You’ve hired a Virtual Executive Assistant, congratulations—you’ve already made one of the smartest decisions a busy leader can make. But hiring an assistant is only the first step. The real magic happens in how you work with them.

And in a remote setup, that takes extra effort. Not extra work—extra intention.

Because here’s what I know from experience: when communication is low, confusion is high. And when you’re not in the same office, there’s no casual catch-up in the hallway or overheard conversation to fill in the blanks. You either make communication a priority or you create chaos by default.

When I supported Simon Sinek, we traveled constantly—200+ days a year together. But when we weren’t on the road, we worked remotely. There was no office to walk into, no desk nearby to pop over to with a question. We had to be deliberate about how we stayed aligned when we were apart.

After a few iterations, we landed on a simple but powerful daily habit: ten minutes. Every morning. No matter where we were. It was a standing call, first thing in the day, and it was non-negotiable.

That ten-minute check-in aligned our priorities, cleared up questions, surfaced roadblocks, and helped us both hit the ground running. No guessing. No surprises. Just clarity.

This is what I recommend for every leader working with a VEA. Not necessarily that exact structure—but that same level of intentionality.

Here are five key ways to bring that mindset to your assistant partnership:

1. Book the Daily (or Near-Daily) Check-In

Five minutes can change everything. A quick daily sync—voice or video—is often the difference between proactive support and reactive chaos. Put it on the calendar and treat it like you would a client call: essential, not optional.

You and your assistant may not be in the same city, state, or even country. Time zones can make scheduling a challenge—but it’s worth the effort. If hopping on a live call isn’t realistic some days, record a quick video message on your phone and send it via text or Slack. Use apps like Voxer. Let them hear your voice, tone, and emphasis. It communicates far more than bullet points ever will.

2. Be Precise, Not Polite

Your assistant can’t act on vague direction. “I need help with scheduling” is too broad. “Move all Thursday meetings except the investor call to next week and send confirmations by EOD” is actionable.

Clarity is kind. Vagueness just leads to delays. When in doubt, the classic “who, what, when, where” framework works beautifully. Name the players. Name the task. Set the timeline. Define success.

3. Share the Why, Not Just the What

Great assistants aren’t just task rabbits. They’re strategic partners. Give them context, not just instructions. When they know why something matters, they can prioritize, problem-solve, and anticipate your needs—often before you even voice them.

For example, instead of saying, “Cancel this meeting,” say, “Cancel this meeting—I need that time to prep for an important investor call, and I want to be fresh and focused.” That tiny bit of context might prompt your assistant to proactively rearrange your whole afternoon to protect your energy, not just your calendar.

4. Give Feedback in Real Time

Too many leaders hold back feedback—either because they’re too busy or they don’t want to seem critical. But feedback is a gift. Tell your assistant what’s working, what isn’t, and what would make your life easier. The more they know, the better they support you.

And remember: words by themselves are not mean or critical. Humans delivering them can be. If your motive is pure—if you’re trying to help them grow and succeed—then the feedback will land the right way.

5. Recognize Their Impact

Recognition isn’t fluff—it’s fuel. A quick “thank you,” a compliment on a job well done, or a moment of acknowledgement can build loyalty and motivation that no bonus ever could. When someone’s entire job is to make you look good, don’t forget to return the favor.

And while giving constructive feedback is necessary (#4), positive feedback goes even further. Acknowledging what went well almost guarantees it’ll happen again. Compliment what you want repeated. Positive reinforcement is one of the fastest ways to shape the support you want.

Working with a remote assistant doesn’t have to feel distant. In fact, some of the most powerful partnerships I’ve seen were built entirely over Zoom and Phone. The difference? Leaders who showed up with clarity, structure, and respect.

If you bring that to the table, your VEA will meet you there—and then some.

Because at the end of the day, you didn’t hire them to lighten your load for a week. You hired them to become a strategic advantage. And that starts with how you show up.