How to set your new Executive Assistant up to succeed

Every recruiter loves to talk about the placement. The moment the offer’s accepted, the contract’s signed, and everyone shakes hands. It’s the natural end of the story.

For the business doing the hiring, that moment isn’t the finish line. It’s the start.

We’re proud of our track record. The vast majority of the people we place go on to thrive in their roles, and that success rate is something we work hard to protect. We also pay close attention to a wider truth about our industry, though. Across recruitment as a whole, plenty of good hires quietly don’t work out, and it’s rarely because the wrong person was chosen. What lets a hire down is usually what happens, or doesn’t happen, in the first few weeks after they start.

We didn’t want to leave any of that to chance. This piece is about what happens after the hire, and why we’ve built it into the way we work.

The hire is the easy part

Finding an exceptional EA, PA or Chief of Staff is hard, and getting it right is what we’re known for. Something becomes clear after a decade in this niche, though. Selection is rarely where things come unstuck. Onboarding is.

Think about what usually happens across our industry. A busy founder or executive finally hires the support they’ve needed for months. They’re relieved. They’re also flat out. The new person arrives, and instead of a proper handover, they get a laptop, a login, and a vague “just dive in.” Within weeks, both sides can quietly drift. The hire feels underused and unsure. The principal feels like they’re still doing everything themselves.

That is almost never a bad hire. It’s a good hire in a bad set-up.

Why good hires can still come unstuck

Two things quietly undermine more support hires than any skills gap ever will.

The principal has never been taught how to use an EA. It sounds obvious, yet most leaders have never had proper support before, or they’ve had it done badly. Delegation is a skill. Trusting someone with your calendar, your inbox and your reputation doesn’t come naturally. Without that, even a world-class EA gets used as a diary manager when they could be running half the operation.

Nobody owns the first 90 days. Once the hire starts, the manager is busy and the new person is often left to prove themselves with no map. That’s a lot of pressure with very little scaffolding, which is exactly when doubt can creep in on both sides.

Neither of these is the candidate’s fault. Neither is something a stronger shortlist would have fixed.

What we’ve built: an aftercare partnership

A strong success rate isn’t a reason to relax. We see it as a reason to push further. We’ve built extra support into the placement itself.

When you hire a business support role through us, you don’t just get the right person. You get a free partnership session designed to set that person up to genuinely succeed. We’ve partnered with eavolve, our dedicated EA and business support training and development specialists, and their team works directly with you, the hiring principal, to make the first weeks count.

It’s a simple idea with a big effect. Rather than hoping the hire beds in, we actively help it happen. How to hand over well. How to build trust quickly. How to get the very best from someone whose whole job is to make you more effective. There’s development support for the hire themselves too, so they grow into the role rather than just settling into it.

We think that’s the difference between placing someone and making sure it works.

What this looks like for your business

The point of all this isn’t to be nice. It’s to protect your investment and your time.

A hire that’s set up properly is productive in weeks, not months. They stay, because people don’t leave roles where they feel valued and supported. They leave the ones where they were dropped in and left to sink. You get back the thing you hired them for in the first place: your own time, freed up for the work only you can do.

Every hire carries some risk. Everything we do after the placement is about taking as much of that risk off the table as we can.

This is what “more than a recruiter” actually means

Plenty of agencies say they’re different. Fewer can tell you how.

For us, the difference is simple. We don’t think our job ends when the offer’s accepted. We think that’s roughly the halfway point. A great placement and a great outcome are not the same thing, and we’ve chosen to hold ourselves accountable for the second one, not just the first.

That’s the standard we hold ourselves to, and it’s a big part of why our clients come back. Quietly, we think it’s what boutique recruitment should have been doing all along.

About the author

Matt Gregson is Managing Director of Lily Shippen, the specialist EA, PA and Chief of Staff recruitment agency, and the creator of its aftercare partnership programme. He writes on hiring, onboarding and getting the very best from exceptional business support talent.