Ask HN: How to shadow a CEO? | Hacker News Reader

Ask HN: How to shadow a CEO?

231 pointsrealrali85 comments

I have the opportunity to shadow a CEO/Founder of a $25 million dollar company. The company is in the fresh produce sector - not an industry that I ever really considered, but the founder has been able to build it up from nothing to one of Inc’s fastest growing companies in just 6 years. I have free reign to attend meetings/calls in all departments, and I have committed to 4 hours, 3 days a week. The CEO is a friend so there’s an established relationship. My longterm goal is to own my company and I want to learn how a successful business is run and the leadership skills required.

I’ve never done this before, so my questions are how do I get the most out of this great opportunity? How can I add value to him? How long should I continue this internship? Any other best practices/recommendations?

Thank you so much in advance!

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Listen. Listening is a multi-dimensional skill. Observe their communication skills primarily their non-verbal communication. Do they attempt to dominate the space around them? Are they receptive to input? Are they patient or hurried? What is their degree of empathy? Are they touchy?

Also watch the non-verbal communication responses of the people who interact with the CEO. Are these people charmed or put off? Is there a receptive common understanding? Is there an eagerness of participation or does the CEO surround himself with cowardly yes men?

Second, pay careful attention to their choice of vocabulary. How does the CEO articulate abstract thoughts? Do they use humor to soften moods? Are they bottom line up front? Do they stutter? Do they pause to organize their words before speaking or does it just flow like a waterfall? Is there a crispness, clarity, or articulation you find particular?

Third, how do they use their time? Focus more on the idle moments when they aren't actively engaging with people or specifically focused on a dedicated planned task. Do they stare off into space brainstorming? Do fidget with a gadget (probably a phone)? Are they calm, restful, or a busy body?

Fourth, what do their notes look like? How they write things down or record things is an indication of how they want they to remember things. It isn't the full picture of how they organize their thoughts, but it is a large picture on what they choose to organize. This is a view into their priorities and may reflect things you would not otherwise consider important.

If you have never been in management yourself you may find yourself focusing on their goals or the things they want you to see instead of the important things you are not yet prepared to look for. Don't worry about the interpersonal relationships or the people they want to introduce you to. This sounds really important, but I promise its a red herring unless you need to engage those same people directly on your own.

You sound like you have a pretty good understanding in this area. Are you in an executive position or work with that type a lot?

I am an Army officer who writes language parsers in JavaScript for a hobby.

Thanks for your service and your spot on advice!

This sounds almost like a rubric for evaluating the CEO rather than learning from them. In the sense that from the paragraphs above it seems you have already an answer for what the good CEO should do.

For example, what does one learn from a successful CEO who is dominant, unempathetic, surrounded by yes men, and fiddles with their phone?

Perhaps I'm not reading this correctly, and you mean look at these traits and note how (perhaps counterintuitively) effective or ineffective they are?

At a certain point in life this sort of listening, or mind reading, becomes non-cognitive. You do this without deliberation and have trouble turning it off. I suppose the idea is to better understand and possibly anticipate the forth coming decisions from how they treat people, self reflect, and plan.

Set the habit from the beginning to do quick debriefs (a few minutes) after each meeting. The most interesting thing when shadowing very senior people is to see why they do certain things.

Try to have 1 question ready after each meeting/call/... Why did you agree to the terms? What was the most important thing about this call? Why did you handle it like that? What did you try to get out of this meeting? How did you know they were going to say X? Try to get a sense of why they make certain decisions, how they think about it.

The debriefs especially are incredibly valuable!

Why?

You may think something happened based on your surface impression of what just occurred. The CEO may view it completely differently based on:

  a. information you don't have e.g. past history etc
  b. non-verbal cues (as other comments have mentioned)
  c. something else

Ideally, the CEO would turn to you after each meeting and ask you "What do you think just happened?", you give your thoughts and then they respond with what they think actually happened.

I've read/heard multiple accounts of where this has been game changing for the non-CEO/manager person as it gives you an insight that you would only ever be able to deduce slowly over time via trial and error.

The terms of immediacy are a great reminder of the importance of the 97 % of nonverbal context. Consider for example, the great American classic essay from Harvard Business Review "How to Run a Meeting" (1976, first published.)

