Jacob Kaplan-Moss

Tag: management

A reading list for new engineering managers May 2nd, 2018

Like many engineers, I got thrown into management without any real guidance. I thought management was just telling people what to do. I thought there wasn’t any real science to it; you just needed to feel your way through it. I was wrong: there’s a whole field of study here, and you can learn a lot by, you know, studying! This is the reading list I wish I’d been given as a new engineering manager.…

My interview kickoff script, annotated November 29th, 2018

When I interview, I say nearly the same thing at the beginning of the interview. It’s a script I’ve practiced and honed over the years . It’s only eleven sentences, but each has a specific purposes. I’ve iterated on this for years, and it’s pretty tightly honed at this point. I published this script in the guide to interviewing I wrote at 18F last year, but never got a chance to break down where it comes from…

Goals aren't enough; you have to talk about performance, too April 1st, 2019

Craig recently wrote about his mixed opinions about OKRs. The crux of his argument, I think, is that communicating goals is the important thing, and that OKRs are a heavyweight tool (with limited success). I agree, somewhat; this post is a “yes, and”: OKRs (when done well) do one other important thing: force explicit conversations about performance. Talking about goals can be fairly easy compared to talking about performance. But talking about performance is a basic management responsibility, and unfortunately it’s frequently done poorly (if at all).…

My questions for prospective employers (Director/VP roles) April 23rd, 2019

Last time I was looking for a job, I wrote up a list of questions I wanted to ask prospective employees. I just ran across the list again, and figured I’d share. I was looking for a senior management role (Director/VP-level) in Engineering or Security, so the questions are sloped in that direction. Also note that I was in a fairly strong position; I didn’t need the a job immediately. So, I was able to ask fairly direct, challenging questions.…

Measuring Hiring Manager Effectiveness September 14th, 2020

Hiring is one of the most important parts of a manager’s job. Over the last few years, I’ve developed a metric I use to measure hiring performance. It’s simple to calculate, and reasonably effective at revealing performance differences between managers. Here’s the formula:

Designing Engineering Organizations January 5th, 2021

How should you structure a larger engineering organization, one with dozens (or hundreds) of engineers? There are many tradeoffs to consider, and no single right answer. But, there are some structures that work better than others.

How to gather consensus before a big decision January 18th, 2021

The next time you have an important proposal to make, don’t wait until the big meeting to ask for support. Here’s how to gather feedback and build consensus beforehand, so you can make that big meeting into a non-event.

SOCCR: the framework I use for decision briefs January 30th, 2021

In my previous article, I wrote about gathering consensus before a decision. Several folks asked for more detail about how I structure those consensus-gathering and decision-making exercises. There’s a specific format I find helpful, which I remember by the acronym SOCCR. Read on for an explanation and example!

Unpacking Interview Questions: “Explain a Topic At Multiple Levels…” February 8th, 2021

Part 1 of my Unpacking Interview Questions series, where I share one of the questions I use when I interview for technical roles. Today: asking candidates to explain a topic at multiple levels. This is one of my favorite questions to ask for engineering roles; strong performance on this question correlates very highly with high job performance on my teams.

Unpacking Interview Questions: “Tell Me About a Project You Led…” February 9th, 2021

Part 2 of my Unpacking Interview Questions series, where I share one of the questions I use when I interview for technical roles. Today: measuring a manager’s ability to lead projects and manage them effectively.

Unpacking Interview Questions: Diversity, Equity, and Inclusion February 10th, 2021

Part 3 of my Unpacking Interview Questions series, where I share one of the questions I use when I interview for technical roles. Today: making sure candidates align with organizational values of diversity, equity, and inclusion.

Unpacking Interview Questions: “Tell Me About a Disagreement…” February 11th, 2021

Part 4 of my Unpacking Interview Questions series, where I share one of the questions I use when I interview for technical roles. Today, an oldie-but-goodie: looking into a candidate’s ability to disagree and resolve conflict professionally.

Unpacking Interview Questions: The Weakness Question February 12th, 2021

The fifth and final part of my Unpacking Interview Questions series, where I share one of the questions I use when I interview for technical roles. Today’s question is the most difficult-to-ask of the series, but also one of the most valuable: asking a candidate to discuss one of their weaknesses.

