But I still need to sometimes also do what a CTO would do in a bigger company, and if things go well and the company grows I may need to incrementally learn more and more of the themes above (up to the point where I hire a CTO to replace me in that role I guess).
The more experienced you are, the more you realize how little you know.
Ultimately, reading the material on these lists is a very small fraction of the job. Personally, I've already read most of the items on the last list years ago when I was earlier in my career and wanted to understand different historical organizational models. That's the right time to read this kind of stuff, because you can use it to pattern match and dig into what others around you are doing in an environment where you are not on the hook for their strategic mistakes.
By the time you're actually doing it, this material will probably not be that much help. You'll be in the driver's seat, not the passenger's seat. You'll need to use driver's seat tools, not passenger's seat tools.
First of all, how many CTO's do you know? And how many of them are good?
Second, is this "mentor-mentee" thing real, or just something business coaches and get-rich-quick gurus claim? Never seen it in the real world.
I'm an old timer. Most of my experience comes from experience. Most of my intellect comes from books an articles written by people who know what they are talking about. Claiming that the latter is a waste of time seems very wrong advice to me.
But maybe your mentor told you differently.
Have you ever learned from one of your more senior coworkers or peers? Worked alongside someone who showed you the ropes or helped you level up your skills? Then you've been a mentee.
Have you ever taken time to guide new hires or junior coworkers in something you're familiar with? Provided advice to accelerate someone's learning? Then you've been a mentor.
Mentor/mentee usually isn't an explicit declaration. It's a very valuable way to accelerate skills, though not the only way.
In the case of a CTO, since it's a unque role, you have to go outside of your company to get mentored. And that doesn't seem so straight forward to me. Because asking a colleague about a problem you are facing is way easier than calling someone and talking about your problem at your work.
Maybe I'm ignorant about this topic, and maybe such things are more normal in US than here in EU. Such things go really against my nature, but I aslo never seen such relationship outside of the same company.
If you're ignorant about the topic, why not explore the other perspective with curiosity rather than gruffly dismissing it as provoking a BS sensor? Mentorship is an enormous part of the lifecycle of executive tenure of the ecosystem I participate in, which is the NYC startup ecosystem.
I've observed that when my colleagues have built a deep relationship with their manager during their tenure, often times, they gain that mentorship permanently whether they stay at the company or not. The reason the mentor does it is because it's just another version of the old adage of paying it forward -- they know that a job they land in the future could come from one of their old reports; in fact, they might even end up working for one of their old reports!
Investing time and energy into cultivating and keeping these relationships going is a large part of how my colleagues have continued to keep their career moving upward as they approach mid-career.
I guess this mentality is common to startup scenes, but not really outside of that world.
I wonder if you're making my point for me. As an old-timer, what you bring to the table that's more valuable than gold is hard fought experience -- not the things you've read. It's easy to read things, but to actually apply them and be responsible for their long-term consequences is rather different.
To answer your other question, I know quite a few CTOs. In particular, there are two that I know very well because I worked for them on the ground-floor building $1B+ startups at the seed-series A stage. So much of what I know came from observing what they did, asking for help, asking them to explain how they came to certain conclusions or made certain major decisions. I wanted to take apart how they did things even if I wasn't responsible for them, so I could put it back together and understand how it works. Not only that, but I kept in touch with them afterwards and found them very valuable sounding boards for when I gave my first CTO gig a shot.
One thing is that it opens up a world that is broader to your own. Another thing is that it can provide clear mental models that you probably won't figure out yourself, and that you can observe only after you know the theory.
Let me give you a clear example.
Early in my career I had to manage a junior. At the time I was reading The 7 Habits Of Highly Effective People. I applied the "stewardship delegation" from that book to the letter. It worked perfect. In my 19 year career, I apply it all the time, with great success (it also works on your kids :D).
But nobody I know knows about it. I could have never learned one of the most important things, from experience alone.
Even when you look at people like Bill Gates for example, they also still seem to get great value out of reading.
Thanks for the conversation, and sorry for my snarky remark, I admit I was wrong judging you :)
I do agree with the overall content of your post, though.
Please leave the unnecessary snarkiness for other forums. I could have said "The most leveraged way to operate as a technology executive" but that's rather wordy. More than happy to engage with any substantive critiques you have with my point of view. It's what has worked for me, and it's based on my own experience.
Once you strip out the pedantic remark, you haven't actually said anything. I think your actual silence speaks volumes and makes my point for me.
The secret to getting good at management is to acknowledge that it is a huge, deep and learnable set of skills. The best managers I know are the ones who constantly seek to improve their skills, and "do the work" to improve.
It's clear that Jim is constantly reading/actively improving, sometimes doing kinda unusual things, like having a specific strategy for priming his REM sleep by thinking a lot about some current problem combined with some kind of meditation exercise.
The most valuable thing for me, and I am a CTO, is exactly the reminder of the breadth of the list. Most of the areas of the list are things I am familiar with, but it is easy to let a few areas fall short. One of the key expectations of a CTO is broad expertise, which is a tall ask.
Being a generalist + working in many separate areas will get you there. It does take time to build experience. I guess you can accelerate it slightly by reading books, but really, most of the lessons are best learned by doing, I think.
Fixed = your talent is fixed, you will not learn, challenges will either show your talent or reveal you're a fake, helpful sheets and reminders like this are a proof of your lack of talent, therefore never admit that you're don't know anything
Growth mindset is basically the opposite.