Starting a retro habit? Start Small🏕️
“Hindsight is 20/20”. Humorist Richard Armour coined this expression way back in 1949. Millions of us have since said this to ourselves or others, only to make the same mistakes again and again. In the tech world, many use a development framework called Agile, which has an essential principle of retrospecting frequently to optimize the team's performance and avoid making the same mistakes. If we want to stop learning the same lessons outside of work also, we need to take this power tool back home.
If you do an internet search on “retrospectives” you will be inundated with formal processes, team building games, and guides on how to run Agile retrospectives. These are great if you are on an Agile team. But these are not approachable for everyone else. Hindsight Retros aims to bring this powerful tool home through simplicity and practice.
Almost any type of change is difficult, for individuals and for groups or teams. As a life hacker, I’ve spent years studying change in various contexts, and no matter how many tricks or science I learn, it’s still challenging to see a change through to becoming a default behavior.
As an agent of change at work, I coach Google teams on Agile development methodologies, and I leverage every trick I’ve learned. When I notice a struggle on the very first steps, I invariably start with one simple piece of advice:
“If you change only one thing about how your team operates, add the simple practice of running blameless retrospectives on a regular basis.”
In this article, I explore my own first steps at life hacking and using the power of hindsight to feed goodness forward in my life.
Humble Beginnings: The Dumbshit List
My family has camped at the same campground in Northern California for over 40 years. Imagine swimming hole rope swings, blackberry bushes, and innertubes down lazy rivers with just the right amount of whitewater. A paradise.
My dad had these family trips down to a science, and every piece of camping equipment fit like Tetris in the big red Ford Econoline van, especially the military grade canvas tent that slept the six of us for 10 days. He had probably owned that tent since he camped in the Australian outback with his best friend in his 20s. It was a big production to unfold and lay out the tent and the myriad of aluminum tubes that fit together just so to create this habitat.
As we grew into teenagers and young adults, our camping trips became a little more care-free, and we drank too much beer, listened to music too loud, and partied till the break of dawn by the campfire.
I was in college in San Diego, sweating through finals and dreaming of that familiar stretch of highway and the first dive into the swimming hole. Finally, exams over, my friend and I packed up my Nissan Pathfinder and hit the road for the 12hour drive, Pearl Jam blasting. The miles all seemed to blur together, the anticipation growing with every dusty roadside town we passed.
We rolled in just as dusk was turning the pines to silhouettes and waved to the family and friends waiting for us. The crack of that first beer echoed through the campground. Time to set up our home-away-from-home, the tent going up with the ease of years of practice… and then that gut-punch moment. No tent poles. We'd forgotten the frickin' tent poles!
It was the 90’s. No cellphones, no Target run, just us, our MacGyver skills, and a tarp. We rigged a makeshift canopy from branches, ropes and duct tape, and woke up suffocating with a faceful of dew-soaked nylon. Soggy lesson very much learned.
I felt terrible, like I ruined this great experience for my friend who drove all this way to join me at my favorite spot. Luckily, she didn’t blame me, and even though I was really blaming myself, my friends and family laughed it off. They helped me see it as not the disaster my brain initially thought it was, but instead as just a breakdown in my process. Over the campfire, the family "Dumbshit List" was born. No complaining, no finger-pointing, just a simple list that reminds us of things we shouldn’t forget. Version 1.0 of the list: no car keys in the outhouse, don't wear your sunglasses on the rope swing, and, top of the inaugural page? "DON'T FORGET TENT POLES."
This list has been used and reused by my family for years to keep track of our lessons learned at the campsite. Expanded to include the good stuff too, like what kind of pancake mix to bring (Krusteez), how to use fresh blackberries (blackberry s’more’s anyone?), and what brand of floaties work best in the river (River Rats).
Now in our middle-age, we bring the next generation to experience this magical place, create new memories, and add more to the list… like don’t forget the bluetooth speaker and Phase10 card game!
Why Hindsight
My memory of the Dumbshit List is actually what inspired me to start the Hindsight Retros website and framework. I was thinking through some future Agile coaching ideas and it occurred to me that retrospective practices don't have to be limited to work. I reached out to John after remembering a “postmortem” that John wrote about an international trip that went awry. I sent John a note and was thrilled when he was as excited as I was to bring this practice to the world.
John and I both felt that “postmortem” was maybe too morbid or off-putting for what we had in mind, but we agreed the toolkit evangelized at Google and published in the Site Reliability Engineering (SRE) books made a lot of sense in the world outside of work. The simple structure and emphasis on shared learning without blame was foundational to Google’s culture of reliability. Combining this practice with Agile retrospectives was a small leap and Hindsight Retros was born.
