TBM 325: Skeptoptimism – Thinking Slow, Acting Fast

This post is for my fellow skeptoptimists (skeptical optimists).

Do you have a mix of skepticism and an enduring faith in the power of teams to make a difference? Read on.

In the book How Big Things Get Done, author Bent Flyvbjerg discusses the importance of thinking slow and acting fast. The basic idea is to take the time to plan right and then act quickly, decisively, and determinedly to minimize risk.

Flyvberg's "slow" is similar to Gene Kim and Steven J. Spear's concept of slowification (see Wiring the Winning Organization). Slowification involves intentionally slowing down to allow teams to plan, practice, and refine their methods.

Critical to both descriptions is that slowing down is not a passive, mindless diversion. Thinking slow is not about circular deliberation and twiddling your thumbs. It is the opposite. It's active. Your brain turns on! Writes Flyvberg:

It's a serious mistake to treat planning as an exercise in abstract, bureaucratic thought and calculation. What sets good planning apart from the rest is something completely different. It is captured by a Latin verb, experiri. Experiri means 'to try,' 'to test,' or 'to prove.' It is the origin of two wonderful words in English: experiment and experience.

A good plan is one that meticulously applies experimentation or experience. A great plan is one that rigorously applies both. A bad plan is one that applies neither experimentation nor experience.

I was thinking about both books recently during a discussion among fellow skeptoptimists (skeptical optimists).

Skeptoptimists assume shit will happen but are also optimistic that the team will eventually prevail. We love thinking slow—messy exploration, pre-mortems, red teaming, going deep, running simulations and scenarios, and discussing risk and "problems." But instead of wallowing there, we know how to kick things into gear and act quickly and decisively—pivoting as necessary. Act fast.

Skeptoptimists often clash with people who interpret thinking slow as wasteful or negative. "Why do you have to make this so complex?" they ask, assuming that thinking slow will translate into analysis paralysis, slow progress, and an overly-complex project. They're worried that you are going to think slow and act slow. "Why can't you be more positive?" they remark, as you flippantly seem to doom the effort with a long, laundry list of risks. They may not share your ability to simultaneously hold complexity, uncertainty, and optimism in your head. You may not appreciate their ability to simplify, rally, and move forward with clarity.

Someone in the conversation put it perfectly:

People assume I'm up in the clouds and can't execute because of how deep I go. And then they get angry when I flip the switch and start executing, blaming me for moving too fast and taking them by surprise. I don't sugarcoat things, but I also really believe in the team's ability to make it happen. Meanwhile, they're positive and paint things as simple in public but seem pessimistic about the team in private.

If this confusion sounds familiar, I wanted to share some thoughts on navigating being a skeptoptimist.

1. Express your optimism! It is one thing to imagine that you are optimistic. It is another thing altogether to express that optimism. You might take your confidence in the team for granted. Do people know you are optimistic, and confident?

2. A simple line like, "We're going to take our time understanding this so we can move quickly when we need to," can go a long way in setting expectations. Set aggressive deadlines for yourself—acting fast is important, and you should tell people you're serious about that.

3. Do your best to contrast normal views on thinking slow (e.g., “an exercise in abstract, bureaucratic thought and calculation”) with something more active, engaged, and tangible.

4. Avoid letting deep exploration seem like a never-ending journey. Regularly connect insights back to tangible decisions or actions. "This is what we learned, and here's how we're going to adjust our plan" is a simple way to ground complex thinking in something actionable.

5. You don't need to show all of your work.

6. Find allies, including people who can act as translators and advocates. I've worked with people who are incredible at simplifying what I do for other people.

7. Realize you may be too optimistic about the team's ability to roll through the punches, pivots, and adversity. Have you talked to them? Are they really on board? Are you grafting your belief system onto how they approach work?

8. Don't keep the "slow thinking" to yourself. Invite other people into the process. This will help you transition from mad scientist to partner.

9. Finally, it's important to remember that frustration might go both ways. Just as others may not understand your deep dives and skepticism, you might overlook the strengths they bring—such as simplicity, clarity, or rallying the team around optimism.

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I have a couple spots still open in my How to Run an Effective Prioritization Activity workshop on Thursday, December 12th, at 8AM PST (US), 11AM EST (US), and 4PM (16:00) GMT. Registration: https://maven.com/s/course/272d87a145

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