TBM 399: 10 Prioritization Traps
Happy 2026, and thank you for reading the newsletter!
I’ve been thinking a lot about prioritization lately. I work at a startup where every second feels like a prioritization decision. There simply aren’t enough seconds in the day, and there’s an endless list of “should-haves” and “musts.” One thing I try to remind myself is that it isn’t about making perfect decisions, but about making marginally better, “good enough” decisions that help us move forward and avoid major crevasses.
To that end, I put together this list of prioritization anti-patterns and traps to watch out for. If we can detect and filter out a meaningful percentage of the duds and traps, it can make a big difference.
1. Burning Down the House
“I know none of this is strategic, but if we don’t deal with it right now customers are going to feel it. Let’s just get through this sprint and we’ll talk about the bigger stuff next quarter.”
Never finding a way to pull out of the high-urgency, low-to-medium-value zone. The company is always in full reactive mode, pulled by urgent things that would cause pain for customers and that would have material impact, but that ultimately aren’t big game changers. These often fit into the “table stakes” category.
The key point is that, in most cases, you can’t ignore these things. You have to do something. If you didn’t, it would be painful. But when you spend all of your time doing these things, you aren’t doing the work needed to avoid these problems cropping up in the first place, and you aren’t doing the work that meaningfully protects the growth of the business. The challenge is to do just enough to make the problems go away, while also figuring out how to make the investments that buy you breathing room or fund expansion in more sustainable ways.
Do This Now: Carve out a fixed slice of capacity (even 10–20%) that is explicitly protected from reactive work and can only be used on prevention, thorny problems, or leverage-building. Treat any exception as an escalation-worthy event.
2. Too Much Time on My Hands
“It wasn’t a failure exactly. We just… kept refining it. By the time we shipped, the moment had kind of passed.”
Medium-urgency, medium-value work where the team fails to find the 20/80, the 20% of effort that produces 80% of the results. They spend far longer than they need to, while avoiding early de-risking, early learning, and early value opportunities. This is the “middling” stuff. You sort of forget about it a couple of months later, or maybe only remember the first few early wins.
Looking back, you say things like, “I wouldn’t call it a miss, but we ended up polishing this way too much,” or “We took too long to get something into the hands of customers.” “It was OK, but in many ways it was more trouble than it was worth,” or “Looking back, the real value was in [some small aspect of the work], not necessarily all that stuff we did with the other 80%.” This is the type of work that expands to fill the available space. If you set a quarterly goal, somehow the work is wrapping up with a couple of days left in the quarter.
Do This Now: Force an early cut: define the smallest version that would let you learn something real in the next 2–4 weeks, and commit to shipping that no matter how uncomfortable it feels.
3. Everybody Wants to Rule the World
“Everyone agrees this is the top priority. That said, no one can really drop what they’re already committed to.”
High-value, high-urgency work. Everyone agrees there’s a real time element here, a window of opportunity to seize, and high confidence in the value. In many companies this ends up on something like the “CEO 10” because it’s high-profile.
Everyone understands how critical it is, or so you think. But the message doesn’t reach everyone. Teams are still juggling that work with other work. Different VPs are balancing their local priorities against the priority of the big thing. Everyone is down in the weeds worrying about overly precise estimates here and there, while senior leaders are wondering if “anyone got the memo about how important this is.” “We keep talking about how much of a priority this is, yet somehow I’m not sensing that we’re taking it seriously.”
At the core, leadership isn’t actually carving out the focus the effort requires. In fact, they’re tacitly encouraging practices that break it into small pieces and cause teams to lose sight of the big picture.
Do This Now: Pick one thing teams are explicitly allowed to drop in service of the priority, and say it out loud. If nothing can be dropped, the priority isn’t real.
4. Just Enough Is Never Enough
“We shipped it, which is good. But yeah, if we’d had a bit more time, it probably would have actually mattered.”
Perpetually doing “the bare minimum” and missing opportunities to capture the actual value. Teams either ship quickly and move on, or take a long time to ship and are forced to move on. They get something promising out there, but only capture 20% of the value. In a sense, with 20% more work they could have captured 80% more value, but the team was under too much pressure to move on.
