Heuristics for Doing Great Work

When Working Alone or With Others

This is a list of principles, not the specifics of how to implement them. There are a lot of dials to turn, e.g., realigning habits and incentives, etc., when implementing principles. Experiment and edit as you go.

1. Work with/find humans you admire.
2. Be kind to yourself and others.
3. Seek and ask the right questions. Seek puzzlement.
4. Do what you hate not doing and do things you fear.
5. If the only reason for which you play is so that you can work better afterward, you're not playing at all…you’re playing because it is good for you.
6. Lighten up. Favor sincerity over seriousness.
7. Experience is not linearly correlated with expertise. If that were true, we'd see more animals escaping from zoos.
8. Easy is what people call things they don’t do or know much about. Throw that word in the trash.
9. Providing feedback to colleagues/friends/etc. is great a thing, especially when we understand them and how they want to grow. Focusing on feedback that identifies with their interests builds trust and achieves outcomes. However, if we ever need to provide feedback that does not align with someone's interests but is instead in service of their best interests as we see it, it is ideal to do this in private. Avoid public-facing feedback. Others will rarely benefit from this public approach. And keep the interaction conversational to avoid perception being your only reality.
10. Trust must be assumed, not doled out conditionally; and, without trust, we have to keep ourselves and others accountable. Each new person we meet or work with starts at 50% trust. This always goes both ways.
11. It is rational to trust your deep instincts since they were shaped through generations of evolutionary pressure. That is not to say your work is done and it won’t take time and hard work to move from head to heart or from mind to gut.
12. Inaction is irreversible. Be decisive. That said, we do take the time to think, as now is not always the best time to make a decision. Incubate on it. We think, debate, persuade, listen, reconsider, and then someone decides. If you disagree, that’s fine, but once the decision is made, it’s time to commit and support it completely. We do like to make decisions as close to the intended action as possible. That ensures we are acting on the most current context of the business.
13. Don’t write. Communicate.
14. Deciding where to go based on where you are is often wiser than deciding where to go based on where you want to be.
15. Say what you mean and mean what you say, listen to understand, read to consider, and write no more or less than is needed.
16. Do what interests you rather than trying to be interesting.
17. We should do the best work we can because that is what we want to do, and that should be all we expect of ourselves and others.
18. Having internal drive and self-reliance, showing up, and not creating unnecessary work for yourself and others are the hallmarks of a good work ethic.
19. It is about the quality of hours you spend not the number of hours spent. Eight hours for work, 8 hours for life, 8 hours of sleep. That’s a fair formula. It’s not work/life balance — it’s work/life/sleep balance. A lack of sleep isn’t a badge of honor, it’s a mark of stupidity — literally.
20. Creative problem-solving progress moves from “Figuring it out” (WIP with unknowns) to “Executing down” (WIP with no unknowns) to “Done”.
21. Great work happens when craftspeople are elevated to artists.
22. Jobs suck. Find a vocation.
23. Cap the downside to manage loss aversion.
24. Do real things and make contact with reality as much as possible, as practice is the most advanced form of theory.
25. Build stuff for yourself to build stuff right. This usually solves a lot of problems if you have the domain knowledge, skills, style, and taste.
26. Keep teams small…like really small.
27. Try not to conform to discrete project plans for more than six weeks at a time, as variability increases with the square root of the time period. A project of twice the duration may experience four times as much slippage, meaning the risk of long-duration projects increases disproportionately with time. Stay focused on the irreducibly independent parts of a big idea while still addressing the target fitness function.
28. Planning evolves alongside execution.
29. Prepare for chaos.
30. To avoid sunk costs and escape Parkinson’s Law, you need limits. Replace estimates with appetites while keeping scope variable.
31. When embarking on something new, eliminate unnecessary processes while maintaining organization.
32. Nine out of ten times you can cancel a meeting when it is not or cannot be converted into a working session.
33. Reactive work and planned work are fundamentally different topologies and must live in separate streams or networks.
34. Delegating work is about serving something useful that can be changed later instead of serving rules to follow.
35. Communicating well is less about transparency and more about creating a shared language of the world—to surface assumptions at the right time, in the right medium as often as necessary.
36. Narrow-scoped questions help you optimize your existing product. Broad-scoped questions help you uncover new opportunities and elicit stories about your direct competitors. Very broad questions can help you uncover new markets and what your product category competes with.
37. Reframe questions, or reframe possible solution paths, not the framed struggles. People get mixed up and think that they should reframe problems. But effective/useful reframing happens at a level above and below an empirically identified problem.
38. When a task is straightforward for people/teams, setting a specific high-performance goal leads to higher performance than urging people/teams to “do their best”; however, when a task requires the acquisition of knowledge, urging people to do their best leads to higher performance than the setting of a specific challenging performance goal.
39. Trade scope for quality, as cutting and shipping are often equally important since doing half a thing well versus doing a whole thing half-assed is a much better approach. Stay focused on the irreducibly independent parts of a big idea while still addressing the target fitness function.
40. When prioritizing, start with things that contain more outgoing than incoming connections and those things that are the most unknown first. Always consider an impact-to-effort ratio but do your best to find the natural sequence of work above all else. We also want to ask ourselves: What can be solved together as one whole, and what can be solved separately? We want to know where we can work on one thing without having to get into the details of another thing, i.e., to set boundaries where you can change one thing without affecting other things. This is about identifying the epicenter or epicenters of an idea and developing the focus to work on the irreducibly independent parts, i.e., separate, but related, scoped-off parts, each solved as their coherent chunk.
41. Zoom in and out, from meta to matter. Use each scale to refine the other.
42. Favor weighted sum (and penalty) functions over Pareto optimizations if you want sharp, differentiated, and opinionated decisions and work output.
43. Now is not always the right time to make a decision or do something; but, if you are inspired, it’s important to preserve that energy and act on it.
44. You do something, and then you see the next step. It is incremental, not monotonic. You need to be ready to make decisions at any point in time.
45. Important things come back.
46. Always consider alternative solutions to a problem/opportunity. Contrast. We like edges. We like seeing edges in our ideas next to each other that are different. That helps to improve our thinking. Contrast creates meaning.
47. Metrics do not lie by being wrong about the thing they are measuring, they lie by being wrong about how important something is and how unimportant all the things you can’t measure are, which leads to focusing errors. Usually, it is just a lot of other things you are not measuring that matter, or can’t measure. Do things that you cannot justify to yourself, which is so important because sometimes those are the most magical things of all.
48. No productive conversation can take place if there is a disagreement on definitions of key terms, underlying assumptions are hidden, and an interlocutor is not open to updating prior hypotheses.
49. Long lists cause delays.
50. Say something rather involved in not much space.
51. Visuals and narratives over constrained linearity (like slides). Syntactically link the words. Worst symptoms: random fragmentation, contextless abstraction, dominance of form over content.
52. A back-and-forth moving down between ideas and problems can make it clear at each step what the questions are that we need to ask. Some steps involve diving into research on the problem domain side or require shaping, prototyping, and spiking on the solution side.
53. Understanding context is critical, as it describes value situationally.
54. Make room in your brain for the germane.
55. Protect your attention.
56. Causality is not a chain, but a network.
57. Calm over ASAP.
58. Be like evolution and double down on what works, not what doesn’t.