No Deep Work in a Vacuum

Thinking about collaborative and deep work together

This week I am writing about work and focus.

I don’t know about you, but for many folks around me who are at startups, agencies or tech companies, work started to feel ‘broken’ a few years ago. This got worse in visible ways during the pandemic. I hear about this almost every day when I talk to people about work.

What’s odd about all this is that if you ask the different stakeholders, everyone wants to make work… work. Company shareholders want businesses to thrive. Leaders want to work with happy, motivated, strong, productive teams. And individuals want to feel productive, motivated and alive at work. But somehow despite these seemingly-aligned perspectives, work just keeps getting worse.

There are various ways to combat this brokenness, as individuals, teams and leaders. I think there is good writing about the individual side, and I think it’s a good time for teams and leaders to think more seriously about their side. The good news is, there are ways to thoughtfully improve how we work. Let’s start by looking at what might be broken.

What does brokenness look like?

Most knowledge workers I know experience or have recently experienced some combination of the following at work - especially in the past year or so as organizations navigate various return to work programs:

  • Back-to-back zoom calls. 

  • An office that’s too busy one day and dead the next. 

  • An office with no spaces to focus. 

  • A remote team you hardly know.

  • Apps designed to compete for your attention.

  • Working at home sometimes feels like a productive refuge of solace.

  • Sometimes working at home feels completely disconnected.

  • Constant messages.

  • A feeling of always being behind.

  • Meetings that are always about catching up.

  • Dozens of projects, but no progress.

  • Work days that blend into night.

How we work is getting in the way of what we do, and why we do it. 

Having just read a book that focuses on the individual ways we can fight back against this brokenness, I want to talk a little about how we need to think more broadly to really solve the problem.

Cal Newport and ‘Deep Work‘

I’m a big Cal Newport fan. He popularized the term “Deep Work” and has found a large following in knowledge workers who have become dissatisfied with the status quo of work distraction, and who want to find ways to produce the highest-quality work they can.

As I’ve written before, Newport refers to Deep Work as a state where you are able to focus single-mindedly on individual work, free of shallow distractions like constant slack messages, screwing around on YouTube, checking email, or scrolling through Instagram.

Deep work is proven to allow you to produce your most thoughtful output, and helps you create the conditions for flow, a pleasurable mental state. It feels better and it produces better work. In my view, the ability to work deeply is a huge asset to any creative individual.

Newport’s new book “Slow Productivity” is an evolution of his previous thinking. It’s fun to follow the arc of his personal motivations from his college days to now. An initial desire to stay competitive, followed by a desire to produce high-quality work amidst the demands of college life and book publishing schedules.

In the book, Newport tends to pull examples from individuals who achieve ‘great things’, like Newton, Jane Austen. He comes up with three core intentions that are designed to guide you towards working practices which foster depth and long-term satisfaction: Do fewer things; work at a natural pace; obsess over quality.

Newport’s three tenets in Slow Productivity

These ways of thinking make a ton of sense. I think Newport does a great job in the book to convince you of their value, and provide optimistic and helpful ways of integrating them into your life. I strongly recommend the book.

Bloodthirsty capitalist reasons to do ‘better work’

I think it’s easy to look at ‘Do Fewer Things’ and think ‘I don’t have time for that, my TPS reports are due tomorrow’ and that makes sense.

But these topics and skills are going to become more and more salient for knowledge workers, not just to remove themselves from the ‘brokenness’ we experience right now, but also to shape their careers and their teams.

Learning how to work well as an intentional practice is a key determinant of the success of individuals and teams, beyond the actual output of what you do, the industry you are in, or your experience. Like, difference-between-having-an-MBA-and-not kind of value.

For individuals, it’s a controllable value multiplier

Accelerating technological change over the next ten years will tend to force most knowledge workers to continually prove and re-prove their value in a corporate setting, perhaps at a higher rate than before. Or rather, that’s how some leaders will see it. You may or may not have the luxury to choose how much you participate in this style of organization.

