The just-stop-it problem
The hardest strategic choice is to stop.
Ask almost any team in a large organisation what’s making their work hard and what you’ll hear will almost certainly include some version of this: the list of things we’re doing grows and nothing ever seems to come off it.
People say this with real frustration and feeling, because the load that most teams are under is both ineffective and unsustainable.
So the interesting thing is what happens with those same people are given the opportunity to identify what should stop. When asked “how do we free up our capacity to work on the important, strategic stuff?”, a workshop tends goes quiet in a way it doesn’t for any other question.
Why the underwhelming response?
I’ve facilitated a lot of strategy conversations, and an ill-prepared for stop-doing exercise is the one that consistently produces the weakest responses.
People intuitively know when an organisation needs to stop things in a conceptual sense. But finding those specific things, offering them up to a group, and committing to stop them is a higher risk activity than most people realise.
Which is why in strategy sessions, the answers that come out are almost always peripheral to anything that would meaningfully reduce the teams load or improve overall performance.
We could change our weekly team meeting to fortnightly?
We could shift the responsibility for monthly reconciliations back to the operations team?
We could reduce the reporting frequency on our internal projects?
These are all real things, no doubt. But they are stupendously minor in proportion to the problem most teams describe of sheer overload, busyness, and ineffectiveness of their most important endeavours.
In fact (and this is quite terrifying to reflect on) I can’t recall ever having facilitated a group who has self-identified an opportunity to stop a priority project that no longer makes sense.
Even with a highly motivated and well-prepared group: the list of what to stop won’t be remotely as ambitious as the list of what to start.
Stopping is harder than it sounds
The easy explanation for the poor response is that people are protecting their own turf. And sometimes that’s true. But I think it’s more nuanced than self-interest on three structural levels.
Stopping is also work
The first is that stopping work is, in itself, work. There’s no such thing in a large organisation as simply ceasing to do something of any substance. Whatever it is, it is likely that processes, rhythms and dependencies have formed around it, people’s roles are partly defined by its existence, and unwinding all of that takes active effort. Which means that the cost of stopping a substantial or long-standing piece of work can feel as significant as the cost of continuing the blasted thing. So teams often keep going not out of irrationality, but because the path of least resistance and least risk is to keep going.
The loss becomes concrete
The second is sunk cost. It’s not just that people have invested and feel reluctant to write it off; it’s also that stopping makes the loss concrete. Continuing to do work that is high effort and low value keeps it in a kind of suspended state where the investment hasn’t formally been wasted yet. So continuing is partly about future hope and partly about deferring the moment of reckoning. And because losses feel roughly twice as painful as equivalent gains feel good, the psychological pull toward continuing work that’s always been done like that is stronger than any options analysis of good alternatives would suggest!
The trade-off becomes explicit
The third is that stopping something forces a trade-off into the open that was previously sitting quietly in the background. As long as everything is nominally in flight, it’s possible to pretend that resources, attention, and political capital are infinite, when already committed. Continuing to carry work that has lost its strategic relevance preserves a kind of comfortable fiction that the organisation can have everything it wants without giving anything up.
Talking about stopping blows a hole in that fiction. It requires someone to say: this matters less than that. Which is why, even when a team privately agrees that something should end, naming it out loud can feel disproportionately loaded. The reputation risk is real, but it's a symptom of an organisation that hasn't yet created the conditions where trade-off decisions can be made honestly and without it becoming personal.
The reverse pilot and its limits
One approach that sometimes helps is what Greg McKeown calls the reverse pilot. Rather than formally abandoning something, you simply stop doing it and wait to see whether anyone notices. If nobody mentions the weekly report after three weeks, the weekly report probably wasn’t being read, and you have concrete evidence now to formally stop it.
This works well for a certain category of work. Reports nobody reads, meetings that have always existed, inherited processes, and the like. The reverse pilot sidesteps the identity and accountability threat almost entirely because there’s no moment of formal announcement, no implied criticism of whoever put the thing in place.
But it has an obvious ceiling. You can’t pilot stopping a major project. You can’t trial the cancellation of a funded initiative with a team attached to it. For the decisions that would create real strategic space for the team, the reverse pilot isn’t available.
The hard choices still need to be made deliberately, by people with the standing to make them, in a context where trade-offs can be openly addressed.
Which is where the question being asked becomes important.
The blank page doesn’t work
The standard stop-doing exercise is brainstorming: a blank page and an open question. It produces weak answers because it asks people to do something cognitively and socially expensive without any scaffolding.
Whether you’ve thought about it like this or not, you’re asking the group to surface their own inefficiencies, implicate colleagues and initiatives they’ve supported, and make a case for stopping things that might be core to someone’s job, or that still have advocates.
Without preparation and a framework that makes it safe to say the uncomfortable thing, the rational response is to offer something small and peripheral. Which is exactly the kind of answers you’ll generally get.
The better approach builds the diagnostic work in before the session starts. Doing the hard thinking in advance by identifying where energy that doesn’t generate proportionate value is going.
When that work is done before people come into the room, it’s possible to have a conversation focused on trade-offs. You’re no longer asking people to generate answers from nothing. You’re asking them to respond to a picture that’s already been drawn that makes the systemic problem visible without making it personal. The question changes from “what should we stop” to “here’s what we found, what sense should we make of it, and what does it mean for what we carry forward?” The conversation can be framed around the core priority as the anchor point, which provides a frame of reference to test all potential work against.
That’s a fundamentally different conversation. And in my experience, it’s the one where meaningful answers are more likely to emerge.
What this means for strategy
A strategy that doesn’t seriously grapple with what to stop is, in practice, just an additions list. It describes new direction without creating the conditions for it — because the accumulated load doesn’t move anywhere else to accommodate new priorities unless something creates the space. People are left trying to execute on a new set of priorities while carrying everything they were already carrying.
The stop-doing conversation is some of the most important work a strategy session can do. It’s also the part that most often stays on the surface, because the conditions for going deeper aren’t built in. Building those conditions — like the pre-work, the right framing, a facilitator willing to call out incongruence — is what makes the difference between a strategy day that generates a list and one that creates genuine clarity about what the organisation is actually choosing.
The facilitator’s job in that moment
When the room goes quiet, or when the answers start coming in small, the instinct is to move on. To take what’s been offered, acknowledge it, and shift to something the group finds easier. It keeps things moving. It avoids the tension.
But moving on is exactly the wrong call.
The quiet and the smallness of the answers are themselves information. They’re telling you something about where the real difficulty is, and a good strategy conversation doesn’t paper over that. It names it.
What I’ve found more useful is to bring the incongruence into the open. To say, as plainly as possible: you’ve just described an organisation that never stops anything as one of your biggest challenges. And the things we’ve identified as candidates to stop wouldn’t materially change that. I’m not saying that critically — I’m saying it because I think it’s worth sitting with. What would it actually take to stop something that matters?
That question tends to land differently than the original one. It shifts from asking people to generate answers to asking them to examine why the answers they’re generating are so cautious. And that’s often where the more honest conversation begins.
Strategists sometimes wheel out the line: choosing not to choose is still a choice. (Guilty as charged).
And here’s an extension to that concept: choosing to stop after you’ve started is a more active choice than choosing not to start in the first place.
The motion that already exists has momentum, infrastructure, and people attached to it. Saying no to something already in motion costs more than saying no at the outset ever would have, which is precisely why strategic choice making is so critical.
Let’s unsquiggle this, good people!
Oh, and if you’re planning a strategy session and want to build in the kind of pre-work that makes the hard conversations possible, that’s exactly what a Strategy Day with the Squiggle Collective is designed to do. You can find out more here.