Strategy & Connoisseurship

Four Pathways to Becoming a Sommelier of Strategy

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I received a request from one of my most engaged readers, Lethal Weapon, for more thoughts on a paragraph from my 2024 piece, Strategy & Artistry. His good question forced me to think more deeply on the topic of personal connoisseurship. I have captured my reflections in this Playing to Win/Practitioner Insights (PTW/PI) piece entitled Strategy & Connoisseurship: Four Pathways to Becoming a Sommelier of Strategy. And as always, you can find all the previous PTW/PI here.

The Paragraph & Question

This was the paragraph:

It took me on a long journey of connoisseurship. For the three decades since, I have been working on my ability to make ever finer qualitative distinctions in my field of strategy. In some sense, I have been working to become a sommelier of strategy. That is, I want to be able to determine that this strategy is superior to that one in these subtle ways — like a sommelier can make distinctions between different wines. My task requires the ability to understand how qualitative dimensions relate to one another — i.e., this aspect of customers interacts with that aspect of competitor dynamics in this particular way.

And this was his question:

Hi Roger, I’m re-reading this post and this copied section [which I replicated above] really intrigued me. Have you written more about this “sommelier” role? I’m sure many of us would love to understand how you “determine that this strategy is superior to that one in these subtle ways.” (I surely would.)

On incoming questions, I try to channel Bill Belichick, former New England football coach and winner of most Super Bowls in history. That is, I decide to not answer or give a relatively curt one on questions that I don’t think involved the questioner putting much thought into it. But if the question is thoughtful, I attempt to give as thorough an answer as possible. This one is in the latter category. And it forced to think more thoroughly and concretely about how I attempt to develop connoisseurship in my field.

After thorough consideration, I believe that I attempt to build connoisseurship in four ways.

1) Engaging in Reflective Practice

Both the practice and reflective aspects are important here — in fact I think of the two as multiplicative, not just additive.

On practice, I believe that people, myself included, have a limited capacity for conceptualization without associated practice. I could read literally everything that has ever been written about strategy and at some point during that journey, I would hit a wall at which my connoisseurship would cease to deepen. Connoisseurship advances only with interaction between conceptual knowledge and practice. The back and forth is critical. And obviously, this is hardly my idea. Aristotle’s phronesis — practical knowledge — and its interaction with episteme — theoretical knowledge — predates me by 2500 years.

I spend about half my time practicing strategy with real clients and the other half writing about strategy, the latter of which requires me to conceptualize/generalize. I don’t know how I would do, let alone get better at, the latter without the former. And I would be dull and boring at the former without the latter.

On reflection, I learned from Don Schön, the primary thinking partner of my mentor Chris Argyris, the critical importance of reflection while practicing. If you simply practice and don’t reflect much, if at all, on what you learned from that practice, you won’t deepen your connoisseurship. You can go to the driving range and hit a thousand golf balls. But if you don’t reflect on your swing and ask yourself to what extent did my swing produce the result I hoped for, you won’t improve. You will just groove your current swing — whether good, bad or indifferent. Not reflecting causes the potential learning to float past your eyes and ears without ever getting into your brain.

On this front, I always try to take note of my reactions. I ask myself: why did I react that way? Was it because I expected x but generated y? For example, if a client reacts aggressively to something I said immediately before, and I feel disappointed, I attempt to ask myself: why was I disappointed? Oh, it was because I expected a joyful reaction from the client. OK, what was my theory about the client that made the actions I took make good sense to me? But at the same time, what about that theory could have been so invalid as to have produced that reaction? What could be a better theory? How could I test that theory next time?

Without reflecting on my disappointment, but rather just experiencing it, I wouldn’t have learned a thing. If instead I reflect each time that there is a gap between the expected outcome of my actions and the actual outcome, my connoisseurship will build slowly but steadily over time. For example, in the case above, I learned how to frame my comments in a way that caused the client to productively react to them — perhaps in very subtle ways.

2) Preventing Myself from Being Overwhelmed by the Numbers

When I talk about this, people go crazy — especially academics — and claim that I am ignoring numbers entirely and going entirely on ‘gut feel,’ which they view on the same level as satanism. In fact, I don’t ignore numbers or encourage anyone to do so. Rather I view numbers as impressionistic not deterministic. In fact, I see them as impressionistic as any other qualitative variable. People not interested in connoisseurship like to treat numbers as ‘true’ — i.e., they tell you ‘The Truth.’ All they can do is improve their quantitative manipulation techniques, as I have discussed before. You can’t become a connoisseur crunching numbers.

