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I am the software lead of a startup which while not struggling, is repeatedly missing goals and commitments to clients. Much of this can be attributed to our CTO.

Some background on her. She is one of those startup founders with a computer engineering degree who never worked any job other than this. One consequence of this is that she has never written code professionally beyond the very beginnings of this company. When she did, she did all her edits in production, didn't use a web framework, didn't know about unit tests, did not know about logging, didn't know about SQL injection, etc. The only non class software project she has ever worked on is this. She makes up for it in sales and leveraging the woman in tech factor.

I was brought in after the first investment to professionalize the software because it could often crash for days on end without her noticing or being able to figure out why and clients were obviously unhappy (and I think the only reason those contracts kept us is because our clients are in a less than flexible industry). I now lead a team of 4 devs.

Here is the core of the problem. We have it so that she needs to approve every feature that goes into production, especially since she often has a role in it, such as writing the text which goes there. Problem is, she just isn't doing it.

We have a substantial number (representing months of effort) of features sitting on Git branches because she keeps promising to review them and just never does. Plenty of bug fixes are stuck in the queue as well.

For example, one thing we wanted to do was implement some kind of logging. It has been stuck in "review" for two months. All the code does is send text notifications when there is a 500 error to the on-call dev (we have a phone we pass around for on call support). Instead, the dev must check the log periodically.

This one is not client facing, just a tremendous waste of developer time. However, plenty of client facing issues are also never resolved. We have one client who wanted to download a table to CSV. She sent the feature request to us, we built it and tested it, and for weeks has sat in the review queue. The client keeps bugging her and me about it.

Another problem speaks to her tech inexperience. Whenever she personally spots a problem, she begins debugging in production. When she inevitably can't find the problem as its written in a language she has never used (I threw out the entire tech stack when I arrived), she calls us.

We use proper tools to debug the issue, but it can easily be days before debug in production is turned off as it must be added to the bug fix and the bug fix must be approved. That is currently the case. Anyone who breaks the site somehow right now can see the IP address of our database server, database names, the libraries we use along with version numbers, and piles of other info. We did a fix on Thursday and she was supposed to review it that evening. It has still not been done despite repeated reminders.

Anyway, a couple days ago one of the major VCs invited me out to lunch this weekend and I accepted. News of all this apparently reached one of our major investors and apparently she is promising him all manner of things and not delivering as well. He straight out asked me if he should replace her.

I declined to answer, saying that it was not my place. But he is insistent on getting my opinion for some reason and wants to have dinner tomorrow. How should I handle this? She clearly needs to be made to step away from the code at least, but I also don't see it as my place to say anything. I don't think she needs to be fired, just moved to a domain she cares about (doing the networking events and women's galas) and away from one she has never seen as more than a burden.

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    Comments are not for extended discussion; this conversation has been moved to chat. – user44108 Nov 13 at 8:42
  • It sounds like a very hierarchy driven place. Does your team expect you to start changing any of these things? – Stefano Palazzo yesterday
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You don't know how your opinion will be portrayed. So, you are right so far, do not pass a direct judgement/opinion. Instead, stick to the facts. Instead of talking about someone in particular (finger-pointing), talk about problems and possible ways of improvement.

If you're asked whether you want her to be replaced, you can take the following approach to answer.

  • List the problems you and the team are facing now and what has been done to overcome that.
  • Point out the cases where you needed help/approval in a timely manner and because you did not get it, how it affected the delivery/commitment.
  • Finally, mention that having some additional help might solve the issues and speed up the delivery process.

Let the higher-ups make the call: whether to replace her or to assign other responsibilities.

If they insist on getting your opinion, you can say,

Based on the facts and current situation, I can surely say any help which enables us to level up the product quality and to deliver on schedule is more than welcome. However, in which form that help needs to be formed, I leave that to your best judgement.

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    "You don't know how your opinion will be portrayed." That is one of the things I am worried about. Is this a loyalty test? Am I also considered to be part of the problem? Problem is, I think he seeks a yes or no answer. SO just keep declining to give that? – FireMyBoss Nov 12 at 7:53
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    @FireMyBoss, No, it's not a loyalty test. This is not a government job. This is a startup. And a VC couldn't care less about loyalty in a startup plagued with technical problems. – Stephan Branczyk Nov 12 at 8:20
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    Yes, this. "Stick to the facts" is almost always a good approach in conflicts. Report the facts you know, and let everyone come to their own conclusion. – sleske Nov 12 at 8:44
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    "Hey, do you think we should fire Nancy?" "I'm not going to answer that, but here's a giant, totally unrelated, list of problems that we currently have under her lead." That's not throwing her under the bus at all – Mars Nov 13 at 1:42
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    This answer doesn't suggest sticking to the facts. This answer suggests presenting a subset of the facts that paints the boss in a negative light. OP may not even be aware of the details of the facts that paint her in a positive light. – Mars Nov 13 at 1:47
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You mentioned that she performs well in sales and as the face of the company. At the same time she is not the right person (anymore!) for development.

So the company has a high profile employee that currently has the wrong task for historical reasons but has important qualifications in another area.

If she started to develop the product, I guess she is still under the impression that she has to control everything and has not learned yet to delegate tasks and to trust other people. Not really surprising for a Techie as founder.

So the task is not to fire her, but to help her (e.g. with coaches) transition fully into her sales role.

