How to Have a Difficult Conversation Without Losing the Relationship
In a small team, the person you need to have a hard conversation with is also the person you’ll be working beside tomorrow. That changes how you should approach it. Here’s a practical way to raise a performance or conduct issue without torching the working relationship in the process.
Get Clear on the Issue Before the Meeting
Write down the specific behaviour and its impact — not a character judgement. “You’ve been late to four of the last six team meetings, and we’ve had to restart the agenda each time” is something someone can respond to. “You don’t seem to care about this job” isn’t. If you can’t point to specific instances, you’re not ready for the conversation yet — spend a few more days noting examples first.
Open With the Purpose, Not a Warm-Up
Don’t bury the point under five minutes of small talk — it makes people anxious and doesn’t soften anything. A simple “I want to talk about meeting timing, it’s not a huge deal but I want to sort it out” tells them what’s coming and lets them meet you there. Say it in the first thirty seconds, then let them respond before you say anything else.
Listen for the Reason, Not Just the Excuse
Whatever explanation you get, treat it as information rather than something to argue with in the moment. Someone who’s been late to meetings because they’re dropping a kid at school every second week needs a different response than someone who’s simply been double-booking themselves. You can hold the standard and still adjust the solution — those aren’t the same thing.
Agree on What Happens Next, in Writing
Close the conversation with a specific, agreed next step — not just a general sense that things will improve. Send a short follow-up email or message afterward summarising what you discussed and agreed, even if it’s informal. It protects both of you: they know exactly what’s expected, and you have a record if the issue continues and you need to take it further.
This is general guidance, not legal advice — conversations that could lead to formal warnings or dismissal have specific procedural requirements, so check with a qualified workplace relations professional before you get there. AHRIK Keyholders can get a second opinion on a specific situation through the HR-of-One Helpline before the conversation happens.