Signs You’re Ready for an Executive Assistant

If you’re reading this blog post, I’m willing to bet you’re an MSP Owner, CEO, or another key stakeholder who sees themselves as the company’s visionary. 

You’ve got big ideas and long-term goals, but also a calendar full of tiny tasks that keep pulling you off track - often at the expense of fixing a broken MSP sales process that needs your attention.

You might be on the brink of burnout. or worse yet, you’re so far into it, you’re not even sure what not being burned out would feel like. 

Have no fear, the EAs of the world are here (to help). The good news is - you don’t have to do it all.

Take a second and think about how much of your day goes to:

• Arranging your calendar
• Replying to emails
• Lining up tasks for the day
• Trying to remember what projects have to get done this week

It's mentally taxing, right? Check your smart watch - did your heart rate just spike? 

Now, shift your focus. What are the things you want to be thinking about?

• Are you hitting your MRR goals?
• Is your ICP as dialed-in as it could be?
• What lead gen efforts are you excited to launch next?
• How do you build retention into your growth strategy?

Still challenging questions, but the kind that move the business forward.  And the kind you can focus on when someone else has the rest handled.

Hiring an Executive Assistant isn’t just about saving time. It’s about creating space to lead, coach, and invest in employing things like MSP sales training that actually moves the needle. There are things in the company that you are the best at. This is more about creating the mental space for the work only you can do.

When you delegate the scheduling, organizing, and inbox chaos, you free yourself up to focus on strategic decisions, growth planning, and team leadership.

The space you free up by offloading admin tasks lets you focus on things like improving clarity in your pitch - something your future clients will notice immediately.

Worried about the cost?
Ask yourself this:
What’s the cost of not addressing the high-impact work only you can do?

Because every hour you spend juggling admin tasks is an hour you're not building, leading, or scaling.

For many executives, knowing when and how to hire an EA can feel like a major stress point. But it doesn’t have to be complicated.

Start by digging into your existing network. Ask your team if they know someone they’d recommend - that’s how I was hired! A personal referral can immediately build trust and eliminate some of the unknowns.

Of course, there are also excellent EAs available on platforms like LinkedIn, Indeed, and other reputable hiring sites.

While it's great to have a full-time executive assistant, part-time is also an option.
If you’ve got the budget and a clear list of responsibilities, go for it. But if you're unsure of the workload or still trying to justify the investment, start small - even 5 hours a week is often enough to begin offloading the mental clutter.

It also gives you space to build trust and train and a manageable pace, which leads to the next point…

Let’s be honest: handing over access to your calendar, inbox, and other systems can feel uncomfortable or even risky. Finding someone who you can trust enough to run your day-to-day operations is daunting. But not trusting..  not providing them with the access and tools they need to make a difference can be a recipe for failure. That’s where many MSP sales leaders go wrong.

If you hire an executive assistant and then hesitate to give them the autonomy they need to actually help you—you’re wasting everyone's time, your own money, and a business opportunity.

Let me tell you a quick story;

When I was 8, I wanted to learn how to skateboard. I spent a year practicing every day on a $20 Walmart skateboard, and eventually a couple years later, landed a kickflip.
Time passed. Many years later, at 17, I decided to relearn it. But this time, I invested in a quality board. Better trucks, smoother wheels, the whole shebang.

You can probably guess what happened next. I nailed the kickflip in 3 months.

It wasn’t about talent or effort. It was the quality of the tool I was using.
 

That’s what an executive assistant is: the upgraded skateboard. 🛹
Yes, it’s an investment, but one that saves you frustration, time, and unnecessary bruises.

If you want an EA to help you go further, faster, you have to trust them enough to stand on the board.

Before you hire an executive assistant at your MSP, take time to get yourself clear on what you really need. This step is #1. Think of it like dating: you can’t assess compatibility until you understand yourself. The same thing goes for hiring. If you don’t know what tasks are dragging you do, where you need support the most, or how to explain what success looks like - there's no way to find the right fit.　

Start with a list:

• What do you wish you never had to do again?
• What decisions are you constantly bottlenecking?
• What would free you up to focus on strategy?

Clarity here makes everything else easier.

Next, be open to change. There’s nothing more frustrating for someone trying to help than meeting resistance at every turn. Yes, your preferences matter. But be honest: is your current process actually the best way? Or is it just what you've gotten used to?

If your EA suggests a new system or workflow and it feels strange - try it anyway. You might find it saves time, reduces friction, or just plain works better. And if not? You can always pivot. 

Trust isn’t just about handing off tasks. It’s about being willing to grow with the person helping you succeed to make this a real working partnership.

If you think hiring an executive assistant is in your future, here’s a few things to ask yourself first:

• Is now the right time to offload some of the tasks weighing me down?
• Can my team recommend someone they already trust?
• How many hours do I realistically need to start?
• What values or traits matter most in the person I’ll be working closely with?
• What’s holding me back from fully trusting someone to support me?
• What are my true needs, and how can someone help me meet them?
• Am I willing to be flexible and try a new way of working?

Your answers will shape the success of the hire far more than any job description ever could.

And just remember: the cost of missing your company goals is far higher than the cost of admitting you need help.

When you're ready to scale your impact, an Executive Assistant isn't a luxury - it's the upgraded skateboard that helps you clear obstacles and pull off the moves you've been dreaming about.