What are you prepared to let fail?
The uncomfortable part of prioritising change is living with the consequences.
You can’t transform everything, everywhere, all at once.
My back garden would like to submit evidence.
After time away, including a holiday in Thailand, I walked into the newer section of our farm garden and felt guilty. Then overwhelmed. The weeds had swallowed a few plants. This amount of wheat would be good if we were playing Settlers of Catan - less so, when that's supposed to be a garden bed.
There were everlasting daisies and cut flowers blooming, but the weeds detracted from the effect I’d imagined: standing back and seeing it all flowering together.
Then I remembered what I’d chosen instead. Family. Friends. Work decisions that needed my attention. Time enjoying the life we’re building. I was still sad about the plants. I was also confident in those choices. That is the uncomfortable part of prioritising. Eventually, you encounter the consequences.
Agreeing priorities is the easy part
In organisational transformation, we can spend hours agreeing what matters most. We sequence the work, approve the roadmap and acknowledge that people have limited capacity. Everyone understands that we can’t do everything at once.
But then something we’ve deprioritised starts struggling. A stakeholder complains. A process becomes frustrating. A team falls behind. An improvement we wanted remains unfinished. Suddenly, the trade-off feels much less reasonable. Someone steps in. Usually someone capable, conscientious and already busy. They keep the thing running, squeeze in the extra work or invent another workaround. The priority list stays the same. The workload grows anyway.
This is where I ask stakeholders: what is the least worst option?
It’s a useful question because it makes room for the possibility that every available choice has a cost. We can step through those costs rather than search indefinitely for a solution where nobody loses anything. We also need to acknowledge that choosing feels uncomfortable. I don’t feel great about letting something struggle. The white stallion is tempting, but riding in to save everything isn’t sustainable.
You can’t mature everything at once
Technology transformation often brings several ambitions together: better information, clearer responsibilities, more consistent processes, stronger controls and people using new systems confidently. Those ambitions may all be worthwhile. They won’t necessarily move at the same pace.
One team might need reliable basic processes before it can adopt anything new. Another might be ready to experiment. A particular service might need substantial attention while an adjacent one can keep operating adequately for now.
Expecting consistent maturity everywhere ignores those differences.
A roadmap needs to account for the people learning, deciding and changing how they work, alongside their existing responsibilities. Listing several initiatives in parallel doesn’t establish that the organisation can absorb them in parallel. Sometimes the right decision is to leave something less mature than we would like. That requires explaining why, what it means in practice and when we’ll look at it again. It also requires accepting that people may continue to find it frustrating.
When “we aren’t rolling this out” becomes a rollout anyway
In one SharePoint implementation, we agreed that it wouldn’t be formally rolled out because the foundations weren’t in place.
But SharePoint can behave a bit like ivy. Once it takes hold, it finds its way into places you hadn’t planned for. It stuck. People started relying on it, without the support, maintenance and governance needed to make it work well. Now we’re working through the consequences, including the perception that SharePoint itself is the problem. People have experienced a frustrating version of it, and that experience is what they judge.
Technology can have limitations. But in this case, replacing the platform wouldn’t resolve the lack of ownership, support and upkeep. The agreed decision hadn’t translated into a clear, workable arrangement for what happened next. Informal use became an enduring reality.
There’s a lesson here for what we let fail: deferring a rollout still requires managing what already exists. We need to decide whether to contain it, support a limited version, retire it or invest in the foundations. Otherwise, people inherit a system nobody properly committed to running. Recovering from that takes more than fixing the technical configuration. It takes rebuilding confidence through a better experience.
Who is paying for the trade-off?
When leaders accept a lower priority, who actually carries the consequences?
Sometimes a team is told an improvement can wait, while still being expected to deliver the improved result.
Sometimes a system receives little maintenance, while its users are expected to compensate for every weakness.
Sometimes we agree that work should stop, but the person who has always kept it alive continues doing it because they can’t bear to let colleagues down.
Those arrangements don’t free much capacity. They make the cost harder to see.
People’s mental health is something I’m unwilling to treat as an acceptable casualty of transformation. I can’t predict every response or trigger. Humans are complex. I do keep watching for signs that the conditions around the work are becoming unsustainable.
Workload matters. I also look at what surrounds it: unclear expectations, competing demands, limited control, unresolved conflict and the feeling that you can never do enough.
If we’re relying on people to absorb every consequence privately, we need to revisit the decision. That might mean changing the scope, slowing the pace, adding support or accepting a lower level of service. The answer can’t always be another request for people to stretch.
Take your fingers out of the bucket
I think of repeated rescue work as putting your fingers into the leaks in a bucket.
It helps for a while. The water stays in. Everyone carries on. Eventually, your fingers need to come out. Some water may have to seep out before the organisation recognises that it needs to invest in the bucket. That doesn’t mean creating a crisis to make a point. It means making the existing problem visible, explaining the consequences and agreeing what happens when the temporary workaround ends.
Every rescue should raise a question: what would allow us to stop doing this?
Sometimes we need a better process. Sometimes clear ownership. Sometimes maintenance, training or investment. Sometimes we need to stop the activity altogether.
If the workaround is always renewed, we may never make that decision.
Decide before the consequences arrive
“Let it fail” is too vague to be useful on its own. We might be postponing an improvement, ending an activity, running a limited experiment or accepting that performance will deteriorate temporarily. Each requires different decisions.
Before stepping back, I want us to work through five questions:
What are we choosing to protect or improve?
What will receive less attention as a result?
What consequences are we prepared to accept, and who will experience them?
What would make us revisit the decision?
Who needs explicit permission to stop rescuing it?
The people carrying the consequences need to be part of that conversation, and when the consequences arrive, we need to distinguish an expected cost from new information that changes the decision. An agreed delay becoming inconvenient may be exactly what we anticipated. A temporary arrangement causing more harm than expected deserves another look. We need enough discipline to hold a decision and enough judgement to change it.
You can regret the cost and still stand by the choice
I’d like my garden to look beautiful. I’d also like time with family and friends, meaningful work and the occasional cocktail by a pool.
Some plants were lost. I missed the full effect of the flowers. I don’t need to pretend those things don’t matter to justify spending my time elsewhere. I’ll deal with the weeds. I may also need to rethink how much garden I can realistically maintain. That’s useful information
for the next decision.
In organisations, choosing priorities means accepting uneven progress, unfinished work and some disappointment. We need to be honest about that before asking people to deliver change.
What are you prepared to let fail—and have you told the people who keep saving it?
TL; DR: The anti-consultant take
You’ve got finite people, finite time and a business to keep running.
If your transformation plan needs everything to improve at once, go back and make some decisions. Choose what matters most. Say what will get less attention. Agree what happens if it starts going backwards. When that happens, don’t act surprised or expect someone to quietly work weekends to make your trade-off disappear. And if a system is already in use, “we haven’t formally rolled it out” won’t maintain it, support its users or decide who owns it.
Take your fingers out of the bucket carefully. Show people the leaks. Work out whether you’re going to repair it, replace it or stop carrying so much water. You can care about something and still choose to spend your capacity elsewhere.
I’m sad about a few lost plants. I still wouldn’t swap the time with family and friends to have kept every garden bed immaculate.
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