Ask HN: How to communicate CTO is not suitable for job to non-tech audience?

2 points by notechthrowaway ↗ HN
Hi there HN,

I work for a non-tech-focused small business that has grown from 50 to 75 people over the past year. Our CTO (title inflation) has always primarily been in charge of infrastructure but much out of it is outsourced and she primarily handles tickets and on-premise gear. Support requests go unanswered, other users assume tech support in order to keep things running, and things break constantly. Without getting into too much detail, a good recent example is a work stopping, critical outage a few months ago where she did not communicate with the firm at all, and no resolution timeline or post-morterm was provided.

This has been barely tolerable over the years but she is not the right fit for the growth of the business. Additionally, she is not involved in the development process at all and this has proven frustrating for recruitment (candidates are confused by hierarchy/red flag) and coordinating on infrastructure needs; developers need to do a ton of work before they can even start writing a single line of code. There's an additional worry that developers are going to get pulled more and more into supports needs given that the person in charge of support lacks the technical ability to do so.

The audience I want to communicate with lacks a technical background, has a very hands off management style, and a pretty short attention span. I want to illustrate that this person is not the right fit for the growth and future of the firm and that they introduce a ton of friction into several teams actually just getting work done. Without overwhelming people, what is a good way to communicate this in a concise, non-ranty manner?

Edit: To be clear, without going into a ton of detail, I am very confident that this will not blow up in my face and that leadership is just not aware of pervasive these issues are and how large the spillover efffects are. I just want some advice on how to properly communicate with this particular audience in a way that they will understand. I won't have multiple opportunities to bring this up without coming off like I have a grudge so I want to make sure the first time is properly handled.

10 comments

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1) Consider first the possibility that this is not a problem you can fix, and you may have to either live with it, or leave the company. Attempting to get the CTO removed from their job, will typically (if it doesn't work) get you removed from your job instead. If it's that bad, perhaps it would be better to just start job-hunting.

2) It is possible that the CTO doesn't care, but it's also possible that they care but just don't know what to do about it. If the CTO had an assistant who was good at managing things, they might be willing to let that assistant do the things they aren't. Convincing the CTO to get an assistant to manage stuff like support requests, infra needs, etc. might fix the problem. She may also be actually good at very high level stuff you don't see, like for example relations with other CxO's, at your company or customers.

Thanks for the response. This is something I want to address as I enjoy my job quite a bit outside of this. As far as the second point goes, she has had assistants over the years but the same dynamic has persisted. I've been with this company with much lower headcount and associated workload - everything was the same.
> Attempting to get the CTO removed from their job, will typically (if it doesn't work)

This is very accurate, the CTO may be in place for reasons you may not fully understand and may be protected. Think of of it as a union job where only the most gross of incompetence will result in the loss of one's position.

The likely outcome is the CTO will find out that you have raised concerns and you will as a result be targeted. Yes workplace retaliation is not allowed, but it is not uncommon, especially if the executive feels threatened.

If you do want to raise concerns, use ChatGPT to word it professionally and carefully and be prepared to jump ship if things go south.

Very often people get and hold jobs they seem unqualified for, or perform poorly in. When they get senior management jobs they can cause or allow dysfunction. You may not know how they got the job. It could be through a personal relationship or nepotism. Their own managers and peers may prefer keeping them in their role.

However the organization management got to where it is, trying to get a senior manager/director removed by rational argument presents a high probability of blowing up in your face. The facts may not matter nearly as much as the perception you got out of line and threatened the hierarchy. You might get fired for rocking the boat.

In other words, think very carefully before you act, and make sure you can die on that hill. In my career experience less than competent managers survive and punish those who challenge them.

I don’t know enough about your situation, but the incompetent CTO may present an opportunity for you to step up and take charge, without directly challenging their authority. Have you thought about offering to take on some of the responsibility?

I know how she got her job and it's strictly title inflation from being an early employee. I feel very comfortable addressing this and have already had initial conversations with an individual decision maker who is frustraed with how several recent incidents were handled. The larger management group is not aware of how pervasive these issues are because our company culture has traditionally been one of putting your head down and working around issues. Traditional approaches such as users supporting other users have been disastrous with growth in headcount and are completely unsustainable.

I have taken on additional responsibility directly (ex: coming up with start to end incident support plans that should be in place already) and indirectly (ex: spinning up infrastructure that should be handled there). This has taken up more and more of my time recently and prevents me from meeting deadlines. I have enough on my plate and taking on more is not an option.

So longevity and loyalty account for the CTO getting that role. In other contexts we would appreciate management caring about those things.

I get what you mean about title inflation, but in a field where people with a year of experience can call themselves “engineers” that’s a pretty weak charge to level.

I once faced a similar situation, loyal early hire promoted to CTO beyond their competence. Lots of dysfunction. A couple of us tried to get senior management to deal with him. We got fired. The world doesn’t work fairly or rationally.

I fully hear what you are saying about being cautious and the only reason why I brought up title inflation was to emphasize that this person is not cut out for the job. I'm not worried about any blowback (I'm confident that our company would continue running if she were gone and I am in a key person role) and even if I were, I am extremely employable. I just wanted to know if anyone had experience with this dynamic between non-technical leadership and communication on tech issues.
Organizations can usually tolerate a considerable amount of mediocrity and incompetence, even at the upper management levels. Organizations usually don't want to allow insubordination or threats to the hierarchy. You see the same thing with cops protecting their own, even corrupt and dangerous cops. Managers and executives work like that too, because if they allow challenges to their authority and competence from the lower ranks that threatens the whole structure.

I don't necessarily like how organizations work in that respect. Maybe you have good reason to challenge the CTO and can accept the risk. I just want to describe the reality of organization dynamics. You can read all kinds of books on management that get into how power structures and hierarchies maintain their authority, putting that before more rational priorities such as competence and job performance.

You should convince them of the need for an independent third party who they trust and has tech expertise to come in and make “digital transformation evaluation and recommendations”.