Think back to when you first started supporting your executive. You probably spent a lot of time figuring each other out.

How do they like their calendar managed? When do they want to meet with you? What information do they need before a meeting? Which things should you handle and which should you escalate? How do they prefer to communicate?

Over time, you developed a rhythm. And that’s a good thing. Until it isn’t.

The challenge with a well-established executive partnership is that it can start running on autopilot. You keep doing things a certain way because that’s how you’ve always done them.

Meanwhile, your executive’s responsibilities have changed. Your role has changed. The organization has changed. New technology has been introduced. You’ve developed new skills. The volume and complexity of the work may have increased significantly. Yet the way you work together hasn’t changed much at all.

If that sounds familiar, it may be time for an executive partnership reset.

This doesn’t need to be a big, formal process. It can simply be a focused conversation about what’s working, what isn’t, and what needs to change.

Here are six areas to discuss.

1. What Has Changed?

Start by looking at what has changed since you established your current ways of working.

Has your executive taken on additional responsibilities?

Are they supporting a larger team? Serving on a board? Traveling more? Leading new initiatives? Working across additional locations or time zones?

What has changed for you?

Maybe you’ve completed training, earned a certification, become more involved in projects, started supporting additional executives, or developed skills you didn’t have when you first began working together.

And don’t forget the changes happening around both of you. New systems, new team members, reorganizations, new business priorities, and evolving technology can dramatically change how work gets done.

You can’t assume that a system designed for your roles two years ago is still the best system for your roles today.

2. What’s Working Well?

A reset doesn’t mean starting over. In fact, there are probably several things about your partnership that work extremely well. Identify them.

Maybe your weekly one-on-one keeps both of you aligned. Perhaps you’ve developed a fantastic process for meeting preparation. Your calendar system may run like clockwork. Or maybe you’ve learned exactly how much information your executive needs before making a decision. Those things are worth protecting.

Ask your executive, “What am I doing right now that is most helpful to you?”

You may be surprised by the answer. Sometimes the things we consider routine are the very things our executives value most.

3. Where Is There Friction?

Now look for the places where work repeatedly slows down, gets confusing, or creates frustration.

• Does your executive wait too long to approve routine items?
• Are you constantly chasing information before meetings?
• Do you send emails that never get answered?
• Are you having to ask the same questions over and over?
• Are calendar decisions getting kicked back and forth unnecessarily?
• Do you regularly find out about important projects or commitments after everyone else?

Recurring frustration is often a sign that the system needs attention. Instead of accepting, “That’s just how it is,” get curious. What’s actually causing the problem?

Maybe the communication method doesn’t work. Perhaps you don’t have enough decision-making authority. Maybe expectations were never clearly established. Or a process that worked when the executive had five direct reports doesn’t work now that they have twelve.

Identify the friction before you try to fix it.

4. What Are You Ready to Own Now?

This is an especially important question for experienced administrative professionals. Think about what you can do today that you couldn’t do when you first began supporting your executive.

Maybe you’re ready to take greater ownership of meeting preparation, project coordination, board support, communications, events, travel strategy, research, reporting, or team operations. Your executive may not recognize how much your capabilities have grown unless you tell them. This is also a good time to look at tasks your executive is still doing that you could potentially take over.

Don’t make this about getting more work dumped on your desk. The goal is to ensure work is being handled by the right person at the right level. If something doesn’t require your executive’s expertise, authority, or attention, ask whether it really needs to remain on their plate.

5. What Information Do You Each Need?

Many partnership problems are actually information problems. You don’t know something your executive assumes you know. Your executive doesn’t know something you assume you’ve communicated. Or both of you have the information, but it’s buried somewhere neither of you can easily find it.

Talk specifically about what information you each need to do your jobs well.

• What does your executive need from you before their day begins?
• What do you need to know about their priorities?
• How do they want decisions presented?
• What information do you need about upcoming projects, organizational changes, or commitments?
• When should something be communicated by email, chat, text, phone, or face-to-face?
• And what information should be captured somewhere so you aren’t relying on either person’s memory?

A few minutes spent clarifying these expectations can eliminate hours of frustration later for both of you.

6. What Should We Do Differently?

This is where the reset becomes useful. Don’t leave the conversation with a long list of vague intentions. Choose two or three things to change.

1. Maybe you start a 10-minute daily check-in.
2. Perhaps your executive gives you authority to decline certain meeting requests without asking.
3. You might create a standard format for presenting decisions that need their attention.
4. Maybe you take ownership of an entire process they have been partially managing.
5. Or you agree to review priorities together every Monday morning.

Keep it manageable. Test the new approach. Then adjust it as needed.

Initiate the Conversation

You don’t have to wait for something to go wrong before having this discussion. And you don’t need to announce, “We need to work on our relationship.”

Try something simple:

“We’ve both had a lot of changes in our roles over the past year, and I’d like to spend 30 minutes looking at how we’re working together. I want to make sure what I’m doing is still supporting you in the best way possible and see if there are things we should adjust.”

That’s not a complaint. It’s proactive partnership management.

The best executive partnerships aren’t static. They evolve as the people, responsibilities, priorities, and organization evolve. If your partnership has been running on autopilot for a while, that doesn’t mean something is wrong. It may simply mean it’s time to check the settings, make a few adjustments, and determine where you want to go next.