The Biggest Mistake CEOs Make When Hiring an Executive Assistant

When a CEO comes to me looking for an Executive Assistant, the conversation often starts with a list of responsibilities. Diary management, international travel, inbox management, meeting preparation, and so on.

All important, of course, but I always like to dig a little deeper.

In my experience, one of the biggest mistakes when hiring an EA is focusing too much on what needs doing and not enough on the person who will be doing it.

A good EA will keep things organised and running smoothly. A really excellent one will understand how you work, anticipate what is coming and know when to step in without being asked.

Finding that person requires a little more thought than simply putting together a job description.

What do you actually need?

No two CEOs work in quite the same way, and I've certainly found that the same applies to the EAs who support them.

Some executives are incredibly organised but simply don't have enough hours in the day. Others are brilliant at what they do but need someone to bring a bit of structure to an otherwise chaotic schedule.

One CEO might want an EA who takes complete ownership of their diary and acts as a gatekeeper. Another might prefer someone who works more collaboratively, keeping them informed and involved in day-to-day decisions.

Neither approach is right or wrong, but understanding the difference is essential.

It's something I spend quite a bit of time discussing with clients before we even begin a search. What has worked well with previous EAs? What hasn't? Where do they feel they need the most support?

Quite often, these conversations reveal far more about the role than the original job description.

Experience matters, but personality and judgement matter just as much

There is no shortage of candidates with impressive CVs. Many have supported CEOs, worked in well-known businesses and managed incredibly demanding schedules.

But having worked for a high-profile executive doesn't automatically make someone the right EA for another.

I'm much more interested in understanding how a candidate operates.

Are they comfortable making decisions independently? Can they remain calm when plans change at the last minute? Do they have the confidence to challenge something when they feel there's a better way of doing it?

And, perhaps most importantly, will their personality work alongside the person they're supporting?

An EA might have all the technical skills in the world, but if the working relationship isn't right, it's unlikely to be a successful long-term appointment.

I always encourage clients to think carefully about this, particularly when they're hiring someone who will be working so closely with them every day.

Don't underestimate the importance of trust

An Executive Assistant is often privy to an extraordinary amount of information, both professional and personal.

They may be involved in confidential business discussions, senior appointments, financial matters and sensitive personal arrangements. Discretion is an absolute given, but trust goes further than confidentiality.

A CEO needs to feel comfortable delegating, knowing that things will be handled properly without having to check every detail.

That confidence takes time to build, but you can usually get a good sense during the recruitment process of whether the foundations are there.

I also think it's important that an EA feels comfortable speaking up. The best working relationships aren't necessarily the ones where everyone agrees all the time.

Sometimes an EA needs to say, "I don't think that's the best use of your time," or suggest a different approach. Being able to do that professionally, and knowing when it's appropriate, is a real skill.

Look beyond the standard interview questions

One thing I always recommend is making interviews as relevant to the actual working environment as possible.

Of course, you want to understand someone's previous experience, but asking them to talk through their CV will only tell you so much.

I think it's far more useful to discuss situations they're likely to encounter in the role.

What would they do if two important meetings clashed? How would they handle a demanding stakeholder who insists on speaking to the CEO immediately? What happens when travel plans change at the last minute, and the CEO is unavailable?

There isn't always one correct answer. What matters is understanding their thought process, how they prioritise and whether they have the confidence and common sense to take ownership.

I also pay attention to the questions candidates ask. A thoughtful EA will want to understand the CEO's working style, expectations and priorities, rather than focusing solely on the responsibilities of the position.

A great EA should make your working life easier

Ultimately, hiring an Executive Assistant is about more than finding someone to take tasks off your hands.

The right person should make a noticeable difference to how your working day runs. They should know what needs your attention, what can be dealt with independently and how to make the best use of your time.

For some CEOs, that means having someone who brings order to an extremely busy working life. For others, it's about having a trusted sounding board who can anticipate problems before they arise.

And that's why I always come back to the importance of finding the right match.

You can teach someone a particular system or way of working, but good judgement, natural initiative and the ability to build a genuinely effective working relationship are much harder to find.

My advice to any CEO considering hiring an EA is to spend as much time thinking about the person you need as the tasks you want them to manage.

It makes a considerable difference to the success of the appointment.

Looking for an Executive Assistant?

At Leaman Consulting, I work closely with CEOs, founders and senior executives to understand their individual requirements and find Executive Assistants who are genuinely suited to the way they work.

Having the right experience is important, but so is finding someone with the judgement, personality and approach to become a trusted part of your working life.

If you're considering hiring an Executive Assistant, I'd be delighted to have a confidential conversation about your requirements.