What Actually Happens Before a Marketing Hire Leaves
There is a great deal written about the first 90 days of a new hire. Onboarding plans, 30/60/90 frameworks, first-week checklists.
There is almost nothing written about the last 90. Which is odd, because that’s the stretch every founder can actually remember.
Ask someone about their marketer’s first month, and you’ll get vague impressions. Ask about the final few and the detail is sharp – the meeting that went badly, the piece of work that was stopped, the moment they realised it wasn’t going to work out.
That detail feels like evidence. It’s why “they just weren’t right for us” survives as an explanation: it’s built on things the founder saw with their own eyes.
The problem is that in the last 90 days, nothing is being caused anymore. It’s being revealed.
What the last 90 days looks like
The pattern is remarkably consistent across the businesses I’ve worked with and across my own experience of being on the receiving end of it.
They stop bringing things
What arrives is what was asked for, on time, done properly, and nothing beyond it.
The unprompted ideas have gone.
Meetings get shorter
Not because anyone is avoiding them, but because there’s less to discuss.
No decisions are being proposed, so decisions aren’t being made, so there’s less to review next time.
Work gets checked more closely
The founder starts reading things they used to skim. Not because they’re suspicious, but because they sense that something needs closer attention.
Conversations become corrective
Now, almost every time the work is discussed, it’s about something that’s wrong with it.
Nobody planned this. It’s what happens when the only trigger for a conversation is a concern.
And the founder starts collecting evidence
This is the part nobody says out loud.
It isn’t calculated, but once you’ve started to wonder whether someone’s working out, you notice things you’d have previously let pass, and each one confirms the doubt that made you notice.
By the time all five of those are in place, the outcome is settled. What remains is the timing.
The four missing pieces
None of that behaviour is a personality. It’s what a capable person does in the absence of four specific elements. In a founder-led business making its first marketing hire, it’s common for all four to be missing.
1. No direction they could work towards
There’s a reason marketers talk about journeys A LOT, and this is it.
Frequently, founders believe they gave direction because they gave a target – grow pipeline, double inbound, hit this number by June.
A target isn’t a direction. It’s a destination with no map.
Direction is the thing that lets someone decide between two reasonable options on a Tuesday afternoon without asking.
Are we going after a new segment or going deeper in the one we have?
Are we building something durable or buying attention this quarter?
Is the constraint awareness or conversion?
Is sales having difficulty articulating the product?
The list goes on.
Without that, every choice is a guess about what you’d have wanted. Some of those guesses will be wrong, and being wrong will look like poor judgement rather than an absence of information.
The tell is retrospective, and it’s brutal.
If you can remember correcting the direction more than once, but can’t produce the document that stated it in the first place, the direction didn’t exist.
It was being discovered, one correction at a time, by someone who had no way of getting it right first.
2. Expectations that were never stated
Every business has expectations that feel too obvious to say;
How finished does something need to be before you show it?
How fast should you reply to an email or Slack message?
Do you flag a problem early or arrive with it solved?
How much detail belongs in an update?
Do you ask permission or ask forgiveness?
None of that is in the job description. All of it gets assessed.
And an unstated expectation can only be discovered one way: by breaching it. So a new marketer spends their first months finding the edges by walking into them, and every discovery arrives as a small failure, in front of people who already knew.
The founder experiences this as a series of minor disappointments.
The marketer experiences it as being wrong repeatedly for reasons nobody stated in advance.
Neither of them names it, because from the inside it doesn’t look like a communication problem.
It looks like a fit problem.
3. No milestones, and no way to bank a win
I’m talking about journeys again. This is the one I’d point at hardest, and it’s the least discussed.
Without agreed success markers, a marketer cannot be doing well. They can only be not failing yet.
Think about what that does over nine months.
There’s no point where anything is confirmed as working.
No moment where the founder says: that’s what I wanted, do more of it.
Effort accumulates, but evidence doesn’t. The person has nothing to point at, AND neither do you.
So when doubt turns up in month six, there’s nothing to benchmark it against. No agreed success markers or milestones to make you think, hang on, they’ve delivered three things I asked for. Just an undifferentiated stretch of activity and a feeling that it’s not going the way you hoped.
Milestones aren’t bureaucracy. They’re the only way founders can see progress and the marketer can start building trust in their work.
And they don’t need to be sophisticated. Three things, agreed at 30 days, that you’ll both look at on day 90.
Whether they were achieved matters far less than whether they existed, because the conversation on day 90 is completely different when there’s something specific to talk about.
4. Nobody to work it out with
The first marketing hire in a founder-led business is almost always the only person in the building who does what they do.
There’s no colleague to sanity-check a plan with.
Nobody who’s made this decision before.
Nobody to say that’s normal, or that won’t work here, or I’d take that to her before you build it.
Everyone else has that. The first marketer has a founder who’s stretched, holds all the context, AND is also the person judging them.
That’s an isolating position even when everything else is going well. When the first three absences are also present, it becomes untenable, because there’s no way to check whether the confusion is you or the situation.
Most experienced marketers, in that position, conclude it’s them.
How the four compound
They aren’t independent problems. Each one of them makes the others harder to solve.
No direction means more guesses.
More guesses mean more corrections.
More corrections, with no milestones to offset them, mean the record consists entirely of things that went wrong.
And with nobody to sense-check any of it, the person has no way of knowing whether the pattern is about them or the environment.
So they do the rational thing. They narrow.
They stop proposing, because proposals get corrected.
They deliver exactly what was requested, because requested work can’t be wrong.
They go quiet in meetings, because there’s nothing safe to suggest.
Which is precisely what the last 90 days look like to the founder.
And it reads, unmistakably, as somebody who isn’t very good at their job.
What the last 90 days is actually good for
Not as a record of what went wrong; it’s too late for that.
But as a diagnostic, it’s excellent, because it’s the part you remember clearly.
Ask yourself these three questions:
When did they stop bringing you things?
Find roughly the month. Then look at what happened in the six weeks before it. Something did.
How many conversations about the work were corrective?
If the answer is nearly all of them, then the only signal that person ever received was negative, regardless of how much of the work was fine.
Could you have told them, at any point, that they were on track?
Not “things are going well.” Specifically on track, against something that was agreed. If the answer is no, then there was never a benchmark for them to have demonstrated their abilities and met your expectations.
None of those questions requires the person’s version of events. All three are answerable this afternoon.
What it's worth changing
The fixes are small relative to the cost, and they’re all front-loaded.
One page of direction, not a target. Three milestones agreed at 30 days and reviewed at 90. Whatever’s currently unstated, written down – particularly the things that feel too obvious to say. And one external person your marketer can talk to who isn’t you.
That last one costs almost nothing, and almost nobody does it. A peer, a mentor, a monthly call with someone who’s built a marketing function before. Sales can be a good sounding board if you have it. It removes the isolation without adding headcount.
The reason to do this isn’t only to avoid another failed hire. It’s that a marketer with direction, stated expectations, agreed milestones and someone to think with does substantially more in their first year than one without – same person, same salary. They spend month one working rather than trying to triangulate.
Most of what looks like a bad hire is a person operating without any of the four. And by the time you’re watching the last 90 days closely enough to be worried, all four have been missing for 6 months.
The good news is that all four are yours to install. None of them requires a better candidate.