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.

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

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

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.

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.

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.

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

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?

> 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.

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.

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.

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.

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!

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.

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.