hiring mistakes founders spot too late

from the job listing to day one: where remote hiring goes wrong

In partnership with

Most founders don't realise they've made a bad hire until 60 days in.

By then the person is onboarded (loosely), in the Slack channels, and starting to quietly disengage…

In today's send:
✅ Why your job listing might be filtering out your best candidates
✅ What bad remote onboarding is actually costing you
✅ What a better remote hiring process looks like

I'd love to know 👇️

When it comes to remote hiring, what do you find hardest?

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Top reads this week:

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Here's something most founders don't realise until it's too late 👇️ 

Your hiring process is probably filtering out your best candidates before they even apply.

The listing is the first filter

Most remote job listings read like in-office postings with "remote ok" added at the end.

  • No salary range.

  • No detail on how the team communicates.

  • No sense of what a typical day looks like.

A vague job listing will filter out your strongest candidates: the ones who have options and won't apply blind.

A good remote listing tells someone how you work (think culture/timezones/management), what tools you use, what async looks like day-to-day, and roughly what the role pays.

Without that, you're not attracting candidates.

You're hoping they take a chance on you 🤷 

The process is too slow

Remote candidates, especially good ones, are usually talking to a few companies at once.

A hiring process that drags past three or four weeks will lose most of them to whoever moves faster.

Two clear stages, quick decisions, respect for their time.

Speed signals something about your company: that you're decisive and that you value people's time.

Onboarding is where most remote hires go wrong

Here's a stat worth noting…

In an office, a bad onboarding is uncomfortable and not fun. Done remotely, can feel be very isolating if done badly.

The new person logs in on day one, nobody knows they're there, and they spend the week trying to figure out how things actually work.

30% of new hires leave within their first 90 days, and poor onboarding is one of the leading reasons.

The thing most interviews miss

Technical skills get tested, communication skills rarely do.

Remote work runs on how people write, how they handle ambiguity, how they give updates when no one's looking. A good async communicator will outperform a brilliant but vague person on a remote team every time.

Most hiring processes don't check for any of it.

What a better remote hiring process looks like

  • The job listing tells candidates how you work, not just what you need from them

  • Hiring takes 2-3 weeks max, start to finish

  • Communication and async skills are tested during the process, not assumed

  • Day one has a structure: tools ready, a buddy assigned, a 30-60-90 day plan in place

  • Onboarding runs for 90 days, not 90 minutes

Remote work gives you access to the best talent in the world.

But your hiring process has to be built for it.

ATR tip of the week

Before your next role goes live, read your job listing as a candidate who has never heard of your company.

Does it explain how you actually work?

Is there a salary range?

Does it make clear what "remote" means at your company: fully async, some core hours, a few team calls a week?

If it doesn't answer those questions, your best candidates are already clicking away.

Forward this to anyone hiring remotely; a few tweaks to the process can save months of frustration.

Other reads:

And here's some more reads for the week:

Most of these mistakes are fixable; you just need to catch them before they cost you.

Have a great week!

Thanks,
Sam

PS 👇️ 

The best candidate for your next role might not live in the same country. Oyster helps you hire globally in 180+ countries. Payroll, compliance, and benefits included.

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PS: Interested in the BTS of newsletters? Chat with Chris.