
Ask HN: How to shadow a CEO? - realrali
I have the opportunity to shadow a CEO&#x2F;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&#x2F;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.<p>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&#x2F;recommendations?<p>Thank you so much in advance!
======
austincheney
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.

~~~
fanzhang
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?

~~~
austincheney
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.

------
petervandijck
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.

~~~
wraithdroplets
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.)

~~~
ZainRiz
Link: [https://hbr.org/1976/03/how-to-run-a-
meeting](https://hbr.org/1976/03/how-to-run-a-meeting)

------
confiscate
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

~~~
paradoxparalax
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".

~~~
speedplane
> 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.

~~~
NewsAware
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

------
wallflower
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!

~~~
realrali
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?

~~~
mft_
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.

~~~
realrali
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.

~~~
crazypyro
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.

------
ChuckMcM
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!

------
subfay
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.

~~~
bergerjac
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.

~~~
paradoxparalax
>"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.

------
no1youknowz
> 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](https://www.youtube.com/watch?v=mNDA-o9yJNw)

~~~
pitt1980
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)

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

~~~
CyberFonic
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.

~~~
timwiththebo
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.

------
ohitsdom
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.

~~~
realrali
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.

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

------
edw519
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.

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

------
jaxn
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.

------
CPLX
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.

------
paradoxparalax
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.

------
dkokelley
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!

------
cynusx
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.

------
timwiththebo
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](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

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

~~~
sombremesa
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.

------
forgotmypw3
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.

------
danrl
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.

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

------
vineet
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.

------
joshstrange
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.

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

~~~
joshstrange
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!

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

------
ugly_but_honest
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.

~~~
realrali
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.

------
simonebrunozzi
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.

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

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

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

~~~
arikr
I strongly suspect they are referring to Mastery by Robert Greene

------
speedplane
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.

------
rajacombinator
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.

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

~~~
realrali
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.

------
kernx16
An idea would even be ask the CEO you're shadowing these questions. Surprised
no one has said that yet.

------
mapster
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!

------
peter_d_sherman
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!