You have some control over how productive you are at work, and how much you enjoy it. Knowledge workers have the chance to rethink legacy work practices, and adopt new ones that enable deep focused work and high-quality collaboration. These skills are the ones that will allow you to do the highest-value, most enjoyable work for your time.

Whether you believe AI is about to ‘take everyone’s jobs’ or finally create an idyllic post-scarcity society, as a human the ability to do your best possible, most enjoyable work is surely the goal of everyone at work. Certainly it seems clear that any time you spend during your workday doing shallow work, or feeling distracted and disjointed, is not doing a lot of good for anyone.

Just as knowledge workers should not assume the organizations they work for will provide the best tools, systems, habits, rituals or expectations for fluid work, organizations should not assume that knowledge workers have it ‘all figured out’ and can mindfully manage their tools and time. There is a dual responsibility for learning, sharing and growth. However, it is possible for most organizations to think far more deeply about this stuff, and make it a core practice of their teams, so that any individual coming through the organization is given a better framework for success.

Or, put it another way, it’s good to think about this stuff because it will not only make you feel better, but you will be more competitive, if that’s what you want.

For leaders, it’s… a controllable value driver

The quality and quantity of work your team produces is directly related to how they work individually and in collaboration. Leaders are focused on what their team achieves, but often don’t have time or proven frameworks to improve how they do it, and seem to be flummoxed by the changes in the workplace that have happened over the past few years.  

If you want to have a team that survives and thrives amid a lot of pressure and unpredictability over the next ten years, the ultimate value of that team depends on how much of the highest-value work individual members are doing, and how much additional value comes from the combination of those members. The function for all that might be something like this:

Individual Multiplier x Individual Potential x (Team Multiplier)

(Where Team Multiplier is some complex function of the assistance of other team members, the creativity they have, the efficiencies of teamwork, etc)

For example, in a design team of five people, if every project is chaotic but each individual designer is a disorganized genius, you might feel like there’s a negative individual multiplier, high individual potential, and a negative team multiplier. In made-up non-real algebra, the team would produce not just 20% more but maybe 100% more if it was working well.

So what you are trying to do as a leader is help that individual multiplier to grow for everyone, and make sure that team multiplier also stays high and grows over time. Investing in ways to help employees do deep work and participate in useful collaborative work is a really high-leverage way of increasing both of those multipliers.

My sense is that over the next 10-20 years, as company leadership comes under pressure to reduce headcount and replace functions with various AI solutions, you will continue to see the eradication of whole teams. So thinking about how a team as whole can stay competitive and create value is something that many leaders will find themselves needing to do.

Or just leave and do something different rather than playing this game at all.

The individual protectionism of Deep Work

I love Cal Newport’s tenets of Slow Productivity. I think they are essential.

But clearly they are also kind of a dead end, because no individual is an island. No amount of protecting-yourself with email auto-replies or blocked-off calendars is sufficient if you are working in a modern organization and a societal culture that doesn’t follow the ethos. Individual tactics are necessary. But when part of the core problem is communication with others, there is no way these tactics are enough.

In some ways only using Newport’s advice is like giving everyone in society a gun to defend themselves. It is an individualist approach to a collective problem.

It reminds me of some of the messaging around ‘self-care’ — a whole industry encourages folks to buy massages and spa treatments as an individual consumer to somehow solve their anxiety and depression with products, rather than having the space to build a life that truly resolves their discomfort. This was completely unrelated to the topic at hand, but it happened that this week Anne Helen Peterson’s excellent Culture Study newsletter featured this paragraph which captures another aspect of what I am getting at - individual solutions:

[…] But a whole lot of this ethos stems from a deep-seated belief in individualism. We think that just because we can “do it ourselves” (and by “it,” I mean raising kids, performing domestic labor, caring for others, finding economic security, living life) that we should do it ourselves….and our ability to do so evinces innate moral fortitude. We’re better people, in other words, because we did it alone.

Anne Helen Petersen

In the same way that most problems cannot be solved by individuals alone, when you take an individual-only approach to deep work, you are missing 50% of the solution. Deep work’s purpose is to produce value for others, and deep work relies on the input/output of others, so the best deep work has a collaborative nature built in.

