Leadership

The Uncertainty Mindset

Thinking in Bets

Understanding Organizations…Finally!

Defensiveness inhibits learning

When you are feeling defensive, that’s a sign that you’re dealing with a big/complicated problem. You are feeling defensive because you don’t want to feel the pain of having your certainties uprooted.

Work toward proximate objectives

Rather than setting overly ambitious goals, which can be demotivating if they take too long to reach, set proximate objectives instead. Proximate objectives are relatively easy to attain, and they give you momentum and context that you can use for your next battle.

Kindness begets kindness

If you ask someone for a small favor and they agree, it’s more likely that the person will then agree to a slightly larger favor, and so on and so forth. It’s a virtuous reinforcing feedback loop.

Every hire defines the next one

The people you hire form the basis of your company’s culture and end up defining the people you hire next—it’s a reinforcing feedback loop.

Empathy gives you perspective

When you’re dealing with a high-stress situation (e.g., your boss or a client is yelling at you), your stress hormones run amok, causing you to quickly lose perspective. You put yourself at the center of your own world, and you feel threatened and betrayed.

Collaboration is either generative or reactive

Collaboration comes in two forms, distinguished by when it happens relative to the act of creation:

Change requires collaboration

When introducing change, whether it be technical, cultural, or of some other form, you will need to collaborate with others to be effective. This is because of two reasons.

Collaboration is not compromise

Collaboration is not about compromise: if you compromise and end up with a subpar solution, everyone suffers.

Hell yes or no

When making most decisions, the outcome should be either a “hell yes” or a “no.” This applies to several areas of life:

Hire for attitude, not for skills

When hiring people, you should focus much more on their attitude than on their skills: someone with the right attitude will learn the job much more quickly than you’d expect. Conversely, someone with the wrong attitude will never be able to perform in the long term, no matter how talented they are.

Peak Performance

The Answer to How Is Yes

Structure sets you free

“Structure” refers to the processes by which people work, both individually and as part of an organization (e.g., operating principles, policies, document templates, recurring meetings, etc.).

Media create new agency

Tools simply make existing workflows more efficient, while mediums create new agency.

How Not to Use AI

Status and Culture

Impro

The Presentation of Self in Everyday Life

Bright spots catalyze change

When creating change, look for bright spots in your organization and use them as examples to replicate the behavior in other areas of the org: which teams are performing well? What’s making them effective?

Build experimentation guidelines

Experimentation guidelines allow you to quickly and safely tackle challenges and capitalize on opportunities, and get closer to your shared vision.

An operating cadence needs shared vision

There’s no point in building an operating cadence in the absence of shared vision. Operating cadences allow you to move faster and with more confidence, but you need to know where you want to go in the first place. That’s why you should Align teams before empowering them.