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PaperclipPerfector  1yr ago (text post)   29842 thread views

Culture War Roundup for the week of October 2, 2023

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Fortune 500 CEOs aren't working bone crushing hours the way a small biz CEO might. (More on that second part later).

But, being an F500 CEO is incredibly hard.

I had the opportunity to meet and interact with one at the F500 I worked for in my mid 20s. This was a non-trivial interaction that occurred because a series of events led me to being on this big strategic thrust planning team that the CEO was half-personally overseeing. Another series of events led to a bunch of us being at the HQ on a Saturday. Right before lunch, the CEO walks into the main "war room" and literally rolls up his sleeves to help out. He was there all day. In that setting, everyone was talking with everyone at some point or another and the various "ranks" that usually created some deferential distance were not as palpable. It was easy to talk to the Big Guns, so I just sat down and started talking with the CEO.

The conversation can pretty much be summed up like this:

TollBooth: "So .... what do you actually do?"

F500 CEO: Chuckling, "I make about four decisions per year and, the rest of the time, am on call to answer questions that the board and wall street investors have. That's the easy part. I'm basically a financial psychotherapist. The first part is way harder."

TollBooth: "Why?"

F500 CEO: "Because those four decisions dictate the 16 - 20 decisions I can possibly make for the next 4 to 5 years. If I make the wrong ones this year, we, as a company, have fundamentally worse options in the out years."

TollBooth: "So, just make good decisions this year"

F500 CEO: "Well, yeah, that's the goal. But these 4 or so decisions I make rely on, without exception, massively incomplete information that I then have to use as part of a decision making model that incorporates what I think our competitors are going to do, what the market will support, and what won't cost us customers. All of those things are interdependent and you can't really say which one comes "first" in the decision making chain. It's like hitting a half dozen moving targets that are all moving in random directions - if you time it right, you can blast three of them at once, and that's a really great year. If you don't, you miss everything and it looks to outsiders like you were shooting randomly."

TollBooth: "Why are we doing this strategic thrust thingy right now?"

F500 CEO: "Because I screwed up one decision two years ago and I think I can salvage it with this. If I can't, I probably am gone 2 years from now."

I'd add one personal/emotional level consideration to this; you have to live with the uncertainty and lack of control leading up to and following making these four big decisions each year. One thing I learned in my first technical sales engineering team was that a sales process might be long, but you can sort of see it developing day to day and week to week. So, you can reduce your overall anxiety by just doing the next obvious thing in the process, even if that thing is banal (scheduling a follow up meeting, asking for a how-to guide review, whatever). A good analogy is training for a sports meet. You put in the work day in and day out, and then, all of a sudden, it's the big payoff day / week and you go out and get it (or don't). All your nervous energy along the way, however, you can divert into the training (or the development of a sales cycle in this case).

The CEO can't do that. There's no training cycle that builds up to something. It's literally four decisions made on four different days across a year. I think he could, and did, think about the decisions a lot before he made them. And I also think he probably had a team of smart people digging through a mountain of data and projections. But, like he said / I wrote above, these decisions had really incomplete information - you can't brute force your way through them even with a million spreadsheet runs. And, there isn't really a way to test and the iterate - you're calling out a new direction for the Battleship and you have to live with it until you hit the iceberg or don't. (Sorry for throwing in another unrelated metaphor)

I think the personality type that ends up as an F500 CEO definitely isn't "work like a dog 16 hours a day" but is, instead, "Be comfortable with weeks and months of utterly not knowing. Then pull the trigger." Is that hard work? You tell me.

Returning to small/medium CEOs working crazy hours. In my experience, that's 90% of the time a failure mode of a founder type CEO who can't give up micro levels of control and build the durable systems you need to scale. I've been in tech startups where the founder was very much the engineering genius type but then there came a time where the best answer was to "hire the MBAs." Everyone's life got better. Everyone made more money. The founder saw their big dream flourishing, albeit without direct control.

Great write-up, thank you. I knew a CEO of a big bank, and I think the biggest barriers to making good decisions were:

  • lack of time: he would have regular lunch with other C-levels, but then there were regular skip-level 1:1s with department heads, meetings with key customers, meetings with directors, public relations, government relations, various steering committees
  • lack of data: there's a reason why all these "visual analytics" software packages blew up in popularity, most of the information comes in the form of carefully curated reports. If you let yourself be walked through one, you'll never see what your C-level exec or department head is not saying.
  • lack of levers: yes, this sounds strange, but these four big decisions each year are usually so big you don't really have a way to course-correct later. Yes, you can sometimes be a Jeff Bezos and write a memo that everyone has to use document APIs for integration or be fired, but usually you can only be a Jeff Bezos, read Chris Pinkham's memo, give him a whole lot of money and see what happens.

For example, there's a shareholder meeting and one of the directors tells you "Bank X used to be #5 retail bank in the country 4 years ago and now it's #8, while Bank Y, your closest competitor, grew from #6 to #3". This basically means you are already on your way out, so let's rewind the time.

There's a board meeting and your trusty advisory office has prepared a memo for you that shows that you'll soon lose your #5 spot in the ranking of retail banks. Your chief retail officer of course has a slide deck that explains that this is a temporary setback mostly driven by a big drop in car sales this year. What do you do?

  1. tell her that you want the bank to become #3? She comes back with an investment proposal of ten billion dollars that should break even in eight years. What do you do then?
  2. tell her to stop the backsliding? Next year you're solidly #6, but that's because there was another black swan that hurt you more than the competitors. What do you do?
  3. fire her and look for a better chief retail officer? What do you tell the new one?

Very interesting commentary. I personally think it's 'work smart' stuff but the meaning of what you say does extend beyond anything a two-word platitude can cover.

Reminds me a little of my experience in crypto, few decisions, lots of stress, lots of waiting on events. Easy things that are difficult to do. Of course, much less money at stake.

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