A few weeks ago I was on a long drive home from a client meeting and I started running through the names of people I’d actually spent real time with over the past year — not the LinkedIn list, the actual list. The ones who’d had my ear, my weekends, my energy and, in some cases, my best thinking. By the time I got home I realised something a bit uncomfortable. A handful of those names didn’t really belong on it anymore. Not because they’re bad people. Because they’re not pulling in the same direction I am.
That’s the part nobody likes to say out loud.
The question worth sitting with
There’s one question I think every business owner should ask themselves once a year, and it’s blunt: is the time I spend with this person making me sharper, or just making me comfortable?
Comfortable is the trap. Comfortable feels like loyalty, like history, like the easy lunch where nothing hard ever gets said. Growth tends to live somewhere else.
I’ve started using Copilot in Outlook to actually look at the data. I’ll ask it to pull together who I’ve met with most over the last three months and the answer is sometimes a surprise. The people I think I’m investing in and the people my calendar shows I’m investing in are not always the same list. Calendars don’t lie. They quietly show you where your time really goes, and once you’ve seen it laid out on a page you can’t unsee it.
Three filters I run people through
When I’m doing this stocktake, I look at three things, and I try not to overthink any of them.
The first is how I feel walking away from the conversation. If I leave a coffee buzzing with ideas and a list of things to try, that’s a signal. If I leave flat and quietly wanting a nap, that’s also a signal. The body keeps a fairly honest scoreboard, even when the head is trying to be polite about it.
The second is whether they’re actually moving. Movement doesn’t have to be loud — I know plenty of quiet operators who are building something serious. But if someone has been telling me the same story about the same plan for three years running, that stagnation will start to drag on you whether you notice it or not.
The third is whether they’ll tell me I’m wrong. The people who only ever agree with me have very little to offer me. The ones who push back, who ask the awkward question, who say “are you sure about that?” — those are the ones I keep close. Anyone who’s only ever told me what I wanted to hear has never once helped me improve.
The hardest cuts are the kindest people
The brutal part of this exercise isn’t the obvious ones. It’s the genuinely lovely humans who just don’t fit where you’re heading next. Lovely doesn’t equal useful. You can wish someone well, mean it completely, and still recognise that the season of regularly being in each other’s diaries has run its course. That’s not betrayal. That’s adulthood.
I keep a private Loop page with my thinking on this — a few names, a few notes, no judgement attached. Copilot helps me draft the reflection prompts when I’m not quite sure what I’m trying to articulate. It’s not a kill list. It’s a way of being deliberate about where my hours go next year, because nobody else is going to be deliberate about it for me.
If you’ve never done a Friendventory, do one this month. Block an hour in your calendar, pour something decent, and walk through the names honestly. The people in your corner shape the business you build next. Pick them on purpose, because by default you’ll just keep whoever was around when you started.
CIAOPS 