TBM 381: Stop Trying To Make Prioritization "Easy"

Hot take: We want prioritization to be hard. That’s the game. If it is easy or transactional, then something is wrong. Let me explain.

Three Frames

When we talk about prioritization, there’s a difference between:

1. Prioritizing goals, objectives, and strategies (our “ambitions” or intents)

2. Given fixed capacity, and assuming the existence of goals, objectives, and a strategy (#1), how do we utilize that capacity for maximum results

3. Deciding whether to make net-new investments to increase/shift capacity

Anti-Patterns

Depending on how you weave together 1-3, you get different anti-patterns:

If you only focus on ambitions (#1), you will be trapped in fantasy land. You will pay a huge context-switching tax. You’ll find yourself perpetually overcommitting. Trust and confidence erode.

“We are crystal clear about the outcomes we want to achieve, but lack any ability to prioritize the priorities. It’s all stretch goals, with no reality.”

If you only focus on playing perfect capacity Tetris (#2), you will be doomed to optimize the trivial. You will fit everything in with the perfect plan, but fail to apply focus where it has the highest leverage. An efficient, reactive, random, strategy-free walk. Premature convergence to fuel overly precise estimates and way too much emphasis on predictability for predictability’s sake.

“Our plans look immaculate in spreadsheets, but half the time we’re grinding on low-impact stuff. We’re busy and efficient, but I’m not sure any of it adds up to meaningful progress.”

Focus on ambitions (#1) and capacity allocation optimization (#2), without ever considering net-new investment (#3). You will find it hard to take novel, new swings or to work down big chunks of debt that resist “just chipping away.” It is all “can” and no “should”.

“Half the time we’re grinding on low-impact stuff. We’re busy and efficient, but I’m not sure any of it adds up to meaningful progress.”

If you focus on ambitions (#1) and net-new investment (#3), you will throw money at unfocused dreams. You will never pressure-test whether the org and operations could deliver more within current constraints (or should let go of existing priorities). You set yourself up for an eventual crash once you realize you never flexed your operational chops (or optimized last year’s opportunities before the shiny objects took over).

“Leadership keeps adding budget and headcount for new bets, but the core machine is messy. We never test if we could achieve more by sharpening how we work today.”

If you focus on capacity allocation optimization (#2) and net-new investment (#3), you will keep throwing money at efficiency games without ever questioning whether you’re climbing the wrong hill.

“We keep adding people to ‘optimize capacity,’ but no one asks if we’re even solving the right problems. It feels like running faster on a treadmill.”

The Interplay

A critical point here is that there’s an interplay between these perspectives. This isn’t a simple funnel where you jam ambition in at one end and get a plan and a stack of hiring requests out the other.

You also can’t just optimize one thing. Many people claim they would be successful if they just had a strategy and objectives, or reduced WIP, or focused on outcomes over outputs, or prioritized tasks by force-ranking.

Note how each of those views is pinned on one of the three pillars we mentioned.

In a functioning product org:

• Reality tempers ambition, but it also forces us to get resourceful.

• Ambition challenges the status quo, pushing us to think bigger.

• It can be useful to reject new investment requests by default to encourage resourcefulness, but then fully support new investments when they enable things that simply wouldn’t happen otherwise.

• You want your team to have an answer for “If we gave you a million more dollars in budget, what would you do with it?” AND have a bias for impact within existing constraints.

Prioritization As Continuous Dialogue

Prioritization is a continuous dialogue, which is why frameworks, almost by definition, are only marginally helpful. Prioritization also occurs across fractal layers, ranging from directional ambitions to specific deliverables.

It is a never-ending journey between aspiration and pragmatism, optimism and skepticism, divergence and convergence, abundance and scarcity, and the dance of challenging constraints while also working within them.

The huge problem is that people look for quick fixes to REPLACE the conversation and the various tensions. We don’t want that.

The tension between limited capacity, limited capital, and ambition/intent is the game. It should be challenging—but the RIGHT kind of challenging. Juggling overly precise estimates and trying to fit arbitrary things into the quarter to prove out a weird say/do ratio is the WRONG kind of challenging. If you eliminate that tension or optimize for just one piece of the puzzle, you’ll end up with subpar results.

I’ll end with a thought provoking quote from a product leader I respect. It seems unrelated to this conversation, but I think it is a perfect example of the tensions we should be leaning into.

Money is generally the easiest part of the equation when it comes to building software. It’s very hard to turn $$$ into valuable software and adding people rarely “fixes” a team, and can make things worse by obscuring the actual issue

Any investment requires confidence in the team and leadership to be a good steward of capital

Asking for more people for an initiative implies everything else on your roadmap is more important and that you can’t find other efficiency gains to achieve the mission/objective with the existing team.