It’s Time to Fire Your Chief Everything Officer

“I’m trying to do way too much.”

***

I remember the specific moment when I realized this. It was back in 2011, and I was the head of MetaLab, a design & dev firm. We were growing like crazy, doubling our revenue and staff every year.

On one pivotal day, I managed to secure a call with an exciting new prospect who seemed like a perfect fit. I glanced at the project spec, and hopped on a call with their point person, who also happened to be the company’s CTO. Now, I was used to pitching to other CEOs, and didn’t have much experience talking serious tech — but at the time, I felt that I was the only one who knew our sales pitch well enough to handle the important sales calls. I thought anyone else would screw it up.

Almost immediately, the tough questions started rolling in about our tech capabilities, and how we ran these types of projects. To be clear, I know as much about the brass tacks of building Rails apps as I do about astrophysics — I find it all very fascinating from an incredibly safe distance, but it’s certainly not something I’m qualified to discuss at any length.

For some reason, though, I thought I could talk my way through this call on instincts alone. I fumbled, and eventually, the call ended with a whimper. The damage had been done: we didn’t get a second chance with this client. It was embarrassing.

A few minutes later, a cruel realization tumbled into my brain: we had our own CTO, ready to rescue me from a situation just like that. I’d allowed my ego to get in the way of making smart decisions. I then recalled numerous occasions where I’d shot down suggestions that I hire a project manager, or an account manager, or that someone else should conduct interviews for important new hires.

I had spent too much time resisting passing the baton to somebody else, and couldn’t bring myself to let go of the trusted rituals that grew the company from the ground up.

Copyright Bill Watterson, 1993

The problem was that the precious authority I once had over a team of three was spiraling away from me as we grew steadily into the double digits, and I was still too proud to cede control and admit that maybe I wasn’t the best person for every job.

It wasn’t just pride, though: it was anxiety, too. Anxiety that maybe the baby I’d helped grow into a wise teenager might turn into something else entirely if I wasn’t at the helm, making all the important decisions.

I knew that everyone’s job might be easier if I took a step back, or focused on different things. It just took a series of colossal screw-ups like the one above to finally make me do it.

We’re all one in a billion… right?

We all like to think that we’re Steve Jobs during the John Sculley era at Apple: that our company, under anyone else’s unique vision, will completely crumble. Well, most of us aren’t Steve Jobs, and most of our companies aren’t Apple.

Believing that we’re the next Apple is exactly the type of delusion that causes 9 out of 10 startups to fail. We place impossibly high expectations on ourselves and our business, and ignore the reality that companies are not built by individuals, but by a complex group of people with drastically unique skills who rely on one another.

This false image of the all-knowing founder-CEO lives on in all of us, as documented in this Harvard Business Review piece describing the Harvard Business School’s New CEO Workshop:

Workshop participants told us again and again that they needed to make a conscious effort to resist the illusion of self-importance, omnipotence, and omniscience…. They have found it difficult and ego-bruising to accept gaps in their expertise and admit that the job is more physically and emotionally taxing than any others they have held.”

We put enormous pressures on ourselves to be the indefatigable superhero CEO, who dispenses ingenious wisdom on a whim and never gets anything wrong. Maybe it’s just my distinctly non-Jobsian ambition, but believing that you’re right all the time sounds exhausting and alienating.

More than that, though, placing this incredibly high expectation on yourself doesn’t seem to work out well: even if you’re one of the 10% of startups that actually succeed, Noam Wasserman points out that eventually 80% of founder-CEOs are forced to step down. And unlike Jobs, it’s almost a guarantee that none of those 80% are getting a second chance.

The paradox of entrepreneurial success

Wasserman has done extensive research on when and why CEOs are replaced, and he compiled his findings in the landmark study Founder-CEO Succession and the Paradox of Entrepreneurial Success. The titular paradox is that the faster a company grows — that is, if the CEO is really doing their job well — the more likely they are to be replaced. He put it this way:

The person who took that company from nothing to $5 million has done a daunting job, but that person, in the view of the VC, is very often not the person that will take them from $5 million to $100 million.”

When we think about people like Jobs, Bill Gates, Elon Musk, or Larry Ellison, we forget that they’re noteworthy because they are the overwhelming exception to this rule. They’re the magical, visionary founders and the successful CEOs, all rolled into one magic package. They’re equally capable of working out of a garage and a boardroom, and understand how to deliver something to the very first person as well as the hundred millionth.

