Playing To Win
Personality & Strategy
What Matters & How to be a Better Strategist
I get numerous questions on the relationship between personality types, whether Big 5 personality traits (Big 5) or the Myers Briggs Type Indicator (MBTI), and ability as a strategist. So, I thought I would tackle this set of questions in this Playing to Win/Practitioner Insights (PTW/PI) piece entitledPersonality & Strategy: What Matters & How to be a Better Strategist. And as always, you can find all the previous PTW/PI here.
Some Groundwork
I have laid some of the groundwork for this topic by defining the mindsets and skills need to be a great strategist in What Makes for a Great Strategist? and Becoming a Better Strategist. The three critical strategist mindsets are that strategy: 1) starts with customers; 2) involves a complex adaptive system; and 3) is about inventing the future. The three critical strategist skills are 4) qualitative appreciation; 5) dialogue; and 6) juggling more balls.
Overlap with Big 5
To review, the Big 5 can be summarized (simplified for purposes of this discussion) as follows:
Openness to Experience: Imaginative, creative, and intellectually curious versus dogmatic and conventional.
Conscientiousness: Planned, organized, dutiful, and industriousness versus disorganized, spontaneous and careless.
Extraversion: Sociable, assertive, and seeking stimulation versus introversion, reservedness, and preferring solitude.
Agreeableness: Cooperative, compassionate, and trusting versus antagonistic, suspicious, and competitive.
Neuroticism: Anxious, sad, and irritable versus emotionally stable and calm.
In terms of the six combined strategy mindsets and skills, I see the following overlap with the Big 5:
1) Starts with customers: There is some overlap with Agreeableness in terms of the compassion and respect a strategist needs to show customers.
2) Is about inventing the future: Openness to Experience would help in terms of imagination, creativity and curiosity. However, the inclination should not be so extreme as to be impractical.
3) Involves a complex adaptive system: I see no real overlap.
4) Qualitative Appreciation: Agreeableness may be a small positive in producing more attention to feelings, not just quantifiable measures.
5) Dialogue: I think Agreeableness would be helpful in welcoming discussion with others.
6) Juggling More Balls: I see no real overlap.
In summary, I see as helpful to strategy the empathy and compassion that comes from Agreeableness and the imagination, creativity, and curiosity that comes with Openness to Experience. Conscientiousness feels not directly overlapping but I will return to the subject below. Extraversion feels orthogonal to being a great strategist. And on Neuroticism, it feels that a strategist just needs to be balanced.
Overlap with MBTI
According to the Myers & Briggs Foundation, the four pairs of opposing preferences are:
Extraversion (E) or Introversion (I): Feeling energized by interaction in the outer world of people and things versus feeling energized when reflecting on concepts and ideas in their inner world.
Sensing (S) or Intuition (N): Paying attention to information that is concrete, tangible, detailed and factual versus paying more attention to the patterns and possibilities in the information they receive.
Thinking (T) or Feeling (F): Putting more weight on objective principles and impersonal facts when decision-making versus putting more weight on personal concerns and the people involved when decision-making.
Judging (J) or Perceiving (P): Preferring a more structured and organized lifestyle versus preferring a more flexible and open-ended lifestyle.
Strategy people tend to assume that INTJ’s make for the best strategists (largely because they test that way) and presume since they see me as a noted strategist, that I must be INTJ. In fact, I test as INFJ, which probably explains my wariness of obsessive analysis and faux objectivity. Apparently, I share my type with Goethe, Mother Teresa, Martin Luther King, Jr., and Nelson Mandela. Cool. And for better or worse, we are the rarest type — only 1.5% of humanity.
In terms of the six combined mindsets and skills, I see the following overlap with MBTI:
1) Starts with customers: I think Intuition and Feeling are helpful in paying attention to what customers are doing and why, rather than judging them for it. At the opposite end of the spectrum, I suspect heavy Judging is problematic because the strategist would be less open to understanding customers.
2) Is about inventing the future: I think Intuition is important in promoting openness to possibilities.
3) Involves a complex adaptive system: Again, I think that Intuition is probably an advantage in being willing to dive into the complexity
4) Qualitative Appreciation: On this I suspect it is the same situation (i.e., Intuition & Feeling — good; Judging — bad) as with Starts with customers
5) Dialogue: Here the best would be not too extreme Introversion because an Introvert would be prone to stay within own head and good to be heavy Feeling because Feeling would have the tendency to reach out.
6) Juggling More Balls: I see no real overlap.
The biggest overlap is that Intuition is better than Sensing for the strategist. On the other three, a reasonable balance is probably the best. Extremes will be problematic for the strategist.
