How Leaders Manage Time & Attention

Some findings on productivity.

May 31, 2023 • 8 min read

Last month, I wanted to better understand into how leaders manage their time and attention. While this seems like a core leadership skill, a lot of the managers I know have a fractious relationship with productivity tools. Given this, I had two high-level questions:

  1. What are the popular approaches in this space currently?
  2. Are there pains here that are worth building a product to solve?

To learn more, I collected stories from two dozen managers, directors, and founders in tech about how they prioritize work, track tasks, and organize their time:

  • Interviewees: 25
  • Company sizes: 10 ↔ 1M employees
  • Direct reports: 3 ↔ 26
  • Career stages: New managers ↔ Seasoned executives
  • Tasks tracked at once: 5 ↔ 1000
  • Productivity systems: Meticulous ↔ Downright shambolic

Here are the four most interesting things I learned, and the shape of this weird-ass market as I now understand it.

1. It’s a hard time to be a manager

2023 has brought with it fundraising woes, layoffs, and an increase in the number of direct reports for many managers. A lot of folks are feeling the pressure, and in some cases it’s leading to a bit of… chaos. You know, the kind where you ask an interviewee how it’s going, and they respond with wild eyes: “Haha well I’m still here!”

Talk to your manager if you’re experiencing more than two of the following symptoms:

  • You have more than 12 people reporting to you
  • You’re hiring new reports, especially rapidly
  • Your boss or wider org is dysfunctional
  • Your startup is currently trying to raise funding
  • You’re increasingly unclear what the strategic priorities even are at this point, seriously what is even going on here

If these sound familiar, then you may be in what we call, in the industry, survival mode. Under this kind of pressure, leaders’ use of time and task management habits and tools will often degrade. People who were using Things or Todoist might revert to paper or one Long-Ass Apple Note.

People like me that use a featureful tool like OmniFocus to stay focused might expect this to make things even worse. But it’s a lot more workable I’d thought, because…

2. A Long-Ass Note works for many people

This was my most surprising finding. Formal task-tracking software can be helpful for plenty of people and plenty of workloads, but it also affords a lot of metaphorical rope. I’d hypothesized that more experienced leaders would use more sophisticated task-tracking workflows, but I found the opposite. Many leaders, especially senior folks with a lot of task relevant maturity and a strong team, end up preferring a Long-Ass Note for organizing their work. Roughly 1/3 of the leaders I talked to use a variant of this approach.

Here’s the typical format for this, in my anecdata:

  1. Keep only 5-15 items in your list of tasks at once – just the critical stuff.
  2. Keep a daily or weekly habit of reviewing your top priorities, punting things, and pulling up the absolute most important items.
  3. Mark the passage of days or weeks as they go by, creating a running history.
  4. Optionally, mix in today’s notes from meetings or in-progress work.
  5. Archive the running history every few months.
  6. Host this somewhere you can get to quickly; either a native app like Apple Notes or Bear, or a tool you always have open like Notion or Docs.
  7. Feel self-conscious that a Long-Ass Note is kind of janky, but stick with it because for you, it works.

Two interviewees described this approach as “like paper, but with links.”

Many note-centric people I talked to appreciate that notes avoid the ceremony of GTD-style task-tracking tools, and the overwhelm that can come from “due bombs” and other anti-patterns in systems like this.

There are a few products built specifically with a note-centric view to task management. NotePlan is a compelling offering here that also has some useful calendar integration. Regardless, most of the note-centric planners I talked to were skeptical of adopting any kind of formal tooling.

Of course, the Long-Ass Note isn’t for everybody. Most leaders whose job includes a lot of project management benefitted from more structure. A note-centric workflow seems to work best for folks who have the discipline to focus on just a handful of high-impact priorities, and a role that affords them the ability to do that.

For the procrastinators and easily distracted among us, there was another popular solution…

3. People love time blocking

Most stories I collected about task management habits came with a dose of antipathy. I’ve used OmniFocus for many years, but on some levels I resent it. Even the remarkably resilient Long-Ass Note was often mocked by its adherents. Time blocking, though, was an outlier in that it’s a well-loved productivity habit. Adherents seem to really appreciate the practice, and in most cases wished they used it even more.

Time blocking is a simple idea: set out chunks of time in your calendar where you plan to do certain deep work. Alternatively, batch together small tasks that can get distracting into a time box. This can be a useful approach for people in any role, but it’s particularly useful for leaders, whose days tend to fill with meetings and distractions and Slack pings and status emails and what is the new vacation policy again and oh shit it’s 5:30.

