The Importance of Cultivating a Deep Work Culture

Rocky Warren
Rocky Warren
October 7, 20227 min read

Protected "maker", "flow", or "deep work" time is important to productivity. It's difficult for larger companies to change their culture around meetings, it's not for startups. Implementing a deep work culture and fostering it as companies grow gives them a strong competitive advantage: increased per-employee productivity. This means delivering high value to customers with relatively low headcount. A low headcount, in turn, keeps communication overhead low, creating a positive flywheel.

Research

Snippets from Maker's Schedule, Manager's Schedule by Paul Graham,

There are two types of schedule, which I'll call the manager's schedule and the maker's schedule. The manager's schedule is for bosses. It's embodied in the traditional appointment book, with each day cut into one hour intervals. You can block off several hours for a single task if you need to, but by default you change what you're doing every hour.

When you use time that way, it's merely a practical problem to meet with someone. Find an open slot in your schedule, book them, and you're done.

Most powerful people are on the manager's schedule. It's the schedule of command. But there's another way of using time that's common among people who make things, like programmers and writers. They generally prefer to use time in units of half a day at least. You can't write or program well in units of an hour. That's barely enough time to get started.

When you're operating on the maker's schedule, meetings are a disaster. A single meeting can blow a whole afternoon, by breaking it into two pieces each too small to do anything hard in. Plus you have to remember to go to the meeting. That's no problem for someone on the manager's schedule. There's always something coming on the next hour; the only question is what. But when someone on the maker's schedule has a meeting, they have to think about it.

I find one meeting can sometimes affect a whole day. A meeting commonly blows at least half a day, by breaking up a morning or afternoon. But in addition there's sometimes a cascading effect. If I know the afternoon is going to be broken up, I'm slightly less likely to start something ambitious in the morning. I know this may sound oversensitive, but if you're a maker, think of your own case. Don't your spirits rise at the thought of having an entire day free to work, with no appointments at all? Well, that means your spirits are correspondingly depressed when you don't. And ambitious projects are by definition close to the limits of your capacity. A small decrease in morale is enough to kill them off.

Each type of schedule works fine by itself. Problems arise when they meet. Since most powerful people operate on the manager's schedule, they're in a position to make everyone resonate at their frequency if they want to. But the smarter ones restrain themselves, if they know that some of the people working for them need long chunks of time to work in.

Those of us on the maker's schedule are willing to compromise. We know we have to have some number of meetings. All we ask from those on the manager's schedule is that they understand the cost.

From a summary of Deep Work by Cal Newport,

Deep work is the ability to focus without distraction on a cognitively demanding task. It's a skill that allows you to quickly master complicated information and produce better results in less time. Deep work will make you better at what you do and provide the sense of true fulfillment that comes from craftsmanship. In short, deep work is like a super power in our increasingly competitive twenty-first century economy. And yet, most people have lost the ability to go deep—spending their days instead in a frantic blur of e-mail and social media, not even realizing there's a better way.

From a summary of A World Without Email by Cal Newport (an unfortunate title, but he specifically and repeatedly mentions Slack in the book as well),

Modern knowledge workers communicate constantly. Their days are defined by a relentless barrage of incoming messages and back-and-forth digital conversations–a state of constant, anxious chatter in which nobody can disconnect, and so nobody has the cognitive bandwidth to perform substantive work. There was a time when tools like email felt cutting edge, but a thorough review of current evidence reveals that the "hyperactive hive mind" workflow they helped create has become a productivity disaster, reducing profitability and perhaps even slowing overall economic growth. Equally worrisome, it makes us miserable. Humans are simply not wired for constant digital communication.

We have become so used to an inbox-driven workday that it's hard to imagine alternatives. But they do exist. Drawing on years of investigative reporting, author and computer science professor Cal Newport makes the case that our current approach to work is broken, then lays out a series of principles and concrete instructions for fixing it. In A World without Email, he argues for a workplace in which clear processes–not haphazard messaging–define how tasks are identified, assigned and reviewed. Each person works on fewer things (but does them better), and aggressive investment in support reduces the ever-increasing burden of administrative tasks. Above all else, important communication is streamlined, and inboxes and chat channels are no longer central to how work unfolds.

Finally, from a summary of It Doesn't Have to be Crazy at Work by Jason Fried and David Heinemeier Hansson,

Calm is meetings as a last resort. Calm is contextual communication. Calm is asynchronous first, real-time second. Calm is more independence, less interdependence.

Takeaways

Startups can cultivate deep work in the following ways,

  • Favor asynchronous communication in ticket trackers (e.g., Trello, Linear, JIRA) over synchronous Slack.
    • Ticket trackers should contain all context for specific features and projects (including links to any documents and meeting notes on the subject) rather than having to search for piecemeal conversations in Slack.
    • In this way, picking up a new story gives you everything you need to know to accomplish it. This may require breaking stories down in more detail so there are fewer implementation questions.
  • Use Clockwise or similar to aid in meeting scheduling.
    • It takes each person's calendar into consideration to group meetings into chunks as much as possible, leaving uninterrupted blocks of time for deep work.
    • There is an option to block off "Focus Time" on your calendar and it integrates with Slack to turn on "Do not disturb" during these times so you don't get distracted by Slack notification noise.
    • Understand this may mean delayed Slack responses. That should be okay! Allow people to remain in deep work and respond when they've come up for air.
  • At least one, ideally two "No meeting days" for makers and optionally managers.
    • No cadence meetings scheduled on these days
    • Slack standup instead of in-person or over video chat
    • Impromptu meetings for blockers are okay, but try to have multiple tickets to work on so you can move onto another if you get stuck.
    • As another option in place of "No meeting days", have bi-modal days where the mornings are for meetings and the afternoons are for deep work (or vice versa).
  • Meeting invites must include GAP: goals, an agenda, and pre-meeting preparation. If they don't, you can skip the meeting — no GAP, no need to attend.

If the company buys into this way of working, the ROI is potentially large. It's a mindset shift. But for me personally, my best work is done when I lose all track of time, forget to eat, and come out on the other side with shit fucking done. Imagine if an entire company could optimize their days to get as much of that time as possible. Your competition is in trouble.