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The CEO in the small startup encouraged me to work on the valuable and interesting project the company needs but asked to discuss it with CTO first because "he worked on that on the past". I really want to get this project but have some concerns that CTO may not be equally supportive - it is taking over his former project that he did not finished (regardless of the reason) and there are other people in the company after this project (once it has been taken away from me before I even started, I do not know who and why decided, that I see now is a hope to get the project back to me). The startup is small enough (just few people) so that all members of it have complete understanding of all technical details. I have prepared a short document/presentation that should convinced I have many useful ideas on how to implement the technical side.

I have at least four options:

  • Approach the CTO directly and and attempt to talk. This would be the most direct approach but he may end the conversation with some vague "I do not think this is a good idea" before me presenting all arguments.
  • Write E-mail. This would allow to attach the presentation. While the CTO may still opt not to read, this seems less likely.
  • Call for presentation involving CEO and CTO and draw the proposal on the desk board.
  • Simply start working on the kind of assigned task. Present when I already have some demonstrable results.

Anything else? I really want this project and I am sure I can do it well.

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Treat your CTO as a resource you can use to help you, not as an annoyance to avoid. You seem very reluctant to discuss this with the CTO, but that seems a bit short-sighted to me:

  • Unless he has some form of power complex or plain doesn't like you, then he wouldn't have any reservations about you taking over a project he started but didn't finish for that reason. If anything that'd be a bonus. If someone came to me with a similar proposal, I'd be all too eager for them to pick up where I left off and get it finished! Unless of course I knew something that they didn't, in which case:
  • If he's been down this road before, he'll be able to offer valuable insight into challenges he came across, why he stopped working on it, and tips he might have for you to get the project going again.
  • If he's the CTO, and therefore presumably more experienced than you from a technical standpoint, he'll be able to offer advice (regardless of the fact he's worked on this before) just from the perspective of being more experienced in the field.

If it were me I'd email and ask to set up some time for a meeting or a call where I could run through ideas / notes that I had on the project, and take it from there.

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I think you are overthinking this - the facts that the project is "valuable" and the company "needs" it and that the CEO is effectively sponsoring it will likely insure that it happens.

Approach the CTO directly and and attempt to talk. This would be the most direct approach but he may end the conversation with some vague "I do not think this is a good idea" before me presenting all arguments.

If you took this option I think the above would make it unlikely that the CTO would attempt to disuade you from doing it - and even if he does respond with your feared "I do not think this is a good idea" then it doesn't really change anything - the CEO has asked you to work on it and you could just carry on.

Write E-mail. This would allow to attach the presentation. While the CTO may still opt not to read, this seems less likely. Call for presentation involving CEO and CTO and draw the proposal on the desk board.

To be honest this is probably what I would do - although I would tweak this slightly; send the CTO an e-mail outlining that the CEO has asked you to take this project on and to get his opinion. Attach the presentation and ask when would be a good time for the two of you to meet and talk about the project.

Call for presentation involving CEO and CTO and draw the proposal on the desk board.

This is overkill IMO, the CEO has delegated to you what he wants you to do, dragging him into a presentation with the CTO doesn't serve any purpose in my mind.

Simply start working on the kind of assigned task. Present when I already have some demonstrable results.

Not a good idea - the CEO asked you to discuss with the CTO first, at the moment the CEO's support is the key thing you have going for you and ignoring his request is a bad idea.

Anything else? I really want this project and I am sure I can do it well.

It sounds to me like you already have it! Go forth and kick a##! As a final note of advice try to stop seeing the CTO as your enemy - you're both on the same side here, you want to do the project, the company wants to do the project. Don't go looking for conflict where it doesn't exist or you'll end up creating it.

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Your CEO has asked you to discuss it with the CTO first (worth bearing in mind - CEOs don't really "ask". This is an instruction.). This limits you to the first suggested approach, but there are different ways to go about it.

You could go directly to the CTO and raise the subject. You could also start with an e-mail to arrange a time to discuss it, for example :

Tom; Eric asked me to look into X project again. I have some ideas how we could implement this. When would be a good time for us to talk this through?

That way, you're not going to blindside the CTO by starting a discussion without him knowing the instruction came from the CEO. You're also approaching it as a request for advice, which is how the CEO suggested you play it.

If the CTO does not think it's a good idea, this is something you could (and should) report back to the CEO, giving the reasons the CTO gave you why it might not work out as planned.

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  • Thinking your way, this eliminates the last approach only. Others are along the lines "discuss with CTO"
    – eee
    Commented Nov 9, 2018 at 9:43
  • @eee - Kind of, but while the second works an an invitation to a discussion, attaching the presentation at that point might look premature. The third might work, depending on your company culture, but if I was the CEO I'd be surprised to be invited to a presentation on something I'd asked you and the CTO to discuss. If I was the CTO, I might think it was a set up. But you could play with the third in your discussion with the CTO, and ask him to arrange a presentation with the CEO. Commented Nov 9, 2018 at 9:51

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