Playing To Win
Dealing with Intuitive, Non-Strategists
Don’t Re-enact The Charge of the Light Brigade
My last two pieces have been Stop Working for Loser Strategists and The Myth of Objectivity & Strategy. On the heels of those pieces, I received a detailed question that dealt with both subjects, so I have decided to create an ad hoc trilogy with this Playing to Win/Practitioner Insights (PTW/PI) piece called Dealing with Intuitive, Non-Strategists: Don’t Re-enact The Charge of the Light Brigade. And as always, you can find all the previous PTW/PI here.
The Question
This is the question, unedited except for disguising the name of the company and its location, adding a link for the article mentioned, and bolding two words:
I’m a corporate strategist at x, an insurance and financial services conglomerate in y. I’m grappling with the challenge of embedding true strategic thinking in a legacy organization — where data is scarce, and the prevailing culture often defaults to intuition or tradition over analysis. In your article “The Big Lie of Strategic Planning,” you argue that strategy is about making bold, integrated choices, not just filling out planning templates. Yet, in environments where data is limited and strategic literacy is low, how can we practically foster the kind of integrative and design thinking you champion? Are there specific actions or mindsets you’ve seen work to break through legacy inertia and spark a genuine shift toward strategic, evidence-informed decision making?
For context, it is a sizable organization with approximately $7 billion in revenues and $75 billion in assets.
The questioner asks about helpful mindsets and actions for working for a weak strategist AND wanting to see more objective data analysis — hence the link to the two previous pieces.
On the Mindsets Front…
It struck me how this question displays a mindset that I see frequently, which is a longing for the perfect situation — in this case, to work for a fabulous, data-oriented strategist. I previously argued against working long-term for a loser strategist — so I understand the sentiment.
While it might sound like a productive mindset — to only accept perfect situations — my view is quite the opposite. I will explain by way of an example: my time as Dean of the Rotman School of Management. Happily, it was viewed as a highly successful stint, at the end of which I was named global business dean of the year.
Lots of businesspeople took note of my switch to the academic world following a couple of decades in the business world and thought it would be a cool second career for them — which it certainly was for me. They frequently call me for advice, often when they have been approached or thrown their hat in the ring for a particular business-school dean job. But they typically tell me that they aren’t very interested because the business school in question has problems of one sort or the other — a deficit, faculty infighting, enrolment problems, etc. — and they are going to wait for a more attractive situation. They hope that I will tell them that they are smart to wait for a great situation.
But my advice is exactly the opposite. The reason my time as dean was considered a great success wasn’t because I took the helm of a great, well-functioning business school and ran it well. It was because I led the turnaround of a dreadful situation. When I arrived, Rotman was running a large deficit, was hemorrhaging faculty to US schools, had just weathered an embarrassing public scandal, and suffered from brutal faculty infighting. I won’t belabor the story here. You can listen to a Whitney Johnson podcast discussing it here if you wish.
The same thing holds for AG Lafley. He is considered one of the best CEOs of his era not because he managed a legendary company well. It is because he inherited leadership of the company at the most perilous crisis point in its then-163-year history and boldly restored its glory.
On this front, my view is analogous to the value investing mindset of Ben Graham and his #1 student Warren Buffett. According to Graham: “The intelligent investor is a realist who sells to optimists and buys from pessimists.” And Buffett offers the following: “I will tell you how to become rich…Be fearful when others are greedy. Be greedy when others are fearful.” Situations in which observers are pessimistic and/or fearful are not toxic — they represent leadership opportunities.
So, the biggest required mindset change is yours. Don’t be so pessimistic! As a corporate strategist, this is a wonderful opportunity for you to add enormous value to your company. Treat it as such.
On the Actions Front…
That having been said, I did argue in Stop Working for Loser Strategists that if after two years, you are still working for loser strategist — quit. But before that, try hard for two years — and this is how to try productively.
If usage of data is limited and strategic literacy is low in your executive management, don’t charge straight up that hill against an entrenched opposition. Don’t tell them that they must do strategy and make data-based decisions, unless you want to participate in a historical re-enactment of The Charge of the Light Brigade — in which a British brigade charged against an overwhelmingly stronger and well-entrenched enemy force and lost 70% of its members before retreating having gained nothing at all.
Those executives will tell you to shut up and get back to work — and arguably they should. You haven’t helped them at all. Collectively, they are your boss. They tell you what to do, not the other way around.
Regarding Strategic Thinking
You can help them to the greatest extent by solving problems that they see. Of course, identifying problems that they don’t see is also helpful. But you must earn-in first for them to listen to you on that front.
So, start by asking them what their biggest problems are, the ones that keep them awake at night. Create a Pareto chart of them and start working to solve them, beginning with the top problem. But don’t insist on calling what you are doing ‘strategy.’ Why use a term that alienates them? It doesn’t help whatsoever in this situation.