Link: https://hbr.org/1976/03/how-to-run-a-meeting

The essay has a few passages about things related to The social skill of Politeness, in a broader sense, The very Skill of Enchanting people. This is the skill ultimately responsible for making money, in my experience, no matter what other skills people will praise. I didn't find the specific mention of the 97%, as it was a long essay, but I will consider that what you mean with nonverbal must be related with the human social interaction.

Understanding exec 2nd level thinking is perhaps the largest opportunity of your internship

Always think about WHY behind their actions. Think about their incentives. Think about what they're trying to accomplish. Same for the other people in the meetings.

> Try to have 1 question ready after each meeting/call/... Why did you agree to the terms? What was the most important thing about this call? Why did you handle it like that? What did you try to get out of this meeting? How did you know they were going to say X? Try to get a sense of why they make certain decisions, how they think about it.

You can sum this up with simple advice... be curious.

1. first and foremost, ask yourself WHY this CEO is giving you her valuable time? It's a lot of inconvenience for the CEO. There must be a real reason (more than just being a friend). You need to know the reason for you being there. Otherwise you are flying blind, and can easily say the wrong thing without knowing

e.g. if the CEO is doing this as a way to recruit you, don't say out loud in the meeting "I am going to start my own company after this". It will embarrass her in front of her team.

2. try to schedule the meetings to near end-of-day, and see if you can get to a social-event (e.g. after-work drinks) with the CEO and other executives. That's usually where the real conversations happen, and you find out the real "behind-the-scenes" info

I second the importance of 2,after the work drink or no-blackjack "behind the scenes" for its where the real business is, the rest is just the "acting". I agree in pointing the importance of the reason he/she was granted that position. Chances are parent is considered smart and polite and capable enough to be there, so maybe parent should just use his skills and go directly to open his company, or don't stay too long there, don't get used to be a shadow, even if you make good, comfortable bucks, if the desire is to open one's own company. Anyway, if the best thing if you are not just procrastinating in opening your own company is to go to your friend who owns 25 million bucks company and ask him if he would put some of his hard-nosed earn money in your plan for a company. Ask him to tell you as honestly as a friend can possibly be honest in this word, why he will not put the money that costed him his blood and sweat in your plan for a company. His honest answer would be enough what you need to learn from him in relation to opening this specific company you plan. Moreover, Whenever and wherever you see the word "opportunity" , be aware "opportunity" is a dangerous word, and all scam in the world comes from the word "opportunity".

> I second the importance of 2,after the work drink or no-blackjack "behind the scenes" for its where the real business is

This isn't true at all. Socializing is important for gaining trust, but the real work still happens in the office.

Let's rephrase: the real work happens in the office, but during informal meetings many underlying motives and decision drivers become visible, so such times allow a deep insight into how a business works

If you are shadowing, it is best to either have them introduce you (if needed) and then say silent. Don’t be part of the action unless specifically invited. Observe and listen. In my opinion, taking copious notes might make people nervous. Try to take notes during breaks or the end of the day. Good luck!

Great, thank you! I definitely don't want to overstep my boundaries, but I want to bring some kind of value. The CEO did initially try to recruit me for his sales team, based on my success at another company. Do you think it's ok to offer to help with some sales calls or essentially anything else that he thinks I can contribute to?

Is this his clever way of trying to get you to join the company? :)

I actually proposed the idea, but he did put the thought in my idea by telling me how successful his sales reps are...hmmm lol. It made me really curious how they do it, and how he was able to build such a successful company.

Offer all you want, but remember that if you're doing something, you aren't shadowing. Offer to take notes in meetings for them -- that's probably the most useful thing you could do.

Also, not to doubt your skills, but someone who doesn't have experience in the space "offering to help on sales calls" probably would be a net detriment.

Have a great time!

Makes sense, thank you!

It feels a little like Schrödinger's cat - if you contribute, you alter not just the direction and content of the meeting, but also the dynamic. By getting involved (opening the box) you would irrevocably alter what you observe.

If my goal was truly to observe the CEO and learn from him, my approach would be to be as silent and 'small' as possible - don't speak, don't draw attention to myself, sit behind the table, not at it, etc. I'd want everyone --including the CEO-- to forget I was even there.

