They won't tell you in July. But that's when they decide.
Here's something I've watched happen more times than I can count.
A founder calls me in September, slightly panicked. One of their best people just resigned. Out of nowhere, they say. No warning. A great performer, someone they were building around, gone.
Except it wasn't out of nowhere. It never is.
That person didn't decide to leave in September. They decided in July. On a beach, or a balcony, or a long drive to wherever they went to switch off. Somewhere away from the day-to-day, with enough space to actually think, they asked themselves the question every good employee asks at least once a year:
Am I still in the right place?
And for a lot of your best people, this is the month they're asking it.
Why summer is when people leave
The resignation happens in September. The decision happens now.
There's a reason for this, and it's not complicated. During the year, your best people are heads-down. Busy. Executing. They don't have the mental space to reflect on their career because they're too deep in the work. Momentum carries them.
Then summer comes. They take a break. The pace drops. And for the first time in months, they have room to think.
That's when it happens. They look back at the year - what they've done, what they've learned, where they're headed - and they make a quiet judgement about whether the next twelve months look better than the last. If the answer is yes, they come back energised. If the answer is no, they come back with a decision already made. They'll be polite about it. They'll wait for the right moment. But the decision is done.
By the time you see the resignation, the conversation that could have changed it is long past.
The people most likely to be deciding right now
It's not who you'd expect.
It's rarely the people who complain. The ones who voice frustration are still engaged - they're telling you something because they want it fixed. The dangerous ones are the quiet high performers. The people who just get on with it. The ones you never worry about because they never give you a reason to.
Those are the people who reflect over summer and leave in autumn. Precisely because they don't make noise, you have no idea they're on the edge. You've been so reassured by their reliability that you've stopped investing in them.
Ask yourself right now: who are the two or three people on my team I'd be devastated to lose? When did I last have a real conversation with them about what they want next? If you can't remember, that's not a good sign. It's a signal.
What they're actually deciding on
When your best people weigh up whether to stay, they're rarely leaving for money. Comp matters, but it's almost never the trigger. What they're really assessing is three things.
Growth. Am I still learning? Am I better than I was a year ago? Is there a version of me in twelve months that's meaningfully more capable - and does this place get me there? Your best people are ambitious by definition. If they feel like they've plateaued, they'll go find the next climb somewhere else.
Recognition. Do they see me? Does what I do here actually matter, or am I just reliable furniture? High performers can tolerate a lot, but being taken for granted isn't one of them. The quiet ones especially - because they never demand recognition, they rarely get it.
Direction. Do I believe in where this is going? Do I trust the person leading it? Your best people signed up for a vision. If the vision has drifted, or the confidence has cracked, they feel it before anyone else does.
Notice that none of these are things you fix with a counteroffer in September. They're things you build over months. Which is exactly why the window is now, not later.
What to do this month
You don't need a retention programme. You don't need a survey. You need three or four honest conversations, and you need to have them before the summer break, not after.
Sit down with each of your most important people. Not a performance review. Not a project update. A real conversation about them. Where they want to go. What they want to be doing in a year. What's frustrating them. What would make the next twelve months better than the last.
Then - and this is the part most founders miss - actually respond to what you hear. If someone tells you they want more ownership, give them something to own before they leave. If they tell you they feel stuck, show them the path. If they tell you they're tired, mean it when you tell them to take the break.
The conversation itself matters, but only if it's followed by something real. A founder who asks the questions and then does nothing is worse off than one who never asked - because now the employee knows you heard them and chose not to act.
Why this is a hiring issue, not just a people issue
I run a hiring business. So why am I telling you to focus on keeping people rather than finding them?
Because the two are the same problem.
Every time one of your best people walks out the door, you don't just lose them. You inherit a replacement search that costs you months, pulls your focus, and - if it's a senior or specialist role - might cost you the back half of your year. You're not just filling a seat. You're rebuilding institutional knowledge, relationships and momentum that took eighteen months to develop.
The most cost-effective hire you'll ever make is the one you don't have to make because you kept the person you already had. Retention isn't separate from your hiring strategy. It is your hiring strategy. The founders who lose the fewest people are the ones who spend the least time and money in the market.
And the ones who lose people every autumn, then scramble to replace them every winter, are stuck on a treadmill they built themselves - one conversation at a time, by never having the conversation.
The July playbook: 3 things to do this month
1. Write down your "devastated to lose" list.
Three names, maximum. The people whose resignation would genuinely hurt. Be honest - it's not always the most senior people. Once you've got the list, that's your priority for the next two weeks.
2. Have one real conversation with each of them before they go on holiday.
Not a review. Not a check-in dressed up as a chat. A genuine conversation about where they want to go and how you can help them get there. Do it this week, while there's still time to act on what you hear.
3. Pick one thing to actually change.
For each person, commit to one concrete action based on what they tell you. A stretch project. A path to promotion. A comp review. A genuine break. One real thing beats ten good intentions. Do it before September, not after the resignation.
What I'm seeing from my desk
The best retention tool is a founder who pays attention. The companies with the lowest turnover I work with aren't the ones with the best perks or the highest salaries. They're the ones where the founder genuinely knows their people - what drives them, what worries them, what they want next. That knowledge is the retention strategy.
Most "sudden" resignations were visible months earlier. When I place someone who's leaving a role, I always ask why they're moving. It's almost never a single event. It's a slow accumulation of feeling unseen, unchallenged or uncertain - usually building for six months or more before they acted. The founder rarely saw it coming. The signs were always there.
The counteroffer almost never works. By the time someone resigns, they've emotionally left. I've watched dozens of founders try to buy back a departing employee with more money or a new title. It works maybe one time in five, and even then, they're usually gone within the year. The time to keep someone is long before they're standing in your office with a resignation letter. It's now.
Tools
DM me on LinkedIn with any of these and I'll send them straight over:
SCORECARD - A 5-line role scorecard template. Forces clarity on what the hire actually needs to deliver.
LOOP - A structured interview loop framework. Who interviews, what each stage tests, how to avoid asking the same thing four times.
OFFER - A checklist for making offers that stick. Comp, work model, timeline, and the soft stuff most founders forget.
Because great teams are Built Different
Hiring question? Building a key team? DM me - always happy to think it through with you