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Group Improvisation

07-03-13 Ben Callahan

To an industry obsessed with process and workflow, Ben offers an alternative approach to web design and development.

In 1959, Miles Davis got a few of the most talented jazz musicians of all time together in a recording studio in Manhattan. The album they were about to record would go quadruple platinum and still be selling 5,000 copies a week in 2013. The title of that album was Kind of Blue, and today it’s considered by many to be the greatest jazz record of all time.

The musicians Miles was playing with didn’t know what they were going to record when they arrived at the studio. In fact, Miles didn’t even really know. The only preparation he had was a handful of modal scales and a few melody ideas. No sheet music or chord charts. No rehearsals or overdubbing techniques. The first time the band made it through a track is the take that’s on the album. Though web design and modal jazz may seem worlds apart, there’s a lot that improvisational records like Kind of Blue have to teach us about our process-crazed industry.

Dazed and Confused

Building for the web has been an exciting journey for the past few years, but it’s no secret that we are all a bit confused when it comes to process. Understanding our deliverables and managing our clients through these changes is not easy when our product has to work—or should I say, “respond”—everywhere.

If you read through the Kind of Blue liner notes written by pianist Bill Evans, you’ll come across this quote:

“Group improvisation is a challenge. Aside from the weighty technical problem of collective coherent thinking, there is the very human, even social need for sympathy from all members to bend for the common result.”

Bill is highlighting two distinct challenges they faced in making this recording. The first is the challenge of the group, which he describes as “the weighty technical problem of collective coherent thinking.” The second is the challenge of the individual, which he explains as “need for sympathy from all members to bend for the common result.” These two challenges are part of every team that’s ever existed, including yours and mine as we build the web. So, how do we build a process within which our teams can fully collaborate and a team that’s willing to do so?

The Balance

It starts with balance. What Miles did in preparation for recording Kind of Blue was just enough to allow his band to improvise together. Too much structure would have resulted in something much like other jazz records of the day. Too little, and they may never have made it through the sessions. We need to do the same as we coordinate our teams’ efforts on web projects. However, this balance can be different for each team, depending on the client, the individuals participating, and the experience the team has in working together.

As I’ve worked to build a company that can perform this level of “group improvisation,” I’ve noticed a few characteristics that seem to be consistent in a truly collaborative team.

Be Great

Quite simply, the skill of the individual is critical to the success of the team. We’ve heard a lot in our industry about becoming a “craftsman.” While I do feel this language is overused, the sentiment is certainly valid.

Had Miles brought a group of average musicians into the studio for the Kind of Blue sessions, the record wouldn’t have been the same. Instead, he gathered individuals so skilled that playing their instruments was second nature, like breathing. This level of mastery is called “unconscious competence,” and it’s quite rare. It means that you’re fluent in your discipline, and this fluency is what gives you the ability to improvise and explore.

Another thought: happy accidents usually happen where you’re fluent. I believe this is one reason many designers who are highly skilled in static design (ala Photoshop) have difficulty transitioning to design in the browser. Instead, a new crop of designers is growing—one that has never designed comps in a static tool. They are fluent in HTML, CSS, and JavaScript, and this is where they are creative.

One warning: be careful about building your team based solely on skill. Having individuals that are passionate about learning can be just as beneficial as a group of hardened pros. Often, this fresh outlook inspires a team to try new things!

Be Humble

Finding individuals who are both skilled and humble can be tough. Once you do, you’ll see what a difference this combination makes. Kevin Sharon, previously the Design Director at Happy Cog, Austin, recently said something quite relevant at Artifact Conference:

“If you can’t say ‘No,’ it’s not collaboration.”

As I look back at my involvement with the web, I realize that it’s taken me a while to get to a point where I can say ”no” to my clients. While this is true in relationships with clients, Kevin’s statement is also very relevant in team interactions. The ability to offer and receive critique is a necessary ingredient for a collaborative team. Likewise, humility is at the core of truly constructive criticism.

But it’s not just critique that requires humility. The individuals on your team also need a willingness to consider the good of the project before themselves. You’ll likely find that you can’t convince or teach someone to be this way—they either get it, or they don’t. Try to find those that do.

Be Empathetic

There has been a lot of conversation around the idea of being empathetic to the needs and desires of our users. This is certainly important, but I’m encouraging a slightly different kind of empathy. In order to sense what’s best “for the common result,” I believe we need empathy for the other members of our team. This level of investment in and care for each other allows a team to think and act as one. Without the ability to put yourself in the shoes of your peers, you won’t be willing to adjust your own way of working. Empathy is a powerful character trait, and a team of people, each having some level of empathy for one another, is necessary for group improvisation.

My friend and colleague, Matt Griffin, describes this quite eloquently as it relates to client meetings:

“You may have some vague plans about what you’re going to do when you sit down. But you’re always listening, watching, and ready to throw all your plans away if a better avenue presents itself. What you really bring to bear in the moment is not a rehearsed plan, but the sum total of your cumulative knowledge and experience to that point.”

Empathetic people are “always listening and watching,” seeking a way to understand what their peers are feeling. Combine this with the humility to be “ready to throw all your plans away if a better avenue presents itself,” and you have the ingredients for real group improvisation.


Even with a team full of highly skilled and humble individuals, the benefits of a deep empathy for the team are not immediately visible. Only with practice can we develop the ability to work as a single unit for the good of the whole.

Miles’ band had been playing together quite a bit. In fact, he invited Bill Evans (the pianist from the previous incarnation of his group) to play all but one of the tracks on Kind of Blue. I wonder if the kind of improvisation he was seeking for this record required a group of players that knew how to work together—one that had practiced improvising together.

I have to believe that the more we work with the same people, the better we’ll become as a team. In short, we need to give our teams opportunities to practice together. Expecting this level of improvisation without time to develop the sensitivities required will certainly result in disappointment. Look for opportunities to allow this kind of practice for your team. It will be messy, but it will be worth it.

One Deliverable

For a while now, I’ve been speaking about our deliverables and our process. The more I consider what’s possible if you have the right people on the team, the more I believe that we only really have one deliverable.

We build web sites.

This is our deliverable. Not wireframes, not site maps, not Photoshop files, not Style Prototypes. I can’t help but wonder if our clients would be better served if we focused our efforts on that end goal. Then, our “deliverables” would look more like progress updates than formal, pretty, pictures of sites. A team truly focused on the end goal, equipped with skill and character, will naturally find paths toward elegant solutions.


We spend a lot of time talking about workflows. We do our best to diagram them, wrap them up in a Keynote file with a pretty little bow, and offer them to the world as if we’ve figured it all out.

If you take only one thing away from these thoughts, consider this: invest in your people over your process. This will have a long-lasting impact on your culture, the individuals on your teams, and the work they produce.

I’d love to hear if you’ve found the same to be true.

Special thanks to Matt Griffin for his feedback on these ideas, and my crew (Ryann, Drew, and Jody) for their help in editing.

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