Ask HN: How to shadow a CEO?
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!
86 comments
[ 2.8 ms ] story [ 116 ms ] threadAlso, 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!
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.
Taking a role in meetings could potentially create a lot of awkward power dynamics between you and the other executives, in my opinion.
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.
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.
> 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?
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.
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.
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.
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!
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!
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.
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.
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.
Why?
You may think something happened based on your surface impression of what just occurred. The CEO may view it completely differently based on:
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.
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.
You can sum this up with simple advice... be curious.
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.
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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
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 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
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.
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?
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
This isn't true at all. Socializing is important for gaining trust, but the real work still happens in the office.
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.
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.
> "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.
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.
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!
If you can, attend meetings with the CEO with the goal of observing these things;
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!
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
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)
Seems you could get more value and give more as an intern. never too old to intern!
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.
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.
- 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.