Where individual contributors, or ICs in management jargon, are often focused on tasks, managers are focused on people. Thus, their calendars are often poorly formed for getting things done.

Meanwhile, there are usually at least a couple of important, high-impact things a manager should really be sitting down and doing today. Making a habit of time blocking helps ensure these things actually get done.

A specific flavour of time blocking that’s especially helpful for those prone to procrastination is to block time at the beginning of a day or week to Eat the Frog. The Frog, in this metaphor, is the critical task that you don’t wanna do. Something that is causing you stress, and you’ll be glad to have off your plate. Get it out of the way first, and the rest of your day is the reward. It’s dumb, but it can work wonders if you do it.

One manager liked the idea of avoiding procrastination using the Eat the Frog method, but found themselves procrastinating the very act of identifying a Frog and scheduling time to complete it. Thus they continued to churn through their task list in an unordered way between meetings, anxious about the handful of overdue tasks they habitually deferred, including the aspirational “Choose a Frog”.

This twisted loop of self-defeat brings me to the penultimate lesson. Time blocking works, but only if you’ve developed the discipline to actually do it. Hence, it’s important to remember that…

4. Everyone’s demons differ

If you’ve led a team, you’ve seen the variation in how different folks struggle. Overwhelm, procrastination, overwork, distraction, demand avoidance, over-commitment, analysis paralysis, and even just boredom can all impede different people. While I objectively knew this, these interviews crystallized for me how most leaders have tamed but not defeated their respective demons. These personal struggles tend to fuel very personal opinions about productivity tools.

For example, in my research I learned about Reclaim, a tool to help teams flexibly block out time and make better schedules by automatically shifting 1:1s and other meetings. I spoke with a couple folks who quite liked using it to manage their calendars, and more who loved the idea. Meanwhile, some interviewees were actively hostile to the concept. One director called the idea of automatically shifting 1:1s “a literal nightmare”.

While personality and biology fuel some of these differences – the folks I talked to who mentioned ADHD had adopted simpler calendars and kept more disciplined task lists in my findings – there are also huge variations as a person moves through roles, companies, and experience levels.

Often folks will develop one set of habits and tools for managing their work, then have their system implode when they get a promotion, switch companies, start an ambiguous new project, or even just develop more self-discipline and no longer need the same tools. All careers have a natural cycle of change, and these changes lead people to churn in and out of different productivity tools.

This is natural, and adaptive, and good. But it has the side effect that…

5. This market sucks

Task management and productivity tools are deeply personal, and each customer’s needs change over time. The market leader in this space, Todoist, has built something that works for 80% of people 80% of the time, and has earned 30 million users in the process. Other than an obstinate refusal to support start/deferral dates, it’s a serviceable task management tool. By being a decidedly middle-ground task manager, they’ve done a pretty good job of reducing how often people need to churn out of it to another tool.

Meanwhile, a lot of people will tell you how much Todoist doesn’t work for them. They bounce between the many tools that make up the remaining 20% of the space, fuelling a massive archipelago of niche and ultra-niche tools, often maintained by 0-3 people each. While I initially thought this indicated an opportunity, I now suspect this is the natural state of the market.

If you’re considering building a product in this space, you need to grapple with two things:

  1. A tool for individuals will have difficult economics – you have to fight for each sale one by one.
  2. A tool for productivity will have high churn – many people will naturally grow out of your tool over time.

Together, these give productivity tools the same market dynamics as self-help products. There’s a lot of interest in the space, and some people will try anything and everything, but you’re always fighting uphill.

There’s a good 2021 article in Wired about productivity apps and their difficulties, which ends thusly:

To-do software [is] unique. The majority of tools we use in our jobs are about communicating with someone else. All that messaging, all those Google docs, all that email—it’s about talking to other people, documenting things for them, trying to persuade them. But a to-do list is, ultimately, nothing more or less than an attempt to persuade yourself.

This struck me. One interviewee, an accomplished founder, had described their productivity approach as “very bad, very ad hoc” but was skeptical they would switch to anything better. This is a market where it seems like the tools are bad – and sometimes they are – but in many ways they’re just mirrors. The needs are personal, and constantly changing. Ultimately, there’s only so much we can do as product developers to help people help themselves.

Where does that leave me? After four weeks of research, I’ve learned a ton about how leaders work across various companies, tuned up my own approaches a bit, and levelled up my product discovery skills, which was a lot of fun. But now I’m on to my next research space.

Next up: a problem that is causing trouble for an increasing number of teams, who seem keen to get a solution in hand. More on that soon.

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© Allen Pike. 👋🏼 You can contact me, or check out Steamclock.