End-of-Year Journey Mapping: How my 2020 Went and How 2021 Is Looking

Four years ago, I started organizing a small end-of-year gathering with other Bay Area collaboration practitioners to celebrate and make meaning of the year together. We would spend the first few hours of our session mapping how our individual years went using an exercise called Journey Mapping, then we would share our respective stories with each other and toast the end of the year with libations and snacks. It was a lovely ritual, and it became an annual tradition.

This past year, we couldn’t do a face-to-face gathering due to the pandemic, so we decided to do it remotely instead. Going remote had three wonderful benefits. We were able to divide it into two sessions, which netted us more time. We were able to invite more people, including folks who lived outside of the Bay Area. And, it was a good kick-in-the-pants for me to write up the exercise so that others could organize their own gatherings. (Several folks did, which made me incredibly happy.)

Journey Mapping is a quick way of visually telling the story of a project’s highs and lows over a bounded timeline. (Product managers may be familiar with customer journey mapping, which is similar in spirit, but different in practice.) You can do the exercise on your own, but it’s nicer in a group setting, even when everyone is doing it for themselves (as we do in our end-of-year ritual). It’s like working out with a buddy — you’re more likely to do it if others are doing it with you, and it’s a wonderful way to support each other and build community. When you do it as a group on a shared project, it serves as a fantastic tool for making meaning together and for discussing and developing shared narratives. I often use it as a ritual for teams to celebrate, mourn, learn, and transition.

How you do the exercise is not as important as simply making time to reflect regularly. The more you do it, the more you’ll understand how best to adjust it for your specific situation. That said, Journey Mapping has three attributes that I think are particularly powerful.

First, it contextualizes your work in your overall life. The toolkit specifically asks you to map highs and lows both professionally (or with a specific project) and personally. In a team setting, the tendency is to skip the personal brainstorming, especially when you have limited time. Sometimes, this is warranted. However, you lose a lot when you do this. Several years ago, I did this exercise with a startup’s leadership team, which was struggling mightily with interpersonal dynamics. Earlier that year, they had been running out of money, and they weren’t sure they would be able to raise another round of investments. Not surprisingly, that was a low point professionally for everyone. At the same time, one of the leaders had also been dealing with a family tragedy and the dissolution of a relationship. The rest of the team never knew about this and only found out about this through the Journey Mapping exercise. Learning about their teammate’s personal struggles many months after the fact caused them to re-examine how they viewed their behavior during that time, leading to greater empathy, a little regret, and ultimately forgiveness.

Second, the Journey Mapping exercise asks you to list the highs and lows from memory first, then to review your calendar, journal, and other artifacts and add anything you might have forgotten. This reminds you that what you might be feeling and remembering in the moment is rarely the whole story and that there may be lessons to harvest or things to celebrate that are worth revisiting. It also reminds us of the importance of having and reviewing artifacts.

Third, the Journey Mapping exercise encourages you to take your somewhat structured set of sticky notes and create meaningful art out of it. For example, these were the sticky notes that I created for my 2020 (using Sticky Studio):

and this was my artistic rendition:

This part of the exercise almost always gets short shrift. We often treat art as optional — nice, but not necessary. Doing this end-of-year ritual with my colleagues the past four years has helped me realize that this is a mistake, not just with Journey Mapping, but with many of my exercises. Practically speaking, when you create something that’s beautiful, you’re more likely to look at it again. More importantly, the act of creation leads to an understanding that’s far deeper and more meaningful than a set of sticky notes can convey.

You can get a taste of what I mean by looking at the art that some of my colleagues created:

Everybody chose to tell their story differently, from emphasizing specific themes (e.g. needing space, “re-“ words) to capturing a larger metaphor (e.g. tree, river). My colleague, Catherine Madden, organized her year into five categories and wove her story into the tapestry on the right — you can read more about her story and process here. Seeing what people created and listening to their stories were incredibly moving. I will remember those stories in a way that I don’t think would have been possible if they had simply told them or shared their sticky notes. Moreover, I don’t know that they would have told the stories the way they did if they had not had the chance to create this art.

My 2020

The personal backdrop for my 2020 was — like everyone’s — all about the pandemic. I was incredibly fortunate to be healthy and safe and not to lose anyone to COVID-19. So many people were not that lucky. The numbers are staggering — 2.2 million deaths worldwide so far, 450,000 in the U.S alone. (For comparison, 400,000 Americans died in World War II.) What made it all the more heartbreaking — especially for someone whose purpose is to help society collaborate more effectively — was how divided and misaligned we were in these trying times.

