes just through honest conversations with peers who’ve been there. Once they realise most of their fears are imaginary, everything shifts.
Create safe spaces to mess up
Managers need places to talk about the conversations that didn’t go well. The feedback that landed wrong. The times they avoided something they should have addressed.
We run peer coaching sessions where managers bring their real challenges- not the sanitised version, but the messy, uncomfortable truth. It’s amazing how much courage people find when they realise they’re not the only one struggling with this stuff.
Why this matters more than you think
When managers avoid the hard conversations, it doesn’t just affect that one relationship. It ripples through everything.
Teams lose trust because issues never get resolved. High performers get frustrated watching poor performance go unaddressed. And managers themselves burn out from carrying all that unspoken tension.
But when you create a culture where direct, caring feedback is normal? That’s when things really start to change.
About the author: Jimi Wall is the Founder & CEO of Upwrd – a coaching-first cultural, leadership and team development business that works with people-first institutions and organisations. Jimi has an extensive background in Higher Education, having previously worked as Organisational Development Manager at City St George’s University of London, and as Client Director in Executive Education at London Business School. Upwrd provides coaching, facilitation and training support to a wide range of UK Universities and private sector organisations.
This article has been kindly repurposed from Upwrd and you can read the original here.