tl;dr:“Navigating deeply ambiguous problems is the rarest skill in engineers, and doing it well is a rarity. It’s sufficiently rare that many executives can’t do it well either, although I do believe that all long-term successful executives find at least one toolkit for these kinds of problems.” Will shares his playbook and approach here.
tl;dr:Will had to solve a common problem — how to make technical decision within a large organization of over 400 engineers. He established Navigators, individuals accountable for these decisions in their area of expertise who report directly to the CTO. (1) Each major area of the business has one Navigator, who is an active contributor to the software written. (2) There is exactly one Navigator for a given area; Navigators do not overlap. (3) Each Navigator is accountable for the technical decisions made in their area. This includes interpreting organizational strategy and applying it to their context. Will elaborates on the roll here.
tl;dr:It’s easy to lean too heavily on benchmarks by believing that they answer questions: they don’t really do that. Benchmarks only ask questions, they never answer them. It’s up to whoever is using the benchmarks to extract the questions and do your own work to answer them. If you look at “R&D costs as a percentage of revenue” across companies, you’ll notice that some are four or five times higher than others. Are the high spenders early in making a calculated bet into releasing a new service, or are they just inefficient? Either, or both, could be true, and that’s the sort of interesting question-answer pair to work through when using benchmarks to evaluate.
tl;dr:Will covers the following: (1) Why executive roles are particularly dependent on having multiple leadership styles. (2) How and when to use three primary styles: leading with policy, leading from consensus, and leading with conviction. (3) How lessons taught early in management careers about micromanagement discourage too many executives from leading with conviction. (4) How to develop leadership styles that you currently feel uncomfortable using. (5) How to balance across these styles, especially when you’re uncertain which is most appropriate for a given scenario.
tl;dr:Will argues that many companies lack a coherent engineering strategy, leading to inefficiencies and frustrations among team members. An effective engineering strategy consists of two core components: (1) "Honest diagnosis that engages with the reality your organization’s current needs and challenges." (2) "Practical approach to move forward while addressing the circumstances raised in the diagnosis." Written strategies are more effective than implicit ones, allowing for feedback, updates, and accountability. Will provides insights into how individuals can drive strategy from both top-down and bottom-up approaches.
tl;dr:Will discusses: (1) The conflicting goals between those designing, operating, and participating in performance and compensation processes. (2) How to run performance processes, including calibrations, and their challenges. (3) How to participate in a compensation process effectively. (4) How often you should run performance and compensation cycles. (5) Why your goal should be an effective process rather than a perfect one.
tl;dr:Will discusses your role as an executive in your organization’s hiring, the components you need to build for an effective hiring process and provides concrete recommendations for navigating the many challenges that you’re likely to run into while operating the hiring process. He gives you enough to get started, build a system that supports your goals, and start evolving it into something exceptionally useful.”
tl;dr:Will reflect on his shift from a 'company, team, self' framework to an eventual ‘quid pro quo' approach during his management tenure at Uber. His ‘quid pro quo' approach is: (1) Generally, prioritize company and team priorities over your own. (2) If you are getting de-energized, artificially prioritize some energizing work. Increase the quantity until equilibrium is restored. (3) If the long-term balance between energy and proper priorities can’t be balanced for more than a year, stop everything else and work on solving this issue e.g. change your role or quit. Will emphasizes the importance of remaining flexible and curious.
tl;dr:Will discusses: (1) Debugging the engineering leadership team after stepping into a new role. (2) Gelling your leadership into an effective team. (3) What to expect from your direct reports in that leadership team. (4) Diagnosing conflict within your team.
tl;dr:“I’ve started to notice recurring communication challenges between executives and the folks they work with. The most frequent issue I see is when a literal communicator insists on engaging in the details with a less literal executive. I call the remedy, “extracting the kernel.” Focus on the insight or perspective within the question.