I suggest you need to figure out what your goal truly is: to learn from him, or to 'bring value' for some reason? I'm not sure the two are compatible.

You make a good point. I think my need to bring value comes from being so grateful for the opportunity - I feel like I need to do something for him because he's doing something for me. I guess my time to 'repay' him will come later.

They're doing this /for/ you, not to get something /from/ you. Show your gratefulness by staying out of the way. Maybe bring donuts in the morning one day, something that doesn't impact the business. You're shadowing, not applying for a job.

I would suggest keeping your contributions limited to 1-on-1 conversations with the CEO, preferably soon after a meeting.

Taking a role in meetings could potentially create a lot of awkward power dynamics between you and the other executives, in my opinion.

> but I want to bring some kind of value.

I can't speak for this CEO, but if I were in the position I think I would get more value out of you being a silent shadow, and then debriefing you and getting a fresh perspective on the operational aspects of the organization.

That does seem to be an important thought...creating some compelling reason for him to talk with you again after this shadow work.

One that worked for me was to listen carefully for some opportunity where I could help. Like, "it sounds like you're negotiating with Microsoft... I just finished doing that with another company, there may be some helpful things I could share..."

Something like that creates a basis for an ongoing relationship. Such that you don't have to try to press a sales pitch in a hurry.

Unless you volunteer to provide minutes/notes for meetings you attend - it's a great way to put people at ease, AND be useful, AND be able to take as many notes as you want.

Brilliant

Note that taking minutes at a meeting is a skill and its possible to be embarrassingly bad at it. Consider finding a few episodes of Car Talk, My Favorite Murder, or another podcast with at least 2 people talking back and forth, putting it at 1.1x speed, and taking notes on that.

Do you consider yourself to be good at note taking?

> Consider finding a few episodes of Car Talk, My Favorite Murder, or another podcast with at least 2 people talking back and forth, putting it at 1.1x speed, and taking notes on that.

This is an interesting idea. I think I'll try it!

Do you recommend this as a way to get better at note taking or a way to assess your ability to take notes?

I find that the hardest part of taking useful notes is identifying and organizing the key ideas that will need to be referenced later; writing down everything that's said in the order it was said seems to be of less value in a lot of cases.

How would you assess the quality of notes taken with this exercise?

That is a super opportunity!

If you can, attend meetings with the CEO with the goal of observing these things;

   * Conflict resolution
   * Group commitment
   * Performance management and expectation setting
   * Information sharing/hiding
   * Individual empowerment and delegation

Those are the key interactions that come to mind when operating a company on a day to day basis. I'd suggest you take notes of all your observations at the meeting and then spend ask the CEO to tell you what they saw. What did they like? What concerned them? Given the meeting what did they see as the actions that would best help the situation move forward toward resolution.

Dan Warmenhoven once told me that he spent a lot of time trying to help people get things finished. As he described it, people can get caught up in the thrill of "doing things" and that is great, but they can also be afraid of the "what am I going to do after this is done?" question. As a result the project they are working on stretches on and on because it pushes off the scary question of "What next?"

It is a balancing act to keep what ever comes next exciting enough that people want to finish the current project and get on to it, versus making the next project so exciting that they cut corners finishing the current project to get on to it!

You learn by doing and putting skin into game not by watching or listening random CEO advice.

The only thing you will learn is that if your friend could create a $25M company you can do this too. This is how we grow--by imitating our closest peers and we start as babies imitating our parents and siblings. Creating a $25m company is btw not that hard, creating a multibillion company is.

Everything else, stuff you will see and his advices won't help you because once you are in the situation yourself you won't be able to use that stuff. Long story, I'll tell why another time.

Found a company yourself now and let him coach you/make intros to investors and let him check your overall pitch. If you don't have any ideas for a business ask him. This will be your first mission.

Shadowing a CEO without having a clear mission is douchy.

"You learn by doing and putting skin into game not by watching or listening random CEO advice." Perhaps you meant: "you learn MOST by doing and putting skin into game, COMPARED TO JUST watching or listening random CEO advice."

