I was fortunate enough to spend about 18 months as staff assistant to my CEO, including access to their email and basically all meetings. This was a PE-backed roll-up that was in the midst of acquiring several smaller companies, and then pursuing an exit.<p>The experience really opened my eyes about the requirements for the job. The amount of code-switching required to communicate well with ownership, the other C-levels, employees, customers, and potential acquirers could make my head swim. The breadth and depth of technical, financial, and human expertise necessary to verify all the parts of the business and smell out where issues might be hiding. All of that before even getting to (in this case) integrating several businesses into a whole, identifying up-and-coming leaders, and keeping the employees happy; let alone actually having a strategy, getting buy-in, and implementing it. And then spending most evenings networking with the elite class that you need to know to have access to capital. You can never have a bad day. Ever.<p>This was for an org that was comfortably under 1000 employees, all located in the US, where none of the VPs were the kind of political operators you get in meatier companies.<p>I walked away thinking that there can't be even 100k people in the country with the ability to do even a non-laughable job as the CEO of a 500ish employee company. Not even do a good job, just do a job that doesn't look like one of those 80s child-parent-bodyswap movies where the kid tries to work in an office.<p>I still think CEO pay is out of control, but I understand better why boards end up paying what they do. Any weakness in any of these skills is an existential threat, and you don't know for sure what will hit you this year.
The "What it's like" posts are really cool. Especially enjoyed this account[1] from a content writer who shadowed the CEO during a half-day meeting with a major investor and got to see the impact of their work in a context they never expected:<p>> Next we met with Vinod, Bruce, and investment partners Brian Byun and Sven Strohband for a company brief and brainstorm session. Sid began with an update on the financials, and detailed our massive growth and expansion both in terms of people and product. There were no slides presented. Instead, Sid used our website as a visual aid. Nearly every question or discussion point was first addressed with a Google search to pull up the appropriate GitLab web page to reference.<p>[...]<p>> I’ve been working at GitLab for two and a half years as a content writer on our marketing team and at times have been extremely frustrated with our marketing website—the content on it, how it’s organized, what we’re presenting, etc. It doesn’t look or operate in a way I’m familiar with so my instinct was to not trust it. But nothing we do at GitLab is “normal,” and witnessing our CEO use the website as a single source of public truth to inform our investors is just one example of what it means to be a transparent company.<p>[1] <a href="https://about.gitlab.com/blog/2019/04/08/khosla-ventures-gitlab-meeting/" rel="nofollow">https://about.gitlab.com/blog/2019/04/08/khosla-ventures-git...</a>
I'm constantly in awe of Gitlab's radical transparency approach. I have no idea if this is actually a good idea (surely every competitor of Gitlab has a huge amount of assymetrical information about Gitlab that Gitlab does not have in return) - but I am fascinated by it and truly grateful for them for daring to go out on a limb and do this experiment. My fingers are crossed that this brings them amazing success as I wish all companies worked this way.
It’s surprising to me that a CEO can allow all of their meetings to be shadowed by a (relatively low-level) employee — surely there must be highly confidential information, performance feedback, sensitive legal matters, etc that can only be attended by specific executives?
I was surprised by the volume of the handbook material that applies to the role of CEO shadow. To me it implied a high level of formality and expectation of rigid adherence. Then I found this:<p>> CEO shadows label the handbook MRs they create with the ceo-shadow label. It's a point of competition between CEO shadows to try to best the previous shadows' number of merge requests.<p>I am no longer surprised by the length of this section of the handbook.
GitLab is a company I've always felt hasn't quite found product market fit.<p>However, its "open source internal practices" model is the gold plated standard for a 21st Business.<p>If you're any kind of manager of anything, do this.<p>See: <a href="http://blog.idonethis.com/managers-write/" rel="nofollow">http://blog.idonethis.com/managers-write/</a> for more.
Looks like a great program that will yield insight, especially being able to travel with the CEO. Anyone aware of other companies doing this or something similar?
I think the reverse would be equally as informative if not more.
(Which has been the subject of a tv show)<p>CEO shadows an employee all day.
Get a feel for how the peons live.<p>Understand why it is so hard to get things done in the company.
I’d recommend anyone who finds this interesting to give a listen to Matt Mullenweg’s Distributed podcast episode with gitlab’s CEO. An abridged version of various different initiatives, which make gitlab different: <a href="https://distributed.blog/2021/05/20/episode-27-leading-with-values-sid-sijbrandij-joins-matt-mullenweg-to-talk-about-gitlab-transparency-and-growing-a-distributed-company/amp/" rel="nofollow">https://distributed.blog/2021/05/20/episode-27-leading-with-...</a>
I really like this idea and want to see if it is possible to come t live as an online service where CEO finds the right CEO shadow.<p>Couple of years ago the idea of CEO Shadowing was mentioned on Kernal. <a href="https://kern.al/idea/shadow-a-ceo-lessons-courses-programs" rel="nofollow">https://kern.al/idea/shadow-a-ceo-lessons-courses-programs</a>
Since then no one picked it up, not sure why. But I'm interested and want to make a real living application for CEO and who want to be CEO Shadow.<p>Is it worth it?
Couple of years ago the idea of CEO Shadowing was mentioned on Kernal.
<a href="https://kern.al/idea/shadow-a-ceo-lessons-courses-programs" rel="nofollow">https://kern.al/idea/shadow-a-ceo-lessons-courses-programs</a><p>Since then no one picked it up, not sure why. But I'm interested and want to make a real living application for CEO and who want to be CEO Shadow.
Is it worth it?
If you are interested in this kind of role, it is usually called Executive Assistant in the corporate world. Had the fortune to support my CEO and attend e.g. all board meetings (because I did the minutes). This is at a >10$ bn revenue established company. Very rewarding, but experience depends very much on the style of your boss.
Gitlab sums up the problems with GIT and the culture around GIT. Do things as complicated as possible. Gitlab mainly solves all the problems it created.<p>I think this role is good though. We have similar staff that been included in all the things and they got up to speed fast.
This is great! I would love to shadow the CEO like this and understand what they do and how they do it. However I fail to understand how this gives the CEO nay feedback about their own job as mentioned in the post.