I’ve hired a lot of people. I’ve also lost a few far too early.
And every time I look back at a new hire who left within the first 90 days, I realize the same uncomfortable truth: the problem rarely started on the day they resigned. It started on day one or, more often, before day one.
Remote work made this harder, not easier. When someone joins an office, they absorb a lot without being told: who to ask, how decisions get made, what “good” looks like, and whether
they belong. Remotely, none of that happens by accident. It has to be designed.
That is why I’ve stopped thinking of onboarding as an HR task. I now see it as a business-critical process. Because when onboarding fails, we don’t just lose a new employee. We lose recruitment spend, manager time, team momentum, and often months of productivity
The first 90 days decide more than we admit
The first three months are when a new hire decides whether they made the right choice.
They are learning the role, building relationships, understanding expectations, and quietly
asking themselves: Can I succeed here? Do I have what I need? Does anyone actually care whether I’m doing well?
If the answer is unclear, people leave. Sometimes they leave loudly. More often, they leave
quietly, disengaging first, then accepting another offer, then resigning when it is already too late
to fix.
That is why I no longer accept the excuse that someone “wasn’t a good fit” after 60 or 90 days.
Of course fit matters. But if we did not give that person clarity, support, access, feedback, and a
real connection to the team, then we contributed to the outcome.
Remote onboarding fails in small ways
Remote onboarding rarely fails because of one dramatic mistake. It fails through small gaps that
add up.
The laptop arrives late. The manager is travelling during the first week. The new hire is added to
twelve Slack channels but introduced to nobody. They receive a 60-page handbook but no clear answer to “What should I focus on this week?”
From the company’s perspective, everything is technically done. The contract is signed. Payroll
is set up. The equipment was ordered. The induction call happened.
But from the new hire’s perspective, something is missing: direction.
I have learned that remote employees do not need more information. They need a clear path. They need to know what success looks like in week one, month one, and by day 90. They need
a manager who checks in before problems become resignations.
Day 1 is too late to start onboarding
One of the biggest changes we made was moving onboarding earlier into the period between offer acceptance and the first working day.
That period is emotionally important. The candidate has just said yes. They are excited, but also
nervous. They may still be fielding messages from other recruiters. If we go silent for two weeks,
we create doubt.
So before day one, we make sure the basics are handled:
● The contract, payroll, and compliance steps are complete
● Equipment and access are ready
● The manager has a first-week plan
● The new hire knows who they will meet and what to expect
● Someone from the team reaches out personally
None of this is complicated. But it signals something powerful: We are ready for you.
Every new hire needs a 30-60-90 plan
I used to think a 30-60-90-day plan was corporate bureaucracy. Now I see it as one of the
simplest ways to prevent early turnover.
A good plan does three things:
- Removes ambiguity. The new hire knows what they are expected to learn, contribute,
and achieve. - Creates early wins. They can see progress instead of feeling lost for weeks.
- Gives managers a reason to check in. It turns vague “How’s it going?” conversations
into useful coaching moments.
For remote employees, this matters even more. In an office, a manager can notice confusion.
Remotely, confusion can hide behind a green status dot.
Managers are the real onboarding team
HR can build the process, but managers make onboarding real.
A new hire does not remember every policy document. They remember whether their manager
made time for them. They remember whether someone explained the unwritten rules. They
remember whether they felt safe asking a basic question in week two.
That is why I ask every hiring manager the same question before a new person joins: What will
you do in the first week to make this person successful?
If the answer is “HR will handle it,” we have a problem.
Fixing the gap is cheaper than replacing the hire
There is a commercial reason for all of this, too.
Replacing an employee is expensive. It costs recruitment fees, onboarding time, lost
productivity, and the disruption of a team that has to absorb the gap. And when someone leaves
early, we often repeat the entire cycle only to risk the same outcome if the underlying
onboarding experience has not changed.
Fixing the remote onboarding gap is not a “nice to have.” It is one of the highest-leverage
retention investments a company can make.
What I would tell every CEO
If I could give one piece of advice to another CEO, it would be this: do not wait until exit
interviews to learn about your onboarding gaps.
Ask your recent hires:
● What confused you in your first week?
● What would have helped you become productive faster?
● Did you feel welcomed and supported?
● Was your manager available when you needed them?
● What almost made you regret joining?
Then fix the answers.
Because 90-day turnover does not begin on day 90. It begins on day one with the experience
we create, or fail to create, for the person who just trusted us with the next chapter of their
career.
