Join me in a little exercise, two minutes tops. I promise that it will change how you see your job, your organization, and your career, for at least…well, forever.  

I want you to close your eyes (seriously, do it at the end of this sentence) and try to picture what your worst work nightmare looks like, in as much gory detail as you can.  

Did you do it? (If not, seriously, do it now. I can wait.) Now think for a moment about what you pictured. What was happening? Not happening? What kinds of pressure were you under? What was going wrong? How did it make you feel?  

I’m not a psychic, but I’m guessing that your work nightmare had at least some, if not most, of these elements:  

  • Crazy, but mostly arbitrary, deadlines 
  • Work piled up with no end in sight 
  • Working well into the evening just to stay “caught up” 
  • Thousands of unread emails you just can’t get to (or filter effectively) 
  • Lots of busy work 
  • Lots of work “in progress,” but nothing seems to cross into “done” 
  • Endless meetings (most of which really could have been an email) 
  • Constant activity, but little actual work done 
  • A cramped office with little sunlight 
  • A cramped schedule with little “down time” 
  • Busy work intended to make up for a lack of direction or vision

I know that most readers will have one or more of these in their work nightmare because I’ve asked a lot of people to do this exercise—in fact, it’s the first exercise I do with people when I run Sketch’s Agile Fundamentals class. It comes from Luke Hohmann’s Innovation Games, a collection of facilitation exercises I highly recommend.  

The work nightmare exercise is one of the most telling things about the modern working world. 

Drawing Our Work Nightmares in Agile Fundamentals Class 

When I ask workshop attendees at one of our Agile Fundamentals classes to think about their work nightmare, I ask them to actually team up with 2 to 4 other people and, as a team, draw what their work nightmare looks like.

What I like about this approach is that you can’t just say, in the abstract, what’s wrong with the work nightmare scenery. You have to find a concrete, visual way of conveying the idea.

For example, one team hated the idea of working well past 5:00 p.m. just to get caught up, so they drew a clock that read 6:30 p.m.…right next to a physical inbox filled with papers that still needed to be processed.

Another group drew a picture of their calendar, showing all the useless meetings, with actual work crammed into a single random hour on a Tuesday. Yet another group drew a programmer sitting at a desk, with a single small window showing the last rays of sunshine as the sun goes down…and that poor coder is still stuck there, working. 

What I have found over the dozens of times I have done this activity is this: The pictures themselves vary wildly. That makes sense, as each team develops its own ideas of what to draw, and how to draw it, independently. But everyone comes up with a similar set of things they dislike about the modern work environment—or there are at least common themes. 

And I’ve never had someone look at another team’s drawing, hear their explanation, and say “I don’t understand,” or “I don’t get why this bothers you.” No, what I get are sympathetic nods from everyone around the room, every time.  

In other words: The images and details we use to express our frustrations with work can vary a lot, because everyone brings their own unique selves to the team. But everyone has had a common experience with all the worst aspects of the modern workplace. 

So Many Workplace Features Are Arbitrary 

I am a big fan of companies that provide jobs, invent things, improve our lives, and generally do the right thing. What I want to criticize here is not the places where people work, but the workplace. Ask yourself these questions: 

  • Why are the two most common ways to pay people by the hour and by a fixed salary? Why not pay according to the value they’ve delivered? Or KPIs met? 
  • Why do most places start the workday at 9 and end at 5? What would happen if the workday was instead broken up into two stretches, 8 to 12 and 4 to 8? 
  • Why are budgets set so far in advance? Why do people work so hard to “protect” those budgets year to year? What would a more flexible, adaptable budget look like? 
  • Why are so many meetings about “getting alignment” rather than “getting feedback”? And why is it that management usually sets meetings, rather than team members themselves? 
  • Why do managers plan who does what work, instead of professionals deciding for themselves what is important to work on? 
  • Why do so many companies measure output instead of outcomes 
  • Why are companies always scrambling to make their resources and budgets fit their projects, rather than finding ways to make their projects fit their people and budgets? 
  • If there is so much communication going on—Slack channels, project board comments, dashboard alerts, sync meetings, and thousands upon thousands of emails—how much of that communication is really meaningful? For the stuff that is most meaningful, who should it come from? And why? 

There is no business rulebook that says when work starts, how you are paid, what meetings there should be, and so on. Each organization starts by adopting some best practices or agreed-upon standards. From there, whatever is not captured explicitly in those standards usually forms implicitly as a set of norms and traditions. Those traditions, though cherished, are largely arbitrary. 

That’s how work nightmares start: When organizations slavishly hold onto practices, norms, or traditions that are no longer working for them, but that people are afraid to let go. 

Overcoming Your Work Nightmare 

I kind-of wish there were a single, simple formula for overcoming a true, real-life work nightmare. There is not, though getting some very targeted training for your teams can go a long way toward unearthing their particular challenges.  

I will, however, leave you with these three tips. These seem to be the kind of “aha” moments that workshop attendees have at some point after the “work nightmare” activity, and that seem to help them think about the transformation ahead:  

#1: It starts with you.
It’s easy to lay the blame for the dysfunction of a workplace on things outside your control: There’s too much work. Clients don’t know what they want. We have no budget. The boss is crazy. Our hands are tied legally. These might be true, but everyone who changes sees that the transformation has to start with them.
  

OK, not every problem literally starts with you. But problems persist because people adopt a mindset that lets them persist. Change your mindset, and you become open to new possibilities (cue ethereal new-age music).  

#2: Everything has a cause; not everything has a reason.
A practice or policy has a reason for existing when someone can point to a solid argument in its favor. Not every practice or policy has a reason, even though it has a cause. For example, maybe your team has a weekly check-in on Tuesday mornings. Why Tuesday mornings? Because that’s when Chad, the first manager, set up the meetings and nobody has switched them since then. There was no good reason Chad chose Tuesday morning—it just fit with his schedule that first week and no one else objected. But the meeting could just as easily happen on a Thursday afternoon, as long as people could plan ahead. The meeting time has a distinct cause, but not a reason. 
  

Now think about other, more consequential, practices that might have a cause but no current reason for existing—like a long, extended discovery process or grueling series of manual tests.  

#3: Get your priorities in order.
Work nightmares are also a product of prioritization gone awry. If you stay late to work on something, you are prioritizing getting that piece of work done over the rest of your life (your life past 5:00, anyway). If you have thousands of emails, you’ve probably prioritized “being informed about absolutely everything, just in case” over trusting others to handle things.
  

I think it’s great that the Agile Manifesto, written as an argument against work nightmares, starts by stating the priorities of those who designed, and choose to adopt, Agile:  

Individuals and interactions over processes and tools 

Working software over comprehensive documentation 

Customer collaboration over contract negotiation 

Responding to change over following a plan

I’m not saying that Agile is the cure-all for every work nightmare out there. But it pays to be explicit about priorities and asking how “the way things are done around here” might be contributing to the more nightmarish elements of our work lives. 

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