Instead just work on solving the problem. Start by reverse-engineering the current set of choices to help executive management gain an appreciation that the current problem is the product of the current set of choices interacting with the competitive environment. That will help them appreciate that they need to make a different set of choices to make the problematic outcome go away.
Then help them think through that different set of choices. That is strategy. But don’t tell them it is or lecture them about it. Get them to make better choices. If you help them make better choices that make their most damaging problems go away, you will have earned in. And after you have earned in, you can tell them what they have been doing is strategy and they will be inclined to accept that and even start embracing strategy.
Regarding Data Orientation
In terms of their use of data or lack thereof, don’t get wound up about data. As I discussed in The Myth of Objectivity & Strategy and elsewhere, objective data about the past is not a critical input to determining strategy for the future. A bigger problem in strategy than weakness in/absence of objective data, is weakness in the logic underpinning strategy.
Choosing strategy is about competing logics not about competing data. We have no data about the future, so the data can never demonstrate that we should do one thing rather than another thing going forward — though data driven (self-proclaimed) strategists consistently make this error. Rather, creating the future is about imagining possibilities and choosing the one for which the most compelling logical argument can be made, as Aristotle argued 2500 years ago. And that is the essence of strategy.
Intuition is a manifestation of logic. Intuition doesn’t come from nowhere. It arises when our minds make connections and inferences that cause us to feel better about one thing than another — in the case of strategy, one path forward versus another. Intuition is a form of what pragmatic philosopher Charles Saunders Peirce called abductive logic — variously referred to as ‘a logical leap of the mind,’ or ‘inference to the best explanation.’ (I discuss Peirce and abductive reasoning extensively in my 2009 book The Design of Business if you want more on this front.)
Based on the wisdom of Aristotle and Peirce, I argue that intuition is a positive thing for strategy — but with one exception. If the logic of intuition is left unexplored and/or untested, it won’t contribute to the logics of strategy competing and the most compelling winning. That is, if an executive is allowed to say, ‘my intuition says X, so we should do X,’ and a choice is made to do X, that is bad for strategy because the logic isn’t subjected to testing by others.
The instinct of data-driven (or obsessed) strategists is to challenge such intuition by asking — or frequently, demanding — its proponent to ‘prove it’ with data. It is at this point that the intuition-driven executive tells the questioner to shut up and get back to work — and never involve the questioner in strategy again.
So, don’t! It is a useless way to proceed. It is a silly question because no strategy about the future has ever been proven to be ‘right’ in advance or ever will be. And the stupidity of the question will just piss off the intuitive executive.
Instead ask the executive to help you understand the logic of the intuition. Use the What Would Have to be True (WWHTBT) question to unravel the intuitive logic. WWHTBT about customers for the intuitive direction to be successful? WWHTBT about our competitors, our capabilities, etc.? Lay out the logic behind the intuition so that everyone involved can assess their comfort level with it. In my experience, executives with the intuition gain valuable insights into the previously implicit logic structure — and sometimes they change their thinking on their own, without challenge from anyone else.
Then encourage others to come forward with alternative strategic logics — not to prove the initial view wrong but to make sure the group is being comprehensive in considering multiple ways of proceeding before deciding. Again, in my experience, the initial executive is not angered or annoyed by the consideration of other alternatives when it is done this way. They just get mad — justifiably so — when they are asked to do the impossible by proving their idea in advance.
Practitioner Insights
As a strategist, you are rarely going to face a perfect context. Even if you are CEO of an organization, you are going to have to get your strategy approved by a board and/or investors — many of whom don’t understand strategy or what it entails.
Don’t be demoralized or discouraged by a context in which they think very differently about strategy than you do. That is an opportunity for you to shine and to create disproportionate value. Embrace the challenge!
But don’t embrace it by re-enacting The Charge of the Light Brigade. That was truly a tragedy because it both caused horrifying loss of life and was delusional. Sadly, it was designed to fail.
Don’t talk strategy or data. Zip it! Instead talk problems and logic. Everybody wants their problems solved and almost everybody hopes to be logically sound. Solve problems by improving the team’s logic and you will get little pushback. You will earn in. And when you have, fess-up and tell them that they have been doing strategy, rigorous strategy, all along. Because they will have experienced it concretely with you, they will understand what strategy actually is and what thinking rigorously about it entails. And they will think you are pretty darn useful to have around!
******
As a reminder, I previewed in January 2025 that I am doing a PTW/PI podcast series with friend Tiffani Bova. The fifth in the series will be on LinkedIn here on Wednesday, May 7th at 12 noon EST and 9am PST. Look forward to seeing you there!