I did this kind of shadowing as part of an MBA and it was super useful. Senior managers are often flattered that someone would want to do this, and they often find the discussions (including naive questions) with the "shadow" useful in providing an alternative perspective. So it's not only beneficial to the "shadow". One of the tasks we were asked to complete, in addition to general observation, was to make a note every 5 minutes or so on what kind of task was being performed, and (of possible to judge), the level of the task e.g tactical (day-to-day / week-to-week) concerns vs strategic (months - years). Tabulating that and writing a short report for the CEO afterwards is helpful for the shadow in order to consolidate and organize what you learned, and very helpful to the CEO, who almost always end up spending most of their time on tactical issues ("firefighting") rather than strategic issues, even though they know they should probably be spending more time on the latter than they currently are.

Yeah, we find each new hire pretty valuable in the first few months because they provide a perspective on pain points that we may have internalized and disregarded.

I would completely disregard this advice.

> "Everything else, stuff you will see and his advices won't help you because once you are in the situation yourself you won't be able to use that stuff. Long story, I'll tell why another time."

How could you know for certain it wouldn't help him?

Moreover, humans have mirror neurons which respond to actions that we observe in others. These mirror neurons fire in the same way when we actually recreate that action ourselves.

So if the student observes with intent, then his brain could subconsciously 'download' the CEO's behaviors.

>"I would completely disregard this advice"

Much to the opposite, au contraire, I would say this is the best of all advices written here, as it goes to the point as if the OP wants to open a company of his own or just procrastinate, to use a less mild tone, as in your comment.

> I’ve never done this before

Really happy you mentioned this because on the face of it, this is a colossal waste of time.

Shadowing someone in the duration you have mentioned is the equivalent to buying a Tony Robbins book about Entrepreneurship, reading it and then proclaiming to be an Entrepreneur when really Mark Cuban has it right and they are just a Wantrepreneur.

I know this sounds pretty harsh, but you have no skin in the game. You won't be making any decisions, you won't feel the weight of them either. You won't be telling staff to start and project and then see all the problems associated with getting it finished.

There's no muscle memory to be gained here.

Here's what I would do. Tell your friend, instead of shadowing to make you a manager with a member of staff. To then give you a small project to deliver. Something that's well outside of your comfort zone. Ask him, to have himself or another manager to be available for mentorship when you need it.

Now you'll be in a position to find out for yourself:-

1) What makes a good leader

2) How to effectively communicate to staff.

3) How to handle problems that come up in running projects.

4) How to plan a project and then to complete one.

5) How to manage a budget.

6) Everything else in between.

Doing is far better than watching and by doing so, gets you a lot of experience for when you want to do it yourself.

-------

Honestly though. I would just start my business today and have the CEO friend as a mentor.

Fail and fail often: https://www.youtube.com/watch?v=mNDA-o9yJNw

idk,

a lot of the internships that people get in college are functionally job shadowing opportunities,

I think most of the advice given in this thread would be excellent advice to a person starting college internship,

Depending on the field, who you're shadowing, they're willingness to share, and your ability to receive what they're sharing

I suspect that can be valuable for a certain period of time

(I suspect that you're correct that returns on that experience can often diminish quickly)

I would not be comfortable having an arbitrary personal friend of the CEO sitting in on my important meetings.

I agree with your concerns. It would also be significant as to how the CEO introduces the "friend" if at all. In business meetings it is usual to introduce everybody to everybody and indicate in what capacity they are attending the meeting. So a silent shadow would raise eyebrows at a minimum.

Agreed. Before my shadow day I get the CEO to send a quick email to everyone in the company introducing myself, why I'm in the office etc. This seems to work well.

Interesting, could you help me understand what type of important meetings you're talking about and why you would not be comfortable?

I haven't experienced people having a problem with me observing their meetings before, in fact most people are really happy for me to learn from their meeting. I understand some meetings could be difficult though eg. HR related

Confidentiality and principle of least authority. Sensitive information should only be disclosed to people who actually need to know it.

You mentioned "adding value" a few times, but if you are truly job shadowing then that should not be a goal of yours. Job shadowing is about observing and learning. Just watch and listen, and do your best to humbly stay out of the way.

Thank you. This gives me clarity. My need to contribute was my way of showing him how grateful I am, but that can come at a later time.