Sometimes this is because everything takes so long that no one has any appetite to iterate. If they had de-risked and gotten something out earlier, they would have had more legroom. In other cases, teams are moving reasonably quickly. They’re skilled at “working small,” but no one is allowed to really “think big” and keep the effort going.
A variant of this is shipping things that are almost there, but never really tying up the loose ends with support, documentation, capturing early win stories, and so on. It isn’t always about pressure to move on, but rather a habit of not really closing the loop. The trouble, of course, is that this is a counterbalancing instinct to the 80/20 problem. Some teams spend forever polishing. Other teams never polish. The features end up with no paint and no sealant.
Do This Now: Before shipping, list the 1–2 follow-on investments that would unlock disproportionate value if the initial release works. Pre-authorize one of them so the team doesn’t have to “re-pitch” momentum.
5. Running on Empty
“We’re close. We’ve been close for a while. It’s just more complicated than we expected, and it’s hard to say what ‘done’ even means anymore.”
Death marches where no one seems able to explain why things are taking so long. They’re aimed at something valuable and urgent, but as time passes, the window of opportunity starts to close and the value proposition or potential ROI gently slips away. One defining trait is that there’s no obvious way to say, “Hey, we’re off track here.” These efforts often involve highly specialized technical puzzles and a lot of pride. No one wants to admit they’ve gotten stuck in a quagmire.
There are periodic “summits” to understand the state of things, but a couple of weeks later everything is somehow back to normal. Leadership teams often bring in an outsider to help wrap their head around it, and the results are similarly unsatisfying: another summit, the outsider sharing their findings, a new “solid plan” emerging, and so on.
Another key element is that these efforts tend to defy adding more people. When asked, “Can we add people to speed this up?” the answer is a confident “no” (for good reasons, in most cases). From a prioritization standpoint, these efforts become permanent fixtures on the roadmap. Other, more urgent things crop up, creating interruptions, but they 1) don’t take up enough capacity to really put pressure on people, 2) are often foundational problems that need to be fixed, and 3) slow everyone else down, even though no one can quite do anything about it.
Do This Now: Introduce a clear “off-track” signal: a date, learning milestone, or decision checkpoint where continuing requires an explicit recommit. If you can’t define that signal, you’re already stuck.
6. Dreamer
“Leadership really believes in this, so we’re protected. We’ll worry about how it fits with the rest of the company later.”
“Innovation” efforts that are lower urgency but high value. Choosing to nurture this work is often the right move. If you didn’t, you’d risk living entirely in the high-urgency, reactive, optimization domain. The CEO wants to see progress on X, so you see progress on X, and the team checks the box.
A couple of problems tend to show up.
One is that the organization tries to treat “innovation” as a project. There are no real opportunities to learn. There are no opportunities to relax governance rules, compliance, and so on. In other words, none of the ingredients for creativity exist. The teams simply aren’t given enough room to operate.
The flip side, of course, is the opposite failure mode: there are no enabling constraints. There’s no pressure to ship and learn. Teams build a bridge to nowhere, basking in the protection of senior leadership. There are also no real efforts to integrate the idea across the organization or to test the ability to scale it, which means the work “finishes” only when it hits the wall of reality (for example, “How will we support this?” or “How will we sell this?”).
Do This Now: Add one enabling constraint: a deadline to ship something real, a forced integration with an existing team, or a concrete scaling question that must be answered. Creativity needs forcing functions.
7. Slow Ride
“Yeah, it’s annoying, but everyone’s learned the workaround. It’s not blocking us — it just makes everything take longer.”
Imagine if Slack or GitHub went down once a day for a couple of hours. It would be the end of the world. Yet there are often areas of friction inside companies that impact everyone and slow everything down, and they get relegated to “tech initiatives.”
From a cost-of-delay standpoint, this work should effectively inherit the opportunity cost of everything it impacts. If the waste were visible, there would be an immediate meeting of senior leadership, maybe even the board. But because the impact is less visible, “qualitative,” mitigated by workarounds, and because a few high-profile teams are lucky enough to avoid the dependency and still produce results, these efforts get framed as lower urgency and lower value. It’s death by a thousand cuts. Nothing so severe that people quit or walk out, but cumulatively it has a massive impact.