Unpacking Interview Questions: Interview Question Series Wrap Up February 15th, 2021

A summary and wrap-up of my Unpacking Interview Questions series, covering why I wrote this series in the first place, some advice on developing your own questions, and answers to a few questions.

Effective Organizations Value Autonomy February 26th, 2021

I believe that autonomy is one of the most important values of effective organizations. But I also think it’s a value that’s misunderstood and misapplied. In this post, I’ll (1) define what I mean by “autonomy”, (2) explain what autonomy isn’t, and (3) try to articulate why autonomy, as an organizational value, leads to higher effectiveness.

Unpacking Interview Questions: Types of Interview Questions March 1st, 2021

There are three types of interview questions: behavioral, hypothetical, and trivia. Behavioral questions are the gold standard; they’re the most effective at predicting job performance. Hypothetical questions can be useful in certain circumstances, if used correctly. Avoid trivia.

How to Give a Status Update To Executives March 5th, 2021

Here’s a weird little skill I had to learn the hard way: how to give a status update to executives, investors, or boards. It’s different from most other kinds of status updates: much shorter, much quicker, much less in-depth. Here’s the structure I use when giving an update to this type of audience.

How managers should respond to defensiveness after feedback March 23rd, 2021

I had a call a few weeks ago with a friend and fellow engineering manager, and we spent most of it talking about someone on her team who wasn’t responding well to feedback. He was performing several parts of his job pretty poorly, but when each time she told him that his work wasn’t acceptable, he pushed back. He argued, sometimes loudly, and refused to make the changes that she was asking for. My friend came to me pretty frustrated, not entirely sure how to respond to this guy. Most managers know this feeling: they’re doing their job as a manager, giving clear, specific, professional feedback but it’s going poorly. What should you do in a situation like this?

“Fair” Doesn't Mean “Equal” March 28th, 2021

Some conversations about my previous piece brought me back to one of the earliest lessons I learned in my management career. It’s a realization that’s embarrassingly obvious in hindsight: treating people fairly doesn’t mean treating everyone the same.

The Fundamental Purpose of Middle Management: Context Down, Information Up April 19th, 2021

On the fundamental purpose of middle management: context down, information up.

Three Feedback Models April 22nd, 2021

Here are three models that I like for delivering feedback. Each is valuable on its own and would make a great starting point for anyone who wants to build their feedback muscle. Together, they highlight some common factors in effective feedback models and show off a couple of “special features” that can help your feedback be particularly effective.

The Mass Email Mistake May 10th, 2021

Addressing behavior through mass emails or new policy rollout is a mistake. Here’s why.

Positive feedback is different from praise May 12th, 2021

Managers need to understand the difference between praise and positive feedback. Feedback is one of the most important tools in your management toolbox, and an absolute must for any manager who wants to be effective. Praise is a useful tool, but it doesn’t directly drive performance improvement the way feedback does. If you’re accidentally giving praise when you think you’re giving positive feedback, you won’t see the results you expect.

The VPP/VPE Relationship June 16th, 2021

For an organization to succeed – to reliably and consistently deliver great products that customers want – Product and Engineering need to work well individually, but more importantly, they need to work well together. The working relationship between these two organizations starts with the relationship between their two leaders. If these two individuals don’t have a strong individual working relationship, the team relationship is doomed. This article covers what a strong relationship between the VPE and the VPP looks like, and how to build that relationship.

Book Review: Team Topologies July 5th, 2021

Team Topologies (Matthew Skelton and Manuel Pais, 2019) is, essentially, a book-length treatment of the Inverse Conway Maneuver. I recommend this book to folks looking to design or refactor product delivery organizations, especially those unfamiliar with the idea of aligning teams to delivery priorities.

Delegation: What's delegation? July 19th, 2021

Most managers know that delegation is part of their job, but the vast majority of management texts are incredibly non-specific about what delegation means. So today I’m beginning a series on delegation to try to fill this gap. I’ll cover the principles and theories that guide how I think about delegation, ending with a concrete example: how to delegate meeting attendance. To kick things off: what does delegation mean?

Delegation: “Give Away Your Toys” July 19th, 2021

My foundational principle of delegation: “give away your toys”. Look to delegate the work you love, not the stuff you dislike or dread.

