[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?

[Cpoll]

> 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.

[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.

[eddieroger]

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.

[pboutros]

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!

[realrali]

Makes sense, thank you!

[tyingq]

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.

[benhiro]

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

[realrali]

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.