Bad Leadership, or, Is it time to leave?

It is like a broken record, where we are doomed to listen to the same grove over and over. New leader, shake things up, finds out that it ain't so simple, then doubles down and bad shit happens.

I originally drafted this with a theme of schadenfreude, the German word for pleasure derived from someone else’s misfortune, but as I kept writing it, I realized that I am on the receiving end of this heinous leadership. There’s not enough White Russians to paper over this.

The story thus far…

We have a new leader. Someone who wants to “shake up” the old order. The came in, guns blazing, wanting to make a huge mark, shift our business, and democratize the processes.

As a new leader is wont to do, they have cocooned themselves with “trusted” people (read: cronies) who tell them that all that we have built over the last 25+ years is bad, and that it is holding our business back. One of these cronies is a new “Director” (or is it Senior Director?) of “Product Management”. But they aren’t the director of product management for our product team, but instead, their charter is to build a small team to break through our archaic thinking, to buy into one of the off the shelf SaaS solutions in our space, and to relegate our custom stack and toolchain to the dustbin of history (and to stick their thumbs in our eyes to show us that we suck, and we should be ashamed of our self).

Yay. This is great for morale for the rest of the team. We have a $300MM business that is down about 15% due to COVID, but is rebounding nicely, and once the in person events can resume, our revenue will return to its old form.

The “Promise”

Or is it premise? Regardless, the incoming leader is convinced that the fossils in the org, with the tools we built, are what’s holding us back. That we can’t see the forest for the trees, and that the new team, with this new Director of Product Management will show us all up.


At first, the dream was to hire a complete team, and develop something from scratch that will be AWESOME.

Awesome Express, from the greatest show of all time, Futurama
Awesome Express, from the greatest show of all time, Futurama

When they finally looked at what was required, they punted, and realized that “Gee, perhaps a tested, off the shelf solution would be good after all…”

No fucking shit. There’s a reason that NIH is a fucking horrible strategy. We built our tool chain originally because our use case is a corner case, and it was needed. In the 15 years since we built it originally, the state of the art has advanced, but our particular use case is still not common enough for a major vendor to build it, and we aren’t big enough for them to build it for us.

But I digress.

So, once they started researching, they realized that the market was crowded. Like really crowded. And the players aren’t well differentiated. And our USP is not something that can be done off the shelf with any of them, so we are going to have to do some major development to shoehorn our solution in around the mediocre APIs offered.

Can it be done? Yes. Will it be easy? No. It is going to be extremely difficult.

The worst part? They distrust all us crusty old salts so much that they do not want our help or advice. It seems like there is a massively negative perception of the team that navigated this, built a solution, and a tool set, delivering significant value to literally millions of customers over many years.

Go figure.

Missed milestones

When the Dude first was made aware of this new direction, he kept an open mind. The commitment was that this coming November (like in 2 months, but this was 2 months ago, so they had 4 months) they would be able to demonstrate this new solution and platform at a major internal event. Hell, the Dude has been killing himself to build a set of modules to be demonstrated for this event.

But they haven’t even chosen a platform (it is down to two) and neither of them is optimal, that is, we will have significant trade-offs regardless of which path the team selects.


Now, it looks like the goal posts have been moved to do a technical demonstration and roll out in late spring, 2022. Uh, that’s one helluva slip, ain’t it?

The Why

Time to go into speculation mode here.

First our new-ish leader fetishizes engineering. Everyone else in the organization is subservient to the development team. It is like the engineers are the church elders in the middle ages. Looked up to, revered, and all our efforts are to enable, and worship the engineers.

Even to the point that our leader sidelined our existing product management structure, and hired a (you guessed it) engineer to create a new “product management team” with the title of Sr. Director of Product Management. In my first conversation with this person, I was impressed by his technical chops. But then I saw his first hire as a product manager under him to be someone with no history of product management whatsoever in their background.

The Dude isn’t against this, sometimes thinking outside the box is fine and needed. But to build a product team from scratch, and to hire people who have no experience? Well, that is beyond risky.

Second every decision takes an agonizingly long amount of time. Classic analysis paralysis in action. Scrutinizing every feature and capability in the platform, pouring over each nit, trying to eliminate all technical debt (where has the Dude heard this before?) while knowing that each of the options has some serious deficiencies compared to our bespoke, existing solution.

Alas, one of the strengths of a strong, seasoned product manager is the ability to make a decision, and move on. We know that there is no perfect solution, so it is better to pick the least bad solution (ugh, that sounds terrible) and then work to make it better, adjusting our plans accordingly.

If you want perfect, you have to build it. So you have to get close enough, and then move forward.

Third and this one is a doozy, is that even with a leader who is heavily biased to engineering over the rest of the business, sometimes, there just plain isn’t a technology solution to every problem. More coding, more engineers, more granular projects, more pet projects, more noodling all are fine if you are Google, where search and ads can fund a fuck-ton of niche projects that you can scale, promote, then ultimately kill off.

But we aren’t in that situation. We do not have a sugar daddy BU that will fund us to tinker to our hearts content. We have to build a business, a sustainable revenue stream, with enough profitability to keep us in the game.

A lot of the bits and bobs that go around that (like commerce, tax, governance and compliance, support, marketing and promotional efforts, and operational efficiencies to turn our point products into salable items.

“Build it, and they will come” is a hope, not a strategy.

‘nuff said.

The last word…

It is review time, and the Dude has heard through channels that the BU leader has decided to reserve 80% of all RSU’s and salary increases to team members with “Engineer” in their titles, even though they are only about 18% of the total team size.

Furthermore, while there are headcount restrictions (dictated by Corporate) the only positions that will be opened and filled will be for “Engineers”. If we lose a product manager, or an operations person, too fucking bad. Live with fewer people.

Hell, our leader just opened up a position for a Director of Engineering that the requirements read like a senior Business Development role. So clearly, they are rejiggering people’s titles to reward favored people, while the rest of the organization will be told to - in essence - “suck it”.

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