Playwright Robert Greene infamously referred to his peer, William Shakespeare as “Johnny do-it all”, in an oblique reference to Shakespeare being an actor turned playwright. Jack of all trades, master of none is an often used phrase today. In Middle Age England, several trades had a jack of some sort – lumberjacks, steeplejacks and Jack-tars (sailors). These jacks were often master craftsmen in their chosen trades. The original, “Jack of all trades” didn’t actually carry negative connotations, until ‘master of none’ got added much later.
Today, most of us can feel this dilemma. At our best, we experience the imposter syndrome of not knowing if what’s the right thing. At our worst, we toot chauffeur’s knowledge & managementese. There are as many specialisations today as ambiguous problem statements, that I often don’t even have the right word to explain that feeling of trying to keep pace.
Recently, Elon Musk, the world’s riches person added fuel dilemma when he said in a tweet [4]:
“I strongly believe that all managers in a technical area must be technically excellent. Managers in software must write great software or it’s like being a cavalry captain who can’t ride a horse!”. This, coming from a business man whose span ranges across diverse domains like space travel, electric cars, tunnel transportation and social media – to put it mildly – was odd.
This is the generalist’s dilemma – “How much specialisation do you need to contribute effectively?” The answer, as I now understand, is both – not much and a lot. Both at the same time.
Expert managers often undermine the work
Ian Siegel, who built ZipRecruiter from his kitchen table to a listed company, recalls this story as pivotal moment for him,
“I had this rude awakening. I remember it so clearly. They had me interview someone who had come out of a marketing media company who was a buyer and in the interview, I had with him for 20 minutes he said not one thing I understood but they were all excited about him. I was like “guys, you are going to hire that guy. I have no idea what he does or how he does it. Like, he made no sense to me. He spoke in jargon the entire time.” So, we hired him over my apparent objection. And the first day he was on the job, he goes, “Hey, where are the audit logs of ads running?” And I was like, “What’s an audit log? He is like “the thing you get from the TV stations that show you that they ran your ad when they said they did so that you can make sure you’re not overpaying them.” And literally the first day he saved us a million Dollars because they had not been running the ads. …
At the stage Zip recruiter was then, a million dollars was probably game changing.
With that in mind, let’s start with the premise Elon’s is wrong. So, How can a good manager without coding skills know the project is well done?
Firstly this questions belittles the creative aspect of coding. It is like saying unless you are a master artist, how can you know my art is good? The simple answer, as eloquently articulated by an expert engineer turned manager Attila Vago, is – “You don’t. Not from looking at the code, for sure. A good manager will ensure they have the right people in the team to enable productive development environments, stringent testing procedures and the skills of each member compliment each other enough to have high enough confidence [that] only quality software goes live.”
Companies and managers hire engineers not to tell them what to do, but the other way around. One hires professionals to rely on them, not put them on a leash.
~ Attila Vago [5]
If, as a managers, your instinct is to roll down your sleeves each time to expertly guide the cavalry, you will become the rate limiting factor.
This raises an uncomfortable question — doesn’t my manager need to understand what I’m doing? The answer is – yes but certainly not at the level you think. Says, Vago, “Your [engineering] manager will need to know that what you’re developing is according to requirements, that you address merge issues, adhere to testing and design guidelines, and you’re conscientious enough to deliver on what you promise. Everything else is between you and your team-members, from the designer to the quality engineer. For great code, you’ll get praise from your engineer colleagues, not your manager. Your manager will pat you on the back for getting the desired results”. Ian takes it a level higher, saying I literally am practicing the discipline of not even giving my opinions anymore. What I try to do is ask questions. Tell me why you are thinking a testimonial-style commercial is a right approach for us at this point? I try to just elicit them to explain their strategy to me, so that they are listening to themselves, explain it out loud, and then, we have a dialogue about their answers instead of me saying like, “I don’t think we should do a testimonial-driven commercial right now. Too many people are doing it.
Yet, if generalists are all about soft skills that are often hard to reflect on oneself or others, how does one know where to improve? Doesn’t this open up room for all the Dilbertese today? To me, the answer is counter-intuitive. The term generalist is a misnomer, often misunderstood as the opposite of a specialist.
