What it really takes to make executive support work.
Knowing when to bring in executive support is not always straightforward. For many solopreneurs, small business owners, founders, and senior executives, it can feel like a difficult step to take.
The diary is unmanageable. The inbox refills faster than it empties. Strategic thinking gets squeezed into whatever energy is left at the end of the day.
But in our experience, the leaders who struggle to get value from executive support are rarely dealing with a capability problem. They are dealing with a readiness problem.
Hiring an EA changes very little on its own. What changes things is being willing to work differently. And that is not always as straightforward as it sounds, particularly for founders and senior leaders who have built their business by staying close to everything.
These are the things that make executive support work. If they feel out of reach right now, it is worth understanding why before making the hire.
- Be willing to brief properly, every time
An EA can only work with the information they are given.
When a task comes back not quite right, the instinct is often to take it back and do it yourself. In most cases, that is a briefing problem rather than a capability problem.
Briefing well means sharing the full picture. What does a good outcome look like? What tone is needed? Which decisions can your EA make independently, and which ones need to come back to you?
This takes time at the start. But it pays off faster than most people expect. A well-briefed EA becomes faster, more accurate, and increasingly autonomous. Over time, they begin to anticipate what is needed before you have asked.
If briefing feels like more effort than doing it yourself, the mindset shift has not happened yet.
2. Hand over your diary and mean it
This is where most leaders struggle most.
Diary management sounds simple. In practice, letting go of it requires genuine trust. It means allowing your EA to decide what gets scheduled, what gets declined, and how your time is structured and protected.
Many leaders agree to this in principle, then quietly continue managing their own calendar alongside their EA. Decisions get overridden. Meetings get added back in. The EA is left working around a moving target.
The value of handing over your diary is not just the time saved on admin. It is having someone protect your time more consistently than you would protect it yourself, so that strategic thinking is not always the thing that gets sacrificed.
That only works if you genuinely let them.
3. Share context, not just tasks
Surface-level delegation produces surface-level results.
The leaders who get the most from executive support are the ones who bring their EA into the picture. They share context on client relationships, explain the background behind a decision, and give their EA enough understanding of the business to act with confidence.
An EA who understands your priorities and how you think can do far more than manage a task list. They can draft communications that sound like you, flag issues before they become problems, and represent you well in situations where you are not present.
That level of support is not possible without trust. And trust must be built intentionally, not just assumed.
4. Give the relationship time to develop
Every working relationship takes time to find its rhythm.
Think of it like going to the gym or picking up a new skill. You do not walk in on day one and perform at your best. It takes commitment, repetition, and time before the results start to show.
Executive support works the same way. In the early weeks, an EA is learning how you think, how you communicate, and what matters most to you. The more context you share and the more consistently you delegate, the faster that understanding develops.
Leaders who step back in at the first sign of things not being quite right rarely give the relationship a chance to reach its potential. The value of great executive support builds over time. The leaders who experience it most are the ones who invest in the early stages.
Final thoughts
Executive support can be one of the most valuable investments a growing business makes. But the return depends as much on the leader as it does on the EA.
The right foundations make all the difference. Clear briefing, delegation, and the willingness to let someone in.
When those are in place, executive support moves quickly from task support to trusted partnership.
If you are not sure whether you are ready, that is a useful question to sit with. The answer usually points to something worth addressing, regardless of whether you hire an EA or not.