Delegation: Make Failure A (Safe) Option July 20th, 2021

Your gut instinct is probably to wait to delegate some work until you’re fully confident that the person can handle it. This is often a mistake. Instead of withholding a delegation opportunity from someone because they might fail, you should instead create a situation where failure will be safe.

Delegation: Delegate Outcomes, Not Methods July 21st, 2021

To make delegation most effective, tell people the results you want, but let them decide on how to achieve those results.

People- vs Results-Oriented Management: Both Work! September 22nd, 2021

Broadly speaking, there are two management styles: people-oriented and results-oriented management. Taken to extremes both styles have failure modes, but seeking “balance” isn’t the answer. Both modes can be successful! Embrace the style that comes easiest to you, while learning enough about the other mode to avoid pitfalls.

Delegation: Briefing a Delegate September 27th, 2021

Some managers think delegation is easy: you just ask someone on your team to go do a thing, then kick back with your feet on the desk until it’s done. Not true: delegating that way is a recipe for failure. To delegate effectively, you need to set up your delegate for success. This means explaining the work and desired outcomes, providing context, and teaching your delegate any skills they’ll need to be successful.

Delegation: How to Delegate Meeting Attendance October 6th, 2021

Wrapping up my series on delegation with an example: how to delegate meeting attendance.

Simple Product Management Tricks October 20th, 2021

Three simple tricks product I’ve picked up that help me be more than completely useless when I need to wear a Product hat.

When you're a manager, your behavior is under a microscope October 26th, 2021

If you want to be a good manager, you need to accept that your behavior is under a microscope. You need to watch your behavior carefully and pay attention to what that behavior communicates.

Work Sample Tests: Introduction to Work Sample Tests November 9th, 2021

Earlier this year, I wrote a series on interview questions. Good interview questions are one key to hiring well, but they’re not the only key. Today, I’m starting a new series on another critical factor in effective hiring: using work sample tests, aka practical exercises. This is part 1: what are work sample tests, and why do we need them?

Work Sample Tests: The tradeoff between inclusivity and predictive value November 10th, 2021

Good hiring processes try to maximize inclusivity and predictive value, but unfortunately, work sample tests bring these goals into conflict. There’s always a tradeoff between predictive value and inclusivity. The guiding principle of work sample tests is: construct a test that balances predictive value and inclusivity. Fair work sample tests will be predictive enough to give you a high degree of confidence that you’re making a good hire, while also being designed to be as accessible to as many candidates as possible.

Work Sample Tests: A Framework for Good Work Sample Tests: Eight Rules for Fair Tests November 17th, 2021

What makes a work sample test “good” – fair, inclusive, and with high predictive value? Here’s my framework: eight principles that, if followed, give you a great shot at constructing a good work sample test.

Work Sample Tests: Coding “Homework” November 23rd, 2021

Coding homework is my default work sample test: I use it for all engineering roles unless it’s obvious that another kind of exercise is better. There are good reasons to make homework-style work sample tests the default: they’re relatively easy to construct, they scale reasonably well to large hiring rounds, they’re accurate simulations of real work, and easier than most other kinds of tests to construct in a way that maximizes inclusivity. Here’s how to conduct a coding homework work sample test.

Work Sample Tests: Pair Programming November 30th, 2021

I tend to prefer asynchronous work sample tests. The flexible scheduling of asynchronous exercises (i.e. “work on this whenever you like”) works better for the majority of candidates. But for some candidates, and some roles, synchronous exercises work better. By “synchronous” I mean: work sample tests that are explicitly scheduled, and that has both the interviewer and the candidate working directly together at the same time. In these cases, I often turn to pair programming.

🔗 Shreyas Doshi on the hiring fallacy December 4th, 2021

Great Twitter thread with some hard truths about “we need to hire more engineers”

Work Sample Tests: Bring Your Own Code December 7th, 2021

If you’re hiring engineers, some candidates will already have code they can share: side projects, open source, and so on. It’s silly to ask those candidates to write new code just for your interview if they already have code they can share. So, if you’re asking candidates to code as a work sample test, you should also offer to let candidates submit something they’ve previously written. Here’s how.

