Exec Development is a Different Game

Epistemic status: I’m not 100% sure of this, and will probably take a few years to verify once I start hiring (and training) again.

This is a companion discussion topic for the original entry at https://commoncog.com/exec-development-is-a-different-game/

I’m confused. What does ‘training’ mean in this piece?

And: If one isn’t ‘throwing problems at’ individual contributors (ICs), what is one doing with them?

There’s a category of operational training that I wouldn’t expect executives to participate fully in - if the business model changes, or technical systems change, or some set of processes gets overhauled, ICs are going to need to get wise to a level of new task detail managers can’t afford to dig into. Given that, I’d expect ICs to require more training time than executives as a matter of course, with the difference in time being driven by the difference in the nature of their respective roles.

But if the distinction is strictly about career development, then I’d argue that a two track system where executives sink or swim but ICs get guidance counselor-like treatment from management is going to result in an adverse selection issue. ICs with an appetite for problem solving will leave to go where they can solve problems, while those who want a ‘high touch’ work environment that feels like an extension of a stereotypical college classroom will stay.

In a scenario like that, one could hire well but not be sure of it, because the problem solvers quit before they get near their potential.

I suspect I don’t buy the premise of the post, but again, I’m not clear on what ‘training’ means.

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This is actually one aspect I’ve been struggling with.

First: yes, when I say training I do mean guidance-counselor type treatment from management. Or at least that’s how I ran things, and for good reason: I didn’t want people to screw things up when working on the product. So there was a standardised (functional) training program, which established expectations, taught them our code style and familiarity with our production codebase, and then people were levelled according to the same set of criteria on the engineering team. Later, when I hired managers, I trained them in management and taught them to do 1-on-1s and to run their own functional training with their subordinates.

It mostly worked: yes, this was an ‘extension of college’, but the flip side was that people loved it. Retention went up. And there was this weird dichotomy going on where any engineer attached to the Singapore office wouldn’t have these benefits, so they were a flight risk; meanwhile employee retention on the Vietnam side of things was way higher. After a great engineer in Singapore left, I mandated that new engineering ICs must be attached to the Vietnam office, under me, so that we wouldn’t keep losing them. Retention wasn’t a problem after that.

But I was reflecting on it and I do think there were one or two people who levelled so quickly they outgrew the company. And now I’m wondering if I could have thrown them in the deep end instead — meaning no guided career path, no training, just chaos and more responsibility than they were ready for.

(My boss’s approach to training — which is to say the Singapore side’s approach to training — is to articulate expectations and then leave you to it. We lost I think a dozen people who hated this and couldn’t handle it. Most people want a clear skill tree laid out for them.)

Anyway now that I’ve explained this, a few things have been bothering me.

  1. Adverse selection of a two track training path — exactly what you said. Might still be doable, though.
  2. Throwing execs into the deep end implies acceptance that things would blow up. Training ICs is to ensure that things don’t blow up! (Grove gives the example of an Intel technician who wasn’t given adequate training, and destroyed $1m worth of chips in a single day. He blames her manager.) How do your reconcile this?
  3. The bit that I didn’t mention, but is closely related to the idea of exec development: in many cases you can’t train a failing exec, or put them on a performance improvement plan. No, you fire them. It’s highly unlikely that an underperforming exec who has lost the trust of their team can ever succeed again. So there’s also this nuance to it.

In practice, I’ll likely have to test this out. Hence the epistemic note at the top of the post.


It sounds like you’re talking about folks without much career experience here; is that a fair assumption? Skill tree guidance is far superior to ‘just go figure it out’ when one is dealing with someone without much experience or confidence, without question.

I don’t reconcile them; I think of them as being in two different categories. And I think everyone needs both kinds in order to execute well and grow.

In the new CFO’s case, they need functional/operational training so they don’t inadvertently cook the books: they need to observe reasonable control barriers between them and accounting staff. And they need leadership training (or the intentional absence thereof) in order to grow in the role. It’s OK for the CFO’s relationship with the audit committee to founder for a while: if they can figure it out they’ll level up in ways a mentor may not be able to predict.

I’d class the Diller related examples you cite as leadership examples - problems of people and coordination between them.

Part of my struggle understanding here is that I can’t imagine working in an environment where technical staff didn’t have the opportunity to do things that might blow things up. Figuratively, I mean (in high school I had a substitute math teacher who had screwed up a critical calculation in a previous job and as a result part of an oil refinery was destroyed), since software screw ups are not usually catastrophic.

If one gives technical ICs skill tree training alone and they’re content, that’s great in the short run, but then one is stuck with technicians rather than engineers, and they’re hard to promote.

My worldview is no doubt heavily influenced by the environments I’ve worked in - corporate research staff tend to be folks who left academic settings to escape the skill tree in favor of a ‘choose your own adventure’ kind of career.

