Product management in a hurricane

A product manager looks for advice from a strategically unaligned workplace

A product manager asks:

As a product team we have to address some of our "product debt" and in order to do so we have to spend engineering resources to improve those features. Our C level management thinks that these efforts do not align with the long term vision. But, in order to be able to have a long term vision we have to focus on retention. Which 2 months ago used to be our short term company goal. It is very difficult to find balance between spending engineering and product resources on retention efforts and at the same time keeping up with a long term strategy which at the moment does not make much sense and/or it is always changing.

Such circumstances are like standing in the eye of a hurricane. External pressures are at odds, a maelstrom of what-the-fuckery creating a fog that neither vision nor strategy can cut-through. All you know for sure is that the wall-cloud is closing in.

What do you do? You do the only thing you can: you look at your to-do list and you start at the top.

The realities of the situation from an outside perspective is that the product ownership of your company seems immature. I suspect there is a lot of resource-churn passing work between teams, there’s indecision and inexperience in the C-Suite, and - judging from your post - the stress from this is pervasive. I’m guessing you don’t have the authority to just pick — short-term or long-term, if retention is effectively a blocker to reaching long-term goals, then you know what to do — so you’re at the whim of the folks who cut your check.

I wrote in “Do your mentors deserve the benefit of the doubt?

How does one best rationalize a statement from a "master" you think is wrong? Should you re-calibrate your opinion of this person? Does this "wrongness" infect this person's other advice? Does this stain of perceived wrongness from other people you respect have value?

If I do [care about this person’s opinion], then before reacting I must still put my emotion to the test. How does one know a person is wrong? Is your sense of this person's wrongness the wisdom derived from due diligence in study, or the feeling derived from pattern-matching intuition? How can you tell?

This is a valid exercise not to discount the value of experience-informed intuition that something smells off about a statement or belief system, but it's necessary to consistently put our intuition to the test in order to suss out cognitive biases.

Disagreement within their area of expertise can signal a leveling-up. Congrats. You're killing it. However, if you decide that, toe-to-toe, this person's area-expertise sufficiently outranks yours, then I think here they deserve the benefit of the doubt.

The choice then isn’t what product strategy is best but whether you choose to defer to C-Suite. If you do, great: your decision-tree has been cut in half. Figure out the to-do list.

If you choose to go another direction, then you have to be honest with yourself:

  1. what actual control do you have over the situation?

  2. with what control you have, can you make the impact you want?

As a stoic designer, you practice not letting your emotions get swept-up in the external forces, so you can make the cold calculating decision - which is the right decision for you.

Defer, or don’t.

In the meantime, start sending out your resume. Who would want to associate with such chaos?

Craft virtuously.


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Remember that design is not art, but a practice,

Michael Schofield