The science of starting small
But how does one take a practice used by thousands of Googlers and high tech workers across the globe and bring it home and back to basics?
It seems intimidating, and introducing a new habit in our already busy lives is notoriously difficult. There are hundreds… no, thousands of books out there that give advice about how to change almost anything about our life. I’m sure we all have some of these on our shelves: quitting bad habits (overeating, not exercising, spending money), developing good habits (cleaning, exercising, gardening), or improving relationships (romantic, familial, work). Here’s just a selection of books I have on my own shelf.
I’ve heard it takes 30 days to develop a habit, but Scientific American research suggests it takes twice as long on average to change habits, 66 days. Many factors determine success or failure such as having accountability partners, habit complexity, and applying different incentives at different times. So if you want to leverage the benefits of hindsight through a regular retro practice, how might you build this habit of retrospection?
In Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones James Clear laid out a simple and approachable framework that resonated with millions. With an unbelievable 4.8 rating and 125k ratings on Amazon, he clearly struck a chord with millions of people who wanted a better life, but didn’t know how to get started. Three quick takeaways are:
Break it down: Sometimes a change is just too big to bite off. The author advocates to take any change you seek and break it down into the smallest possible chunk that you know you can do. An example he shares is about a regular flossing habit. For him, he started by just flossing one tooth, and adding one each day.
Stack it: Smaller habits stack and build on top of each other and lead to more profound change.
Build Systems: Focus on building the right systems over ambitious goals, trust the process and system, and the rest will follow. For example, setup environments that enable better choices and that discourage bad habits, such as putting the candy jar out of reach so you need a stepladder to get to it.
Joseph Grenny and Kerry Patterson, the coauthors of Crucial Conversations and David Maxfield, Ron McMillan, and Al Switzler did extensive research and distilled factors of successful change in Crucial Influence: Leadership Skills to Create Lasting Behavior Change. In their research they verified 6 sources of influence that are at the root of successful change. They cover Motivation and Ability, as well as Personal, Social, and Structural motivators.
Well, this is a lot more than baby steps! So, how can we “start small” and apply these ideas to introducing a retrospective practice?
Make it fun: if you find it enjoyable to review your experience and celebrate the wins and learn from the failings, you will do it more often.
Make it easy: If the notepad, list, photos, or whatever you use to capture lessons is at hand and always at the ready, you won't have hurdles to capturing those lessons.
Bring in support: Make it something you do together with your partner, family, friends, or team. When you encourage each other it will remind you all that learning matters.
Yet a third impactful book on my shelf is The Checklist Manifesto: How to Get Things Right by Atul Gawande. This book is small but mighty, and the author drives home that complicated leads to errors. So we should be consistently driving to remove complexity from situations where success matters. He used surgeons and pilots as common examples, but even lower stake ventures like my camping trips can use this trick. For me, that meant getting the packing list out of my head, and onto paper, freeing my mind to work on more subtle matters, like what favorite songs to add to the road trip playlist.
What are some small ways to introduce a retro practice?
Even though I hadn’t read these books in my 20’s, my Dumbshit List (DSL) passes the test of time for reasons we now understand:
Small: It doesn’t get much simpler than a list
Memorable: The experience and the simple lesson was unforgettable. Thanks to the visceral story (wet soggy tent), I will literally never forget the tent poles for the rest of my life. Not to mention, the name “Dumbshit List” is fun, glib, and sticky, though of course not for small children.
Ritualistic: It’s become a family ritual to ask at the end of every trip: ok what’s for the DSL? We have a process and a system for keeping it updated.
Central: In a central spot that everyone knows about, we keep a notebook in the camping gear bag, and after we set up camp it sits on the camp table in case anyone has something to add
Something like the DSL works great for important events that don't happen very often, when it’s easy to forget those little things:
Moving homes
Annual Parties
Family reunions
Spring cleaning
Home improvements
Maybe your family keeps a notebook in a drawer with sections, or a file folder that stores the scribbled lessons learned from each year's garage cleanout.
For events that are more frequent, there are many apps you can put on your phone to capture quick notes to search later. I have a myriad of “Lessons Learned” notes in Google Keep for example.
Google Keep
Trello Boards
Documents, Spreadsheets, OneNote
Even a photo album you title “Remember this!” could be an easy way to remind your brain about something that worked, didn’t work, or what you want to do next time.
So the next time you have an opportunity to learn from a foible, fail, or big win, take a few extra moments to jot down a few reflections. And at Hindsight Retros we’ve boiled it down to four key questions:
What Worked?
What Didn’t Work?
Where did you get lucky?
What will we do differently next time?
The answers stack up and drive big improvements over the long haul.
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