Actionable Tactics to Navigate the 'Messy Middle' of Strategy with John Cutler
Hey! Nacho here. I’m continuing the series of podcast episodes in which I interview thought leaders about hard strategy topics. Last week’s episode was with Teresa Torres, and in upcoming episodes, we will feature Marty Cagan, John Cutler, Jeff Gothelf, Bruce McCarthy, Dan Olsen, and more!
So, if you are not a subscriber yet, this is a great time to join :)
Strategy is messy. It happens simultaneously at different levels, with different lenses and time horizons, among many other stakes.
My guest in this episode, John Cutler, has a remarkable ability to bridge the world of theories with what we actually face down the road when executing. Together, we unravel the intricacies of the 'messy middle,' that challenging space between lofty company aspirations and the day-to-day grind of teams.
The conversation was extremely valuable to me because it brought actionable ideas to complex topics like:
helping the team think bigger and broader,
what is important to define to have a solid strategy,
how to (or not to) align,
and many more topics.
John shared valuable tips on how to overcome the major obstacles leads face.
Listen now on Apple, Spotify, Google, and YouTube, and read on for my takeaways and highlights of the episode.
Takeaways
The messy middle is where product strategic thinking happens: the space between the company strategy (the “big pillars” the CEO may mention in an all hands and everyone nods) and the day-to-day activities you do to move the needle.
John described the maps we use to tame this problem as chains of input-output causal relationships. All are essentially similar and help get the conversation going.
Some teams have difficulty identifying these chains. John recommends asking the “one step up” question: if you are seeing a 1-3 week bet, ask what the 1-3 month bet is and then a 1-3 quarter bet. These help identify the connections to the higher-up strategy.
Once we get one step up, we can ask: what are other 5 ways to solve this 1-3 month bet? It’s an easy trick to widen the opportunity space.
To define strategy, John recommended thinking what are the relevant questions and our current answers. This may be what customers we will serve for some teams, but for others, that question can be irrelevant or non-actionable.
John explained his “alignment trap” concept, where we spend to much time trying to gain alignment, when in reality is actually good that people have different perspectives.
Looking at the value of having good strategies, John gave an interesting view on capital efficiency. The consequences of strategic choices will play out in a few years in how the company can leverage the assets it created through the strategy.
When communicating strategy and impact, it’s important to build the storytelling around the second and third-order consequences of the bets we are placing to make it meaningful for stakeholders and budget approvers.
John clearly differentiated Strategy creation and deployment. The artifact to synthesize strategy is not what we use to create it. All-hand strategy documents are frustrating because, in reality, you probably need different versions for different levels of interest people will have. So, the all-hands one-pager has been watered down to the lowest common denominator.
You can see a list of all episodes to date here.