Episode 222: Cowboy CTO and underpaid after promotion


In this episode, Dave and Jamison answer these questions:


  1. Hey, long time fan of the show!

    Our current CTO came in as the result of a merger. For most of his life, he was a solo developer and owned his own company.

    The struggles we are facing now are:

    • He is not responsive at all, neither via chat, nor email, nor any other communication tool.
    • He often says “I’ll do it” but then takes weeks to finish
    • He has thousands of unread emails in his inbox
    • When he writes tickets, the details are unclear for others
    • He codes way too much for a CTO, in my opinion, and his code is a bit messy compared to the other developers

    Since he is a really nice person, we all want to give him feedback that makes him understand his role better, and to avoid being a bottleneck.

    I know that changing another person is hard, but at the same time I know that he is motivated to become a good CTO.

    How do I help him?”

  2. Hi. I’ve only recently discovered your podcast this quarantine, and it’s been really helpful at work already. So when I was faced with this problem, I immediately thought of you!

    I have been a professional software developer for just over a year and have received great feedback from my manager and team. During my performance review, I asked what I would need to qualify for promotion. I got the news that I had already been recommended for a promotion!

    Meanwhile, a friend still in university got an entry-level job offer from my company that pays more than I would make if my promotion went through. Where I come from, there are no negotiations when companies recruit at universities, so it’s not a matter of them negotiating a better deal.

    If the promotion does not come through I have no qualms trying to negotiate. If the promotion does comes through, would I come off as ungrateful if I bring this up? Am I asking for too much by wanting to be paid more at a higher position than what a new grad would be paid at entry level? I know it’s not an ideal world and I feel greedy as I type this, but I just want to be compensated for what I think I’m worth. I also think that it also comes down to my ego at some point. SEND HALP

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