16 Comments

It's a bit present in all your points, but strategy is one aspect why I often prefer to compare a company to a caravan rather than a boat. A caravan can split, goes in different directions, disassemble and reassemble later, etc. It could be to scout a new path or to make a detour to get some water for the rest of the group. Some can homestead at some points, to exploit a small lot, while others continue. Seeing a company as a boat going in one direction indicated by one captain feels a lot like a surreal utopia in this sense.

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Another of saying the same thing is that a strategy can be a portfolio of bets.

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This is a great analogy!

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+1 for the preeminence of intuitive strategic thinking. It’s often maligned because an intuitive early in their career must make bad decisions to learn how to make good ones. (I know I did!) Gladwell’s “Blink” is one that resonated deeply in my neurodivergent brain.

Nit: I don’t often see “negotiated” so much as “competed” or “fought” or “defended” or “imposed” in the places I’ve been. I see strategies like frames of reference (as described by Klaff in “Pitch Anything”) with the strongest frame/strategy winning. By winning, I mean in the sense that the market is never wrong. Strategy can’t be separated from its conscious and unconscious components any more than it can from its intended and unintended components (money/time invested versus luck/timing). The “best” strategy always wins. But beware the fool who tries to copy someone else’s “best practices” without copying the exact circumstances in which they were best. 😏 Better to look for principles upon which to make intentional trade offs.

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The market is never wrong but it can be manipulated and it can change. One question is: what timeframe do we define “winning” in? Because strategies can perform well in the short term but suck in the longer term.

E.g. Startup land and the choice to blitzscale vs bootstrap. Blitzscaling can produce awesome short term results in terms of ARR growth and valuation but it may ultimately leave the founder with no equity. Which is presumably not the strategic outcome they were looking for.

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All fair points, Matt. If the strategy isn't dead yet, it hasn't lost yet. Survival is one key aspect I often hear armchair strategists overlook, regardless the timeframe.

Having been crushed by vulture capitalists down to nigh zero percent by Round E in the last startup I played in, I feel ya'. However, watching the same suckers vote for the 5-year earn-out rainbow that I counseled against was vindictively satisfying. They also got zero pot o' gold at the end because the acquirer set the expense cap too high, but a contracts a contract. The M&A pros got the company and the tech for song. Three fire sales later, Berkshire owns my tech and is still presumably turning the crank on it. C'est la guerre.

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All is fair in love, war, and venture capital.

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The written strategies for most organizations are… not their actual strategies

https://strategy-madlibs.herokuapp.com/

https://blog.gardeviance.org/2014/07/a-quick-route-to-building-strategy.html

And the differences between written and actual strategies are similar to those between espoused theories vs theories in use: https://coachingleaders.co.uk/espoused-theory-and-theory-in-use/

So in large organizations

1. You have as many strategies as you have people capable on developing and implementing a strategy.

2. None of this matters because the organization has typically transformed its environment to ensure long term success. You have to work really hard to screw it up.

Strategy typically matters for:

1. Small, young organizations who typically face regular existential decisions.

2. Any organization facing a real challenge / change to its basic operating assumptions.

Probably the best thinker and writer on strategy is Roger Martin: https://rogermartin.medium.com/

I have some thoughts here: https://tempo.substack.com/p/dont-tell-me-your-strategy-budgeting

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Very perceptive post. I especially like the characterisation of Corporate Strategy as a "negotiated narrative".

The organisations that I have worked with that have managed to do the best job with strategy have been explicit about the "negotiation". I agree that realised strategy is often emergent ... but I also think organisations can play a role in how that realised strategy emerges.

The worst case is that everyone just does their own thing and chaos emerges. The best case is for a combination of coherent actions across individuals and teams that direct the organisation forward whilst still allowing for serendipity to enhance the opportunities available. And rapid adaptation when such opportunities present themselves.

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The rationalization of emergent strategy reminds me of the narrative fallacy and it's definitely something I've been guilty of. Sometimes by overindexing to things going smoother than in reality, others by emphasizing more the struggles that were overcome, but it definitely takes conscious awareness to avoid defaulting to creating narratives more coherent than actual events.

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Number 7 is so often the case. I have seen this process unfold. An uncomfortable truth is that luck enters into the success of more businesses than we would care to admit. It’s better to be lucky than smart. Of course when luck turns your way, you have to recognize the opportunity and execute against it, but let’s not kid ourselves that there was some a priori strategy that foresaw all those circumstances.

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To be smart is to be prepared to grasp the right opportunity (which is often unknown and hard to recognize) when it presents. So, for me, it's a bit more than just lucky, although luck is clearly part of the process (to think the contrary is likely a kind of delusion).

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When luck meets preparation, magic happens. Both luck and preparation are necessary ingredients, albeit in differing percentages from case to case.

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Your post has prompted a more fulsome response: https://tempo.substack.com/p/strategy-the-good-the-bad-and-the

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Excellent post again, John.

An underlying pattern in some of the points you raise is that of the principal-agent problem. What might be closer to an "objectively right strategy" for an organization is elusive or negotiated down to meet the needs of many disparate agents within the org.

Another element you touched on, rightly so, is the need for influential & repeated communication to ensure that the strategic context becomes part of the "collective brain" of the org. Tough problems to work through, no doubt!

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Great article! The right strategy still needs to be well communicated and understood at all levels and it requires a supportive environment to ensure expected outcomes are met. I believe that a dual strategy approach where you protect your core while exploring new avenues is easier to implement.

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