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Great advice but I disagree that “most executives aren’t awful”. Leadership is a hard and opaque role. More often than not the wrong people are promoted to management. Poor leadership is the norm, not the exception.



It really depends on the company we are talking about. If you look at where Will has worked, it's easy to see why he thinks this way: His executives really were pretty good in general, and some downright great. It's just that his selection of companies, and industries, is not necessarily representative of the world at large.

There are many companies, often older than the ones Will has worked at, which, as you say, tend to have executives with a far lower quality. A non-trivial amount that yes, I'd call awful, especially after seeing the difference with the excellent ones. It's hard to run a good company with a bad executive team though. Therefore, I'd argue that the right take is that, if you are working for a firm that is doing well over average, Will's take is the right one, and that when it isn't right in your environment, you should consider greener pastures.


Being a good executive or good manager is actually very hard and thankless. When you're at the top there's no one to pat you on the back and say "good job" or "how are you feeling?" and everyone either sees you as a villain or is waiting for an opportunity to slit your throat and take over. The last few years i've been surrounded by execs and high-up managers at my clients and firm. I don't envy their positions honestly, maybe the comp is good but the stress and pressure isn't something i could handle. And i say that has someone in a fairly stressful and pressurized role.


"CEO's get it right 17% of the time" was a great quote that I read.

Seems about right. We draft 10-20 design documents for every one implemented.


Regardless of whether a majority or plurality of leaders/managers are bad (because there are definitely tons of them, I may be one myself), I think a lot of people use personal outcomes to blame leaders/managers for structural issues.

Perhaps a team delivered a mediocre or poor outcome, but was that outcome potentially the best result due to organizational constraints? I suppose that I’m just pointing out that since leadership can be “hard and opaque” judging it’s effectiveness can be just as hard


Maybe this is just because leadership is hard, and more people are needed in leadership positions than are capable of fulfilling the role?


There are probably too many managers tbh


Leadership is not managing though.

I think the problem is in conflating the two so the leading gets forgotten because most of the time is spent managing.


Maybe the criteria for selecting leaders is based on connections as opposed to personal qualities.


Are you talking about actual C-level executives at major corporations, or just mid-level managers you've had?


I think it depends.

A lot of large institutional companies effectively work "on rails", so loads of C-level execs there are glorified middle managers whose only talent is climbing the greasy pole.

Young companies though, they have "real" go-getter execs.

Finding out who is who, is a skill in itself.


100% correct. You are extremely lucky to get one good executive at a company nevermind several.


In my career, I've met a single executive that I feel would not stab me in my face to further their own career (assuming it won't be found out or they could blame my stabbing on someone else).

I think you are wrong.

"Most executives arn't awful" - true. They are sociopathic.


Who are the right people? Mind contrasting …

- values?

- characteristics?

- abilities?

- experience?

- education?

Best way to tell them apart in interviews?




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