Totally understandable. Later seems appropriate, and your feedback after completing this process will probably be pretty valuable to your friend.

Eat fresh produce.

Seriously. Believing in the mission is the first step. Acting upon it is the second.

I bet nothing ingratiates you as much as this. It shows them that you "get it", are serious about your own aspirations, and are willing to do whatever it takes to get there. And it will probably open every little door and window just a little bit further.

That's a great idea! I'm already all about eating well and fresh produce so I'm all set :)

I am a CEO, but not a particularly excellent one. If I were to Shadow a CEO, I would be interested in...

- the speed they make decisions, especially in terms of how much they know and don't know at the time of the decision. - the "level" of conversations they are having. Are they strategic or tactical? Or maybe more relational. - how much time do they spend doing any sort of deliverable work? - how do they take notes or set reminders? - how frequently is their admin with them and what sorts does the admin NOT handle? - how do they deliver corrective feedback? - how is their time divided between strategy, finance, and people?

Then observing those things would lead to lots of questions.

Also, I would ask who they would pick to lead the company if they retired tomorrow.

The most important insight to have going into something like this is that there’s absolutely no guarantee whatsoever that the CEO is good at his job, or that any given thing you observe should be taken as a positive example.

By definition there is something he is doing or has done that is exceptional, but he may be succeeding in spite of many terrible habits or behaviors.

With that in mind it’s a guarantee that you should be able to learn quite a bit from spending time observing.

But don’t fall for a classic beginners mistake of assuming that because just someone is successful all of the things they are doing should be counted as causes of that success.

I have had a few times, the experience of being all the working time and extra-time together with CEOs of different businesses, in different countries, and I have met some wealthy people on this "job", I wont risk saying amounts, but probably only one or two of them has more value in companies than the 25 mi you describe. I have met, in few days meetings, or one-time meeting, people with an order of magnitude, at least, the value you mention in personal wealth. In my case, I was regarded as advisor, right-hand, "friend" and "partner", and to this very day some of them are still sending me messages to ask me to go back to work with them. I have concluded its all just delaying me in starting my own company, and I ignore everything now, literally eat Ramen noodles, and focus on my programming project, that I have been delaying for years, despise all close people calling me crazy, when they see people driving a million dollar car knocking at my door and I say I don't have time, send them away! and they know I'm eating noodles just, I will keep on the field I choose and I believe is the one for me to make money, even with zero experience in this field besides a half-complete toy program, and having years of experience and sizeable knowledge in other profitable fields, in the end I have to do what I believe will make me my Own money, and is better to start my own business, otherwise one can spend his life helping other peoples' business.

If you want to contribute/bring value, learn as much as you can about the company. Why are things structured the way they are? What needs to happen for the company to be successful? What things are that way “for a good reason”, and what things have just “always been that way”?

The most valuable thing you can bring to your CEO friend is a trusted outside perspective on his company. Go in with humility and an open mind.

As far as getting the most out of the opportunity, there are 2 big takeaways I would look for:

1) Learn all about the types of work required for the job. If you’re early in your career, it’s good to try lots of things and see what sort of work you enjoy (even if you want to own your own company, you’ll want to know what sort of work you’ll want to bring in help for).

2) Meet as many people as you can! I believe that a huge part of the compounding “interest” of career growth is in relationships built. If you’re shadowing the CEO, that gives you lots of access to other executives (but don’t count out anyone at any level - everyone you meet can teach you something!).

Build your network by making good relationships with the people you meet. Who knows? You may meet a future co-founder there. And if not, the people you meet may be able to make good introductions: “A” players know other “A” players. Invest in the relationships with the A players.

Finally, you should be on the same page with the CEO with the direction or outcome of the internship. Are you looking to land a job at this company? Do you want an introduction to other opportunities? If your CEO friend wants to help you, make it easy for him by letting him know exactly how you want to be helped.

Good luck!

