The Art and Science of Prioritization

Managing Everything From Your Time To Your Meetings To Your Backlog

I’ve been fascinated by the navy SEALs since I was young. From the intense training it takes to become a SEAL, to the mental and physical discipline, and the missions they undertake, they have always been interesting to me. In fact, as a young man one of my friends got hold of their pre-training physical fitness guide, so he gave a few of us copies (this was before you could find things like that on the internet, so it was a great find). And we all used that to train weekly, trying to increase how many push-ups and pull-ups we could do. I think I consistently plateaued in week 4 or 5, where I stayed strong but couldn’t quite get past the number of pull-ups they wanted you to do.

That may be one reason I love the book book Extreme Ownership. At one point, Jocko Willink tells about his team of SEALs as they moved deep into an enemy occupied neighborhood. They fought for most of the day, and as they were moving out again to get back to their base, one of their team fell off a roof. They were in a vulnerable spot with many issues happening at once. As the leader, he needed to secure his team, get everyone down, tend to his fallen soldier, and make sure he has everyone with him still. It’s a long list of things to prioritize when you are under fire. And some of them seem more urgent. But the key to good prioritization isn’t to spin in every direction at once, or let the urgent things trump the important.

“Prioritize and Execute. Even the greatest battlefield leaders could not handle an array of challenges simultaneously without being overwhelmed. That risked failing at them all. I had to remain calm, step back from my immediate emotional reaction, and determine the greatest priority for the team. Then, rapidly direct the team to attack that priority…I could not allow myself to be overwhelmed. I ha to relax, look around, and make a call.”

As much as everyone wanted to rush to their fallen friend, they first needed to secure the area and account for everyone. Then make their way down off the roofs to the street and secure that area. It wouldn’t do to make mistakes and lose lives by prioritizing the wrong things.


This month we’ve focused on prioritization. In my weekly newsletter, we’ve done a deep-dive into different areas of prioritization. We’ve shared some laughs and some tears. But for those who don’t subscribe yet, I’m going to review the key points here.

Guarding Your Time

Inevitably, our time will get filled. Call it a variation on Parkinson’s Law. Things will expand to fill the time available. If we don’t take control of our time, other people or other events will.

Importantly, that means that we won’t have the time or ability to focus on the things that matter most.

The problems we face are many these days. They aren’t new, just easier to access than ever before.

  1. Emails - Average employees spend 35-40% of their days on emails and communication. That is insane. Absolutely insane.

  2. Meetings - Meetings are occupying more and more of our days. More on this one below.

  3. Too Many Opportunities - We have lots of excellent opportunities, but if it’s not a “hell, yes”, it should be a “no from me.”

  4. Fear and Discomfort - We are often afraid of being alone with our thoughts and without distraction. And that pushes us toward lower value tasks. In one study, participants who were left alone preferred to shock themselves out of boredom than be left to their thoughts.

  5. Habits - Bad habits from relying on meetings to always being on-call have a way of taking our time.

  6. Dopamine Hits - Hello Twitter and Instagram.

The solution to our problems is to work deeply. That can mean everything from cutting out distractions like social media to time-boxing lower value tasks. And scheduling (and keeping the commitment) of working on high value tasks. Emails and meetings don’t fall into that bucket.

(De)Prioritizing Meetings

Meetings have found a way to take up more time than ever before. How did it get to be like this?

The problems again are numerous. We rely on meetings for too many things and use them as a crutch. But that occupies so much of our own time and so many other people’s time.

  1. Task Management - We use meetings as a tool for task management rather than managing our own tasks.

  2. Information Dissemination - Yes, it really could have been an email.

  3. FOMO - We become our own worst enemy, wanting to be part of meetings to not miss out on important decisions or discussions, further propagating meetings.

  4. Politics/Perception - We use meetings (or we participate in them) to enhance our position. And so they grow unnecessarily.

  5. Purpose - Too many meetings lack an obvious purpose. Our default has become to call a meeting whenever we feel uncertain about something.

  6. Structure - And our meetings too often lack structure and agenda. If you organize a meeting, you need to think through the purpose and how to achieve that purpose.

  7. Number of People - Going along with FOMO and politics, we often involve way too many people in meetings. Rather than thinking about the greatest number of people who need to be involved, we should think about the smallest number that can help us achieve our goal.

To get out of this meeting spiral, we need to own our tasks. We shouldn’t rely on meetings to mark milestones for getting things done. Or for disseminating information that can be done effectively in other ways. Or for achieving status.

It’s definitely harder in our Covid environment. In my experience and the conversations I’ve had, it appears we’ve swung hard to having to many meetings and Zoom calls. There is certainly a place for meetings and in-person communication, especially as we are all separated. But we’ve gone too far in most cases. We need to reclaim our time to get meaningful work done and spend less time in meetings. And that starts with asking hard questions about why we’re having meetings and if they are valuable (and if you need to be there).

If you need some good ways to say no to a meeting, this is an article I linked in a newsletter earlier this week: How to Decline a Meeting.

Strategic Prioritization

I’ve often said that prioritization is one of the hardest parts of product development. Understanding what problem to tackle next, how to balance requests from stakeholders and leaders and users, and putting it all together into a cohesive product experience. It’s the art of product management. And it’s hard.

