Intentionality is one of the most important founder traits.
This is true in part because building businesses is harder now (low hanging fruit is gone + management matters more) – but also because Intentionality is a proxy for judgement and decision making:
Over the course of their journey, a founder needs to take in millions of data points, process them, and make sounds decisions.
The expected value of their decisions must be consistently positive; additionally, they must discern which decisions take priority and triage accordingly…
The best proxy is intentionality: Are they thoughtful — quite literally full of (quality) thoughts — about what they're doing and how they're going to do it?
One of the ways I evaluate intentionality is by asking questions. The right ones can quickly uncover intentionality (or a lack of it); unsurprisingly, they usually revolve around the why of the matter.
But one of the less appreciated nuances to the why is how someone can articulate what the why is, and where it came from.
Consider any plan — if you ask someone why they made a particular decision, they’ll often say something logical, but not that insightful.
Why did I bring two water bottles on my run?
Because I knew there was no rest stop until mile 8, and knew I’d need it two bottles before then.It’s hard to evaluate anything in isolation; plans are no different. Founders often have vastly different plans though, which means it’s also difficult to compare plans outright.
But even though plans (and founders) aren’t apples to apples, there’s still a comparative component to this. Some people have much more interesting analyses of their actions. They can speak at far greater length, and far greater detail.
Why did I bring two water bottles on my run?
Well I knew there wasn’t a rest stop until mile 8, and the first 5 miles of this race are really hilly, which means I’ll not only expend more energy but also exhaust more of my electrolytes. So even though it’s suboptimal to carry two water bottles because my arms will get more tired, it’ll actually net out better for me to bring them.
I also added electrolyte packets to each water bottle, and changed the lids from screw caps to squirt tops so I could drink the water more easily. I set two alarms to remind me to finish each respective bottle by a certain time, and have two friends stationed along the trail ready to take the empty bottles when I’m done.Explanations like this provide such great detail that it becomes easier to understand almost all the components of the individual’s thought process. This level of articulation gives greater observability into someone’s intentionality. The more they talk about their plans, the more you’ll know how they think.
Ideally, you want close to a 1:1 ratio between words and insights. If the ratio is 3:1, then you’re listening to a rambler. If someone somehow speaks with a 1:3 word to insight ratio though, that’s immediately worth your attention.
The reason this is important is because on top of evaluating an analysis of the plan, you can also evaluate the plan’s outcome.
Historical plans provide a score card against someone’s judgement. How did they get to where they are now, and what was their plan to get here? Did their plan pan out? Where were they wrong (and do they know that)? What part changed the most? What are their takeaways and how are they applying them moving forward?
Reflective founders can answer all of these questions, and while you also have to account for lots of external variables, this line of questioning helps you create a mental model of a person’s judgement, and calibrate on the accuracy of their decisions. Once you do that you can then dig into their plans for the future.
One of my favorite scenes from Sherlock Holmes captures this well:
It’s a great fight scene because the fight’s over before it even begins; Sherlock enlists his intellect to predict the entire fight, and once he finishes navigating the different decision trees to the outcome he wants, he goes on to actually fight his opponent.
Great founders have a similar ability; they can walk you through all of the details of what their actions are and how they will transpire. They use their intellect and resources at hand to give you their own mental forecasts of the future.
This is a future they have direct control over. They don’t have complete control — no one does. But they have a lucid understanding of what their actions are and the context in which they’re making them. They see the playing field, and they know what game they’re playing.
“Good startup ideas are well developed, multi-year plans that contemplate many possible paths according to how the world changes.” – Chris Dixon, The Idea Maze
Not only is intentionality the best way to navigate the Idea Maze, it’s also the best way to create a plan to execute against it too.
When Contending with Frameworks it’s important to remember the golden rule:
“Plans are worthless, but planning is everything” — President Dwight Eisenhower
This quote and the movie scene above aren’t incongruous; one of the less noticed details from the movie is that the actual fight does not follow Sherlock’s preordained plan. From one of the YouTube comments:
For anyone who didn’t notice, at around 3:08 Holmes did a chop to the neck instead of breaking the jaw. I love how they included this little minor detail, as not everything Holmes calculated actually came to pass. However Holmes is clever enough to think of other possibilities to give him an edge in the fight. Human error [applies to] everyone, not even the smartest man alive can avoid it, but the most clever can adapt. I love it.
I like what another commenter says:
Whether you had 10 minutes or 10 years you cannot predict people so consistently. The best fighters in the world use strategies that will cover as many possibilities as possible and try to setup for safe predictions. They are always considering multiple options and usually won’t commit to a prediction unless they can account for being wrong.
Evaluating intentionality is all about assessing a founder’s ability to take in new information and make strong decisions. Good founders will take in an absurd amount of information over the next few decades. You want to believe that they'll be able to ingest this info and then make directionally strong decisions day after day.
It’s less about making sure they have a plan and more about understanding how they make plans. Greatness cannot be planned, but plans help the great ones get to the mountain top.
The best way to examine them, and their plans, is through inquiry.
“Now you know my methods, Watson.”
