Multi-Track Storytelling

Context

Your reality is full of uncomfortable constraints, messy facts, and shaky assumptions. Goals are shifting fast and you do not have high confidence in your roadmap. But you rely on an external party for funding, and they're demanding that you make long-term commitments.

Discussion

I try to speak directly as much as possible. When I was younger my directness sometimes got me into trouble at work. I guess it's because I was raised in a family where lively, even aggressive debate was the norm. My mother says we got this from my Swiss grandfather, who had absolutely no filter and was especially generous with negative feedback.

My directness served me well in the first few years of my career, working in small businesses and early stage startups. As a developer, nobody expected me to be anything but direct. In one early performance review, I was delighted that one of my peers wrote, "Alex is an absolute straight shooter."

So the iterative, agile development style–where we estimate, measure our velocity, and constantly update our forecasts to meet delivery dates– was natural for me.

But I struggled with longer-term plans. I knew that any 12 month roadmap was nothing more than a forecast. When leaders wanted commitments to deliver items of unknown complexity that were many quarters away, I argued with them. I felt it wasn't rational to commit to the unknowable.

Years later, I was leading product in a company with a particularly volatile strategy, and the CEO demanded a committed 24-month roadmap. I was asked to gather PMs and engineering leaders together and produce the thing in a week.

It broke my brain a bit. Based on my experience with him, I was sure that this guy was going to change strategy on us again in 3 months. No matter how careful we were with buffers, hedging, and estimation, this 'committed roadmap' was going to be pure fiction. And I felt it was unethical for me to create it.

But it was made clear to me that either I make the roadmap or find a new job.

So we made the roadmap.

When we shared it with the executive team, I was careful to start the presentation with caveats:

This is a forecast. We believe all this is possible given the current team. If the team composition changes, or we lose people, this won't be possible. So we need to proactively hire ahead of attrition. And if new needs come in from the board or customers, we will either not address those needs, or this roadmap will have to change.

None of them cared. This was just 'Blah blah blah' to them.

Only later did I realize: Execs speak with confidence amid high degrees of uncertainty all the time. They know things are going to unfold differently. They know roadmaps are forecasts. Their days are chaotic. Often they don't even know what they will be working on the next week!

But amid all this uncertainty they use high-confidence words like 'commitment'. If an exec asks for a 90% confidence roadmap, often what they mean is the same thing an engineer would call a 50% confidence roadmap.

(Now, that's no guarantee they will behave in a fair and rational way when the change comes, but that's a different issue!)

In my case, the CEO just wanted a forecast, a story. The uncertainty was understood, and I was getting too hung up on the word "committed", which did not not mean the same thing to me as it meant to the CEO.

3 parallel business stories

Business storytelling operates in multiple tracks at the same time, with different concerns. Here are three tracks PMs should think about: