You hired an Assistant. Now what?
You finally did it—you hired an assistant. 🎉
You imagined that this would be the game-changer. The thing that would finally clear your plate so you could focus on the big picture.
But here’s the reality: If you don’t set this partnership up for success, you’re going to find yourself in the same cycle of overwhelm—except now you’ll also be frustrated that you’re paying someone and still drowning in work.
The problem isn’t the hire. The problem is what happens after the hire.
Most executive-assistant partnerships fail, not because of bad assistants, but because of bad onboarding.
Executives bring in an Assistant, assume they’ll “figure it out,” and then wonder why things aren’t clicking.
Let me save you months (or even years) of frustration:
A great Assistant isn’t just someone who knows how to manage a calendar or book travel. A great assistant is someone who knows how to manage you.
But that doesn’t happen overnight. It takes intention, structure, and communication.
So, let’s fix this. Here’s how to make sure the first 30 days with your assistant set you both up for long-term success.
The 5 Non-Negotiables for Your First Month with an Assistant
1. Make time to get time.
Executives who tell me they “don’t have time” to onboard an assistant are the same ones who come back months later saying, “It’s just easier to do everything myself.”
If you can’t find 8 hours in one month to build a partnership that could save you hundreds of hours later, ask yourself: Do you even need an assistant?
Action Steps:
Commit to two 1-hour meetings per week for the first month.
Use these meetings to set expectations, align on goals, answer questions, and clarify priorities.
2. Communicate like it’s your job. (Because it is.)
Your assistant cannot read your mind. If you don’t communicate clearly—your expectations, priorities, preferences, and quirks—they will never be able to fully support you. Remember: Your assistant doesn’t know what you don’t tell them.
And before you say, “I’m just not a talkative person,” let me stop you right there:
Being a leader means stepping out of your comfort zone when it matters. This is one of those times.
Action Steps:
Be upfront about your work style, decision-making process, and communication preferences.
Share personal details—your values, work style, hobbies, passions, pet peeves, non-negotiables, and personal preferences. It all matters.
3. Define “success” in exact terms
A moving target is impossible to hit, so ensure your instructions are actionable and easy to follow. If you don’t define success clearly, your assistant is left guessing—and you’ll always feel like they’re missing the mark.
Action Steps:
Set expectations for communication: Phone, email, Slack? What’s urgent vs. what can wait?
Define how and when decisions should be made, and how much authority your assistant has to make them.
4. Treat this like a real partnership.
Hiring an assistant isn’t like hiring any other employee. This isn’t a transactional role—this is a relationship.
Your assistant isn’t just there to complete tasks. They are there to help you think, plan, anticipate, and execute. That only happens if you treat them like a trusted partner.
Action Steps:
Don’t just tell them what to do—give them insight into why it matters.
Loop them in on big-picture goals so they can actively contribute to your overall success.
5. Build a feedback loop immediately
If you’re waiting six months to give your assistant feedback, you’re waiting too long. The first month is the time to course-correct, fine-tune, and refine expectations.
Frequent feedback now will save countless hours later spent wondering why things aren’t working.
Action Steps:
Schedule weekly check-ins during the first month to review what’s working and what’s not.
Ask your assistant: “What do you need from me to be successful?”
Final Thought: Your Assistant’s Success = Your Success
The executives who get the most out of their assistants are the ones who invest in the relationship from day one.
A great assistant can be the single most valuable hire you ever make. But only if you give them the structure and clarity they need to thrive.
Set the foundation right, and this partnership will transform the way you work.
Want the full roadmap?
I put together a free guide that walks you step-by-step through how to get your assistant up to speed the right way in the first 30 days.
Because hiring an assistant should make your life easier—not harder.