In some ways this reminds me of the ‘ergonomic’ frenzy that happened in the 1990s. The older segment of the workforce, that had started their careers away from computer screens found themselves at a keyboard and mouse for hours at a time, and developed various mysterious repetitive strain injuries, back problems and eye strains. Clearly transitioning from a typewriter or pen to constant screen time was uncomfortable for those people.

The fleshy wrist rest of an ‘ergonomic’ mouse pad is a bit like ‘only checking your email once a day’ in that it only acts on the last stage of the problem.

This fostered a huge industry of ‘ergonomic’ mouse pads with wrist wrests, keyboard rests, split keyboards, endless chair designs, foot rests and more. The number of products you could buy to somehow alleviate your discomfort was incredible — and most of those product types remain in some form. But most younger folks just don’t seem to need them because they grew up with the tech rather than having it thrust on them at the age of 45.

But none of these products really changed the underlying hard problem - a tiny screen, a fixed working posture, hours spent tapping away at a desk that people were just not used to. No amount of silicone padding really fixes that.

This kind of ‘how do I learn how to adapt to what’s happening in a way that’s comfortable for me?’ - can feel defensive and temporary and unsatisfying when you have to buy products or set up complex email automations to protect yourself from some large, unstoppable force. Because the leverage of individual protection is too small.

Instead I think there’s an ideal in knowledge work that we can strive for, which is based on a positive state of connectedness rather than solitude: A state where we feel like we are able to work individually with focus, flow and pleasure, and producing really great stuff. We are also given the benefits of collaborating frequently with others on something really meaningful, enjoyable and challenging that also produces flow at a team level. For example, you get really good at problem-solving together.

To achieve this requires as much work at the team level, as it does alone.

When I talk about this stuff I end up using the phrase fluid work — the idea that you are able to both dive into deep work and pull back into a collaborative mode. Fluid work has many two-sided aspects to it, because of its interconnected nature — versus just looking at deep work on its own. For example, the opposite nature of deep versus collaborative work has a counterpart in the way we think about realtime and asynchronous communication.

Balance and harmony in fluid work

I think there are a few examples where fluid work is about mindfully navigating between two different forces like this. Here are some:

1. Deep ←→ Collaborative

Deep individual work is required to ensure that collaborative work is successful, exciting and productive. Most often, the quality of any specific piece of individual work impacts the work that other team members have to do, and the quality level to which they do it. Over time, successful individual deep work ideally raises the bar for the team as a whole, and provides access to more interesting, exciting and valuable work for the team to do. You hope!

High-quality collaborative exploration lays the groundwork for further deep work on an individual level. It reinforces and reminds us of the personalities, the qualities and the skills of our coworkers, and allows for implicit adjustments (like casual remarks made during a brainstorm) and explicit readjustments (like a reallocation of work) that mean a deep work session can be fruitful.

Many folks in the workforce now have very little direct experience of high-quality realtime in-person collaboration. Getting 10,000 hours of this stuff is harder and harder. It became less widely practiced during COVID, and now we have folks who had a college experience of no in-person collaboration, who now have a work experience of the same. Beyond skill development, there’s a social anxiety component that I see more and more people experiencing, which is making them less likely to resolve this.

I think this is an area where organizations can really help folks learn how to do this stuff well, create safe environments for experimentation around, and see an immense increase in value as a result. Even starting with simple questions, like, how do 3-4 people get around a whiteboard or digital tool and collaborate?

2. Realtime ←→ Asynchronous

In the abstract, fluid work means awareness of realtime versus asynchronous needs. When you are working on something, how often do you need to bug your coworker, and in what situation? Are you bugging them because you really need an answer or because it is an effective distraction technique from doing the thing? How effectively can you all proceed on your individual projects without either interrupting each other or holding each other back? How can you help each other by doing more, rather than less?

Abstractly, the ideal is that each node in a system can perform some tasks without needing constant communication with the system as a whole. And the system as a whole can function smoothly without requiring constant input from any given node. Ideally you are able to mindfully navigate between these scenarios. This means being aware of when realtime information transfer is useful, and when it is not. There are probably good biomimicry-inspired approaches to this! And this is where explicit planning as a group, and using frameworks rather than some unplanned default, will be better.

