Facing Up to Difficult Conversations: Why It Matters and How to Do It
Sometimes doing good work means saying things that feel uncomfortable – like giving tough feedback, questioning an idea, or calling out behaviour that doesn’t sit right. These moments take bravery, but they’re essential if we want trust and genuine relationships at work.
The problem is that, in today’s distributed workplace, tough conversations are being avoided. A 2023 survey by Crucial Learning found that 70% of employees hold back from difficult conversations.
Why we’re keeping quiet
Through our Connection Heroes training, we’ve seen the same challenges come up again and again. Many people avoid difficult conversations because they don’t want to upset their colleagues – especially those they don’t feel close to. They end up confusing politeness with kindness, choosing short-term harmony over honest, constructive feedback.
In remote or hybrid teams, this gets even harder. When relationships are more transactional, it’s difficult to know how someone will take feedback – and without strong connection, confidence drops. People worry they’ll be misunderstood, that speaking up will cause unnecessary tension.
And sometimes, people simply don’t care enough to speak up. They’re not invested in the outcome, or not willing to face the discomfort that comes with saying something difficult. If it’s not their problem, they’d rather keep their head down than take a perceived risk.
Avoiding these conversations may feel easier in the moment, but it comes at a cost: problems grow, performance stalls, development needs go unmet, and trust never deepens.
Managers can lead the way — but they need support
Teams take their cues from managers. If leaders are open, honest and respectful in the way they give feedback, others are more likely to follow. But many managers haven’t been trained to handle tough conversations — or have only ever seen them done badly.
This is where tools like Radical Candor® can really help.
A practical approach: Radical Candor®
The Radical Candor® model, created by Kim Scott, is built on two simple principles:
- Care personally – show you value the person
- Challenge directly – be clear and honest about the issue
When both are present, you get feedback that’s thoughtful and useful. When one is missing, it either feels too soft to be helpful, or too blunt to be productive.
Here’s how practising Radical Candor® might sound:
Giving feedback on work quality
“I really appreciate the level of detail you bring to our reports – clients notice that. On yesterday’s draft, a few figures didn’t quite line up, and that could knock people’s confidence. Let’s go through them together so the final version is as strong as your usual work.”
Challenging behaviour in a senior colleague
“I know you’re focused on getting this over the line, and I respect that. But in today’s meeting, a few people felt rushed and didn’t get a chance to speak up. I’m worried we’ll miss something important if that keeps happening. Could we give a bit more space for questions next time?”
Bottom line
Brave conversations build better teams. When people learn how to give honest feedback with care, trust grows, issues get fixed faster, and relationships deepen. Managers can set the tone, but they need tools, practice and support.
Photo by Kelly Sikkema on Unsplash