There are multiple levels of prioritization. I break them down into this hierarchy:

  1. Strategic - At this level, we focus on the high level opportunities for our business and market. This is about company or department objectives and goals.

  2. Product - At this level, we focus on how to achieve the strategic goals. This is about problems to solve, product direction, and roadmaps.

  3. Backlog - At this level we focus on execution. This is about prioritizing what gets done to achieve the product goals, to solve the problems we’ve identified and deliver the value and outcomes we intend.

A lot of discussion and articles like to jump into different methods for prioritization at this point. But I think that is premature. A suitable method can be a useful tool, but it is part of a larger framework that we need to do prioritization.

  1. Vision and Strategy - Before you can prioritize, you need to have a clear vision and strategy. Otherwise you are left to the whims and wishes of anyone with a strong opinion or senior position.

  2. Understand the Context - Understanding context should be an ongoing pursuit. You should be doing research and interviews and market analysis. For product teams, this is part of the ongoing product discovery process. I wrote about it recently in an article Product Discovery: The Beginning of Good Product Development

  3. Gather Inputs - With a good strategy and good context, you can gather specific inputs, both qualitative and quantitative. These should be specific to your prioritization decision.

  4. Use Methods to Visualize - Now is the time for methods to visualize. There are many to choose from. I break them down into three primary groups. First is ranking methods. These are methods used to calculate scores and rank priorities. Whether it is strictly ranking, using MoSCoW or some other formula, I group these as “ranking” methods. Next are matrix methods. These methods put initiatives or items into different quadrants in a matrix for visualization like Kano or Value/Effort. Finally, I have “functional” methods. These are more focused on broader discussions and bigger functional areas, like user story mapping and lean canvas. 

  5. Decide on Priorities - Don’t outsource your decision to any framework or process. Use the methods as guides and tools, but know that they are only tools. You still need to decide. And not every decision will be clear-cut. 

  6. Align and Realign - Once you have decided on priorities, whether for broad initiatives, your product, or your backlog, you need to align with your team and organization. Make sure everyone understands how you reached your decision and why.

This is a big topic, and one of keen interest to many of us. It takes a lot of practice and a lot of work.

What is Really Important

We’ve focused a lot on prioritizing our time and our meetings and our products. But some of the most important prioritization we do is between our work lives and our personal lives. It is so easy to let work encroach more and more on the personal side, especially when the boundaries have been so blurred.

Personal Life

If we don’t specifically make time for our families, friends, and ourselves, other things will inevitably encroach. I’ve called it a variation on Parkinson’s Law, meaning that work will enlarge to take over any time we give it if we don’t box it in somehow.

As I’ve been meeting with people over the past weeks and months, one of the recurring themes has been how quickly life has changed for so many of us. Many of us were working hard, crushing our roles, when the world changed. And just like that, companies bid so many people farewell without much of a second thought. It doesn’t take a crisis like Covid-19 for that to happen either. It can be a leader who believes their way is the only way to work, and you don’t fit into that. Or a company restructuring.

We should work hard. We should do our best work. But we should keep in mind that the most important things in our lives—our families, friends, etc.—are more important than an extra hour in the (virtual) office.

Personal Projects

In a similar vein, diversifying out of our primary 9-5 is a great idea. Whether it is to develop additional skills, extend our expertise, or increase our network, I’m a big advocate.

Some of the best things I’ve done for my career have been outside of my role. My writing online, in places like this newsletter and on Medium, has opened doors for me professionally. And led to other things, like my podcasts.

I also have completely unrelated projects that expand my skills in other directions and help me think about problems in alternative ways. And they are just a good creative outlet. I’ve done woodworking for several years now (you can find more at Evans Woodshop), and dabbled in graphic design as a hobby.

Not everything needs to be side hustle, though. In fact, pick something that you don’t plan on monetizing in any way. Maybe it’s music or art or crafting or baking. Find something that you want to be good at that you won’t make into a side hustle. While I don’t foresee some of my side projects ever becoming massively profitable, I still have a few hobbies that are strictly creative releases that I know will never be for anything but pure enjoyment.


Prioritization, in life, in work, and in our products, is the key to success. It takes a tremendous amount of effort and thought. But by focusing on the right things and devoting our effort to the highest value items, we’ll get the biggest returns. And that is worth it.


Best of the Rest

Books

The Biggest Bluff - Maria Konnikova set out to learn poker, and how to master the thinking behind decision-making with incomplete information. Poker, it turns out, is a great way to do that. And this book is that story. It’s great from start to finish, and one of my favorite reads this month (and this year).

Bobiverse Books - These books have been on my list for a while, and I read We Are Legion, For We Are Many, and All These Worlds this past month. They are a fun sci-fi read exploring ideas around von Neumann probes, the Fermi paradox, and how humans will handle the end of the world and AI.

Podcasts

The End of The World - If you haven’t listened to this series, it is worth it. I did this past week and really enjoyed it. If you’ve done reading on pandemics, you know just how serious they can be (and how our current pandemic, as bad as it is, feels like a warm-up to something much worse). But don’t stop there, because there are many more things to worry about! I guess it’s that 2020 feeling.

Prioritization: Choosing the Right Things from Strategic Initiatives to Products To Features - As if on queue, we did a podcast episode on this very topic recently. Take a listen for some more insights as we dive into product prioritization and discuss some topics above.

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