Steve Jobs, minimalist (and magician?), 1982. -Photo: Flickr CC, culturalelite

For most of us, though, it’s incredibly important to recognize the moment where we feel things spiraling away from us — ideally before we’re on a disastrous call we shouldn’t have been on in the first place. It’s at this point that we can make the most significant additions to our team, and ensure that we’re future-proofing our companies. Ignoring these signs has the potential to be what quietly suffocates a company, even when the numbers are showing nothing but growth.

Stop acting, start directing

A good CEO — and a good leader in general — does not hold their company’s best practices as some magic personal gospel, written in a language that only he or she can understand. The best CEOs instead become educators in what makes the business work, and they do this through shifting their leadership style “from direct to indirect means — articulating a clear, easily understood strategy; institutionalizing rigorous structures and processes to guide, inform, and reward; and setting values and tone.”

When the CEO focuses their attention less on day-to-day work and more on the big picture of how their team gets work done, control becomes infinitely easier to cede.

Numerous CEOs I reached out to echoed how difficult it became to be responsible for every decision as their business grew, including Allen Walton from SpyGuy Security, whose experience mirrored my own:

I’d gotten to a point where I just couldn’t do everything myself. Over time, I started doing things that cost my business in big ways. Phone calls were getting missed, emails were going unread, and basic things I needed to do in order to grow my business were going undone. My business had stopped growing — and I was coasting.”

Many CEOs intelligently identify this tendency to coast as a trust issue, and explore ways to remove themselves from the team.

For Andrew Graff, the CEO of full-service agency A&G, this meant setting clear standards for the work people were doing to ensure that they were always aware of the right course of action. Graff explained:

We created a culture code that explains who we are on our best days, which in turn gives the team a great barometer check when making decisions.”

Allen Walton created a similar document for his first employee, which he called his SOP (standard operating procedure):

I told my employee that practically any question he had could be answered by the SOP. This started off with taking phone calls and responding to customer emails.”

Walton and Graff’s ‘best practices’ strategy matters immensely to not only their ability to interfere with their team less, but also to empower their team to make decisions completely on their own: the document acts as a kind of pre-approval from the CEO. Removing yourself from a decision entirely is meaningful. Paul B. Brown put it this way in Forbes: 

“When employees feel you are going to make the final decision anyway, they don’t always think through fully what they are doing. Once the decision is theirs, they tend to be not only more creative, but careful.”

Replace yourself with experts

Of course, there’s also the question of hiring those first few people to trust with your newly minted marching orders — the people who will allow you to step back and focus on growing your business.

Chris Maddox, the CEO of Seneca Systems, suggests that you incrementally fire yourself as roles become too time consuming, and allow them to completely own parts of your business: “Find someone you trust to own a specific function and trust them to own it. While it’s tempting to look for a generalist who you can offload any of your work to, that quickly ceases to scale.”

The thought of hiring a generalist is indeed tempting (it was certainly tempting to me), but hiring a jack-of-all-trades who requires training in numerous areas does not solve the riddle of the hurried CEO who cannot cede control.

Katie DeCicco, CEO of Celebration Saunas, points out that hiring proven experts won’t only improve certain aspects of your company, but will do so much faster and with much more finesse than you could do alone: “I recognized from the many jobs I’d had prior to starting my own company, how limited CEO’s were when they had to be the smartest person in the room. The minute I started my business, I gave control over to vetted experts.”

“You’re fired.” —me, to myself

At the end of the day, the best thing you can do for your business is identify what you do incredibly well, and make that your focus. For everything else, find talented & trustworthy lieutenants and be great at educating them on why your business has been successful. And more importantly, don’t be afraid of their new ideas: just because they’re not your initiatives doesn’t mean you’re not being a great CEO.

For me at MetaLab, I soul-searched and talked to almost everyone on the team before concluding that my strengths were in building relationships with clients and shaping projects. I made the decision that the moment we signed a contract with a new client (and my job was ‘done’), I’d hand off the project completely to a skilled, experienced project lead who could take the work through to completion.

As Chris Maddox suggested above, I “fired” myself from project management — and it felt great.

***

Are you a recovering Chief Everything Officer? Did you ever watch one in action? What advice would you give a leader who is taking on too much?

-Photo: early Egyptian juggler art. User: Oxymoron. [Public domain] via Wikimedia Commons