What the f*ck do CEOs do?
At a high level: Make sure the company is more valuable at the end of the year. At a low level: Lots of coffee chats.
👋Hi, it’s Greg and Taylor. Welcome to our newsletter on how to make high-stakes professional and personal decisions in your 30s.
Read time: 10 minutes
I was lucky. I grew up in a business household, with a dad who eventually became CEO of the company he’d worked at his whole life, starting in the mailroom. I grew up listening to his stories at the dinner table, and it seemed like being CEO was the best gig you could get in business.
But even with my dad as an example, I didn’t really understand the job of a CEO until I was doing it. There was no CEO bootcamp – I learned everything on the job.
I’m 62 now, and after 6 early-stage CEO gigs, I think I’m a decent CEO. But with more training and less trial and error, I could have been a decent CEO a lot sooner – probably by 40.
Maybe you’re thinking you could be a CEO one day. Or maybe you’re just curious what the hell your CEO does all day (except Slack you at 11 PM and say “I need this ASAP for the board meeting”).
Here’s the explainer I wish I had in my 30s – my no-bullshit take on the job, and the skills needed to do it.
– Greg
The CEO’s mandate: Build a more valuable company
The CEO is measured by enterprise value. In other words, a good CEO’s company is more valuable at the end of the year vs. the start.
The board cares more about this than anything else … and the CEO reports to the board. Boards want value creation and only have one lever to get it – hire or fire a CEO to generate that value. Period. So if you’re good at generating enterprise value, you can do pretty much anything else you want, even if you’re a raging fraud or asshole (Adam Neumann, Elon Musk, etc.).
Everything in a great CEO’s day, month, and year ladders up to this mission – making the company more valuable in the future. But often, even if you do everything right, there is no value creation – recessions, competition, interest rates, and technology changes can beat down even the best CEOs.
What a CEO does all day (aka diagnosing, selling, and looking for leverage)
The myth of the CEO is well-defined. According to the myth, their week might include: swooping in to make genius last-minute changes to the product. Spinning stories on stage about the future. Raising more capital than the annual GDP of half of the countries in Europe. Ringing the bell at the IPO.
The reality is more like this:
Interviewing. This is particularly true in a CEO’s first 12-24 months, but it never really goes away. A good CEO is always interviewing, even if they’re not hiring. They’re interviewing for the future (if someone on the management team leaves or doesn’t work out). And they’re interviewing for other senior roles in the org – usually selling the best recruits on why they should join the organization.
Diagnosing problems. This is the CEO’s main role in leadership meetings, product reviews, pipeline calls, and 1:1s. Great CEOs get to the root of an issue and quickly size its risk (or not) to the business. It’s why you might get late night Slacks from your CEO asking “what’s going on with [X project]??” They’re not trying to annoy you – they’re diagnosing: digging into different parts of the business to understand what’s working and what could be working better.
Looking for leverage. Like we wrote about last week, great executives work high-low, meaning they’re making this month’s plan while doing work that won’t pay off for 1-2 years. Great CEOs spend lots of their time on the latter. I take 3-5 coffee chats per week. 90% of them won’t lead anywhere. But I’m looking for the other 10% – a future partner, a potential acquirer, or a new large client.
Selling the business/vision/product. To clients, to consumers, to employees, and to investors. Being CEO means developing and delivering your manifesto to the outside world. Pitching enterprise customers, preparing remarks for weekly all hands meetings, and writing monthly board updates. It’s all about consistency and repetition.
Crisis management. When shit hits the fan, you’re on the hook. In my 25 years as CEO, I’ve managed through probably 20 different crises, of varying degrees of severity. Some are inevitable in a career this long (especially among startups) – layoffs or unhappy clients. Some are more unusual – a security breach or a terms of service violation. They all require the CEO to drop everything and focus.
A typical week in the life of a CEO
Your CEO’s calendar is probably private. So here’s what mine looks like in a typical week.
Week of November 27, 2023
I try to reserve 20% of my week for focus sprints – writing, editing, and thinking. But this was a heavier meeting week.