I always look at the numbers associated with any problem on which I am working. Numbers represent useful data and I try to use all the useful data at my disposal. But I practice thinking about what picture of my subject the numbers help me to paint — not what the numbers deterministically say. And if the numbers run counter to everything else that I know about the subject, I don’t automatically change my mind. That is being overwhelmed by the numbers. Instead, I focus on getting ever better at — yes — painting with numbers!

3) Guarding Myself Against Being Drowned Out by Other Voices

I don’t believe that you can develop your own connoisseurship if you spend the majority of your time listening to other voices. Does that mean don’t listen to or read other voices? No. Just don’t do too much of it. It is your voice that you need to develop. You can’t do that if other voices are simply drowning you out.

On this front, I don’t read much. I am not proud of that and I always have a fear that it will hurt me eventually. Instead, I spend a disproportionate amount of my time writing. Over the past quarter century, my write-to-read ratio of time spent is at least ten-to-one — maybe more.

The reason is that I don’t think you can become a connoisseur if your mind is totally full of other people’s thoughts. I don’t think you can discern what notes you are tasting in that lovely cabernet sauvignon if people around you are screaming leather, slate, cranberries, chocolate in your ear. You have to be in your own mind as you practice in, experience, and reflect on the world.

You have to develop your own ideas and take in other people’s thought with great care. You need stillness in your mind to consider what you are considering without distraction.

4) While Remaining Open to Other Connoisseurs

It is a balance. While I guard against being drowned out by other voices, I know that I can’t muffle all other voices or I will miss insights that will contribute to my connoisseurship. In my experience, plenty of good stuff comes from connoisseurs in fields other than my own.

A great example of that came courtesy of my longtime Procter & Gamble friend (now retired) Craig Wynett, one of the most innovative people with whom I have ever worked. He phoned me up out of the blue one day and said that we have to go visit Dr. Gerald Edelman at the Neuroscience Institute in La Jolla California. The late Dr. Edelman was a Nobel Laureate and father of the Theory of Neuronal Group Selection (TNGS), often called Neural Darwinism due to his 1987 book by that name.

The dominant conceptualization is that the brain operates like a computer executing code. His alternative conception is the brain as a Darwinian entity that evolves and adapts based on its experiences. And he demonstrated that with repeated efforts on the same kind of problem, neuronal groups form in the brain that become much more efficient at thinking about that class of problem.

There was little obvious connection to strategy in the visit — and it meant going all the way across the country to San Diego International and then a 45-minute drive. But if Craig thought it would be useful, I was all-in.

And he was right. Dr. Edelman completely changed my way of understanding how humans think. In particular, he caused me to become more confident in strategy inferences that I make, even if I don’t understand completely how I made them. He also helped me double down on practice — to build my neuronal groups!

I was open to his ideas because he was a genuine connoisseur in another field — how the brain works. Interestingly, he was also a masterful violinist who once imagined a professional violin career before turning to biology. Because his field of connoisseurship was so far from mine, I didn’t feel compelled during our time together to focus my mind on the connections. I just chilled out and learned. Only later did I start to make connections with my work in strategy, design and innovation. And I believe that one-day encounter has contributed meaningfully to my connoisseurship of strategy.

I don’t solely open my mind to connoisseurs from distant fields. Sometimes it is in my own — as with Peter Drucker, Jim March, Chris Argyris, Mike Jensen and Don Schön. But it is very few because my bar is very high — and always has been.

Practitioner Insights

You need to work assiduously on your connoisseurship to become a connoisseur of strategy. It won’t happen automatically by itself. A core requirement is to be a reflective practitioner. If you don’t practice, you have zero chance of becoming a connoisseur. If you practice without reflection, you also have zero chance of becoming a connoisseur.

I worry more about reflection than practice. I learned that the hard way at my old firm, Monitor Company, which I loved. It was chalk-a-block full of exceedingly bright, hard-working consultants. One of my directorial jobs was head of our R&D function and I asked our consultants to contribute to building out knowledge (I didn’t call it that but it was my attempt to build the strategy connoisseurship of the firm) by doing one non-onerous task. At the end of each case they finished, write me a one-to-three paragraph note on what they learned on the case. I got less than 1% adherence. It helped me realize that these bright, hard-working consultants liked to practice but not to reflect. Don’t fall prey to the same thing.

Also, pay attention to protecting your mind. Don’t let it either become overwhelmed by numbers or drowned out by other voices. It needs stillness for reflection.

Be open but be careful to let in only what contributes. Only integrate into your connoisseurship a fraction of what you experience. You will sense when there is something truly valuable — don’t overrule your sense.

And welcome to the journey!