Cultures of Chaos

A product roadmap can actually be detrimental to the business if the gameplan keeps changing.

I am the last person to write about discipline. I am trying to stop eating after 9pm and it’s nearly killing me. Yes, 9PM. In a world where folks fast through, say, Wednesday, I am struggling to cut snacking one hour before I go to bed.

Still. I’m going to talk about discipline. Please tell me (comments, like button, blink twice) if this has ever happened to you. You get an impromptu slack message, email or meeting request where the team is told to stop working on the strategic initiative they’ve been slugging away at and to work on something new. Sometimes it makes sense. But when it becomes a pattern, it’s crushing.

It happened to me this morning. We were to stop what we’re doing and pursue a new strategic directive “ASAP”. This was prompted by one prospect request in our sales process. (If you’re wondering, it’s not a “white whale” prospect. It’s just … another prospect.) The new directive isn’t bad for the product. If we stick with this plan, it’ll help some customers and help our product positioning. But it’s still a reversal of what we had been currently working on. This has happened at our company several times this year.

Call it context shifting. Call it startup culture. Call it agile (although it’s not). I call it a lack of discipline. How can a team rally behind ideas if they are constantly at risk of getting shut down? Why produce high quality? Why talk about these ideas excitedly with clients? Why do the necessary research?

It’s like building the perfect sandcastle too close to the ocean. It’ll be gone in a matter of minutes, so how much of my heart and soul do I invest?

I call this a “culture of chaos”. In a startup, it can make sense if you’re finding product-market fit or perhaps landing on the right problem to solve. But for an established company (as mine is)? It’s crippling. It means that what was planned, designed, developed and perhaps even marketed won’t likely be realized. Sure, we can go back to the thing we were doing. But if we abandoned that thing so easily, why would we?

This brings up the next question: How solid was the strategic direction if it could be replaced on a whim? In my case, it was pretty solid. But apparently not bulletproof. It had been validated and there was a go-to-market opportunity attached to it. The new direction also has a market opportunity attached but now our team of settlers need to pack up our belongings and hike to another destination. Right when we had the campfire going too…

In a culture of chaos, the roadmap becomes less valuable. Sure, a roadmap can - and some would say - should change. But when the product vision gets turned upside down at an alarming frequency, the roadmap becomes less valuable to its audience. It becomes littered with risk if the intent is to excite customers, partners, analysts or our own team. In some ways, an ever-changing roadmap looks like execution failure and unfulfilled promise.

The solution? In the short term, hide the roadmap. Don’t use one. And then turn toward the larger issue - fixing the culture. Take the necessary steps to instill patience, focus and discipline into the planning. This is a really hard thing to do. In many cases, like mine, you are looking to change the behavior of senior leaders. However, by outlining the risks to the business and to team morale, perhaps the culture can begin to change. By calling out the opportunity costs, and putting that into real numbers, one might be able to dissuade leadership from breakneck changes in direction. Might. But also, worth the effort.

The good news is that the really strong teams don’t alter strategy this often. For established companies (post product-market fit), there is a clear strategy of what the company aims to be and a general field guide for how it’ll get there. A complete change in direction requires substantial new information or a change to the environment. This could be a market event (perhaps a financial recession), technological breakthrough (perhaps AI) or corporate event (perhaps an acquisition).

The best leaders acknowledge and set aside shiny objects and stay focused on the strategy in place, until it’s realized or discredited.

It’s like driving. If you constantly change direction, you’ll never reach a destination. But you will eventually run out of gas.