How to handle working at a startup when leadership plans do not make sense to me

[quaythuxsmb]

Working for startups the past 6 years I have noticed a pattern where leadership priority is delusional from my perspective.

* We seem to be surprised when our schedules continually slip despite it being brought up that our schedules are very opportunistic when they are first made.

* We pick metrics that justify us making certain decisions while discrediting other options that perform better on the measures that our customers tell us they plan to measure us by.

* We are focusing on the long-term selling points of our product as a higher priority than solving issues that are causing our product to fall short of our current contracts, causing us to not be paid due to falling below performance targets.

I am currently working on my second start-up both companies started by first-time founders. The first one I joined after series A and left after series C.

the second one I joined after series A we are currently on our B, the founders were directors in FANG.

I am technical and a manager.

Do you have any suggestions on how to proceed when you don't agree with or understand the reasoning behind leadership choices and are beginning to be labeled as pessimistic within the company ?

 

[pmsh]

@quaythuxsmb If you no longer believe in the company/vision, or it's no longer what it used to be, why not quit? Unless you're very passionate about the problem being solved, I don't see why you should remain in an environment that gets you agitated.

 

[berlin_worship]

@quaythuxsmb Unlike the other commenters, I wouldn’t say that the automatic solution here is to quit. Especially because it seems like this is a pattern. One thing I would point out is that the only thing consistent in these experiences is YOU! That’s not to say that you are the source of the problem. But you are probably more attuned to noticing the (anti)patterns here.

First I would say that software projects are notoriously difficult to estimate. It might be easier to plan backwards. If you set the release date, then by what date should QA start. If QA starts on that date on what date should you be dev complete. So on and so forth. Once you miss your first milestone it should be clear that the schedule is at risk and easier to communicate to leadership proactively. But this is just a tactic. Founders, and leaders in general, have to convince themselves of certain “untruths”. After all, starting a company is the ultimate expression of doing something “untrue” despite all the rational reasons that it won’t work. So this behavior is understandable, though maladapted at some point.

Second, I would say that it’s actually laudable that they are thinking about long term features and laying groundwork now. However, this is a founder trap. You have to “buy” the “luxury” of working on these long term features by getting short term wins. Having said that, if they can sustain the current business and invest for the future that’s great. Even better would be to quickly, cheaply, and iteratively test their way into those long term features. They have a hypothesis about what will sell in the future. How quickly and cheaply can they retire the risk that it might not sell in the future?

Something I would suggest is something I absolutely fail at. Don’t surface your skepticism in “public”. Meaning meetings with more than one other person. Some people will feel the need to save face or double down when “challenged” in public. Working “softly” 1:1 is much more effective. If you can convince an individual leader that you are aligned with their goals but have a constructive suggestion for alternative tactics to get there, you may find yourself being more effective (and thus less frustrated).

You’re lucky in that being a manager you have a certain amount of influence over your team culture. Ultimately, though, people will emulate the behavior of the founders. Regardless of what they say, what they do is the de facto culture. It may ultimately be that you can’t fit in. However the fact that these companies got to series A and beyond says A LOT about the Founders and the business. Very few companies reach that stage. So, like I said, they have a lived experience that says that belief in the unlikely can payoff. Best of luck.

P.S. Every company, without exception, is messier on the inside than the outside. Sometimes we magnify that mess because we’re close to it. I also struggle with perspective sometimes. Hyper-conscientious employees struggle with finding the line of focusing on their realm of responsibility. We feel like any problem in the company is our problem to fix. Unless we are the founder or in leadership, it’s not. Our role is to surface it at the appropriate time in the appropriate setting and then to let the chips fall where they may. That feels uncomfortable but will ultimately lead to less friction and be better for your mental health. Hope that helps.

 

[quaythuxsmb]

@berlin_worship This is a really good answer, Thank you!

I agree and have been coming to grips with how much of this issue is due to my personality and anxiety. I have an aversion to when I hear schedules or plans that appear so high risk that the expectation is they will fail. In many ways I still operate the way I did when we were a 15-person company and the price of miss gauging a risk is we go bankrupt. I think that risk still exists but the timetable is much longer and it is not a failure but an acquisition or lack-luster exit is the punishment.

The part that I am still not bought fully into is ignoring problems that I see that fall outside of my department. In theory everyone takes care of their own part then everything will work out, in practice I have never seen this work. It feels wrong to sit by and see things go bad that appear they could have been avoided. The part I am coming to grip with is it is not my job to fix these problems.

The back of my mind is questioning is it that I need to become more trusting or am I being gaslite by our founders.

 

[berlin_worship]

@quaythuxsmb Yeah I would not suggest ignoring problems. If you’re like me (and many folks) once you see a problem you’re “constitutionally” unable to ignore it. That kind of hyper- conscientiousness is well adapted most of your career, but as you see here it’s causing friction and frustration (on your part and the part of others around you). Rather than ignore problems, I would suggest just being judicious in terms of how and to whom you surface these concerns. And then be clear on the distinction between being heard vs being followed. That is, if you’re convinced that the person to whom you’re communicating fully understands your point, then be willing to accept that they may still not follow your advice. If you’re ok being heard and can trust/accept the judgement of the folks you’re expressing to then you’ve done all you can. If you ultimately don’t trust them, then you should look to exit. In some sense you’re asking them to trust you. Extending that trust to them may be a key unlock.

Again, I’ve never been successful in this domain. Mostly because I don’t follow my own advice. But hopefully this is useful.