Talk to Your Boss About Deep Work


A Deep Case Study

Tom works in marketing for a venture-backed tech start-up in Silicon Valley. After reading Deep Work, he realized that prioritizing uninterrupted concentration would help him excel in his job, which centers on cognitively demanding research and writing.

But he despaired that regular deep work was impossible given his company’s culture.

As he explained:

Our company uses email and Slack as our primary means of communication. I get so many emails and chat messages every day, and there’s this unspoken expectation in my department that if someone emails/messages you, you should respond almost immediately, even if you were in the middle of something. If you didn’t respond quick enough people would assume that you were slacking off (this expectation was especially strong with instant messages).

Communication environments of this type are increasingly common in knowledge work (and near ubiquitous in tech). And they can be quite distressing.

As Tom admitted, he really didn’t get much “actual work done,” as his days were filled with “putting out fires” and “reacting to other people’s needs.”

Fortunately, however, all hope was not lost…

The Deep Discussion Strategy

I suggest in my book that employees interested in depth should discuss the topic with their boss. In more detail, during this respectful conversation you should try to accomplish the following:

  1. Explain the concepts of deep and shallow work, noting, of course, that both are important.
  2. Ask what ratio of deep to shallow work hours you should be aiming for in your job.
  3. Then promise to measure and report back regularly. (Most bosses will be interested to gain these extra data points.)

With some trepidation, Tom decided to give this strategy a try. Here’s his report:

I explained to [my boss] the concept of deep and shallow work.  I asked her about her expectations: how much time does she expect me to spend each day researching/writing, and how much time does she expect me to spend communicating through email and chat?

Her reaction?

As soon as I brought it up, it was immediately obvious that if she said she wanted me to spend large portions of my time communicating rather than doing my work, it would have been ridiculous. The only reason this had become a problem in the first place is that we’d never been deliberate about setting expectations.

Tom and his boss quickly settled on a plan in which Tom would have a 1.5 to 2 hour chunk of uninterrupted deep work time in the morning and in the afternoon.

Outside of those chunks he would be answer emails and instant messages promptly.

After talking with his manager, Tom then explained the plan to the team members with whom he communicated most frequently. It took them about a week to adjust to his deep work schedule, and now it doesn’t come up.

As Tom concludes:

It’s been three months now and nothing broke. Checking email and slack less didn’t result in any catastrophic issues. In fact, it’s helped me improve the quality of my work and my ability to focus, and my brain doesn’t feel fried at the end of the day from multi-tasking/switching contexts all day long.

This deep work discussion strategy is simple but it really does work. Many draining work cultures are more flexible than employees expect (see also: Leslie Perlow’s research on the Boston Consulting Group).

Put another way, just because your office seem hostile to deep work today doesn’t mean that it wouldn’t support it tomorrow…if you bring it up.

Just ask Tom. But not between 9 to 11 or 2 to 4, because he’ll be too busy creating valuable things to answer.

(Photo by Kai Hendry)

21 thoughts on “Talk to Your Boss About Deep Work”

  1. I like this real world example Cal, it reminded me that my wife needs to have this conversation as well. However, she has a slightly different set-up. As a small business owner she leads a team of 13 in much of the manager-role work, but I think she can set up a chunk of time in the AM and PM – much like Tom in the example – to finally score some Deep Work hours. Really appreciate your research & writing, keep it coming!

    • The boss needs to have uninterrupted time as much as everyone else. If you have 13 staff and they each ask you 2 questions a day that is an interruption every 20 minutes or so (and you can never achieve focus).

      I have times when I am free to be interrupted and off-limit times. So long as the boundaries are clear, it works really well.

      • Thanks for this perspective. As line staff, I had never thought of this, but so many of us bugging the boss would destroy her concentration as much as mine is when my peers IM me for dumb things. I am going to concentrate on making an agenda list for her instead of opportunistically contacting her at each moment. I have also unfollowed all my peers on Skype because I find it distracts me to view their presence / who is working and who is not. This takes away one more target for my attention when I should be focusing on deep work.

  2. A while back, the company I work for sat down and wrote up our expectations on our different mediums of communication and how quickly we’ll respond. Those expectations have changed a bit, but just the act of sitting down and deliberating about who expects what was incredibly helpful for us. We all know that an email needs a response within 24 hours and a direct message in Slack requires a response within an hour or so. That being said, if you’re out of pocket for a bit, everyone assumes you’re head down and busy and that you’ll get back to them later.

  3. At my new job employees are encouraged to put up outside of their office or cubicle if the need arises. They’re laminated and have either a stop sign or hotel do not disturb sign on them, and then these words: “I’m concentrating on a project. Thank you for not interrupting me. I will be available at:” with a place for you to write the time you’ll be available with a dry erase marker. When I saw that during my interview, I knew I’d be joining this company. It’s a great culture where you’re encouraged to put the same message as an auto-reply in your email and to not answer phone or IM while you have the sign up. This simple practice totally floored me, because I keep reading about it from Cal but didn’t think any company could actually pull it off. (especially not in biotech, where the culture tends to be “act first, think later”!)

  4. This is a great example. These conversations are important. I wonder if these are possible without building up some career capital in the same organization or perhaps without a stellar resume.