I was way luckier than most, but pandemic life was still hard. I spent the spring simply trying to cope. Like many people, one mechanism I tried was growing plants. I found a wilted mint sprig in the back of my refrigerator, which I rooted in water for several weeks, then transferred to a pot. I observed and documented the process every day, occasionally sharing what I saw on Instagram. My partner, amused by the loving care I was showing my plant, named it, “Mo.” I was awed by how resilient my mint was, and I was also surprised how gratifying this simple, regular practice of paying attention to Mo Mint felt.

Resilience. Paying attention. These became recurring themes both personally and professionally. I went into 2020 hoping that I could spend 30 percent of my time on coaching and training individual collaboration practitioners. I felt that this would be the best path to maximizing my impact, and it’s also where I felt the most energy and joy. A third of the way into the year, as the lockdowns were starting, it was clear that I wasn’t getting enough traction to hit that number.

I also went into 2020 adamant that I would only take on organizational clients willing to try my muscle-building approach to addressing their challenges. Convincing clients to do this has always been difficult, but my yield in the first half of 2020 was even lower than what it usually was. In an interesting twist, both the pandemic and the racial unrest created demand around collaboration practitioners who could help with remote work and equity work. However, most of the prospects who came my way were more interested in quick fixes than the kind of deep work that real change requires.

Grappling with those two things in concert was hard enough. Doing so during a pandemic was even harder. Paying attention and focusing on resilience made all the difference in the world.

The previous year, I had started to experiment with video as a way to better communicate my frameworks and practices, and I had more ideas and partially written scripts than time to produce them. Several conversations I had been having with colleagues inspired me to revisit one of these videos, Acting Strategically, which I published in April.

The response was universally positive, with many people asking me, “What would it look like for me or my organization to do this?” This led me to dust off some workouts I had developed over the years and start piloting them with colleagues and friends. The pilots performed well, and I loved doing them. I started preparing an “official” offering for late 2020, when something unexpected happened. Focusing on strategy was helping prospective organizational clients understand my workout approach in a way that had failed to click otherwise. Even when it was clear that they needed to focus on areas other than strategy, because they were better primed for this approach, they were more open to using workouts to address other aspects of collaboration.

By late summer, I found myself doing workouts with several organizational clients. It was gratifying and generative, but it was also taking my energy away from my individual practitioner offerings. I was conflicted, but I ultimately decided to go with where the demand was taking me and to hold off on my individual offerings indefinitely.

Looking Forward and Backward and Forward Again

Doing the Journey Mapping this past December had one more interesting twist. A few years earlier, Catherine Madden had suggested doing the exercise as a way of looking forward, not just looking back. At the beginning of 2020, I decided to try her suggestion, drawing what I imagined my professional curve might look like at the end of 2020. Here’s what I drew:

It was fascinating to compare this with how my year actually went. I had imagined a choppy beginning with a gradual upward trend, and I wasn’t completely wrong. However, the choppiness ended up being twice as long with an overall downward trajectory, there was never any “big” win, and while my year did end on an higher note, it wasn’t as high as I had hoped.

Still, as with all scenario work, the goal wasn’t prediction, it was to prepare for possibilities. Because I had imagined that my year would be choppy initially, I was mentally and emotionally prepared when that turned out to be true. I had also adjusted my strategic goals accordingly, so even though they ended up being off, they were not as off as they probably would have been otherwise. Finally, because I had written it all down, I had something to look at and reflect on at the end of the year.

I am determined to do this exercise again for 2021, but it’s already February. I’m about two months behind where I usually am in terms of planning, and I find myself more unmoored than I’ve been since starting this Faster Than 20 experiment seven years ago. I’m trying to be compassionate with myself. Last year was not normal, and while there are some positive signs, we’re not out of the woods yet, and there’s still a lot of uncertainty moving forward. I’m still excited about providing workouts, coaching, and community for collaboration practitioners. I have a set of clients I’m currently supporting, I have some ideas of what I want to offer individual practitioners later this year, and I will undoubtedly continue to experiment. Beyond that, I just don’t know.

What I do know is that rituals, community, and time to reflect matter. I am always grateful for my peers and our end-of-year gathering, but I feel especially so now. I hope many of you find Journey Mapping valuable as well.

