What Makes a Great Executive Assistant to a Founder?

Having recruited Executive Assistants for founders over the years, one thing I've learnt is that there really isn't a one-size-fits-all approach.

You can have two founders running equally successful businesses, both looking for an exceptional EA, but with completely different ideas of what that person should bring to the table.

I've worked with founders who want someone incredibly tech-savvy, who can introduce AI tools and automate processes wherever possible. I've also worked with founders who prefer a much more traditional approach, where documents are printed, instructions are dictated and established ways of working are very much respected.

Neither approach is right or wrong, but finding the right person for each is a very different recruitment exercise.

Understanding the person behind the role

When I take on a new EA search, one of the first things I want to understand is how the founder actually works.

Are they someone who likes to delegate and leave their EA to get on with things? Do they want someone who will challenge them and suggest different ways of working? Or do they prefer to be closely involved in the day-to-day and have someone who will follow their lead?

It's also important to understand the pace of the business, the founder's personality and what has or hasn't worked with previous assistants.

Quite often, it's these conversations that tell me far more about the type of candidate we need than the initial job description.

Two very different founders

A good example of this was a recent search I worked on for the founder of an AI start-up.

Understandably, technology was a huge part of how he operated, and he wanted an EA who was just as enthusiastic about it. He wasn't simply looking for someone to manage his diary and inbox. He wanted someone who would actively look at ways to make things more efficient, whether that meant introducing new systems, automating tasks or finding better ways of managing his workload.

For this particular role, curiosity and a genuine interest in technology were just as important as previous EA experience. Someone could have had a fantastic CV and years of experience supporting senior executives, but if they weren't interested in embracing new technology, it was unlikely to be the right fit.

At the other end of the spectrum, I've worked with a founder who had a much more traditional style.

He liked to dictate correspondence, have documents printed and work in a very particular way. He wasn't looking for someone to come in and overhaul his systems or suggest a new app for everything. He wanted an experienced, organised EA who would quickly understand his preferences and ensure everything ran smoothly.

And there is absolutely nothing wrong with that.

The point is that both founders needed excellent support, but what made someone excellent in one role wouldn't necessarily make them right for the other.

What I look for in a founder's EA

Of course, there are certain qualities that I would expect from any strong Executive Assistant.

Good judgement is essential, particularly when supporting someone whose time is constantly in demand. Knowing what needs their attention, what can wait and what can be handled independently makes an enormous difference.

Initiative is equally important. A good EA shouldn't need to be told what to do at every turn, although how much autonomy they have will naturally depend on the founder.

Discretion, adaptability and the confidence to deal with people at all levels are also things I look for.

But perhaps one of the most important elements, and often the hardest to assess on paper, is personality fit.

An EA can have an outstanding background, excellent references and all the right experience, but if the chemistry isn't there, the relationship is unlikely to work.

This is particularly true when supporting a founder, where the working relationship is often very close and can involve a considerable amount of trust.

Why the CV is only part of the picture

I always say that a CV is a starting point, not the whole story.

It tells me where someone has worked, who they've supported and what their responsibilities have been, but it doesn't necessarily tell me how they approach their work.

When interviewing candidates, I want to understand how they think, how they manage difficult situations and what sort of environment brings out the best in them.

Some EAs absolutely thrive in fast-paced, entrepreneurial businesses where no two days are the same. Others prefer a more structured environment with established processes and clearly defined responsibilities.

Neither is better than the other, but putting someone in the wrong environment is rarely going to end well, however impressive their experience might be.

It's also important to consider what the candidate wants. Recruitment should never be just about finding someone who ticks the client's boxes. The opportunity needs to be right for the EA too.

What difference does a great EA make?

For me, the real value of a great Executive Assistant is the amount of time and headspace they give back to the person they're supporting.

A founder's attention is often being pulled in several directions at once, and having someone they can genuinely rely on makes a huge difference.

That might mean introducing technology that saves hours of administration each week, managing an increasingly complicated diary or simply knowing exactly how the founder likes things done without needing to be reminded.

It's not always about doing things differently or being the most proactive person in the room. Sometimes it's about understanding when to take the initiative and when to follow someone's preferred way of working.

The best EAs tend to get that balance right.

Finding the right fit

At Leaman Consulting, I've always believed that successful recruitment comes down to really understanding both sides.

When recruiting for a founder, I want to get to know how they work, what they expect and what sort of personality they're going to enjoy having alongside them every day.

From there, it's about identifying candidates who not only have the right experience but are genuinely suited to that particular individual and business.

Because ultimately, the best EA isn't necessarily the one with the most impressive CV. It's the one who makes the founder's working life easier, and who enjoys doing it.

If you're a founder considering hiring an Executive Assistant, or perhaps wondering whether you're getting the right level of support from your current setup, I'd be delighted to have a confidential conversation.