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Situation I'm a PM (Product Manager) currently working in a small startup (15 people) where we have about three developers, one of whom is the CTO (call him Bob). Bob drives the technical aspect of the product (not very surprising) and contributes a lot of code and created the initial product themselves.

Bob likes to work out of the office typically and maybe comes into the office for a couple of hours each day. Furthermore, there are some days when he is completely absent. We try to communicate through Slack or WhatsApp and I try to gain some understanding what is being worked on so I can understand any roadblocks and what should be next.

The problem is that, more often than not, he will make product decisions and prioritize product features / timelines without telling anyone. Often times, I learn about something new either when I inquire about a surrounding issue or when I see it in the product myself.

We are in the process of building a roadmap so there is some cohesiveness but he is slightly averse to it.

Question How can I communicate effectively with the CTO and get a better understanding of the decisions they are making and the path they are taking?

Thank you!

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    Is Bob essentially unsackable? I'm guessing "yes", which makes this harder.
    – Philip Kendall
    Jan 23, 2019 at 7:19
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    Why woud you sack him? If the CTO is competent and delivers, the problem to be addressed is the process, not the quality.
    – Czar
    Jan 23, 2019 at 7:43
  • The CTO is definitely competent and does deliver. The main issue is communication or lack thereof.
    – anonpm
    Jan 23, 2019 at 7:51
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    You say the CTO is "slightly averse" to the building of a roadmap. Do you feel he supports you and your role or do you feel he regards your efforts as superfluous?
    – Daniel
    Jan 23, 2019 at 9:09
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    The "slight averseness" to have a roadmap looks to me as a yellow-ish flag, like Bob doesn't want to completely stick to a plan because that would hinder his power to decide random changes/features/timelines without telling anyone. I would try to make sure that this is not the case.
    – busman
    Jan 24, 2019 at 15:11

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Bob likes to work out of the office typically and maybe comes into the office for a couple of hours each day.

Ignoring the odd day where he's absent, this gives you a couple of hours window each day to grab him and keep up-to-date with any changes he's made. Make the most of that!

It doesn't need to be a long chat, just a case of "Hi Bob! Just wanted to check you're still working on x, or have there been any other priority shifts / new features that have come up? Any other updates at all, or anything that'd be helpful to have the other guys take on?"

That might prompt a response saying "same as yesterday", or if things change frequently, you might get a "Ah yeah, I'm now working on y feature because Mark requested it so that's bumped up in priority. If you could get Alice to work on z, that'd be really helpful." Either way, it should keep you up-to-date and in the loop.

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    even make it formal, organise a standup meeting every day for when he is there, with the whole team, this only need be 15 mins long
    – WendyG
    Jan 23, 2019 at 9:40
  • @WendyG Absolutely, that's a great suggestion.
    – berry120
    Jan 23, 2019 at 10:10
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    Great! Thank you Berry! I tried this yesterday and it worked well. I'm going to make a habit of this and take copious notes when he speaks.
    – anonpm
    Jan 24, 2019 at 6:09
  • @anonpm Awesome, happy to help.
    – berry120
    Jan 24, 2019 at 9:12
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Tricky situation. In the hierarchy he is your superior as CTO. On a functional levle he is your subordinate as engineer. You need to manage him, where it concerns your product, but you can´t play on any authority over him. So you need his buy in, to support you in your role.

This is called "Managing up" and there are a lot of books and articles for you to read up further.

The main points are to:

  • Make it easy for him, offer a benefit. If he knows things run smoother when he keeps you in the loop, he will do it.
  • Ask him for support. As you have no leverage to command him, you have to ask him to help you out with the collaboration you need.
  • Stay constructive. Sometimes you will have a disagreement. If you can´t get your way sometimes it´s better to take what you get and do with it what you can. Don´t create a big fuss and risk loosing his trust. Better to state that you would prefer a different approach, but accept his decision.
  • Open communication. If he is creating problems for you, let him know how he could support your better. If you have information relevant to him, pass it on. Try to get at least a small informal face-to-face talk of 5 minutes with him.

Links:

About Managing Up - Online Article

Tips for Managing Up - Online Article

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    I wasn't aware that this a thing! Thank you for sharing these links!
    – anonpm
    Jan 25, 2019 at 11:05
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How can I communicate effectively with the CTO and get a better understanding of the decisions they are making and the path they are taking?

Schedule periodic meetings with the specific goal of going over the decisions regarding the technical aspects of the project.

The meetings could be weekly, daily, or whatever frequency is appropriate. And the could be in-person or over the phone.

Provide an agenda to make the best use of your time and his. Keep notes, and distribute them or publish them to the project website.

This may also help with building the roadmap.

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