Interviewing: 5-10% of my time
Call with a friend (Calvin) who could potentially help us with AI product management (a role we’re not yet actively hiring for)
Diagnosing: 20% of my time
Internal meetings (leadership meetings, weekly curriculum review)
1:1s
Looking for leverage: 30% of my time
Partnership calls (e.g. UNC Charlotte)
Peer company calls
Pitching the business: 40% of my time
Content creation (e.g. AI Primer Sync, Newsletter Drafting Session)
Webinar creation & delivery (e.g. MEA & Section, AI Session – both free workshops I did for companies/associations to promote Section)
Client engagements (e.g. Axel Springer AI workshop)
Student office hours/1:1s
Crisis management: 0% of my time
This is a typical week, but it probably gets blown up 4 times a quarter. In these scenarios, 50% of the CEOs time gets redirected to an issue that can last anywhere from a week to 1-2 months. Everything goes to shit, and you do the rest of your job on the weekend.
The most common reasons this happens:
Internal or external crises (e.g., major unhappy customer, failed product launch)
Layoffs
Fundraising
Departure of a key executive
Personal issues (e.g., illness, family emergency, etc.)
Like any job, being CEO is low-stress on some days and a nightmare on others. Weeks with layoffs, phishing schemes, and other crises take years off my life. Average weeks are stressful but manageable, and in good weeks, the job is clearly worth it.
Five skills a good CEO has
I recently asked Larry Bohn (partner at General Catalyst and a board member at Section) what he looks for in a CEO. He’s been a venture capitalist for 25 years, and worked with hundreds of CEOs. He listed three traits: brutally realistic, resilient, and has gumption.
If you want to be a CEO, there are five skills you should be honing every day.
1. Storytelling – CEOs are salesperson #1 for the business. Get good at selling – to customers, clients, your manager, and your team. The most common source of stress I see in new CEOs is someone who’s a great builder or operator, but a terrible storyteller. They’re usually miserable, because half the CEO job is selling.
2. Getting to V1 – CEOs set the DNA of a company, especially in startups. You set the strategy and write the operating principles. You make the first hires to set the talent bar and the first fires to maintain it. You drive the team to build new products, test new marketing channels, and explore new markets. Get good at building and shipping V1s fast.
3. Business analysis – CFOs own the business model, but CEOs own the implications of it. Develop your own financial fluency, and get good at pulling insights out of numbers – margins, CAC, LTV, runway. CEOs are fluent here – learn these metrics and get good at understanding what they mean for the health of your business.
4. High-low – We dedicated a whole post to this last week, but great CEOs move between these two modes constantly. You can’t find leverage if you’re not working high, and you can’t diagnose problems or pitch the business if you can’t work low.
5. Firefighting – When needed, CEOs lead the team in a crisis. You can practice this skill – when things go wrong in your company or team, be the one who steps up. If your org faces layoffs, a product recall, or a bad few quarters, observe what the CEO and leadership team do well (and don’t do well). Look for low-stakes opportunities to flex this muscle yourself – it will come in handy when you’re CEO.
My advice
Being a CEO is the one job at a company where you are graded every day, by everyone. What other job has the equivalent of a Yelp rating? It’s the first requirement of being a CEO: being comfortable with that level of accountability and transparency into your performance.
I have an 83% approval rating on Glassdoor. Not awful, but not great. That approval rating is made up of a thousand things. The layoffs I’ve greenlit. The big bets that didn’t work out. The All Hands meetings where I said something stupid. Lots of good stuff in there too, but my point is – you need a very thick skin.
If you have that, start training now on the other skills you need. Start to take more risk at work, start to speak up and out, volunteer to lead the high-risk and high-profile projects.
I want you to put yourself in situations where you can test your abilities to handle the CEO job. Find out if you have the resilience, risk tolerance, business chops, storytelling, and firefighting capabilities.
If you are a CEO already, then get some help and support to do it better. Don’t do what I did in my 30s and 40s (go it alone or assume you are supposed to know how to be a CEO). Invest time and money to be a better CEO – a CEO bootcamp, a CEO coach, a fellow CEO for monthly coffee chats, or a good book.
Most days I love this job. It combines the accountability and (potential) glory that I crave, with the opportunity to work on problems I care about, alongside people that I chose (since I hired them). But the job comes with costs – and those costs are higher if you are not prepared or trained to do the job.
To the next 10 years,
Greg & Taylor