The Five Conversations Every Manager Should Be Running (And Most Aren't)
"I'll raise it next week."
If I had a dollar for every time I've heard a founder or manager say that, I'd have a very healthy coffee budget.
Here's the pattern I see again and again in growing businesses. Something small pops up. Someone isn't quite sure what's expected of them. A great team member is getting quietly restless. A behaviour is starting to rub the team the wrong way. The manager fully intends to say something. They really do. But it's busy, it feels a bit awkward, and maybe it'll sort itself out.
It rarely does.
Most people problems in growing businesses aren't really people problems. They're conversation problems. The conversation that didn't happen. Or happened too late. Or happened so vaguely that nobody realised it had happened at all.
The good news? The fix isn't a 60-page management framework. It's five conversations, done well and done often.
Why good managers skip the conversations that matter
Most managers in growing businesses got the job because they were brilliant at the work. They were the best salesperson, the sharpest designer, the most reliable operator. Then one day they had a team, and nobody sat them down and said: "By the way, your job is mostly conversations now."
So they keep doing the work they know. And the conversations get squeezed into the gaps, or skipped altogether, because they feel optional. Right up until they're not.
This matters more than most founders realise. Your managers are your culture. The day-to-day experience of working in your business is shaped, more than anything, by the conversations people have with their manager. Get those right and a lot of other things take care of themselves.
So, what are the five?
1. The expectations conversation
This is the conversation that makes sure every person knows what great looks like in their role. Not their job description. Not a set of KPIs buried in a document from two years ago. What great looks like right now, this month and this quarter.
It gets skipped because it usually happens once, at onboarding (if you're
lucky), and then never again. Meanwhile the role has evolved, the business has grown and the priorities have shifted three times. Then we wonder why someone is "underperforming".
People can't hit a target they can't see.
Try this in your next one-on-one:
• "What do you think the most important part of your role is right now?"
• "Here's what I think it is."
• "Where are we different?"
The gaps are where the gold is. Jot down what you agree, even as a few dot points, and come back to it whenever priorities shift.
2. The check-in
The check-in is a regular, human conversation about the person, not the project. It's not a status update. You can get that from your project management tool.
The managers I see doing this well keep it regular (weekly or fortnightly, 15 to 30 minutes, protected in the diary), let the team member bring their own agenda, and follow up next time on anything that came up.
Most importantly, they go one layer deeper than "How's it going?" Because we all know how that one ends. "Yeah, good." And… cut.
A few questions that get a more honest answer:
• "What's taking up most of your headspace at the moment?"
• "What's one thing that would make this week easier?"
• "Is there anything you need from me that you're not getting?"
• "What's something from the last fortnight you're proud of?"
The check-in is where you hear about the workload that's quietly getting out of hand, the thing at home that's making this month hard, or the idea that's been sitting in someone's head for weeks. It's also where trust gets built, fifteen minutes at a time. And if your business has an Employee Assistance Program, it's the perfect moment to remind people it's there.
If your team spans a few generations, how people like to check in can vary too. I've written more about that in How to Manage a Multi-Generational Team.
3. The feedback conversation
Can we please retire the feedback sandwich? Nice thing, actual thing, nice thing. Everyone knows the recipe, so the moment you open with a compliment, your team member is bracing for the "but". The real message gets lost somewhere between the bread.
Good feedback is simpler than that. Three parts:
• What I saw. Specific, recent and observable. "In yesterday's client call…", not "You always…"
• The impact. Why it matters to the client, the team or the work.
• What's next. A question or a clear ask. "What would help?" or "Next time, could you…?"
Positive feedback deserves the same care. "Great job!" is nice. "The way you handled that complaint, calm and clear with no jargon, is exactly the standard we want" is useful, because it tells people what to do more of.
Two more things. Feedback works best little and often, in the moment. If something is a surprise at review time, it's too late. And it goes both ways. The best managers I work with ask for feedback as often as they give it. Try: "What's one thing I could do differently that would make your week easier?" Then listen without getting defensive. (Harder than it sounds.)
4. The growth conversation
Not everyone wants a promotion. But everyone wants to grow.
This is the one a lot of growing businesses miss. In a 30-person business there often isn't an obvious next rung on the ladder, so managers skip the growth conversation altogether. Nothing to offer, so why bring it up?
Then a great person leaves for a role that looked like "more".
The growth conversation isn't a promise of a promotion. It's a genuine question: where do you want to be in a year, and how can we help you get there? Sometimes the answer is a bigger title. Often it's a new skill, a project they'd love to own, more time with clients (or less), or flexibility that lets the rest of their life work. Most of those cost far less than a replacement hire.
Have it twice a year, separate from performance reviews, so it stays about them and not the org chart. Questions to start with:
• "Where would you like to be in a year?"
• "What part of your work gives you the most energy?"
• "What would you love to learn next?"
• "What's one thing we could do in the next three months to help?"
5. The tricky one
The conversation you're putting off. A performance issue, a behaviour everyone has noticed but nobody has named, or a conflict that's been left to simmer.
Here's the thing about the tricky conversation: it doesn't get easier with time. It gets more expensive. The manager hopes it'll resolve itself, the team watches to see if anyone does anything, and the person involved often has no idea how serious it's become. By the time the conversation finally happens, it's not a conversation any more. It's a process.
The short version of doing it well:
• Have it early. A small conversation now beats a big one in three months.
• Say it straight and kindly, in the first minute. No warm-up lap.
• Bring examples, not adjectives. "Three missed deadlines this month" lands. "You seem disengaged" doesn't.
• Get curious. There's often more going on than you know.
• Write it down and follow up.
And if it's heading towards formal performance management, get advice before you go any further. I've put together a full step-by-step guide here: How to Have a Difficult Conversation at Work
A simple rhythm for all five
Management isn't a set of annual events. It's a rhythm of small conversations. Here's what that rhythm can look like:
Conversation | How often | A question to start with |
Expectations | Whenever priorities shift, and at least quarterly | "What does great look like in your role right now?" |
The check-in | Weekly or fortnightly | "What's taking up most of your headspace at the moment?" |
Feedback | Little and often, in the moment | "Here's what I saw, why it matters, and what's next." |
Growth | Twice a year | "Where would you like to be in a year?" |
The tricky one | As soon as you notice | "Can we talk about something I've noticed?" |
For founders: how to back your managers
If you've got a new layer of managers, here's one small thing you can do this week. Ask each of them which of these five conversations they're having regularly. Then ask which one they'd like help with.
That answer will tell you exactly where to invest.
A few other things make a big difference. Model the conversations yourself, because your managers will copy what you do far more than what you say. Give them the time, and treat conversations as part of the job rather than something to squeeze in after the "real work". And if they've never been shown how, teach them. Nobody is born knowing how to run a good one-on-one.
Where to start
Pick one. Probably the one you've been avoiding.
When managers are having all five conversations regularly, you feel it. There are fewer surprises, fewer resignations out of nowhere, and a team that actually talks to each other.
If you'd like help building these habits across your leadership team, that's the kind of people foundation our HR Lift Off program is built to set up. Book a discovery call and we'll work out where to start together.
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