tl;dr:Senior leadership roles are often unposted and delegated to exec firms. Will outlines several ways to find such roles: (1) Through peers. (2) Exec recruiters through your network. (3) Crowd-sourced searches, such as small mailing lists. (4) Twitter.
tl;dr:Will believes the most valuable leadership skill is "how to think correctly," inspired by the book Thinking In Systems. Despite many considering themselves as system thinkers, they "model casually." Will provides 3 rules for thinking in systems safely: (1) When your model and reality conflict, reality is always right. (2) Models are immutable, but reality isn’t, it's always changing. (3) Every model omits information; some omit critical information.
tl;dr:Most hiring funnels miss a closing call and the end of the hiring process. This is 2 steps: (1) Ask for the candidates concerns. (2) Answer them by telling the best version of the truth. "The artistry of the closing call is finding the most compelling path between their starting concerns and accepting your offer. Infrequently... you’ll come to realize that the role really doesn’t give the candidate what they’re looking for. It’s far better to realize now than after they’ve joined."
tl;dr:"It’s more effective to capture existing capacity than create new capacity" in a large company. The opposite is true in startup & growth companies. In large companies: "If you need more headcount, convince leadership to require every team to send a volunteer to work on your project. If you’re missing a leader, oblige one on a peer team to move to yours." Hiring is slow and restrictive.
tl;dr:(1) Think about what you need engineering managers to do. (2) Refine those tasks into four or five key skills for the role. (3) Create an interview to evaluate each skill. (4) Create a rubric to score each of those interviews. (5) Train the interviewing team on the new rubric. (6) Remove interviewers from the loop if they refuse to use the rubric.
tl;dr:Two pieces of advice if you feel burnt out: (1) Avoid making career decisions while in a bad mental place - take a two week vacation. (2) Great careers are not linear but often have a number of lulls. When you’re high energy, these lulls are opportunities to learn and accelerate your trajectory. When you are low energy, they are opportunities to rest.
tl;dr:Infrastructure teams have 2 modes of operation: (1) A foundation mode where tasks are mandatory e.g. compliance, security, scaling a popular product. (2) Innovation mode where teams have the flexibility in prioritizing and solving problems - teams have less experience here so Will guides us through the process of problem discovery, prioritization and validation.
tl;dr:A strong team concept is where "ownership, work, and accountability are generally assigned to teams." In a weak team, work is assigned to individuals and is driven through "interpersonal connections rather than process." Will reflects on both, and how our environment is geared towards strong teams.
tl;dr:Will's tips on managing staff-plus engineers include: (1) sponsor and support more than direct.(2) Help redefine what success. A staff engineer’s "flywheel of feedback" is less immediate and that should be managed accordingly. (3) Give frequent feedback and explain why.
tl;dr:Title gives a sense of seniority amongst peers, a seat at the table of higher engineering discussions, a bump in compensation at larger companies and potential access to interesting work. Pursuing title alone can be counter-productive, and "focusing on developing your approach and skills will be far more impactful."