What I’ve Learned About Building Collaboration Muscles

It’s now been seven years since I first started exploring a simple hypothesis:

  • Collaboration is a muscle (or, rather, a set of muscles)
  • You strengthen these muscles by exercising them repeatedly (i.e. practice)

Our current orientation toward collaboration is knowledge-centric, not practice-centric. No one expects anyone to get good at playing the guitar by handing them a book or sending them to a week-long “training,” yet somehow, this is exactly how we try to help folks get better at communicating or navigating hairy group dynamics.

I’ve spent the past seven years trying to change this. I’m currently on the fifth iteration of my experiments, which I’m currently calling Collaboration Gym. The other iterations (slightly out of order) were:

  1. Changemaker Bootcamp (2013)
  2. Collaboration Muscles & Mindsets (2014-2015)
  3. Habits of High-Performing Groups (2018-present)
  4. “Personal” Training for Organizations (2016-present)
  5. Collaboration Gym (2020-present)

I’ve failed a lot and learned a ton with each iteration, and I thought it would be fun to summarize what I’ve been learning here. I’ve also been having provocative conversations with Sarna Salzman and Freya Bradford about what a Collaboration Gym (or, in their case, a “Systems Change Dojo”) might look like in their community of Traverse City, Michigan. We’ve stayed mostly big picture so far, but recently decided that it was time to get real and specific. With their permission, I’ve decided to do my thinking out loud so as to force me to write down these scattered thoughts and also get some early feedback from a broader set of folks. That means you, dear reader! Please share your thoughts in the comments below.

Changemaker Bootcamp (2013)

The first iteration of this experiment was Changemaker Bootcamp, a face-to-face workout program that met for two hours every week for six weeks. I designed a series of exercises focused on developing muscles I considered to be critical for effective collaboration, such as listening actively, asking generative questions, navigating power, and having challenging conversations.

My participants — all of whom enrolled individually — generally found the exercises valuable and appreciated the practice-orientation. They also got along well with each other and valued the peer feedback. I designed the workouts to feel like physical workouts, only without the sweating and exhaustion. They consisted of warmups followed by intense exercises, with “just enough” explanations for why we were doing what we were doing. Most found the experiential emphasis refreshing. A few found it slightly dissatisfying. Even though they trusted me, they still wanted me to explain the why of each workout in greater detail.

These initial pilots helped me test and refine my initial set of workouts, and they also helped build my confidence. However, there were three key flaws.

  1. We weren’t repeating any of the exercises. In order to do this, I needed more of my participants’ time and I needed to focus my workouts on just a few core muscles.
  2. I needed an assessment. This would help me figure out the muscles on which to focus, and it would also help participants sense their progress.
  3. I was having trouble explaining the specific value and impact of this kind of training to people who didn’t already know and trust me.

Collaboration Muscles & Mindsets (2014-2015)

I tried to address these flaws in my next iteration, Collaboration Muscles & Mindsets. I almost tripled the length of the program from six to 16 weeks to create more space for repetition and habit-building. I created an assessment that folks would take at the beginning and at the end of the program, which helped me focus the workouts and also enabled the group to track their progress. Finally, I made it a cohort training rather than a program for individuals, which also helped with focus.

I also shifted the trainings from face-to-face to a remote, decentralized model, where I paired people up and made them responsible for scheduling their workouts on their own. After each workout, folks would share one takeaway on an online forum. This created group accountability by signaling that they were doing the workouts, but it itself was also a workout focused on muscles for sharing early and often. Every four weeks, everyone would get together for a full group workout.

Not being face-to-face meant I couldn’t (easily) do somatic workouts and that the instructions had to be clear and compelling. Not leading the pair workouts meant that I couldn’t make real-time adjustments. These constraints forced me to be more rigorous in designing and testing my workouts. In return, doing them remotely made it easier to participate and shifted agency away from me to the participants, which was in line with my desire to de-guru-fy this work.

I consistently faced early resistance from folks about the time commitment. I tried to explain that the workouts were in the context of the work that they were already doing, so they weren’t actually doing anything “extra,” but reception to this was mixed. Even though people got the metaphor around practice and working out, they didn’t have their own felt experiences around what this might look like, which made my description of the program feel abstract.

In the end, I asked participants to trust me, explaining that they would be believers after a few weeks. Most folks are hungry to talk about their work with someone who will empathize, be supportive, and offer feedback. Talking with the same person regularly enables people to get to the point faster, because their partners already know the context. Even if folks ignored my instructions entirely and just talked, I knew that they would get value out of simply having regular conversations with other good people.

This almost always turned out to be true. After the first week of workouts, folks would generally report having an excellent conversation with their partner. After about six weeks, people would often start saying that their workouts with their partners were the highlights of their week. Even though people generally had a felt sense of progress by the end of the program, they especially loved the final assessment, because they could point to and talk about the progress they had made in a concrete way.

