What I learned about Agile teams and building better software by coaching Little League

In March 2021, following the one year mark living through the global pandemic with two young sons at home and both of our jobs rapidly changing to full-time remote, my partner and I took a leap of faith and signed our boys up for Little League. In our past life, this would have been no big deal. We’ve done soccer, swimming, summer camps, and baseball would have most likely felt like another page in the book of “do all the activities” to provide our kids with a Well-Rounded® upbringing.

This time around, Spring baseball suddenly felt monumental. At that moment just a few months ago, COVID vaccinations were still restricted and not yet widely available. The league president reached out to me and asked if I would volunteer to coach my older son’s team of 7 to 9 year old boys and girls playing at the “Farm” level. Having coached youth soccer and swimming before, I agreed to take a swing at baseball. I was a Little League player as a kid and a lifelong Chicago Cubs fan, so I thought “how hard could it be?” Thankfully, it turned out to be just the right level of difficult and challenging, while always being enjoyable.

Here’s a summary of some of what I learned, re-learned, or finally admitted to be true about coaching and the different ways I saw its parallels to the work of software and technology that I have been engaging in over the past two decades.

Coaching is Work

• The first thing coaching Little League reinforced for me: coaching is work.
• To be a good coach, you must prepare before the event, be it practice or game, then must perform during the event itself, and finally must do the “after work” to process, learn, adapt, and begin the preparation for the next iteration. Can you do that on the fly? That’s great, but there’s no paradox in preparing to be adaptable in the moment.
• It feels like “coaching” in the Agile software development space has somehow been cast in a negative light, or with cynical opinions about the efficacy and utility of coaching. Combined with examples — good and bad — of coaching or coaching-as-a-metaphor everywhere in our culture, it’s not difficult to put together how this devaluation has anchored itself in our imaginations.

Trust the Personality of the Team

• You may have ideas about what your team will become, but they are just one input. The team will grow and evolve — form/storm/norm — based on your inputs, but also independent of your desires and influence.
• You may feel the urge, as the coach, to steer this growth process for the team. Let go of that mindset to attempt to exert control and trust the team. If it’s heading off the rails, step in to course correct, but otherwise let the team step into and embrace — or struggle with — its own self identity.

Flexadaptability (aka Exercise Flexible Adaptability)

• Flexible adaptability in the workplace refers to a person’s ability and willingness to respond and adjust to changes by balancing your core beliefs and the appropriate reaction to the change.
• So much of the game of baseball (and software, I swear that’s the last time I will do that) is simply being focused and “seeing” the field as each individual play unfolds, then preparing yourself mentally and physically to react with speed and coordination when “something happens” in the game.
• For players still learning the basics of the game, they will become better when they can field and throw from any position on the field. Much like XP or “pairing/mobbing” development practices, players should rotate, move around, try something new, and practice embracing change and finding ways to make it fun and meaningful.

Include Everyone in Everything

• Sometimes you want to put people in their favorite spot, either because they are the best at that position on the team or they are working to become better.
• Other times, people will learn by practicing on their least favorite tasks (positions), as well as from watching someone else perform in their favorite.
• The best team members know what they prefer and what they don’t, but they’re willing to perform in either spot in order to help the team. Going outside of your comfort zone is the only way you’ll expand it and grow.

Practice is Key

• Repetition is how we build our skills. Put your hand in the glove and get better fielding a grounder, catching a fly ball, throwing to a teammate, catching their throw back to you. It’s okay to fail, that’s what practice is for so that we can learn and try again, over and over.
• I decided to treat each practice as a “sprint” with a beginning, middle, and end. First, we come together and greet each other, we warm up our bodies/minds, state our goal(s) today, then break into different spots on the field to practice discrete skills (fielding, throwing, batting), before finally everyone coming back together at the end to demonstrate what they can do in a scrimmage.
• Low-stakes opportunities to try, fail, learn, adapt will provide people the safety to take risks, attempt new solutions or methods without the fear or pressure of “the game” weighing on their minds.

Winning or Losing is the Wrong Metric

• When you’re coaching 7–9 year olds, some of whom have never played organized baseball before, the goal of each game is smaller than the end result. We want to make “baseball plays” in the right way — fielding a grounder and throwing to first, touching the bases when we run, knowing the difference between a force-out and a tag-out situation, etc.
• If you focus on who won or lost the game, you’ve paid attention to the wrong things. How many outs did we make at the base in each inning? How many times did we refuse to quit? How many fouls did you get before ultimately striking out? How many grounders did you stop? Each play becomes a new opportunity to attempt again and either succeed or learn from failure.

And, Failure Teaches You How to Succeed

• Ultimately, doing something the right way often depends on first (or many times) doing it wrong.
• Missing the ball, over throwing your target, dropping the catch, getting hurt — and bouncing back — these are all the building blocks that you must put in place in order to become skilled — automatic — at making the right play at the right time. Seeing, reacting, moving, and following through in the moment are the sum of the equation (repetition + adjustments / time).

Stay in the Moment

• Baseball is a game that challenges the best attention span, not to mention the limited “pay attention” meter of your average 8 year old. It’s a game with long lulls of inactivity interrupted by moments of fast past, and exciting, developments.
• Being present in the moment, as a coach, is about helping others improve their ability to focus, let go of distracting thoughts, and visualize the possibilities of each play before it happens.

And, Keep the Future in Mind

• One of the most difficult things for a young baseball player to learn and internalize is the lesson that “you’ll get another chance”. Everyone wants to hit, but no one likes striking out. But you only get a hit if you’re willing to take a swing. You only get better at connecting with the ball once you’ve experienced the bitter reality of missing enough times that it motivates yourself to experiment, change, and improve.

Coaching strategies will necessarily differ for kids and adults, for baseball and software development. But, the striking similarities, in my mind, come down to a foundation of building a baseline of trust, safety, and striving to find a balance between understanding our present reality with designing our best possible future.