Conventional discussions of prioritization assume something like: “We have several plausible things we could do. Let’s compare value, risk, effort, confidence, etc. and decide which ones to invest in.”

But in my experience, the real problem starts AFTER that. We often know what we should do — that isn’t the problem. We know what the existential threats are. We already know we’re overinvesting in some things. We already sense which projects need a reset. What we’re struggling with, or don’t have the conviction to do, is how to create the organizational conditions required to act on that knowledge.

Meanwhile, you’re currently doing a lot of things you should either not be doing, should spend more time on, or should radically change your approach. The challenge is two-part: yes, you need to be considering the right or less wrong options, but it is also HOW you approach those things.

Try this with your team. Fill in the blanks. If you can’t fill one in, skip it.

“We keep coming back to __, but no one has a clear solution. And we seem unwilling to jump headlong into it. Every pre-mortem singles it out. Every quarter there are half-hearted efforts. But the threat is just abstract enough that there’s always a plausible story for why it might __. We keep pushing it off to ___ and hoping that’s enough.”

“No one debates that ___ is important, and that is part of the problem. It’s fun. It feels productive. Saying yes is a well-worn habit. But unless we set limits, we’ll keep polishing it forever, well past the point of diminishing returns, while ___ starves. We’ve probably already captured ___% of the value.”

“Unless we agree to do ___ in principle, we’ll keep wasting time trying to prioritize each and every little piece of it. No single item is big enough to survive a prioritization meeting. But collectively? People should just be able to pull from this pile whenever __. The value comes from doing it in __, not batching it into some giant future initiative.”

“Everyone in the room knows something is off with __. Confidence has dropped since __. But the momentum is crazy. Ask a question, you get shot down. Nobody wants to be the person who held up the train. What we actually need to prioritize is permission to ___ it.”

“___ has been almost done since __. Everyone is tired of it. We keep giving it scraps of attention, and it keeps lingering. __ stays blocked waiting on it. We need a short-lived period of extreme focus, or we need to stop pretending. That means explicitly saying ___ slows down for a bit.”

“We keep discussing ___ but never actually learn anything new. Someone is always ‘doing discovery’ on it amidst ___ other things, but nothing real emerges. We need to spend real, concentrated capacity resolving ___ before we can move.”

“___ needs room to grow. We can’t judge it by the same standards as __. We need to protect it and give the team leeway, but also hold them accountable for __. The question isn’t ‘Is this paying off yet?’ It’s ‘Is this developing in a healthy direction?’”

“We keep calling ___ important, but no one will fund it, stop ___ for it, or hire against it. Is it important enough to displace ___? Important enough to add capacity for? Or neither? We either invest or say no.”

“What’s really stopping us on ___ isn’t the work itself. It’s the investment to be able to do it. We keep wishing we had ___, but we haven’t prioritized building that muscle. We have to prioritize our ability to do this, not just doing it.”

“The scope on ___ is huge. But there’s a credible path to radically less scope that still captures most of the value. What if we just did __? There’s an 80/20 here if we’re willing to seriously test __ before committing to the full thing.”

“___ feels urgent because __. But is that window actually real? What specifically changes if we wait until __? Sometimes the answer validates the urgency. Sometimes it exposes something people just want to do now.”

“On paper, ___ looks like just another effort. But if you consider everything that would benefit, it’s critical. ___ gets faster. ___ gets cheaper. Unless you explicitly account for what it multiplies, it will always lose the prioritization conversation.”