Collaboration Muscles & Mindsets was a vast improvement over Changemaker Bootcamp, but people were still not practicing enough to see the kinds of dramatic, persistent improvement I wanted to see. I needed to focus the workouts even more and find ways to get people more repetitions.

I was also still having trouble explaining how doing these workouts would lead to the promised impacts. People understood the theory, but without felt experience, it felt too abstract. If you think about it, telling folks who are out-of-shape that they could be running a 5K in two months simply by running a little bit every day also feels abstract and far-fetched. The reason people are willing to believe this, even without felt experience, is that they know that many others have done it successfully. I probably need to get to the same place before folks truly believe the story I’m telling about collaboration muscles and practice.

Habits of High-Performing Groups (2018-present)

In 2018, I decided to shift the frame of my trainings to focus on four habits of high-performing groups:

Throughout the course of my work with groups of all shapes and sizes, I noticed that the best-performing groups do all four of these things consistently and well. These also serve as keystone habits, meaning that doing them regularly often unlocks and unleashes other important muscles and habits. Regularly trying to align around anything, for example, forces you to get better at listening, synthesizing, and working more iteratively. Only having four habits made focusing my workouts much easier.

My monthly Good Goal-Setting Peer Coaching Workshops was an attempt to help people strengthen their muscles around the first habit — aligning around success. Participants were asked to fill out a Success Spectrum before the workshop, then they got two rounds of feedback from their peers and optional feedback from me afterward. People could register for individual workshops, or they could pay for a yearly subscription that enabled them to drop into any workshop. The subscription was priced low to incentivize regular attendance.

Almost 30 percent of registrants opted for the subscription, which was wonderful. However, only 40 percent of subscribers participated in more than one workshop, even though their evaluations were positive, which meant that the majority of subscribers were essentially paying a higher fee for a single workshop. One subscriber didn’t show up to any of the trainings, which made my gym analogy even more apt.

Another subscriber attended four trainings, and watching her growth reaffirmed the value of this muscle-building approach. However, not being able to get more folks to attend more regularly — even though they had already paid for it — was a bummer.

I think I could leverage some behavioral psychology to encourage more repeat participation. One trick I’m keen to try is to have people pay a subscription fee, then give them money back every time they attend a workout. I also think cohort models, like Collaboration Muscles & Mindsets, are better at incentivizing more regular attendance.

The most negative feedback I got from these trainings was that some participants wanted more coaching from me as opposed to their peers. I designed these trainings around peer coaching as part of my ongoing effort to de-guru-fy this work. Just like working out with a buddy can be just as effective for getting into shape as working out with a personal fitness instructor, I wanted people to understand that making time to practice with anyone helps develop collaboration muscles. Still, I think there’s an opportunity to strike a better balance between peer feedback and feedback from me.

In this vein, this past year, I started offering Coaching for Collaboration Practitioners as a way to help leaders and groups develop the four habits of high-performing groups. This has been my most effective muscle-building approach to date, which makes me somewhat ambivalent. On the one hand, I’m glad that acting as a personal trainer is effective at getting people to work out. On the other hand, not everyone can afford a personal trainer. We need more gym-like practice spaces if we’re going to help folks at scale.

“Personal” Training for Organizations (2016-present)

Finally, over the past five years, I’ve been experimenting with customized organizational workouts focused on specific needs, such as strategy and equity.

I’ve found decent success at convincing potential clients to let me take a muscle-building approach toward their work. For example, rather than help a client develop a strategy, I will lead a client through a series of workouts designed to strengthen their muscles for acting strategically. Still, I often have to strike a tricky balance between more traditional consulting and this workout approach.

I’ve gotten much better at striking this balance over the years. In the early days, I tried partnering with other consultants to handle the more traditional work so that I could focus on the training. That almost always failed, especially with more established partners, because they didn’t fully get and believe in my approach, and in the struggle to find the right balance, the workouts would usually fall by the wayside.

Working by myself allowed me to be more disciplined in my approach, but I still struggled to maintain the right balance, and I failed a lot. I feel like I’ve only begun to turn the corner in the past few months. One thing that’s helped is getting much clearer about what clients need to already have in place in order for the muscle-building approach to succeed, specifically:

  • Alignment around the what, why, and how
  • Structures, mindsets, and muscles to support their work

For example, attempting to help a group develop muscles when they don’t have the right structures in place can cause more harm than good. To help demonstrate what happens when you’re missing one of these critical ingredients, I created a model inspired by the Lippitt-Knoster Model, to which Kate Wing introduced me:

Alignment Structures Mindsets Muscles = Performance
Alignment Structures Mindsets Muscles = Confusion

“Why are we doing this?!”