Or, if the parting is meant to be amicable, you let them down easy: take their staff away, make them a de facto IC, give them a fancy new title and three to six months to ‘manage the transition’ of their old team to new leadership. Plenty of time to find a new gig.


I took some time to think about your reply, because I realise that I didn’t always think this way. I used to assume that we should treat subordinates as capable of figuring things out on their own, and throw tasks at them to figure things out on their own. And then I had to stop, because it was very obviously not working.

Of course, to some degree this might be because I was operating in Vietnam, and the expectations might be … lower, given that I started out hiring from non top-tier universities? But then I remember talking to friends in FAANG companies around the same period, and they were also dismayed that they had to hand-hold name-brand university graduates and show them a path to career advancement. We kinda assumed that they had their shit figured out. (Being from Asia, you hear stories about name-brand universities in the US, and then when you meet actual graduates from them, the reality sometimes doesn’t match expectations. Except maybe MIT?)

Eventually we read HOM and concluded that Grove had it right — most people don’t have a clear career plan in their heads and feel some degree of happiness and certainty when their direct manager works out a plan with them. So we all did similar things with our subordinates (with variations, of course; since it had to fit the org they were in).

I’ve been so won over to this form of thinking that I had a jarring feeling when I read Diller’s account. And it does sound like you’re so used to Diller’s perspective that you find it jarring when you read my account!

In my context, definitely. In my FAANG friends’s contexts, I think some of their subordinates may have experience, but not confidence (though I’m just guessing here), so that might be true also.

I think this was what I was missing. I mean, even when training junior subordinates, I’d let them make mistakes in low-stakes environments. I’ve also let more senior subordinates make mistakes at higher-stakes environments (e.g. deployments, but only because I trust them to be able to handle themselves if things blow up and cost us $$$). But I’ve not done the equivalent of throwing someone with no operating experience into a CFO role of a major subsidiary. (Because I don’t have a major subsidiary to throw them into, heh :wink: )

I look forward to giving that a go in the future.

Good point.

As an aside, I was reading Simon Sarris’s https://simonsarris.substack.com/p/the-most-precious-resource-is-agency and I think it’s tangentially related to our discussion here. Sarris has this to say:

The world until recently was overflowing with onramps of opportunity, even for children, and we seem to do poorly at producing new ones. Modern complexity may have erased some avenues for agency (no boy can meaningfully learn the telegraph), but I suspect how we have oriented the world, not technology, is the main problem. 13-year-old Steve Jobs called Bill Hewlett and received a summer job at HP, which would be unsurprising in Carnegie’s time, was certainly surprising for 1968, and is obviously verboten today.

We seem to have a political (public) imagination so shallow that it cannot conceive of what to even do with children, especially smart children. We fail to properly respect them all the way through adolescence, so we have engineered them to be useless in the interim. We do not need children to work, that is abundantly clear, but by ensuring there is nothing for them to do we are also sure to destroy more onramps towards making meaningful contributions to the world.

Much of the fault for this lies in an attempt at systematizing skill and knowledge transfer so thoroughly that people begin to conceive of it as the task of school, rather than a normal consequence of work. Because of this shift, childhood contains the age where one can intuit very well how the world works while being prevented from acting upon it meaningfully. Instead of an adolescence full of rites of passage, where one attempts to master something and accept responsibility, we have made it full of waiting, and doing work—for school is work—that nearly everyone knows is fake.


Ah, but that’s not what Diller did in this case. He had what looked like a rising star on his hands. Dara Khosrowshahi had come up through the ranks of Allen & Company for seven years before he got the CFO gig. And as the son of a conglomerate founder he was probably on the fast track the whole time. No generic ‘business orientation’ time needed.

If he had some team-of-teams management experience by the time he got named subsidiary CFO, then he’d already be at a level where management jobs are more alike than different, regardless of the role, and his experience gaps would be mostly CFO function-specific.

If not, that’s a harder climb, but not impossible.

Yes, having once been a corporate intern, and having trained interns fresh out of college, I would definitely not recommend throwing someone who had no operating experience into a senior role.

Over the course of 5 years or so I saw about 100 interns go through a six month program, about 50 get hired permanently, and about 5 get to the level of managing teams, with 2 or 3 eventually managing teams of teams. The hires found direction in the process (probably half of them quit the company to do something they found more engaging, like law school or startups) with a lot of help from management and prior interns.

So I’m with you RE: the struggle to manage folks who don’t have a business orientation when they show up. Starting at step 1, one needs to grow for a while to get on the short list of a Diller type in the context in which Diller was operating.

RE: the Sarris piece, I was inadvertently lucky in that I went through a peculiar undergraduate program (with no promise of worldly success on the other side) that one had to self select for. So when I and fellow alums showed up for post-college work we knew that whatever work was going to be, ‘like school’ wasn’t it. I didn’t realize until much later how much help that was.

P.S. Digging a little further into Khosrowshahi’s CV, there may have been more than seven years between his starting at Allen & Company and getting the CFO job at IAC. The public details are fuzzy.