/Jacob Kaplan-Moss

Thinking About Risk: Mitigation tl;dr: Jacob presents a simple framework to help frame discussions about risk mitigation. “It’s intentionally very simple, a basic starting point. I’ll present a more complex framework later in this series, but I want to lay more of a foundation before I get there, so we’ll start here.”

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An Introduction To Thinking About Risk tl;dr: “How dangerous is it to launch this new feature if it hasn’t gotten a proper security review yet? How much risk is left after we do that review?” So welcome to a new series about how to think about risk. This series is a crash course, a high-level introduction to the most important concepts and risk frameworks. It’s intended for people who encounter risk from time to time and need some basic tools, but don’t want to make a deep study of it. 

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Mentorship, Coaching, Sponsorship: Three Different — And Equally Important — Tools For Developing Talent tl;dr: “One of the main responsibilities of a leader / manager is helping their staff develop. Mentorship, coaching, and sponsorship are import tools in the staff development toolbox. Good leaders should be adept in all three, and know when (and when not) to use each. In my work with new managers, I sometimes see confusion about these three different tools, and I see people using them in the wrong circumstances.” Jacob provides a glossary, high-level explanation of what these three things are, how they differ, and where to use them.

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Tracking Engineering Time tl;dr: How should a manager discover what their team is working on and figure out if time is being allocated correctly? Jacob shares his playbook: (1) Measure the time engineers are spending using story point, ticket counts. This doesn’t need to be super-precise. (2) Split that time into “buckets” that map activities that influence output. Jacob starts with 3 buckets: features i.e. time spent developing new things, debt and toil i.e. time spent on routine tasks. (3) Agree on the appropriate ratios for each bucket, and then adjust over time to influence the outputs you care about.

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Estimating Software Projects: Breaking Down Tasks tl;dr: Jacob describes his process: (1) Begin with a list of tasks or sketch. (2) Think through the steps you need to take to accomplish that task and write them down. Don’t worry about completeness. Each pass just needs to expand on the previous one. (3) For each item, ask the following: Do I understand what change is desired? Do I understand what “done” looks like? Can I define all the steps I would take to get to “done”? Do I have all the information I need? If the answer is “no”, take that task and break it down further using this algorithm again. (4) Repeat until all tasks are sufficiently broken down.

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My Diverse Hiring Playbook tl;dr: (1) Adopt a “Rooney Rule”, which requires teams to interview at least one ethnic minority candidate for senior roles. (2) Use opportunistic hires strategically. (3) Focus outbound recruiting on underrepresented candidates. (4) Focus outbound recruiting on underrepresented candidates. (5) Cultivate a network of “connectors”. (6) Be explicit that you’re looking to build diverse teams. 

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First Decide How To Decide: “One Weird Trick” For Easier Decisions tl;dr: "The heart of this process – the move that I think makes it work so well – is that it includes an explicit step to first decide how to decide. That is: when a decision appears that it’ll be controversial or difficult to make, instead of immediately starting to discuss the matter at hand, the stakeholders first come to an agreement about how they’ll eventually decide. In fact, this happens twice: first at the macro scale when the organization agrees to adopt this process overall, and then in the micro scale, for each individual decision." Jacob discusses an example. 

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How To Build Trust tl;dr: "These are all going to be fairly high-level, just skimming the surface – I could probably write a full post for each point, but will keep them brief to avoid making this article into a book." Jacob elaborates on the following: (1) Act consistently. (2) Communicate clearly and transparently. (3) Be reliable. (4) Set and respect boundaries. (5) Use role power sparingly. (6) Give feedback. (7) Give credit, take blame. (8) Delegate effectively. (9) Sponsor and coach. (10) Respect confidentiality but be clear about limits. (11) Ask for permission to give feedback, suggestions. 

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Hire For Floors, Not Ceilings tl;dr: Jacob uses the sports performance analogy of "floors" and "ceilings" to discuss hiring practices. In sports, an athlete's "ceiling" denotes their peak potential, while their "floor" represents their worst performance. Jacob identifies four performance archetypes, from consistently excellent athletes to those who are unpredictably variable. Drawing parallels to hiring, Jacob argue that employers often mistakenly prioritize a candidate's potential (ceiling) over their consistency (floor). He emphasizes that a consistently average performer is often more valuable than an unpredictable one, stating, consistency and reliability should be prioritized over sporadic potential.

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When Is Short Tenure A Red Flag? tl;dr: "Here’s a question that comes up a lot. It goes something like: “I’ve only worked 10 months at this job, and it’s terrible. If I look for a new job now, will my short tenure be a red flag?” Or, from hiring managers: “I’m looking at a resume showing they’ve worked three jobs in the last four years. Is that something to be concerned about?” Jacob discusses his perspective here, as well as how hiring managers and candidates should evaluate and respond. 

featured in #363