Alignment Structures Mindsets Muscles = Frustration

“We can’t succeed in these conditions.”

Alignment Structures Mindsets Muscles =

Resistance

“I don’t want to be doing this.”

Alignment Structures Mindsets Muscles =

Anxiety

“We’re not capable of doing this.”

Collaboration Gym and Future Iterations

I’m mostly resigned to more “personal training” work, if only to accumulate more Couch-to-5K-style success stories, so that people can develop more faith in the muscle-building approach. (If you or your organization would like to hire me for coaching or to design a custom workout program, drop me an email.) But I continue to be committed to experimenting with more scaleable and affordable approaches to muscle-building than hiring personal trainers. I’m hoping to unveil the Collaboration Gym early next year, and I’ve already successfully piloted a number of new workouts that will be part of it.

Epic success for me is to see others participate in similar experiments on their own and to share what they learn. A Collaboration Gym is only useful if there are lots of gyms all over the place. I give away all of my intellectual property so that others can copy and build on it, and I will continue to share my learnings here to further encourage replication.

The Secret to a Good Retrospective? Actually Having Them!

People often ask me how I structure retrospectives — meetings where a team debriefs and harvests its learning. As with all of my techniques, I am happy to share, and my framework and template is freely available on this website. As a process geek, I love exploring the art of leading good retrospectives. But when it comes to most groups, I prefer talking about some of the more mundane aspects of retrospectives.

Scheduling them, for example.

First, a story. One of the hardest, most time-consuming problems in software development is finding bugs — mistakes in the software’s code. Bugs are inevitable, and fixing them takes up large chunks of a programmer’s time. When I worked in tech over 20 years ago, I met with a vendor that had an extraordinary debugging tool. It would analyze your code and automatically spit out a list of bugs. It wasn’t doing anything magical, it was just clever automation of some oft-practiced techniques.

I was blown away by the simplicity of what they had done. I asked them how others were receiving their tool, figuring that it was selling through the roof. The representative furrowed his brow and responded, “Most people don’t react positively.”

“Why?” I asked in surprise.

“When we demo our tool,” he explained, “we ask people to point it at their actual software, so that it’s working with real data. When it starts spitting out bugs, people start freaking out. They don’t have the resources to fix all of the problems it finds before their scheduled release. They’d rather not know about them.”

It was hard for me to fathom at the time, but as I spent more time in tech, I started seeing this for myself. As I transitioned out of tech into organizational work, I started seeing this manifest in a different way.

Simply put, in my experience, most teams never schedule retrospectives. If we’re being honest with ourselves, I think this is because most of us are afraid of what we might discover. Maybe we’re worried about our ability to fix the problems. Or maybe we’re afraid of negative feedback and challenging conversations. Either way, what it boils down to is that getting better has to wait… possibly forever.

When we do schedule them, they are often the first to get canceled when things get busy, which for most groups is always. I say this with the utmost humility, because this is absolutely true of me. I try really hard to be disciplined about doing them with my teams, and I’m probably better than most. But that’s not saying much, because the bar is really low, and my track record is mottled with canceled meetings.

Perhaps you’ll understand why, then, if you ask me how to lead a successful retrospective, I will often respond, “By scheduling one.” I’m not being facetious. If you’re actually having retrospectives, you’re already doing better than most.

Scheduling them, unfortunately, is only step one. Step two is integrating what you learn. As I wrote last week, people forget things at an exponential rate. It doesn’t matter how artfully you facilitate your retrospective if you’re not building in time to review what you learned, because you will likely forget all those lessons anyway. If you can’t remember what you learned, you’re not going to have anything to integrate. What’s the point of learning if you’re not integrating those lessons?

Step three (which is actually step one) is aligning around goals and success as a group. If you haven’t aligned around goals and success at the beginning of the project, then how can you assess how well you did? For most groups, the answer is generally that whoever has the power gets to decide. There’s no accountability to actual results, because you haven’t decided as a team what you were aiming for. It’s too easy to rationalize anything as success.

If you’re truly serious about learning and improving, then you are, at minimum:

  • Aligning around goals and success as a group
  • Having retrospectives
  • Taking time to review and integrate what you learn

Make sure these are on your calendar, and protect those times.

Photo by Cathy Haglund. CC BY-NC 2.0.