What it Takes to Serve a CEO

The role of Chief of Staff is pretty unique (and I mean the kind who work with executives, not the KPI/OKR type). I knew nothing about the role going into it, but I never let that stop me before. Now, a few years later, I know a bunch.

Why Does a CEO Hire a Chief of Staff?

I got a call that basically said, "Hey, I'm going to grow out my executive team and the business and I could use your perspective and help." I think the challenge with a CEO is that every executive on their team is tasked with making their area of the business thrive. No one has a "floating" role, meaning one that works "on" the business a bit more than "in," though some companies use their COO this way.

On the one hand, I work as a sounding board and give advice to the executives. I help with our quarterly board meetings. And in my case, I also do a lot to be aware of the pulse of the company. It's hard for a CEO to be everywhere, especially with a global organization of mostly remote people, so I am the "first call" when something's not quite right or someone wants a bit of advice.

A CEO uses a Chief of Staff as a kind of "Hamburger Helper," stretching out their capabilities by being able to take meetings they can't and work with the rest of the executive team to advance their initiatives. I'm able to have more 1:1 sessions than the CEO, because my only role is to make this all work better.

What Does a CEO Need that a Chief of Staff Can Do?

I think this is unique to the CoS. For instance, I have a lot of executive communication and storytelling skills that I apply. I have coaching skills and make a decent trusted advisor. Other people might be far more detail oriented (I'm absolutely not). But even that item, detail, I have an ability to play out what kinds of details will need covering. (I just stink at covering them myself.)

A CEO needs an augment and a mirror and an extender. Think about any CEO's day. It's often a battle between all the decisions that need making, each of which requires absorbing information, and all the other larger challenges, like thinking through larger strategic goals. I'm lucky because my CEO opted to put highly capable leaders on his executive leadership team and thus, I mostly conduct the orchestra. They know the music. They very rarely need CEO input to make great decisions. And I get the opportunity to help them think through some of their decisions.

It's Not About Me

Coming from running my own small business, especially one where I was the "face" and the talent and the person on stages, there was surely a little bit of adjustment. But I've always very much appreciated the concept of "servant leadership," and this is the ultimate form of that. I get to work with people at every level of the organization, and I get to help really smart people make their best decisions in service of our strategy.

I work with very smart people and serve a world changing CEO. What's not to love?

One of the parts of my job that I love most is that, though. That it's not about me. It's about being able to observe, and consider, and look from different angles at what's happening, and offer advice. It's like I run overwatch for a highly qualified team. I get to be another set of eyes on problems. Plus, you can deploy me when necessary, to pick up things that fall. I've always got capacity, because I'm not meant to run at 100%.

A CEO Benefits from Guidance

One challenge a lot of CEOs face is that it's hard to get useful input and guidance. My CEO can't turn to me and ask me what it'll take to get to $1 billion in ARR. We have a smart CFO and President for that. But he can ask me to work through other angles we might have missed. All the other big goals we plan to tackle are ones others have done. Not usually right around us, but in the larger world, there's always someone to meet with and learn about a new turn in the road.

Scenario planning is a lot of what a CEO can't spend a ton of time on, but I can. Again, I'm hamburger helper. Though in the case of my CEO, he does a lot of his own thinking, as well. Heck, it's his fault I had to start journaling again. He can pull up mountains of information, detail by detail, from any point in time over the last several years. I wouldn't have a fighting chance keeping up, if I didn't try to do even a little bit of that.

It's a Great Learning Experience

Speaking greedily about my own "career," such as it is, my role as Chief of Staff puts me at eye level with a lot of big and intricate and complicated and rewarding experiences that I can translate into more and more growth. I know that over the last few years, I've built up a lot of experience with navigating complex decisions, enhancing quality performance, providing clarity and strategic considerations.

All of that, I feel, translates to any kind of role, and I know it will be useful in executive coaching capabilities. I'm learning so much. I love that I have even more to learn. What's not to love about serving a CEO when that's the outcome, eh?

I guess this is a selfish post more than an "insights" one. But who knows? Maybe you've thought about doing the Chief of Staff role, and maybe this gives you some perspective. Or maybe you're contemplating hiring one, and at least you can think through what it might bring to your organization to have those capabilities.

Who knows? I was just musing.

Happy 2025!

Chris...