Work Sample Tests: ‘Reverse’ Code Review December 15th, 2021

For most software engineering roles, the best work sample test will be some combination of the exercises I covered earlier in this series. But not every role; there are some circumstances where other types of tests fit better or are better at revealing some critical piece of information relevant to hiring. This post covers one of them: a “reverse” code review, where instead of you reviewing the candidate’s code, you have them review yours.

Work Sample Tests: Labs & Simulation Environments December 24th, 2021

The work sample tests I’ve covered in this series so far all involve software development. But what about roles that don’t involve day-to-day coding: roles like security analysis, penetration testing, technical support, bug bounty triage, project or program management, systems administration, technical operations, and so on? For those roles, I turn to simulated, “lab”-style environments. Here are some examples of that kind of test.

Work Sample Tests: What doesn't work (and why) December 30th, 2021

I’ve written about a bunch of effective work sample tests and the “rules of the road” that make them effective. One thing I haven’t talked about is counter-examples: types of work sample tests that don’t work. I tend not to do this sort of thing: I find it’s usually more useful to talk about what does work than to pick apart what doesn’t. But here, I think it’s illustrative: looking at why certain kinds of work sample tests fail can help illustrate the principles of effective tests. Let’s look at a few kinds of work sample tests that (usually) fail, and why.

Work Sample Tests: Wrap Up and Q&A January 6th, 2022

This is the final post in my series on work sample tests. It’s a wrap-up post: I’ll address a few random points I couldn’t quite fit in elsewhere, and answer some questions from readers.

🔗 Maintaining a healthy work culture is the first role of every executive - Graham says wrong things January 12th, 2022

“This is the part where I say something about how more diverse teams build better products, and how diversity of backgrounds, identities, and opinions leads to better decisions. That is all true. However, in this organization we value diversity and inclusivity because that is the morally and ethically correct thing to do. That it benefits us, our customers, and the company is nice. We will do it regardless of how true that is.…

Book Review: Powerful (Patty McCord) January 18th, 2022

Patty McCord was Netflix’s first head of HR and a member of its executive team for 14 years. She (along with Reed Hastings, Netflix’s founder and CEO). She’s probably best known as the co-author (with Hastings) of Netflix’s famous Culture Deck, a 125-slide deck that lays out Netflix’s unusual culture. Powerful is a deep examination of that culture and its ramifications. It’s one of the better dissections of what “culture” really is and how it works. I recommend it to anyone in a position to influence company culture. You may or may not want to mimic Netflix, but thinking through which parts of Netflix’s culture you do and don’t want to mimic is an excellent exercise – it certainly was for me.

🔗 Managing people 🤯 | Andreas Klinger February 7th, 2022

“your job is not to manage people but to manage processes and lead people”

🔗 Jade Rubick - What do great engineering managers need to know about compensation and equity? May 15th, 2022

Really fantastic crash course in pay systems.

DORA Metrics: the Right Answer to measuring engineering team performance June 17th, 2022

“What metrics should I use to measure my engineering team’s performance?” Believe it not, there is a Right Answer: the so-called DORA metrics.

Role Title Terminology October 12th, 2022

In my writing about hiring and management, I often talk about role titles – terms like “manager”, “director”, “executive”, and so forth. I’ve found that many readers find the precise definitions of these terms confusing. So here’s a glossary of the terms I use when I’m talking about job titles.

Performance "Seasons" Are Useless — Use Anniversary Reviews Instead October 25th, 2022

Stop doing performance reviews based on the calendar year. Instead, schedule performance reviews around each person’s individual calendar — a year after they join the team, switch roles, get promoted, etc.

🔗 How to plan? October 28th, 2022

How to plan? How hard could it be? 4k words scribbled down on a sunny October afternoon for people in tech observing the Season’s Traditional Annual Planning Process, inspired by a recent interview question (and 25 years of variously painful planning processes).

🔗 Prioritizing and Planning within Heroku Postgres - Craig Kerstiens October 31st, 2022

My favorite planning exercise

Professionalism: You should maintain a transition file November 9th, 2022

When you change jobs, ideally you’ll have the opportunity to brief your successor directly. But that isn’t always possible: you might get fired or laid off, you might leave for another job without a clear successor named before your last day, you might have to take sudden medical leave, etc. Situations like that will be disruptive, it’s unavoidable, but a transition file will help minimize that disruption.