A generalist is a different kind of specialist
It is usual for CEOs to be generalists but rarely so for a head of finance or legal or technology, right? Wrong. To be really good at their jobs, each of these functional leaders need to be generalists. So what then constitutes a generalist?
To me generalists are folks with a special skill set, a secret ingredient – systems thinking. In business this is a deep understanding of the company’s environment, its business and operating models. Generalist are experts in understanding & building complex systems. Each functional leader needs to build unique and intricate mental models (& system models) in the domain they oversee, which also has myriad specialisations. However, it also needs to be expansive enough to overlap with others domains. To be able to see interlinkages and to identify both opportunities and possible points of stress and failure in the system.
Collectively the management team’s models form the company’s system, which evolves dynamically. The CEO operates similarly, but from a different perspective of integrating functional management, shareholders, regulators and lately, even the society.
Why do so many of us love to work with specialist bosses then? That’s often because, we usually don’t have all the skills for that role and expect our managers to teach us. Teaching you is not their day job, although learning to be effective is yours. Rarely, it can happen that the knowledge involved is so specialised and intricate that you need an apprenticeship model to transfer knowledge. That, however need not be a manager-reportee relationship. As in Ian’s media buying example, the inverse of this is more common.
However, organising work with system design principles has two key challenges. First this needs a dual mindset that is not intuitive at an operating level; and second we need to learn a new mental toolkit to help us design, build and observe system flows..
The generalist’s mindset
Kenneth Boulding’s personality itself is a great example of the dual mindset needed for system thinking. Kenneth, was an economist and one of the founders of general systems theory. He had varied interests spanning across peace studies, general systems, volumes of poetry, ecology and social theory, to name a few. Elise Boulding, his wife, wrote:
Kenneth delighted in life. Nothing was too small to escape his absorbed attention. He always carried a tiny but powerful magnifying glass in his pocket so he could absorb details invisible to the naked eye of any object. By the same token, nothing was too large or too far away to escape his interest. At night he would mount his trusty telescope on the porch and lose himself in the stars.… his way of seeing things was so unique that what people remember best about Kenneth was the unexpectedness of his observations, the unusual connections his mind was always making. Kenneth’s mind at work was a mind at play.
The book, System Thinkers [7]
This mindset is the ability to zoom in with curiosity and zoom out with wonder and yet always look for new patterns, unexpected connections in an imaginative, playful manner.
The mental toolkit
I don’t consider myself an expert in system thinking, so I wont delve into some of its core concepts yet [8], but I’ve discovered a broader toolkit that is helpful as a starting point. I’m only including brief ideas summaries here as inspiration
- Learning quickly: The ability to learn something new fast enough from a diverse set of resources – books, articles, people, courses and more
- Creating new abstraction models: Summarising learnings into abstractions & models that an eight grader can understand and technical experts reluctantly agree
- Rethinking these models: When something doesn’t make sense, slowing down to listen deeply for critical learning so you can upgrade your models
- Reverse mentoring: Learn from younger folks, create abstractions they agree with and rethink those models as you learn something new
- Sythnesis : The ability to combine two or more things to create or infer something new or novel
- Attention to feedback : Pay attention to the feedback loops. Look for things that confirm and for those that don’t conform.
- Ask better questions: The simple act of searching for the right question is more powerful the knowing the right answer. I’ve written a separate essay on this (here ).
This is, but a starting point in resolving the generalist’s dilemma, not the solve. What are some others ideas that you deem worth exploring ? Let me know in the comments below.
Sources
[1] The saying ‘Jack of all trades’ – meaning and origin.
[2] Nandan Nilekani on rethinking how to regulate
[3] Unified Payments Interface – Wikipedia
[4] Elon Musk on Engineering Managers
[5] Managers who are experts undermine the work
[6] https://www.linkedin.com/in/attilavago/
[6] 2021: The year UPI became the undisputed payments champion
[7] Systems Thinkers | SpringerLink
[8] The 6 Fundamental Concepts of Systems Thinking
[9] [An introduction to systems thinking | Draper Kauffman
[10] 20VC: The Job of the CEO is Do As Little As Possible