3. Individual ←→ Leader

Newport spends most of his effort in the book talking about what an individual can do to protect their own workflow. I find that some of these approaches (as mentioned above) feel effective for an individual but perhaps harmful for an organization.

Just as economic protectionism can be a healthy policy for a nation, it on the other hand weakens the overall economic trade system. One nation that is protectionist and holds all the resources can slow down the pace of an entire global economy. Is this good or bad?

Ideally, each individual has useful ways to maintain what makes them the most happy and productive, and those ways do not cause negative impacts on the network as a whole.

On the other hand, the job of a leader is partly to design and evolve the network so that it encourages the best collective and individual output. In my experience, most leaders have very little time or desire to look closely at whether they are creating the conditions for deep work and strong collaboration. The evaluation of ‘how did that brainstorming session go’ is tied far more into the content than the design of the session.

We are far more concerned with what than with how. That’s a classic process vs output debate — but I think this topic is a really critical place for it.

4. Short-term thinking / Long-term thinking

I think there is an overarching dynamic that also affects the environment for deep and collaborative work. It’s about using short-term thinking and scarcity, versus long-term thinking and abundance.

If you take Newport’s three tenets like ‘do fewer things’ above, you can see them as a defense against short-term thinking — the thinking that tends to cram our inboxes with concurrent projects.

Doing fewer things is an exhortation to focus.

The drive to do ‘too’ many things at once is ultimately a scarcity mindset. As a side note, I don’t want to go around accusing folks of ‘having a scarcity mindset’ — there are countless people around the world who genuinely live with scarcity of money, health, attention and safety, and are perfectly rational to feel that scarcity in a visceral way. I am talking more about an abstract and somewhat detached-from-reality sense of scarcity that pervades a business culture, populated by people who mostly experience no real scarcity in their day to day lives whatsoever.

As a child, we would visit Sovereign Hill in Ballarat, Victoria to pan for gold and play around a recreation of an 1850s mining town. It was fun although I clearly remember another small boy crying because a fake teacher in the fake school chided him for being left-handed, in accurate reenactment of the tradition of the Victorian era. Awkward situation all round.

More relevantly - this was my first memory of the concept of a gold rush, which occurred almost simultaneously in California and in Australia, thousands of miles apart. That’s why there was a tent maker from California, thousands of miles away, in the original town - and recreated in the modern tourist version you can still visit today.

In a gold rush, you have the following ideas around scarcity:

  • there’s an open area ‘up for grabs’ where gold might be anywhere

  • getting hold of that gold is the most important goal

  • the gold may be gone in just a matter of years

So you have this incredible ‘abundance’ and ‘scarcity’ at the same time which encourages people to rush around very quickly because of a social reality that only emerged a few years previously.

It might feel the same way with AI right now — there appears to be immense value to be captured, there will be a few ‘winners’, and there is ‘so little time to waste’ because many companies are making announcements and releasing products left and right. The traditional startup exhortation to launch an MVP and get in front of customers amplifies the ‘scarcity’ as launch cycles are accelerated.

I met an exec at an event last week who is working on AI-assisted carbon accounting at a startup with an internal culture that ‘demands’ working seven days a week. He was a big believer in the product, but visibly drained and (politely) expressing frustration at this brutal lifestyle that seems to have been set by the CEO and the investors. He said over and again that they ‘had’ to work this way.

The need for the kind of technology they are building is immense, as the EU and other regions create good legislation to ensure companies keep track of their emissions. Imagine how complex, time-consuming and expensive it is to comb through thousands of invoices each year for a Fortune 500 company, and how much more you can achieve with an AI that scrapes through this data and extracts meaning instantly, for ‘free’. So this does fall into the category of ‘important climate stuff’ to which we must focus our attention and effort.

