Can I nerd out on prioritization for a second?

It’s so common to get asked to prioritize projects or pieces of work as either “High”, “Medium”, or “Low” priority. But that has never quite worked for me; it never seems to capture the nature of the situation. I find myself wanting to add a “yes but…” or “that depends if…” on every single item.

Of course I understand why that prioritization system is so common. At some level prioritization is the business of taking the messy and complex and forcing it into a simplified punch list of projects or tasks. And that duty is critical since it enables your team of experts to know what to work on — to start with the top item from the pile, dig into it, and work their way down. Doing that execution work takes skill and expertise, but it’s emotionally and strategically straightforward for those experts. You tell them what to focus on, and they give you good work in return.

But the deciding of what to do? Now that’s the tangle. That’s the hard, murky, and magical bit. Sorting out what to do when takes another level of understanding, of active and strategic engagement, of critical thinking and extensive communication, of perspective and humility. That’s the key gap most organizations experience, and it’s the gap hurting them most.

When we get called in to help run the show, prioritizing work is among the first and toughest challenges. The landscape always feels impossibly murky at first, and I question my sanity for getting myself into this mess. Everyone is looking at us to make decisions around prioritization in an incredibly complex environment with things moving in every direction, and very little time to get up to speed on all the background context.

In these moments, having to use a High/Medium/Low prioritization scheme feels like the wrong medicine. It makes me feel like I’m just guessing. What does prioritization mean in this scenario? Are we focused on urgency, triaging the things needed most quickly? Are we focused on importance, building the long term foundation we need? Are we running towards the loudest voices asking for help?

Typically everything feels like a high priority, otherwise it wouldn’t have come up to begin with. But what can your team do with a stack of equally high priorities? Not much besides getting overwhelmed.

Fortunately for our own sanity, we eventually landed on three essential elements to understand which suddenly shift everything into focus. Those are:

• Urgency

• Importance

• Level of effort

Urgency is the most obvious consideration. Donor data needs to be fixed by next week or your major annual fundraising campaign is going to crash and burn. A bug has broken your website signup page. Better get on those. But an exclusive focus on urgency keeps you in reactive mode, constantly solving near term problems while falling ever deeper into a hole, neglecting the longer term foundational work that will keep you out of trouble.

Importance is a little trickier. Have you ever seen the importance/urgency matrix? The “important but not urgent” quadrant is the one that is getting neglected if you’re always focused on urgency. All that maintenance work, the long term planning, the platform updates, the data integrity work, and so on — those are rarely urgent enough to get the attention they deserve. But this important-not-urgent work is where you not only prevent problems, but you keep your entire machine evolving to keep up both with your evolving needs and the evolving world around it. So you’d better find a way to keep those items in your priority mix, urgent or not.

Level of effort is the final piece that you need to be able to prioritize. Is each item a quick fix, a small bit of work, a good amount of work, or a larger project? How you estimate it can vary. Fine with me if you prefer using hours and minutes, or story points, or t-shirt sizes. I just need a sense of how big this thing is.

Often we don’t yet know how big it is yet, and there’s no shame in that either. In that case just break off the scoping into its own task and prioritize that piece. Sure, scoping takes some time and some money, but it’s a small investment with an incredible return. Even the seeming worst case scenario where you to pull the plug on a project after scoping is a huge win compared to committing to a failed path before you had the full picture.

Urgency, importance, and level of effort. With those in hand, prioritization clicks into place. This becomes a game you can play. This is when you start to see the matrix and can back-bend your way out of the path of an oncoming bullet.

With those estimates in hand, we now have the elements we need to prioritize and budget work over a unit of time. With those I feel like I can confidently say to the assembled experts: let’s knock these three urgent-but-smaller tasks this week, along with these couple important-but-non-urgent maintenance tasks, while scoping these two things for next month. Meanwhile let’s get this longer term project onto our roadmap so our foundation is where we need to be six months from now.

Are all of those items “high”, “medium”, or “low” priority? I’m not sure. All high, I guess.

But give me urgency, importance, and scope out level of effort, and now we’re talking. Now we can make sure everyone is making great, satisfying use of their time and skills. Now we can see the chessboard. Now we have a game we can play and win.