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    No. I am serious. Show her (especially with data) that the delegated process is faster and safer and convince her to trust her employees. – FooTheBar Nov 12 at 12:25
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    You can also have a conversation along the lines of "this kind of low-level debugging and bugfix approval is beneath you as CTO, you need to be in the high-value roles of strategy, networking, building the brand, blah, blah." It plays to their ego, while at the same time hopefully prompting them to step-back from the areas in which they are in the way. – Phueal Nov 12 at 17:13
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    You could also tell the investor her strengths, then emphasize challenges you face on the development end. If the VC has heard enough to even suggest something of that nature, the things you could tell them would be nothing new, and would let them decide as to where the problems lie and the actions they should take. – Anoplexian - Reinstate Monica Nov 12 at 17:50
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    @Phueal not "beneath you" per se. Make it clear that her supervision on this small of a scale is not needed and takes time and energy away from important things. – xyious Nov 12 at 21:31
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    This is an answer to the question of "what the investor should do", not "what OP should do". OP is not in position to decide what role his superior would take in the future. – dbkk Nov 13 at 4:39
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The question isn’t what the company should do, but what you should reply to a major investor. Not the same thing. So take my reply as “what you should say” not “what the company should do”.

Of course she shouldn’t be fired. She is doing an excellent job in sales. But you don’t think she is quite the right person for her current position. She is not a very technical person (don’t say ‘can’t program her way out of a paper bag’), and her being deeply involved in the development process slows things down, mainly because of her other responsibilities. She doesn’t have time to review changes, so you have a few months worth of changes that are ready but waiting for her, which would be much improved if she focussed solely on sales. And with purely a sales role, she wouldn’t have to debug problems on the production server anymore, but leave it to more experienced developers. And then you wouldn’t have to undo her changes anymore.

See, you don’t have to say anything negative about her. Point out her strengths which unfortunately lie elsewhere.

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A general rule to work by at this level is 'Pass information up, pass decisions down'.

Give the investor your fair opinion of the CTO. Don't lead them into any decision you might want, or let them lead you into agreeing with their decision. Pass your information up, and let them pass a decision down - it's rarely correct to pass a decision up the management tree.

Going only from your information, it's pretty obvious that the company would be better off if she were out of the direct line of development; but it's also obvious that she's a great asset to the company. Hopefully the investors will see the same thing, and move her sideways and you up.

6

There's people, and then there's politicians. There's no difference between them, other than that politicians talk about policies. But anyone can talk about policies, hence the saying that everyone's an expert in football and politics.

Up until now, you've been a regular folk, but the moment you answer anything to that investor, you're a politician. Just like the investor, and just like the CTO.

You can just insist it's none of your business, and stay away from the politics. If the investor is sane, nothing wrong can come out of that.

You can also start playing politics, but then, there's good politicians, and weak politicians.

A good politician has goals, leverage, and a contingency plan.

You clearly want the CTO, out of its current role, that's your goal. A better goal would be to support someone else for that position, maybe you?

If you believe you cannot be fired, or not easily fired (by the CTO, or investor, or any of their friends), that's leverage.

But what's your contingency plan? What do you do if the CTO finds out, and fires you? What if the investor asking you is just a set up of the CTO? What if it's not a set up, so the investor decides to fire the CTO, and you, because you're not the loyal kind? Do you have the means to move on fast? If the answer is no, and if I'd be you, I'd keep my mouth shut.

There aren't enough details for anyone to tell you exactly what to do, but based strictly on what you described, I'd guess going with your raw, original instincts, and refusing to discuss the matter with the investor is the better approach.

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    I don't totally agree with this -- you can talk to the investor without being a politician. In that case you're more like, a tool of the person you're talking to. That can be fine, if you think they are aligned with your goals / will help you with your problems, and you don't actually want to be a politician. It's always possible that might get screwed, but that's something that might happen anyway. This doesn't read to me as a situation where the investor is trying to screw you. They're trying to get support/evidence to screw the CTO, more likely. But it sounds like the CTO is a problem. – Glenn Willen Nov 12 at 19:38
  • @GlennWillen If you have goals that can be aligned, you are doing politics already. – Andrei Nov 13 at 9:35
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Is the CTO good for her current role?

If the CTO is mired in detail, becoming a perpetual bottleneck and consistently missing her commitments then this sounds like a No. CTO's normally have a much more strategic focus on evolving the tech stack, reducing risk, designing and building new enabling technologies and technical and architectural standards. Also I'd argue that if you develop and test your code to an agreed definition of done (including all acceptance criteria) then why wouldn't you release via CI/CD tools through the SDLC. Relying on one person to release every feature (especially if they're not a Product Owner) sounds like madness to me.

Is the CTO good for the organisation?

Since the CTO is a co-founder and you've mentioned that she has strengths in other areas (sales, events etc) it sounds like she could certainly be of value to the organisation. So it could be a classic example of good person who's not in the right role. I'll temper that by saying if she has difficulty in delegating tasks, managing priorities and managing expectations then I would personally be hesitant in offering her a senior role unless I was confident that those shortcomings could be overcome and/or any related impacts minimised.

Is it appropriate to discuss the CTO with a major VC?

Personally I would not be inclined to discuss operational matters with any director unless an executive was aware and had given the discussion their "blessing". Even if the discussion took place, I would be very careful to keep statements factual, constructive where-ever possible and try as hard as possible to keep any personal bias out of it. It's much better to find a better fit for someone that enables them and the organisation to improve their performance rather than turf them out. And unless you know the VC personally, you have no way of knowing if and how any statements will be used. So I would be inclined to treat the conversation as a peer review. But the reality is that this sounds like more of a Management decision first (wrt the CTO's work performance) and a board decision second (wrt the CTO's role as a Founder).

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