How You Can Cultivate a Deep Work Culture: Part 1

corporate to entrepreneurship
Episode 047: Navigating the Path From Corporate to Entrepreneurship
May 8, 2018
deep work
My Attempts at Deep Work – A Journal
May 16, 2018

How You Can Cultivate a Deep Work Culture: Part 1

deep work

If you’re reading this, you’re likely pretty fed up with our typical vicious cycle of shallow work. It goes something like this:


We do some sort of shallow work task, like responding quickly to an email enough times, and we get praise from peers and bosses. We are seen as reliable and a team player. We all want that right? That’s lauded in our culture, our job descriptions, our companies’ credos.  Then we get a promotion, which invariably leads to a heavier workload. This then leads to a time squeeze, where we have even more competing priorities on our plates (and yes, the need for more deep thinking is even more critical here, but there’s no room for that here moving on!).  Then, in the absence of any structures at our company or within ourselves, we continue to opt to complete the shallow tasks, thus continuing the vicious cycle you see here on the screen.


This leads to less impactful work output, more frustration on your team and in many cases, higher turnover, as people seek potentially better opportunities to make a contribution elsewhere.


Q: So, you recognize this is happening with your team and your work product. How can you start to untangle the mess?



A: This is not a simple answer, and different organizational dynamics will change the approach. For example, some teams may only primarily interact with one other team within the company, but other teams may touch all sorts of different teams and external customers. This makes the application different but there is one thing everyone can do, regardless of specific situation, to start to address this challenge.


It starts with you.


As a manager of direct reports or a manager of managers, it really really starts with you. So, in this particular post, we’re not going to get all fancy with how to apply this to your team or company. Instead we’re going to talk about how you – just you- can stop ‘hustling hard’ every day to actually put the building blocks in place for deep work.


How do we start this process?


  1. Start to shift to the anti-hustle mentality. This can be hard to embody when you’ve been ‘crushing it’ and ‘hustling hard’ for your entire career, so enter into this with baby steps and some gentle discipline. Start to cultivate your mind to discern between the important and the urgent and develop ways to either say no to the urgent fires, or create systems that enable them to be taken care of in another way that doesn’t involve you. Say no more frequently (and most importantly, LEARN how to say no. Leave buffers between tasks because everything takes us 1.5 times longer on average than we think it will. (Which is probably a result of the hustle hard mindset, actually).
  2. Embrace the benefits of being unavailable. In our always-available world, we have totally lost track of the idea that we don’t have to be always a text or ping away from someone’s needs. Instantaneous response is the norm, as is people apologizing for their delay in responding and it’s only been 2 hours. (Stop doing that people!) But what if, you just simply weren’t available? I know, there are always gasps and looks of horror when I suggest it, but just allow yourself to imagine it for a minute. What would it be like if you didn’t look at your phone or email from 6pm to when you arrive to work the next day? What if you didn’t have notifications come through on your phone? I tried this as an experiment- I only get texts and phone call notifications on my phone and the first week I thought I was insane. But, after awhile, it became the norm and I don’t expect to get back to people immediately and they don’t expect it either. Lastly, embrace the idea of blocking out your calendar for deep work time- what online marketing expert Amy Porterfield calls “Tiger Time” that cannot be messed with by anyone. Just dare to imagine the perks of being unavailable and try ONE of them on for size this week.
  3. Get Flexible, Baby. I heard Simon Sinek speak in NYC recently and he summed up flexible work in a way I hadn’t been able to articulate before. He said that if an employee decides they need to go on a run at 4pm on a Tuesday- which is technically during the current technical workday- he encourages them to go do it. Why? Because paying attention to what your body, mind and being need is not something that should only happen outside of the traditional 9-5 day. It’s not like you confine all your ideas about work to that period- a great idea often strikes at 9am on a Saturday and you may spend an hour writing ideas or thinking about it. So, the notion of flexibility goes both ways – embrace it, and allow your employees and colleagues to embrace it.
  4. Reorient yourself to your work. This is the most mind-bendy of the potential approaches I’m sharing with you here. I’m in the business of helping people do meaningful work and have fun while doing it. A lot of people come to me thinking their work is bogging them down, that they don’t do anything impactful, that they need a career change. Ultimately they feel that their choice in career has left them unfulfilled and dreading every Monday, yearning for every friday, in the worst kind of shallow work vicious cycle. But, maybe you don’t need to hit snooze 500 times every day- maybe you just need a different relationship to what you do, There is a flawed approach to job satisfaction in this country. We are conditioned to yearn for a once in a lifetime dream job and if we don’t have it, everything is bland and meaningless. What if instead, it’s about the skill and appreciation of the craftsmanship you bring to a job, much like how a small batch food maker approaches his or her craft?  In other words, you don’t need a rarefied job but instead a rarefied approach to your work.



Try these steps to aim for this unique approach to your work:

  1. Spend some time taking a step back from the day to day grind and the constant hustle to really see how your role impacts the greater mission and goals of the organization. If you’re unclear, talk with your leadership team about it.
  2. Make a master list of all the tasks and responsibilities you have. Directly map out how those responsibilities link to the greater mission. Be as specific as possible.
  3. Where there isn’t a strong link, those are the areas to dig into and see how that part of the job can be made more efficient or different, for example, so it does more directly link. And if you still can’t find a connection, gently question the importance of it. Maybe it becomes eliminated and you feel like your job is more impactful.
  4. Engage in a little trial and error. See what can be done differently and question things that have ‘just always been done that way’ (the kiss of death for many a company!)
  5. Rinse and repeat every so often. Dynamics within organizations change so stay hip to it.



This kind of introspective (need I say, “deep” again?) work doesn’t happen overnight, and it’s not something you can necessarily check off that to-do list we so badly want to complete every week or day. But only by truly digging into this work for the next couple of weeks or even months can you really understand where YOU fall on this spectrum. And only then can you help your TEAM start cultivating this habit for themselves, their customers and the overall mission of the organization. We’ll get to that next time. For now, go try these exercises on for size!