When you should apply
This week I sat down with a Head of Product who was hesitant to apply for roles.
Not because the roles were bad. Because they weren't sure they were a fit.
If you've been job searching for more than a couple of weeks, you know the feeling.
Everyone sits somewhere on a spectrum of fit for any given role. And the question you keep silently asking yourself is some version of: should I apply, or should I skip this one?
Get it wrong in one direction and you're firing off applications to roles where you're a 3/10. No replies. Quiet rejections. Why am I not hearing back from anyone?
Get it wrong in the other direction and you're passing on roles where you're a 7 or 8 out of 10 — because one or two bullets in the JD don't perfectly line up with your background.
Guess what? The role goes to someone else who wasn't a 10/10 either. They just applied.
The work we did together
He'd built a shortlist. Roles he liked the look of, from companies he respected. But for most of them, he'd gone as far as reading the JD and then stopped.
So we sat down and went through them, one by one. Out loud.
By the end, four of the five were absolutely worth applying to without making any meaningful changes to his CV.
Think about that for a second.
One role was a genuine no. The top requirement was deep trading platform experience he simply didn't have. The other four were self-imposed rejections.
That's a real pattern. And if you've ever caught yourself reading a JD thinking "well, I don't have that one thing, so probably not"then you're doing it too.
How to calibrate fit without fooling yourself
Fit isn't about matching every bullet. It's about matching the top two or three things the role is really hiring for. Almost everything else is negotiable.
If you hit roughly 3 out of 5, or 5 out of 7, of the real requirements, apply.
The harder part is knowing which requirements are the realones.
That usually means rereading the JD and asking: if this company only got to check one or two boxes before hiring, which ones would they pick?
There's one clear no: if the top stack-ranked requirement is a specific experience you genuinely don't have — five years in retail, deep exchange infrastructure, FMCG scale — save your time.
No amount of CV tweaking will save you there either.
Everything else is much more forgiving than you think.
A few heuristics I use with clients
Apply or skip, in under a minute:
Top requirement is a domain you've never touched.Skip.
Screening question: "how many years of X do you have?" and your honest answer is zero. Skip. You'll get filtered automatically.
Interesting company, wrong role. Don't apply. DM someone there instead and get closer to the right role.
Everything else that feels like a 7/10. Apply. You are the worst possible judge of your own application.
Most people over-index on their own gaps and under-index on how forgiving hiring processes actually are at the screening stage.
The cost of applying to a role that's an 80% fit is fifteen minutes. The cost of not applying to the one that would have hired you is the rest of your search.
The reason this keeps happening
When it's your first real job search in years you don't have a calibration point. Every gap in the JD feels huge. Every nice to have reads like a must. Every thing you've never done becomes a reason to close the tab.
The fix isn't confidence. It's a system.
A repeatable way to look at a role, weigh it against what you actually want, and make a thirty-second apply, skip, or outreach decision. Without spiraling.
That's what I spend a big chunk of coaching on.
That's what this Head of Product now has, walking into next week.
Next week: a Resume Workshop for PMs
I built a Resume Workshop for exactly this bundle of problems: calibrating which roles to apply for, making sure your CV actually earns interviews for the ones you do, and knowing when to stop tweaking and start sending.
It's running next week.
If you've been staring at a shortlist, half-drafting applications, wondering why the pipeline feels slow, check it out.
Wishing you success,
James