Big 5 & MBTI Together
In summary, I don’t see a strong overlap between the insights from Big 5 and MBTI for being a great strategist. It is probably better to lean toward Agreeableness and Open to Experience and somewhat toward Intuition and perhaps to Feeling. But these features of personality don’t jump out for me as super impactful.
Carol Dweck and Angela Duckworth
For me, the insights one can take from the personality-related insights of Carol Dweck with respect to growth mindset and Angela Duckworth with grit are more important for being a great strategist. The fundamental reason is that ability to produce great strategy isn’t innate. It comes from practice, practice and more practice.
Dweck argues that you need to believe that you get better from practice — i.e., have a growth mindset — rather than believing that the most important determinant of accomplishment is your native intelligence — a fixed mindset. The worst people I run across in strategy are one of two sorts.
One sort spends their time telling me how brilliant they are. They are mainly strategy people who don’t think they need to practice because they are just so smart. They suck at strategy because they have a fixed mindset and don’t do the work necessary to get better. I remember back at Monitor Company in the 1990s, we fell out of love with hiring Baker Scholars from Harvard Business School (they are top 5% of the graduating class). Had Dweck’s book been out by then, we would have better understood why our observations led us to that conclusion. Too many of them didn’t get better over time — even though they were obviously exceedingly smart — and I am sure Dweck would have assessed them as having fixed mindsets.
The other sort tells me — proudly — that they are ‘an operator’ and ‘are practical,’ and that is why they don’t spend much time on strategy. I wouldn’t be surprised if they test Sensing and don’t test Open to Experience. But the key is that they just don’t work on getting any good at strategy because they too have a fixed mindset. So, they put strategy off forever — and end up failing at their executive jobs.
The people who are good at strategy have a growth mindset. But in addition to a growth mindset, you need to have grit, per Duckworth. You need to have the determination to keep at it even if it is really hard. If you don’t have grit, you will settle on mediocre strategies — playing to play rather than playing to win, fooling yourself that a play is really a win. I foreshadowed that I would loop back to Conscientiousness because I think that Conscientiousness encourages grit and in that way is a useful personality trait.
This is why I feel that in strategy the combination of a growth mindset and grit are more meaningful than the particular elements of Big 5 and MBTI. Great strategy involves going to the extremes of growth mindset and grit — that is, when you hit a wall, you believe that you can work your way through it, and in addition, you do so because you believe by doing so, you will get better. That having been said I am sure Big 5 and MBTI experts will tell me that features of each personality model underpin a growth mindset and grit. I would just rather go directly to growth mindset and grit.
On this front, people tend to think that I have achieved my observable success in practicing, advising and writing about strategy because I am very smart. I appreciate the generous sentiment, and it may be true to some extent. But I will never believe that determines any gap between me and others who haven’t gotten as far as I have in the domain of strategy. I believe that the biggest difference, to the extent there is one, is that when I hit the wall either in thinking and writing about concepts or problem-solving with clients, I just keep going.
If I don’t see a way of understanding the mystery in front of me, I think about it until a framework comes to me. If I am seemingly forced to choose between two options I don’t like, I keep thinking until a better answer is revealed. If there doesn’t seem to be any winning strategy available, I think longer, harder and differently. Unsurprisingly, all of this is reflected in my books including The Opposable Mind, Design of Business, and Playing to Win. Those books are me.
Maybe I have a healthy dose of Agreeableness, Openness to Experience, Intuition and Feeling. But I consider those traits secondary to the practice plus determination that come from a growth mindset and a lot of grit.
Practitioner Insights
While I think there is something to be gleaned from understanding personality types based on Big 5 and MBTI and their relation to ability in the field of strategy. But I don’t think that the inferences you can draw on the relation are terribly powerful.
That having been said, if you are naturally Agreeable, Open to Experience, Intuitive (but not too extremely so) and (slightly weighted to) Feeling, just follow your natural inclinations as you do strategy, and these characteristics will likely help you maintain a productive path. If your natural tendencies are to be Disagreeable, Closed to Experience, Sensing and Thinking, you’ll have to be more conscious of going beyond your first instinct when working on strategy.
One way or another, you must have compassion for customers. You need to exercise your curiosity before locking on a course and proceeding to next steps. Get and crunch all the facts and objective data but then use your intuition and feelings to consider more qualitative insights and possibilities.
But also think about adopting — to the extent you can — a growth mindset that keeps reminding you that with more work and practice you will become a better strategist. And think of walls as features not bugs. When you hit one, it provides you an opportunity to create great value, but only if you have the grit to figure out a way around, over or through it.
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As a reminder, I previewed in January 2025 that I am doing a PTW/PI podcast series with friend Tiffani Bova. The third in the series is on LinkedIn here on Wednesday, April 9th at 12 noon EST and 9am PST. Look forward to seeing you there!