Do This Now: Quantify the drag. Pick one workflow or dependency and measure how much time it adds per week across teams. Put that number in front of leadership and reframe the work as cost-of-delay, not “tech cleanup.”
8. Someday Never Comes
“We all know this would be huge. We just don’t have a clear enough solution yet to really start.”
The “shoulda but can’t” trap. If you ran a poll across the company, there would be strong consensus around an opportunity that could change the shape of the business. The problem is that no one can come up with a “solution” that feels high-confidence enough. “Everyone knows this would change the game, but we’re not sure how it would work.” Instead of thinking probabilistically, “OK, we’ll probably fail at a lot of things, but we’ll learn and gradually move the needle,” the organization treats this area as a far-off, aspirational opportunity that will be figured out “later,” once the higher-confidence work has been knocked out. The problem is that “later” never becomes today.
At Dotwork, we sometimes call these “forever problems,” because there’s undeniable value in solving them, but fear of lower probabilities seeps in. The result is that companies only approach these areas through walled-garden “moonshots,” rather than integrating them into a portfolio approach across teams. In reality, all teams should be thinking about how to assemble a balanced portfolio of risk, with some longer bets mixed in. When there’s a strong focus on “can’t,” leaders should spend real time figuring out how to remove the implicit or explicit blockers.
Do This Now: Run one low-cost experiment designed only to reduce uncertainty, not to “solve” the problem. Make learning the goal, not success, and explicitly budget for failure.
9. The Logical Song
“This one feels risky, so let’s focus on the thing we’re more confident in, even if we won’t really know until the end.”
Spinning up prioritization frameworks that include “confidence” for things like value and urgency, while missing the potential cost of increasing that confidence. Imagine an effort that’s genuinely open-ended. You’re not sure yet. It could be a game changer. It could land somewhere modest. But the cost of increasing certainty is low, and the path to learning is clear. Now contrast that with a high-confidence, middling effort where the assumptions are hard to test. You only really know when you get to the “end.” What gets missed is that confidence is not free. We need to take into account how easy it is to learn, to increase confidence, to reduce risk, and to collapse uncertainty early, not just how confident we feel at a single point in time.
Do This Now: Add a column to your prioritization that asks: “How cheaply can we increase confidence?” Favor work where learning is fast and reversible, even if initial confidence is low.
10. Takin’ Care of Business
“We didn’t really have anything small and useful lined up, so when we got blocked we just kind of… made something up. It kept people busy, but looking back, none of it actually mattered.”
Prioritization Tetris. This is only marginally related to prioritization, but many teams “pack” their timeboxes, quarterly goals, and plans based on the premise that, if the stars align, they’ll get everything done. Prioritization becomes an input into the madness.
The anti-pattern is not having a set of very small-batch items at the ready, and not making sure that work is generally accepted as moving some needle. Without this, teams end up inventing work on the spot, without much thinking behind it. Meanwhile, they could be “mopping up” slack in higher-leverage ways. The core point is twofold: loading teams up through prioritization is counterproductive, and if you intentionally give yourself more slack and flexibility, make sure you have small-batch work ready to go.
Do This Now: Build and maintain a small-batch “pull queue” of universally accepted, low-risk, needle-moving work. Make it visible and legit, so blocked teams don’t invent work just to stay busy.
Some prioritization related posts:
Thanks for sharing this — I really resonate with how you frame startup life as a constant stream of prioritization decisions under severe constraints.
Startups are essentially a marathon of interconnected decisions, each one influencing the next and the ones before, all made under uncertainty and against many unknown or assumed elements of the business model. Time, resources, and attention are always limited, so “good enough” decisions are not just acceptable, they’re often the only viable option.
That said, prioritization often looks like good decision-making, but it’s usually already in convergence mode.
What I’m missing is the divergence phase: which assumptions were deliberately challenged before narrowing down?
Without that, convergence just locks in the obvious option, the same one everyone else ends up choosing.
Great summary ... I think I recognise all 10 of those traps!