But it does not feel to me like there would be much difference in outcome if his team worked four or five days a week, as opposed to six or seven. Over a year, their current approach represents 30-40% more effort (going over a threshold of comfort, creating risk of burnout, poor decision-making and team turnover) and perhaps only 10-20% more productivity (realistically, having seen the studies). You might possibly achieve something in, what, ten months as opposed to twelve, if you’re lucky.

What’s the point? The number of other factors in startup success are so numerous and unpredictable, that I find it very hard to believe it will be ‘working Saturdays’ that will predict their victory - despite the lore about investors scouting tech winners and losers by visiting their car parks to see which teams are working Sundays. Embedded in the surrounding culture of founders and VCs is the idea that Steve Jobs did this and Sam Altman does this and Elon Musk does this and so the intelligent/competitive/’smart’ things these guys did also equate to being smart about how they apply their time, and how they expect teams to work. So why is this still happening in 2024?

In my experience, both economic downturns and boom times are capable of producing a scarcity mindset which encourages short-term thinking, and ends up to be counter-productive for fluid work.

In downturns, there is less money around, more of a sense of companies fighting for the last scrap of business, employees concerned they will be in the next round of layoffs. Funnily enough there are also startup folks who are delighted with the idea that ‘this is the best time to start a business!’ and so are desperate to make progress against the other startups thinking the same. It felt like this during 2008/9 in the startup world.

In frothy times, there is more money, so more motivation to work harder and reap the oversized rewards, to increase the speed of progress so that you can raise another round of financing. While there is less downside risk for employees, there is more upside opportunity and a kind of ‘get it while it lasts’ mentality. Several markets felt like this from around 2017-2021.

So it’s easy to see how companies (and especially startups) end up in short-term thinking and a sense of scarcity around their own employees’ time and in the availability of resource in the world. I am not saying these responses are necessarily logical, but they happen.

Conveniently and converseluy, there is something about deeper focused work that I think can help reduce the pressure of that social reality of scarcity. If you go live in a cave, there is less pressure, ability or distraction on you to follow the hourly ups and downs of the market price of gold. Part of my hope is that if you focus more on producing deep work, that work might just tend to veer towards abundance than scarcity.

Choose high-leverage ways to improve work

When an organization relies on individuals to self-control their own working environment, they may not expect much change — these individuals can only control a limited sphere around themselves and without coordination, their own individual demands may end up decreasing the overall amount of collaboration. This reduces the overall value of the team, unintentionally making it less than the sum of its parts.

Instead, there should be a coherent framework for fluid work throughout an organization, where deep work is balanced with high-quality collaborative work, either asynchronously or in realtime.

Donella Meadows created a heuristic for intervening in systems in ways that have more and less leverage depending on where and how you act. It’s a really popular systems-thinking tool. It’s not gospel, it’s a set of findings that she developed over her career that mostly-work most of the time.

We see leverage points in almost any interaction.

For example, if two kids are fighting, you can either give them pillows to fight with so they don’t hurt each other (reduce the strength of the feedback loop), or you can completely change their focus of attention with a visit to the park (transcend the paradigm).

I’m reproducing Meadows’ list here in decreasing order of effectiveness. The least impactful things to do if you want to improve a system are at the bottom, and the most impactful at the top.

As you go up and down the list, in your mind you can think of a topic, and judge where your power of influence is and what you are actually able to affect. For example, if you are a middle manager at a large tech co, you probably are able to do things with a lot of freedom within your team - e.g. #2 - change the mindset or paradigm even.

Outside of your team, within a bigger organization, you might have a much weaker mechanism for leverage, and so have to resort to things like changing the quantity of your output or the structure of information flows.

Here’s the ‘ranking’ of Meadows’ leverage points:

  1. The power to transcend paradigms.

  2. The mindset or paradigm out of which the system — its goals, structure, rules, delays, parameters — arises.

  3. The goals of the system.

  4. The power to add, change, evolve, or self-organize system structure.

  5. The rules of the system (such as incentives, punishments, constraints).

  6. The structure of information flows (who does and does not have access to information).

  7. The gain around driving positive feedback loops.

  8. The strength of negative feedback loops, relative to the impacts they are trying to correct against.

  9. The lengths of delays, relative to the rate of system change.

  10. The structure of material stocks and flows (such as transport networks, population age structures).

  11. The sizes of buffers and other stabilizing stocks, relative to their flows.

  12. Constants, parameters, numbers (such as subsidies, taxes, standards).

5 aspects of fluid work life

With this in mind, you can start to think about what you want to change in order to achieve more fluid work, and how effective that thing might be.

