Making plans is not trivial, but it's the easy part.
It's sticking to those plans where most of us fail.
We promise we'll get something done. We prioritize and allocate team capacity. There's a big presentation to show our commitment. And then we go to work with steely resolve.
When we revisit our plan a few months later, we notice we're not on track. Not even close.
Life has gotten in the way.
Shit happened.
We worked hard, but not towards advancing the roadmap.
How did that happen?
What are those forces that keep us from doing what we said we would do? What nudges us to neglect our plans?
Out of touch with the base
You've created your OKRs and your annual roadmap. You know the problems your teams are supposed to work on. But are you sure that's what they're doing?
I often see teams working on a backlog with hundreds of tickets that have nothing to do with the strategic goals in the roadmap. If teams are working on other stuff, it's no wonder they're not doing what you thought they would.
A plan is not a picture in a slide deck. It should be reflected at all layers of the organization. If your roadmap shows that Team A should be working on a Hubspot integration, their backlog should only contain tickets toward that goal.
Make sure to clean their backlog and measure their focus level.
Tools proliferation
Another common issue is when different parts of the organization use different tools. Product might plan their work in Monday, while Engineering uses Jira and the C-level looks at Powerpoint. More tools mean more room for error.
While there might be good reasons for multiple tools, they pose a risk of things slipping through the cracks.
We need to make sure each of these stays in sync. With every tool, the cost of syncing goes up. Keep your toolset simple.
Feature optimism
We have plenty of ideas for new features, and we can't wait to ship them. Our plans often reflect that. We'll cram feature after feature into our roadmap. Not only do we underestimate how long it takes to build such a feature, but we also seem to forget about maintenance and operations completely. Good teams spend 25% to 50% of their time maintaining the software they've already built.
Is that reflected in your plan?
Not sticking to the timebox
Timeboxes are vital for planning. They are our best weapon to stay on track. Instead of coming up with "the scope" and trying to get that "done", we'll build small vertical increments of our solution until the time's up. That's the magic behind Focus Blocks or Sprint Goals. It's what allows us to plan in the first place.
Yet I often see work getting carried over to the next sprint. That defeats the purpose of timeboxing! Pushing a ticket to the next timebox should be an exception, not the rule.
Every time that happens, we actively ignore the plan.
Sticking to the plan shouldn't require discipline and willpower. It requires systems that make it hard to fall into the traps above.
Have a hierarchical, unified plan so you can track almost every task to a roadmap item.
Measure how much time teams spend working on the right things.
Limit the number of planning tools.
Plan 25% to 50% of the time for non-feature work.
Delete backlog items at the end of the timebox instead of carrying them over.
Let’s treat our plans as a process rather than a one-off communication of intent.