There are many things that he wouldn't know because he gets presented a filtered view that makes his direct reports look better

1/ how processes actually work (theory versus reality)

2/ inefficiencies (wasted time/wasted money)

3/ opportunities (to make more money/save money)

4/ If people are actually happy or just saying they are

5/ If his middle management is any good or not

6/ People at risk of leaving

7/ Training issues (people asking how things work who have worked there a long time)

8/ Attitude issues (laziness, turf wars, "it's not my job", shoving problems to somebody else)

9/ Surfacing ideas from people dealing directly with clients or the actual work (skip-level reporting)

I think that your time commitment is too low to really get into it but given that's the time you have I would start at the bottom to gain trust and neutrality and work the way up. You need a credible "role" that would make people open up to you but where it would make sense you talk to everybody (e.g. MBA student from a business school doing an internship and associated dissertation).

I wouldn't return value to the CEO until you stop the experiment because the moment you communicate it, things will change and you lose neutrality and trust.

This is a great opportunity, I'm excited for your inevitable professional growth from doing this.

To help my own professional growth I have now shadowed 5 CEOs for 1 day each and have found it the highest ROI growth/training exercise I've done.

I have a doc that provides lots of advice, templates etc feel free to use and share: https://goo.gl/BJ8GTT

My general pieces of advice

- every CEO is different, so do this 1-2 times a year to gain a breadth of insights

- take advantage of lunch time and the few mins between meetings so that you can ask follow up questions from your observations

- to add value back to the CEO you're shadowing, summarise your observations of them and their business

- talk to 3-5 employees (all levels) to understand from them what makes their CEO great and what they could improve on

- you'll gain lots of insights into how to run a startup, culture learnings etc so don't limit your learning to just CEO insights

Feel free to contact me if you have any questions.

Timbo

How many people can find 5 CEOs to shadow 1-2 times a year?

To be clear, my recommendation is to shadow 1-2 CEOs a year.

People who live in silicon valley can probably do it easily. I was there for an interview a few years ago and met 2 CEOs just at the local bar.

What are some of the bullet points you've learned here?

I learned a ton from working for other CEOs, which put me in a great position to see what to emulate and what to ignore.

I'm having a hard time understanding what can really be teased out of watching someone do a day's CEO work for 4-8 hours, so curious what you have personally taken away.

(PS - I am going to give this a try because I do think it can be valuable, but I feel like you'd need to go in with a mindset that you shouldn't just blindly copy others)

I searched the comment thread for the word "notepad" and found nothing...

Bring a couple of notepads and pens and take notes relentlessly. Stuff that you think you'll remember later is likely to slip away very quickly if you don't write it down. When you have notes, it is much easier to recall other details.

There are several drivers for human behavior in an organization (e.g. compensation, satisfaction, loyalty, etc.). According to Simon Sinek's "Start With Why" book the most powerful driver is having a common sense of purpose. A bigger goal that the organization wants to achieve and that defines WHY they to WHAT they do (here: fresh produce).

I think getting to know the "Why" and finding out how the CEO communicates, establishes, and motivates people towards the "Why" is a valuable lesson. It imagine it to be very hard given the limited time you will be spending with the CEO, but since you are in an established relationship with them, it could be easier to get to the point in conversations.

It's a great opportunity that you have there and I wish you the best of success in your shadowing.

Thank you! I will also check out Simon Sinek's book.

The challenges of starting a company are different form the challenges of running/growing a $25 million dollar company. That being said, you will still learn a lot from shadowing him.

I think you have a few options: a. Shadow him. This in itself will be fairly useful.

b. Shadow him plus. If you want to do this, I feel like offering to potentially sending him an end of month report later-on on a particular aspect he wants might not be a bad idea. To do this well, you might want to spend 25%-50% of your time in meetings where he is not there depending on the report topic.

c. Offer to help on a top strategic initiative of his - This is personally what I would do. You will have an awesome project under your belt and will learn from the experience.

d. Work for him - If he is paying you he will likely want you in a specific role. I feel like this might be the least helpful to you in the long term.

A lot of good advise here, I think that even though you want to be helpful and useful your best bet is to be seen and not heard. People are going to behave differently with you there already, don't "taint" the observation by reminding them you are there. Also I saw one of your comments about wanting to help, possibly the sales team. I'm sure you are coming from a good place but I really think you would be best off just giving a "report" to the CEO at the end with anything you've noticed rather than trying to jump in and help.

Thank you! Any suggestions of useful topics/notes that I should track of to include in a report?

Disclaimer: I don't know you, your personality, or work ethic so please don't think I'm trying to be condescending or think you don't understand basic social norms, I'm just trying to cover all the bases and make sure you don't slip up like I have or have seen others do in the past.

It's a little hard for me to say not knowing the full situation but given you are friends/friendly with this CEO some level of constructive criticism or inefficiencies that you see. It's important to temper that advice and make sure if come across as "here is what I saw" and not "here is what you are doing wrong". Remember, your advice might not be new and they may have already attempted or researched some of your ideas and found them lacking. Just don't go in with a know-it-all attitude, be gracious and potentially hold back any criticisms until asked.

Also I would make a point to write down and convey to the CEO things you see that are being done right/efficiently. This will help balance out any issues you report and, to be brutally honest, make the CEO feel better about letting you shadow them. You don't have to brown nose but don't be a negative Nancy either.

It's going to be hard to for me to give you "useful topics/notes that I should track of to include in a report" because I just don't know that industry and frankly if I were in your shoes I would just go in with a blank slate and record everything I saw/heard of note then try to reflect on what I've recorded at the end of the day instead of looking for specific things.

Best of luck to you and I hope it goes well. I'd love a followup (not with any specific details necessarily) about how it goes!

This is awesome, thank you so much! I will definitely follow up.

You can also stop kissing ass and start your own thing, making mistakes is part of the process, you learn by doing, not by "shadowing" someone successful. Just be a human being , if is your job to br the guy's assistant and you like this kind of role, enjoy! But if what you want is to become someone like him, go out and do crap. Your naivety is your greater weapon. Just be a human being , no someone's pet/servant.

I appreciate that and I totally agree. I haven't figured out quite yet what I want to do, and thought this would be a good opportunity to learn while I'm sorting things out.

I was CEO of a small startup until recently, and then I stepped down (one of my other co-founder took the CEO role).

It was a tough moment for me, and I am still wrapping my head around things that didn't go as intended.

What do you think are the most important traits of an early stage startup CEO?

And, if you live in the Bay Area, would any experienced CEO reading this willing to spend an hour with me to help me review the feedback I got, and my story? It would be really helpful.

I would make your request to sit down with another CEO a separate Ask HN, so it does not get lost. Good luck!

I wouldn't say I'm an experienced CEO but I'd be interested in sitting down to review your feedback over coffee or beer or whatever. My email is in my profile.

Mastery is a book that talks about this concept of mentor-apprentice I strongly recommend this book for your case.

Mastery by George Leonard, right? I've read it before and still have a copy that I will reread.

I strongly suspect they are referring to Mastery by Robert Greene

I would focus more on learning the industry than learning the CEO. The CEO's choice of lunch or idiosyncratic work habits matter less than the ton of insider knowledge that you'll get in the specific area that they work in.

I’d try to treat it as an extended interview for a chief of staff type position, if that’s what you want. Find ways to help this CEO, don’t just randomly attend meetings, which sounds totally useless.

For those who have no clue like me, what does shadowing mean/entail?

It entails sitting in on meetings, following the CEO around during his day to day work and seeing how things generally run at a company this size. He has allowed me to sit on meetings/calls in any department so I will probably be switching between being with him and the sales team.

It would be akin to being a fly on the wall.

More specifically following, and learning from a person doing their work. It is used widely in the medical field among medical students when referring to shadowing a GP for a week for example.

An idea would even be ask the CEO you're shadowing these questions. Surprised no one has said that yet.

great attitude, but is shadowing also interning? Intern add value, but if you are shadowing - that implies being seen/never heard.

Seems you could get more value and give more as an intern. never too old to intern!

Everybody else has some good advice here.

But for me, if I were in your position, I'd only want to learn the answers to 3 simple questions:

1) Tell me about your first sale in this market, and all of the circumstances surrounding it.

2) How did you get that first customer?

3) Before you made that first sale to that first customer, what was the set of problems you realized or experienced that led to the value creation that resulted in that first sale?

In other words, what's the inception point of this $25 million dollar company?

The answers to those simple questions should answer a lot...

Bonus Question: What was the toughest problem you faced in getting this company to a $25 million company, and how did you solve it?

I'll bet that will open up a great discussion!

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