When Should a Founder Hire an Executive Assistant?

There is no magic revenue figure, number of employees or stage of growth that tells a Founder when it is time to hire an Executive Assistant.

The better question is:

What are you spending your time on that someone else could be doing?

For many Founders, hiring an EA can feel like something to do “later”, once the business is bigger, the team has grown or the diary becomes completely unmanageable.

In reality, waiting too long can be costly.

A good Executive Assistant doesn't just take administration off your plate. They can give you back time, create structure and allow you to focus on the parts of the business where you add the most value.

So, how do you know when the time is right?

Your diary is running your life.

If you are spending your day moving meetings around, responding to invitations, arranging travel and trying to work out where you are supposed to be next, something needs to change.

Your diary should support your priorities, not dictate them.

A good EA can take ownership of your calendar, understand what matters and protect time for the work that actually requires your attention.

You are doing things someone else could do.

This is probably the biggest sign.

If you are booking your own travel, organising meetings, chasing people for information, managing expenses, arranging restaurants or dealing with endless administration, ask yourself:

Do I really need to be doing this?

Your time as a Founder is expensive.

Every hour spent on tasks that could be delegated is an hour you aren't spending on strategy, clients, hiring, fundraising, product development or growing the business.

You are becoming the bottleneck.

As a business grows, more people want access to the Founder.
Meetings increase. Decisions increase. Messages increase.
Suddenly, everyone needs something from you.

An experienced EA can become a filter between you and the noise.

They can manage access, prioritise requests, keep people moving and make sure you are spending time where you are most needed.

Your business is growing quickly

Growth creates complexity.

What worked when you had five employees doesn't necessarily work when you have 30, 50 or 100.
Your diary becomes more complicated. Travel increases. You have more senior stakeholders. There are more decisions to make and more people competing for your attention.
This is often the point where an EA can make a significant difference.
And you don't necessarily need to wait until the business reaches a particular size.
If your own workload is already becoming unsustainable, that may be the more important indicator.

You are constantly travelling.

For many Founders, travel is one of the first areas where an exceptional EA can make a huge difference.
Flights, hotels, transfers, meeting schedules, time zones and last-minute changes can quickly become a job in themselves.
A strong EA can manage the logistics, anticipate problems and keep your schedule workable while you're on the move.
More importantly, they can ensure that travel doesn't completely take over your working week.

You are working longer hours just to keep up.

Working hard is part of being a Founder.

Working late every night because you're spending hours on administration isn't necessarily productive.
If you find yourself catching up on emails at midnight, booking travel at the weekend or spending evenings reorganising your diary, it may be time to delegate.
The goal isn't necessarily to work less.
It's to make sure the time you are working is being spent on the right things.

You are starting to need a right-hand.

There comes a point when you don't just need someone to manage your diary.
You need someone who understands how you work.
Someone who knows your priorities, remembers what you have forgotten, anticipates what is coming next and can tell you when something needs your attention.

That is when the role starts to move from traditional administrative support towards a genuine right-hand Executive Assistant.

The difference can be significant.
A good EA responds to requests.
An exceptional EA anticipates them.

You are spending too much time managing your own support

This sounds counterintuitive, but it happens.

A Founder hires an EA, but still manages every detail of how that person works.
They continue to make every diary decision, organise every trip and approve every small task.
The result is that the EA hasn't actually created much additional capacity.
If you are hiring at a senior level, you should be looking for someone who can take ownership.
They should reduce the number of decisions coming to you, not create more.

You need someone you can trust

Founders often have to deal with highly confidential information.
Commercial discussions, fundraising, acquisitions, recruitment, personal matters and sensitive relationships may all cross the EA's desk.
Trust and discretion are therefore essential.
You need to feel comfortable giving your EA access to information, your diary and your working life.
That relationship doesn't happen overnight, which is another reason not to wait until you are completely overwhelmed before starting the search.

But do you really need an EA?

Not every Founder does.
If your diary is manageable, your travel is limited and your administrative workload is under control, you may not need one yet.
A Team Assistant or shared support resource may be more appropriate.
The important thing is to match the level of support to the actual requirement.
You shouldn't hire a £80,000+ senior EA to solve a problem that could be managed effectively by a more junior support professional.
Equally, if you need someone to operate as your right hand, a junior hire is unlikely to deliver what you need.

So, when is the right time?

There isn't a single answer.

But if you recognise several of these signs, it is probably worth having the conversation:
* Your diary is becoming unmanageable
* You are spending too much time on administration
* You're travelling frequently
* More people are competing for your attention
* You have become a bottleneck
* You are working longer hours simply to keep up
* You are missing opportunities because you don't have enough time
* You need someone to take ownership rather than simply complete tasks
* You want a trusted right hand

Don't wait until you are completely overwhelmed.

The best time to hire an EA is often before you desperately need one.
That gives you time to find the right person, establish the relationship and allow them to build an understanding of how you work.

The right EA can change how a Founder works

A great Executive Assistant doesn't simply make your life easier.
They give you back something far more valuable: your time.
They allow you to focus on the decisions, relationships and opportunities that only you can handle.
And as your business grows, that can become one of the most valuable investments you make.

Looking to hire an Executive Assistant?

At Leaman Consulting, we specialise in recruiting Executive Assistants for Founders, CEOs and senior executives.
We take the time to understand how you work, where your time is being lost and what level of support will genuinely make a difference.
Whether you need an experienced Executive Assistant, a senior right-hand, or you're not quite sure what level of support you need yet, we can help you define the role and find the right person.

If your time has become your most valuable resource, it may be time to stop doing everything yourself.