There are five aspects of work life where I think we have good leverage — as long as we are working as a group with leaders, and not trying to solve everything as an individual.

  1. Screens and tools: Our digital working tools can be calm, ordered, helpful. You can develop ways to work that feel comfortable and motivating. You get to decide if AI or any other technology is a positive multiplier for your team or not - same for any project management tool or messaging system. This is in some ways a low-leverage activity, but it is so visible and present that it can have an immediate benefit and set a principle for a team.

  2. Written communication: You as a team get to decide how we message, how we email, how we notify, how we respond. You get to decide people’s expectations around this stuff inside the team and when interacting with external stakeholders.

  3. In-person communication: You as a team get to decide how we work together in-person, communication styles, methods that work well for everyone.

    Both the above two aspects of communication can directly improve deep work and collaborative work.

  4. Direction: Deciding in collaboration as a team and with leaders how goal-setting, schedules, review methods can foster focus and collaboration. The implicit assumptions about what deadlines you accept from customers, and how the pace of work impacts your overall quality of life.

    This is a high-leverage place to focus - changing the goals and structure of the system.

  5. Meta: You get to design and adjust how your team learns competency in the above aspects and finds management methods to improve them over time. You can control your destiny, and also make it an internal and external facet of company culture.

    This may be the highest-leverage activity.

I think there’s an opportunity for organizations to show how good they are at this stuff. It can be codified into something resilient, and it can be communicated as part of the brand. I think if they do it well, it can be an asset for retaining and hiring talent.

Individual, team and leadership interventions

Let’s sum up how and what we might focus on at each level.

Individuals can set themselves up for fluid work:

Cal Newport’s books are pretty good in this area. The general advice to focus on fewer things, work at a natural pace, and strive for quality are evocative of Michael Pollan’s advice to eat real food, mostly plants. In terms of individual practice, this advice might be worked on like so:

  1. The mindset and skills for deep, focused productivity

  2. Workplace setup to enable focus and make work fun again

  3. Tools to communicate with your stakeholders/team

  4. Rituals to continually refine your own practice

Teams can be given the power and knowledge to construct systems and hold experiences to enable fluid work:

  1. Engaging in-person experiences to bring teams together authentically

  2. Frameworks and standards for high-quality in-person collaboration
    Some good prior art around this is here.

  3. Methodology around collective communication to enable deep work

  4. Rituals that serve as maintenance to not only bring teams closer but also continually improve and self-correct how they work

Leaders can be coached on the frameworks and training to foster the conditions for fluid work:

  1. Learning how to create the conditions for high-quality remote, hybrid and in-person collaboration (and achieve it for themselves). And the same for deep work.

  2. Paradigms around objectives and working expectations - how are these creating different dynamics. Are they increasing or decreasing that team multiplier and individual multipliers?

  3. Ways to continually improve and refine these working practices

When this works, I think you can end up with an own-able team culture that helps retain and attract talent. I think this is achievable for most companies in most situations, and it’s something that companies can continually improve over years.

And I think that the juice of doing it is worth the squeeze - we can be happier at work, calmer, make better decisions, and make cooler things. I think that approach ‘trickles down’ in our economy far more easily than money — the way you work with your team is likely representative of the way that your bosses behaved to you. The way you respect and work with your team is normally aligned with how you respect and work with vendors. I think it’s the responsibility of all of us with any agency to improve the way we work so that it improves the way others work with others, along the chain.

I’m working with Paige Carter on developing these ideas further. We are developing specific ways we can help companies struggling with the brokenness I talk about at the beginning of this post, and ways to help individuals to develop these skills for themselves and the teams around them.

We are getting all kinds of interesting responses. If you are interested in working with us on a trial project for your team, please get in touch.

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