October 2026 Newsletter

Burning Questions from the C-Suite

From a Right Hand: How Do I Manage My Workload?

Let's acknowledge that workload is high for any executive, and especially for the Right Hand who is the trusted implementer of the ideas and assignments flowing from the CEO.

For many Right Hands, this is the first role where the volume of inputs is so high and so unfiltered. Requests come from every direction: the CEO, direct reports, peers, customers, email, messages, meetings, hallway conversations. Nobody's sifting and sorting that noise for you. In previous jobs, you probably had a manager who helped you prioritize and figure out what to ignore. At the Right Hand level, nobody prioritizes for you. Sure, your CEO will tell you that you’re too busy and you should delegate more or develop a leadership bench. But the CEO won’t actually show you how to do that. They’re expecting you to figure it out.

Here are three suggestions:

1. Listen to everything, but don’t act on everything.

My brother, Scott, once told me, "The To-Don't List makes more difference than The To-Do List,” and he’s right. Success in a Right Hand role is figuring out what to ignore. The noise is so high that the signal can get lost. (Here’s a good article on signal vs. noise if you’re not familiar with that concept.)

Effective time management for executives is sacrificing the myriad of pretty goods in order to get the one or two really greats done. You have to become awesome at making and communicating trade-offs. Pick one or two things to accomplish this week and put the rest in a parking lot to think about next week. You shouldn’t ignore anything your CEO tells you, but that’s not the same as doing everything your CEO says the minute they say it. Be a possibility thinker open to change, but don’t get blown about by every new idea. Your CEO wants you to listen and really hear what they say, but they also want you to make rational decisions about how to spend your time. You flopping all over the place doesn’t help anybody.

2. Organize your tasks into buckets.

Managing forty initiatives, if they're all equally important, forces you into an unsustainable and constant state of plate spinning. Take your enormous pile of things to do and organize them into three, four, or five key areas you're responsible for. Maybe by business initiative, functional responsibility, or major areas of your job description.

Then pick one important task from each bucket to accomplish this week. Suddenly you're not managing forty initiatives anymore, but instead managing four areas of responsibility, and you're moving each one forward.

At this level, busyness is often a focus problem, not a calendar problem. You can optimize your calendar, reduce meetings, and block off planning time. Those things are useful, but they won't solve the problem of working constantly and still feeling ineffective.

3. Don't expect your boss to set boundaries for you.

At this level, nobody's managing boundaries or pressure for you. You could run yourself into the ground and nobody will prevent it. Of course your CEO cares about you. They may tell you to rest or slow down, but they will still send you twenty more issues to take care of. There will never be a world where the CEO stops dropping observations and assignments on the Right Hand. In fact, if you ever see that happening, you may have a bigger relationship problem because—remember—you want to be the brain partner. It's one of the things you like best about the job. 

But you also need to take charge of your own schedule. Decide when to leave work, when to stop checking email, and how responsive you're going to be after hours. You can’t set your boundaries in a vacuum because your boss will want to weigh in. However, most of the time, when Right Hands actually have the conversation, they discover that their CEO’s expectations are more reasonable than the Right Hand’s expectations for themselves. Who is actually making you answer that email on a Friday night? Because it might not be your boss.

If you’re wondering how to start having these conversations with your Lead, check out Chapter 6: Tetherball and Astronauts in our book, Winning Together.

Famous Right Hands: Hiccup and Toothless, How to Train Your Dragon

One of my favorite things about Hiccup and Toothless in How to Train Your Dragon is that somewhere along the way, they stop being a Viking and his dragon and become brothers. Hiccup fixes Toothless’s tail so he can fly again, but he doesn’t just fix it and send him on his way. They learn to fly together, lead Berk together, rescue each other, get irritated by each other, and argue about what to do. And when one of them is in trouble, the other one shows up. That’s something we don’t talk about enough when we talk about a really good CEO/Right Hand relationship. Yes, you get capacity through another senior leader who can carry real responsibility and make the company better. But if you get the relationship right, you get something else too: you get a brother.

Now I don’t mean your Right Hand becomes your best friend, I mean there is a particular kind of closeness that develops when two people carry something important together for a long time. You know what the other person is trying to accomplish, where they’re strong, and where they need you. You can disagree, get mad, go do separate work, and still know which side you’re on. Hiccup and Toothless don’t lose their independence as their relationship gets stronger; they become more themselves because they trust the other one to be there. A good CEO/Right Hand relationship can become that kind of partnership. You start out looking for someone who can help you carry the company and if you’re fortunate—and you do the work to build the relationship—you may discover you got a brother too.

Links: 7 Leadership Lessons from Hiccup, Leadership Wisdom: 10 How To Train Your Dragon Tips

The Book

If you haven’t picked up your own copy yet or are looking for a holiday gift for an executive in your life, here’s the link to the print, audible, and Kindle versions of Winning Together: How CEOs and Right Hands Build a Relationship That Works. Please consider posting a review on Amazon or sharing the book with a friend who could benefit.

From Heather’s Quote Library

"It's remarkable how often the real problem is not what happened, but how it was communicated."

James Clear, Author of Atomic Habits

Can We Help?

Getting the Right Hand Right isn't something you have to do all by yourself.

Maybe you’re trying to figure out if you need a Right Hand or how to hire one. Maybe you are wanting to strengthen or assess existing leaders. Or perhaps you're preparing for transition and need a real succession path. All of that is easier–and more likely to work–with an expert to guide you.

If you’re looking for a partner in all things Right Hand, reply to this email or click here to schedule a conversation.