Lessons for Leaders Hiring Their First Assistant

You’ve built something amazing. You’re growing, busy, and successful enough that you can’t do it all anymore. Congratulations! You’ve hit the point where you need help. And not just any help — an Assistant.

If you’ve never had one before, you’re what I call a “Freshman Executive”. You’re stepping into a new kind of partnership, one that will change how you work, how you think, and how you lead. But you’ve never done this before, and you’re not entirely sure what to do or where to start.

Here’s the truth: hiring your first EA isn’t about just adding another pair of hands. It’s about expanding your capacity, redefining what your time is worth, and learning how to delegate to someone who gets giddy over making spreadsheets.

It’s not as simple as “finding someone organized.”

Having coached and recruited dozens of executive–assistant teams, I can tell you the first-time experience can be magical or miserable, and most of that depends on how you approach it.

So, if you’re a Freshman Executive, here are a few things you should know before you start the search.

The Best First Hire Is Part Assistant, Part Teacher

The biggest mistake new executives make is assuming they can hire a top-notch EA, plug them in like an office lamp, and they’ll just “turn on.” It doesn’t work like that. If you’ve never had an assistant before, you’re not just learning how to delegate, you’re learning how to be delegated to.

That means your first assistant can’t just be skilled at supporting, they need to teach you how to actually use that support. They’ll have to show you how to share information, how to give context, how to stop double-checking what they’ve already done, and how to actually let go.

It takes patience on both sides, but especially theirs.

So when you’re interviewing, look for someone who can toggle between getting things done and coaching you through the process. You want someone who knows how to both do and explain.

Ask about times they’ve worked with executives who’d never had an assistant before. Ask what worked, what didn’t, and how they helped their executive learn to trust them. You want to hear things like “I coached him through…” or “I built systems so she could see progress in real time.” That’s a sign you’ve found your EA-slash-teacher.

Values-Alignment Is a Non-Negotiable

Your assistant will be closer to your life than almost anyone else. They’ll see your inbox, your calendar, your credit card statements, your travel quirks, and your bad moods after a fight with your partner. If your values don’t align, or you simply don’t like them as a person, it’s not going to work.

This is someone you’ll talk to constantly. They’ll be in your headspace, anticipating what you need before you do. If you don’t actually want to talk to them, or if they drain your energy instead of giving you peace of mind, it’s going to crumble fast.

My rule of thumb has always been simple: if you can’t picture calling this person at the end of a stressful day and feeling relieved afterward, they’re not your person.

Beyond likeability, you need shared values. Integrity. Honesty. A sense of calm when things go sideways. A mutual belief that excellence matters. These things don’t show up in a job description, but they will define your working relationship.

And, some real talk: this person will, at times, be your coach. They’ll teach you better systems, remind you to slow down, and occasionally tell you that your way isn’t the best way. If you can’t take guidance from someone you employ, this won’t work. You’re not just hiring an assistant. You’re hiring a truth-teller who wants you to win.

Your Systems Will Evolve. That’s a Good Thing.

One of the hardest parts of hiring your first assistant is letting go of “how you’ve always done it.”

You’ve always managed your own calendar. You’ve always booked your own travel. You’ve always answered your own emails. And for the most part, it’s worked. But “working” and “working efficiently” are not the same thing.

Your EA’s job is to take what you do well and make it smoother, faster, and more consistent. That’s not a criticism of you, it’s a benefit of having someone who lives and breathes operational flow.

At first, it will feel foreign. You’ll wonder why your assistant schedules meetings differently or organizes your inbox in that way. You might even think they’re overcomplicating things. But here’s what’s actually happening: they’re building systems that make your success repeatable.

Be open to their methods. Let them show you a smarter way. They’ll spot inefficiencies you don’t even notice because you’ve been running on adrenaline and instinct. Trust the process. The goal isn’t to make you less involved, it’s to make your involvement more intentional.

Get Comfortable Being Uncomfortable

Nobody tells you that hiring an assistant is basically professional vulnerability on a fast timeline.

You’ll be sharing things that might feel too personal at first—passwords, credit card details, your spouse’s birthday, your gym schedule, your kid’s school calendar, the hotel chain you prefer, even the reason you avoid window seats on flights.

It’s a lot. But that’s how partnership works! The more your assistant knows, the better they can protect your time, your reputation, and your sanity.

You might also have to reveal habits you’re not proud of. Maybe you’re terrible at follow-up. Maybe you procrastinate on big decisions. Maybe you can’t stand small talk and need your EA to buffer introductions. Whatever it is, owning your quirks isn’t weakness, it’s efficiency. When your assistant knows how you really operate, they can build guardrails around it.

And here’s the good news: the vulnerability doesn’t last forever. Once the trust is built, you’ll realize how liberating it feels to not carry it all. 

It might take a few months to find that rhythm. There will be awkwardness and missed cues. But once it clicks, you’ll look back and wonder how you ever survived without this level of support.

Don’t Wait for Perfect Conditions

You don’t have to have it all figured out before hiring your first assistant. You just need to be ready to evolve.

Many executives tell me they’ll hire an EA “once things calm down,” or “once they figure out what the assistant should do.” 

Spoiler: things never calm down and you don’t know what they do.

What matters most is your willingness to communicate, to give feedback, and to stay open to a new way of operating. The rest you’ll learn together.

The truth is, hiring your first EA will stretch you in ways you don’t expect. It will expose your habits, your blind spots, and your leadership style. But it will also give you something you’ve probably been missing: space to breathe.

You’ll finally be able to focus on growth instead of juggling a hundred small tasks. You’ll feel less reactive, more in control. You’ll start to remember what it feels like to think strategically instead of just trying to survive the day.

That’s the magic of a great assistant.

Need help finding your ideal first assistant?

I help overwhelmed executives hire and work well with their assistants. Learn more here.