Jack of All Trades (and Master of None?)

Very shortly, my old blog site, kevin.generalizingspecialists.com will be shut down. A lot of my older posts here, like The Coach part of Agile Coaching was taken from this site. A colleague and I had envisioned launching an agile podcast 3 years ago, recorded one episode, and concluded we did not have the time to pursue the project further. The most fun from project has been bringing it up in conversations around the concept of Generalizing Specialists.

The concept of Generalizing Specialists is near and dear to the heart of a Jack of All Trades like myself. I’ve held every role on a typical Scrum team, I’ve spent 6 months on a DevOps team, and am currently a Release Train Engineer. From this eclectic background, I have numerous skills that I bring with me. A Jack of All Trades like me is the ultimate Generalist, capable of filling any role, wherever the need arises. It’s characterized by the ability to plug in the gaps, when they are found, and ensuring things continue to move forward.

Jack of All Trades get a bad rap though, as they are often derided as being Masters of None. Some argue that they are over generalized to the point that they have no single area of mastery.

In discussing the concept of Generalizing Specialists, the ancillary concept of ‘T’ shaped skills is often mentioned. The idea is that a capitalized ‘T’ represents one’s skill level in a number of skills. It’s not very deep in ost skills, save for one in the middle. A Jack of All Trades, on the other hand, would have a ‘-‘ hyphen shaped skills. The hyphen may be wider than the ‘T’ shaped skills of another, but there is no one area of mastery.

Except, I think there is one area of mastery that Jack of All Trades are masters in - playing in the white space between roles ang groups. By being adept and filling any role, these individuals have learned how to maximize their ability by recongnizing gaps and doing what it takes to get the job done. Those that get a thrill from doing anything and everything will find a way to discover where they are needed and make themselves useful.

In startups and small companies, you see many Jack of All Trades out of necessity - without a large group of people, the need hasn’t risen for granular role specialization. For the business to keep operating, everyone must fill in the gaps wherevery they may be.

Large organizations, with the economies of scale that they operate at, seek out specialists. Look at most job descriptions, especially for those for a developer in a large organization, and you will see very specific languages and tools referenced, as the organization has setup specific roles. But a large organization needs Jack of All Trades too, to play in the white spaces between their specialists. In a software organization, these Jack of All Trades are often the leaders, the managers, Scrum Masters, and Release Train Engineers, who are all adept at identifying those gaps and calling attention to them. The way these gaps get filled will vary from person to person and role to role. But identifying these gaps and where teams are impeded is the speciality of agilists at any level.

The term Jack of All Trades was preceded by a British term, Johnny-do-it-al. It also had a bit of a negative connotation when it was introduced to describe Actor, Playright, Poet, and Businessman William Shakespeare. Just because you do it all doesn’t mean you can’t be wildly successful.