A running list of observations on work working well. 

Day-to-day culture

  • Feedback culture > Approval culture
  • Publish a short, public manifesto about the specific worldchange you’re after. What are you asking your buyers to become? What are you asking them to be a part of? (ex Tesla, Khan Academy, Substack, Axios, Slack, by Basecamp)
  • Share peer-to-peer kudos in every team meeting. Celebrate success.
  • Publish a client wish list. (ex Big Human)
  • Make work visible with regular stand ups and shared boards.
  • Build the low-fidelity version and stick with it as long as possible. More likely to see the potential over the flaws. Makes it easier to justify changes later. Higher fidelity, harder to talk yourself into evolving.
  • When designing systems for teams of smart people, give them something to work from, not a template to adhere to. (Brian Collins)
  • No Blame culture. (Toto Wolff at Mercedes)
  • Respect blocks for focused work.
  • People like being asked for help. “Helper’s high.” (Defining Decade)
  • Write things down. Render decisions explicit.
  • Start meetings on time.


  • You are the agenda setter, not the problem solver.
  • No goals. Focus on healthy habits and quality decisions, not outcomes (Thinking in Bets; Basecamp).
  • Invitations, never coercions (Daniel Stillman)
  • Tell people that you need help (especially as a leader)
  • The team wants to get to know you. What are you personally working on? Long form weekly memos (Eg Seth on burnout, David Cancel’s “One Thing”)
  • When faced with a decision, identify whether the door is two-way or one-way. Most are two-way, low impact for getting wrong. Focus your deliberations on the one-way doors. (Bezos)
  • Set it in motion. (You should probably not execute it yourself)
  • With your team, ask, “what are you interested in?”
  • Keep a decision log.
  • Ask: Are you excited about what you’re working on?
  • Seniority = more abstract problems to work on. (“Design a form field” -> “encourage authenticity from users” -> “work on an important problem for the customer”) (Julie Zhuo, How to work with designers)
  • No struggle, no learning. Best way for someone to learn is to face down and struggle with an uncertainty. Even if you (the manager or SME) know a “better way,” resist doing it for them or even giving hints. Short term struggle, far more durable learning AND stronger sense of self efficacy.


  • Job descriptions pitch the investment in the role. We need you because we are falling short in these specific areas. Describe what isn’t working anymore, why this hire, why now. What you’ve tried and where it fell short. Kinds of problems you might work on. (Basecamp Head of Marketing)
  • For new hires, ask: Do they create clarity? Do they create energy? (Satya Nadella)
  • Ensure job descriptions are easy to discover from any device. The application process must create a great first impression of the employer.
  • Send every applicant a simple note. Every applicant who reaches the interview stage receives brief feedback.
  • Hire for culture enhancement, not culture fit
  • Hire with blind auditions (ex orchestras, Daily Show via Adam Grant)

Product development

  • Aim for defensible bets, not perfect plans.
  • Win at the emotional peaks of the customer’s journey (discovered via storyboard). Not the UX sizzle, but the actual human moments (ex feeling especially nervous or excited).
  • Set direction, embrace uncertainty. Stubborn on where to go, flexible on how to get there.
  • Be clear whether a project is in a state of experimentation (clearing unknowns) or execution (clearing knowns). (ex Basecamp Hill chart)
  • The team working on the experiment will not be asked to work on the core products. They are not reserves. But they will also be expected to work under pressure, timelines, milestones (not stress).
  • Name investment plans. (Ex D2L’s Oxygen plan)
  • Hold an investment pitch day to cultivate practical curiosity. Make it feel competitive, but recognize that everyone ultimately wants to work on things that have organizational commitment.
  • Roadmap based on problems, especially for things that are further out. (We want to solve for _____, not we’re going to build _____)
  • Report publicly on failures and successes. (ex Impact Hub)


  • Name it.
  • No stock photos.
  • Invest in graphic identity. Distinct, but not repetitive. (ex Beau’s, David C Baker, Knowledge Project)
  • Mess with the brand mark. (ex. The Museum Kitchener, Google Doodles)
  • Promotions must show the product, even if briefly. (ex. Wealthsimple flashing a screenshot on a device at the end of ads)
  • Make customers awesome, heroic. Not awesome products: awesome customers.
  • Give away unapplied insights for free, make applied insights very expensive. (dcb)
  • It is tempting to make changes (messaging, etc) just because you are tired of them. Your audience needs to keep seeing it.
  • Your job is to help customers make sense of the changes in their world / context, the old game vs new game. Not to describe their problem and your solution (bleh). (Andy Raskin)
  • Everybody learns to demo.
  • Customer stories captured by default, programmatically.
  • Every customer interaction is a chance to be more human, show more joy. Ex. Put a happy, visual message at the end of the contract.
  • Publicize pricing and do not discount. (ex Tesla)
  • Invest in original, signature research content. (ex Crayon State of Market Intelligence report)

Customer experience

  • No “do not reply” email. If someone replies to an automated email, a person will get back to them.

Other inspiration

  • Game design: A well calibrated, voluntary challenge. Immediate feedback loop, clear goals. The mind craves resolution. What’s behind that door?
  • Security research and journalism: Go to the source, see how it works, try weird things.