  5. Great book Cal. I am in med school studying for USMLE Step 2 (aka “the boards”) and have changed my routine. I don’t check email immediately upon waking up. I check it one time a day at night just before sleep. Deactivated Facebook. Have found I’m much more calm and less frazzled and can study for long stretches of time.

    • Facebook isn’t a distraction but not keeping in touch with people will eventually become a mental distraction.

  6. Passing of Prince yesterday. Sad loss. What a musical genius. He played multiple instruments, wrote songs, sang. Since he produced so much I was curious about his ability to focus for long periods of time. Here is what I found:

    “His ex-wife Mayte once told London’s Daily Mail, “Being with him was like being at the centre of a twenty-four-hour creative machine. If we weren’t on stage, we were rehearsing. If we weren’t rehearsing, we were in the studio.” That’s why Prince, for a long time, put out an album per year while most artists were releasing one every two years, and Michael Jackson once every four years, like a president. These are albums he wrote, produced, and played most or all of the instruments on. He was legendary for work­ing day and night, an inexhaustible music monster. As he says in “All the Critics Love U In New York”: “Body don’t wanna quit. Gotta get another hit.”

    Several people told me Prince often worked sessions that lasted twenty-four or even thirty-six hours. Chuck Zwicky, one of his engi­neers, told me, “I’ve always admired the diligence and discipline that Prince has and his work ethic. He just kept going and kept working until he had it. I’ve had more than one forty hour day with him. Pretty intense. He’s extremely hard working and, much to the chagrin of women, he’d rather spend his time working on his music than hanging out in a club.” Zwicky said that Prince’s time in the studio was almost always spent efficiently, moving at a rapid pace compared to his music-business peers. “He never spent an inordinate amount of time on one song,” Zwicky said. “I’ve worked with artists who will agonize over a single song for many, many days. I’ve never seen Prince do that. He’s got a very, very clear idea in his head about what the song needs to do, what it needs to sound like and he could get through it very quickly. So, typically, a session started with three written songs and ended with three completely mixed songs. He never second guesses himself and he never scratches his head. He never says, I wonder if this is good or not?” “

  7. In my former company (a mid-size firm) one of my KPI of the Head of the office was the (Total number of unanswered phone calls in the office)/(Total number of calls in the office). Given that offices were open-spaces occupied by 10-20 employees, every time the phone rung, everybody was expected to check if on the desk there was someone ready to answer or, otherwise, get the call redirected to his/her desk. In other words: 10/20 people where distracted on each call. There was no real need to act in that way, it was just a silly order to execute.

  8. Great blog this time and great comments. Finally we are all recognizing that most people must get permission to do their deep work w/o interruption, from both their boss and their assistants. Only quibble is that this particular case was ideal. Would be good to blog on harder conversations with bosses and coworkers and how to deal with those. If you explain deep work, people tend to agree w/ it in principle, but not when they really need something from you. That is why signs on your door or a partially closed door don’t work. Only a closed door works. (Plus phone shut off and email closed and only emergency online searching during deep work periods.)

    I used to be in a busy office shared with 2 other people and in a main thoroughfare of my lab. Now my office all my own and is located down a quiet hallway well off the main thoroughfare and I can work behind TWO locked doors when I need to. Guess which situation leads to better concentration and deep work? Only danger now is falling asleep because of all the peace and quiet!

    Most people don’t have this luxury nor did I most of my life, but I can assure you there is always a quiet place to work somewhere. For most of my career, mine was at home when the family was asleep.

  9. The concept of Deep Work is so badly needed by our society, Cal. I am a graduate student and a large part of my day is spent replying to emails, data analysis, and figuring out administrative hurdles needed to graduate. I have begun blocking out 2 hours of my morning right after I wake up to think deeply about my research and this has made an immense impact on how my work is going. I honestly feel like I’ve put in a full day before I even show up to my lab. It is fantastic.

    Thank you very much for pushing this much-needed principle out there.

  10. I like the example here. I often work on teams with others who are my junior. They interrupt my concentration frequently, reducing the amount of deep work I get in a day. That work is key to maximum personal productivity, so I’m less productive than I could be if I were uninterrupted.

    On the other hand, the people interrupting me save time and they learn something. That has a certain value too.

    What matters most is not my personal productivity. No man is an island. It’s the total output of the ecosystem that matters. A sacrifice to my own ability to deep work in order to get someone else unstuck may enable more total deep work to occur. A 40 minute interruption to my own deep work could allows someone else to get in an entire additional day or two of their own work.

    There is a sweet spot between maximum personal deep work and the shallow work of efficiently managing subordinates that maximizes total value creation. For some it may even be at either extreme.

  11. People who overperform are almost universally taken advantage of. They’ll be promoted only up to the point where they can be taken advantage of the most – middle-management, aka senior management’s bitch. At the lower levels your job performance doesn’t matter anywhere near as much as your skill as a politician. Making friends and influencing people is paramount.

  12. If I work deeply I don’t check my emails. Yes, and then it happens that a collegue comes to me and ask. Then I answer: “I didn’t check my emails because I’m just working on XY. But let me see if I’ve received your email….yes, I have. ….How urgent i it?” I’m doing that always and collegues already know that if I’m busy working on a specific task but I check their issue later. I think you need to control your work environment otherwise the work environment controls you.


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