If and how should I raise a warning flag as a non-management employee?

Question

TL;DR As an employee, should I report to my boss' boss (the CTO) that we are far from our objectives, and if yes, how?

I work in the software industry. Recently our company decided that our API was too old and created a new team to develop the next software that will replace our current. I was excited about it and asked to join the team.

However the architecture and the design laid out by our manager is overly complicated, remains unclear (even for him) and seems to me different from what the board asked for. I tried to discuss this with my manager, but he received it badly. He limited the discussion to my capabilities and didn't discuss the software design.

Last week, we finished our sprint and we had to produce a demo. Our CTO expressed his displeasure because it was not what he expected (in terms of features and stability). But our manager convinced him that the goal was very complicated and would require more time. We worked another sprint hard (with extra-hours) and finally got the requested features.

However the implementation has bugs, doesn't have tests, and remains extremely complicated.

I'm a bit concerned because the foundation of our upcoming software is so buggy and badly designed.

I'm committed to this company and consider it more than just a paycheck. Therefore should I report it to my CTO? If yes, what is the better way to raise this warning?

EDIT (To answer a comment): We don't have officials meeting altogether with the CTO, it's just our manager with him; or our CTO come to our open space to see how things are going.

Answer 1

I'm a bit concerned that, the foundation of the next software is already so buggy and badly designed.

Therefore should I report it to my CTO?

That may depend on how much you value your job.

Doing an end run around your boss and tattling to the CTO is not a good career move. Certainly your boss won't be happy. And it's likely your CTO won't be happy with you either.

If your CTO wants to know the state of the project, I suspect he is perfectly capable of finding out what he needs to know by himself.

If he asks you questions, you can answer them. But everywhere I have worked, running to the CTO and skipping your boss because you are "a bit concerned" doesn't make sense to me.

Answer 2

Therefore should I report it to my CTO?

Basically, what you're proposing doing is telling your manager's boss that your manager is not doing his job well. Assuming that you're right, you are in a difficult situation.

In most cases, if an employee circumvents their manager, it's viewed as a bad thing, for multiple reasons: it suggests that not only do you not have faith in your manager, you also don't have faith in the CTO to recognize a bad design or a project behind schedule. It is very hard to win, and even if you are correct and eventually convince people, it can still taint their opinion of working with you (although this depends a bit on them as well as how you go about it).

If yes, what is the better way to raise this warning?

I assume you meant if no, and I'm going to answer it that way. I would assume that you have design and or status meetings for the project. You should take opportunities to express concern and ask questions about these issues whenever appropriate. You mentioned that you are doing sprints, so you should be having retrospectives and planning meetings around each sprint. (If you aren't having them, then you should suggest it.) At any rate, whenever you're discussing how things are going or planning the next phase of work, ask questions about preventing high bug counts and developing the features that are required.

Since your manager already hasn't received your original feedback well, you need to express your concerns, but be diplomatic. A lot of this will come down to phrasing. For a simple example, you'll want to phrase things like:

Can we some time discussing test plans in order to make sure our code is up to par by the end of the sprint?

Instead of:

Do you have a plan for reducing the bug count so we don't get yelled at by the CTO?

Answer 3

I had a similar situation twice in my career when I had to report my manager to their managers-managers. TL;DR - I ruined my relationship with my manager, but don't regret it, and I believe that it improved lives of team members (they weren't pushed as hard, to uphold unrealistic criteria) and the project itself.

My "checklist" reads as follows:

• Write up a proposal, with a problem statement, a solution or two, it doesn't have to be detailed but should show your perspective. You are not aware of all the moving parts that your Exec is.
• Make a short presentation, based on the proposal. To be able to present a short version on the spot.
• Show it to the manager first, invite them for a lunch or dinner, and have a chat.
• If you manager ignores you - decide whether you care about your relationship with the said manager if you don't go and chat to execs.