First off be honest and tell the COO right up front that you build a competing solution and want to meet for a specific reason. If it means having discussions with the CEO then so be it.

You are both in the trenches. So in a sense you are frenemies.

As a 3x co founder and career startup guy, don’t waste your time or theirs.

CEOs all have the same problems for the most part and if they seem open to discussion after disclosing who you are then have a gameplan.

Otherwise why did you reach out? To play spy games? You win by being better or offering something mutually beneficial.

Don’t beat around the bush and play mind games. It will bite you in the ass later if either of you are around long enough.

Not always, but here are some signs to look for:

- Are they experienced in raising capital? Have they had success in past ventures? Or first rodeo?

- Have they offered you any paperwork that explicitly outlines the agreement? ex cash for hours

- What research have you done on your part with the solution in the market?

- Have they pitched to you how and why this will be a success?

Great question!

From experience, list out what you are looking to achieve based on a few example use cases to narrow down the solution:

- Have you sent a quick Q&A to your existing customers asking them you are looking to run a pilot program for this community based solution?

- Does the engagement need to be in real time? This may point to more of a topic based Q&A solution like a forum (such as reddit)

- Are you expecting this to be self moderated or will you be promoting the channel (host live Q&A’s with other companies/teams/internal?)

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I would start with a test for sure and run it for 6 months or so as a trial run to get some feedback. Something free and something that you can ask your users if they are on before going gung ho.

All of the options mentioned are excellent, but I think you really need to see what your clients really want from community based engagement.