Jacob Kaplan-Moss

Tag: Management

🔗 Reflections on Palantir (#)

I suspect the tone here — largely laudatory, abd looking up to people like Peter Thiel and Paul Graham — will rub most of my readers the wrong way.

Look past that, and pay attention to the notes on what makes Palentir work. I completely agree with a lot of the conclusions about how important being embedded with real customers is. It happens also to be the model that I saw working at 18F and USDS!

October 17th, 2024 • engineering management palentir

All I Need to Know About Engineering Leadership I Learned From Leave No Trace

Sumana challenged me to apply the principles of Leave No Trace to engineering leadership, so here we go.
July 12th, 2024 • leave no trace management

Mentorship, coaching, sponsorship: three different — and equally important — tools for developing talent

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. So here’s a glossary, a high-level explanation of what these three things are, how they differ, and where to use them.

🔗 How to Actually Build a Better Boss (#)

We promote people into management and we just hope that they figure it out. And then we stand, mouth agape, when things go sideways. And this isn’t just a problem for our new managers. We are 40 years into this strategy and now the overwhelming majority of the workforce came up through this same form of occupational hazing. Here’s a new job. It’s very high stakes. It’s totally different from what you’ve done to date. And the skill set isn’t intuitive at all. You’re smart. You’ll figure it out. And if not, you’re fired. Good luck.

February 29th, 2024 • management

🔗 Navigators (#)

An alternate pattern to architecture teams for determining technical direction.

November 25th, 2023 • decisions management

Performance Is Contextual

Managers often talk about performance as a static thing. We say that someone is a “high performer” or “low performer”, as if performance is a fixed attribute of their personality. This fixed mindset is a mistake. Performance is contextual: how well you perform your job is deeply dependent on the conditions around you.
November 20th, 2023 • management performance

Does someone need to be a good manager to give good management advice?

In a management Slack I’m in, someone responded to a list of commonly-recommended management books by asking, “are these people good managers though?” It’s a fair question! But it’s not quite so simple.
November 16th, 2023 • management

How to Build Trust

What are the major management behaviors that can help build trust? Management books often cover the importance of trust, but abstractly. There’s precious little writing about the nuts and bolts, the day-to-day tasks of trust-building. That’s the gap I’d like to try to fill with this article.
November 16th, 2023 • behavior management trust

🔗 (People on) Nice Teams Finish Last (#)

“So remember, much like many other management problems, trying to be “nice” where you should be clear is one of the worst things you can do. “

October 6th, 2023 • management

RTO vs WFH: my default recommendations for remote vs colocated teams

As companies start to roll out so-called “Return to Office” (RTO) policies, I’ve found myself disappointed by the hyperbolic arguments being made by remote work / Work From Home (WFH) proponents. I believe that neither remote work nor colocated work is globally “better”: which one works best is contextual, depending on the role and the needs of the team. In this post I’ll break down how I view that context, and share my “default” recommendations for which teams should be primarily remote, and which benefit from a shared physical space.

Team size isn't a measure of success

Most managers have internalized the idea that team growth, in and of itself, is a unalloyed good, and a sign of success. This is wrong, but it’s understandable. Team growth feels like success, but headcount by itself isn’t a measure of success. Instead, we should judge management success by impact and efficiency.
September 11th, 2023 • management

Do I need a consultant, contractor or employee?

When is it the right choice to hire full-time staff, and when should you use consultants or contractors instead? The short answer: hire consultants for guidance, contractors for execution, and employees for stability and flexibility. For the long answer, read this article.

🔗 The one about scientists & engineers & mechanics (#)

So this came up in a slack and then i had a long expansion and someone asked me to make it a post so they could link it to people and well ok fair enough  

It’s gonna be heck…

August 16th, 2023 • management

Follow-ups to "Incompetent but Nice"

I received a ton of replies to my previous piece in “incompetent but nice” people. I’ve collected some of those replies, and some of my own follow-ups. I’ll cover: what managers should do; the theme that this is almost always a management failure; and my advice for people who are worried that they might be the “incompetent but nice” person.
March 31st, 2023 • management performance

Incompetent but Nice

A question I’ve never been able to answer to my satisfaction: how do you manage people who are nice but can’t do the work?
March 28th, 2023 • management performance

🔗 Meetings for an effective eng organization. (#)

Great (as usual from Will) roundup of the kinds of meetings effectve eng orgs have.

My only addition: I find demo days (mentioned breifly) quite useful; they seem to really drive a culture of shipping.

January 17th, 2023 • engineering management meetings

🔗 Getting a job as an engineering executive. (#)

I’ve gone through this myself – unsuccessfully – and wish I’d had this guide. Great information about a confusing and opaque process.

January 8th, 2023 • career executive interviewing management

🔗 Measuring an engineering organization. (#)

For the past several years, I’ve run a learning circle with engineering executives. The most frequent topic that comes up is career management–what should I do next? The second most frequent topic is measuring engineering teams and organizations–my CEO has asked me to report monthly engineering metrics, what should I actually include in the report? Any discussion about measuring engineering organizations quickly unearths strong opinions. Anything but sprint points! Just use SPACE!

January 3rd, 2023 • engineering management metrics

Professionalism: You should maintain a transition file

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.

🔗 Prioritizing and Planning within Heroku Postgres - Craig Kerstiens (#)

My favorite planning exercise

October 31st, 2022 • management planning product

🔗 How to plan? (#)

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).

October 28th, 2022 • management planning

Performance "Seasons" Are Useless — Use Anniversary Reviews Instead

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.

Role Title Terminology

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.

DORA Metrics: the Right Answer to measuring engineering team performance

“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.
June 17th, 2022 • dora engineering management metrics

🔗 Sometimes you have to choose between being right and being effective (#)

My latest in Quartz… My partner and I had a hellish move recently. We were lucky in that our landlords are nice, reasonable people, and unlucky in that they were quite disorganized and hadn’t done …

February 7th, 2022 • conflicts management

🔗 Managing people 🤯 | Andreas Klinger (#)

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

February 7th, 2022 • management

Book Review: Powerful (Patty McCord)

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.
January 18th, 2022 • books culture hr management netflix

🔗 Maintaining a healthy work culture is the first role of every executive - Graham says wrong things (#)

“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. If inclusivity fails to benefit us, our customers, or the company, we will seek to realign that conflict rather than cease being inclusive.” (The whole thing is this good.)

January 12th, 2022 • culture leadership management work

Work Sample Tests: Wrap Up and Q&A

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.

Work Sample Tests: What doesn't work (and why)

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: Labs & Simulation Environments

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: ‘Reverse’ Code Review

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: Bring Your Own Code

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.

🔗 Shreyas Doshi on the hiring fallacy (#)

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

December 4th, 2021 • engineering hiring management teams

Work Sample Tests: Pair Programming

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.

Work Sample Tests: Coding “Homework”

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: A Framework for Good Work Sample Tests: Eight Rules for Fair Tests

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: The tradeoff between inclusivity and predictive value

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: Introduction to Work Sample Tests

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?

When you're a manager, your behavior is under a microscope

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.
October 26th, 2021 • behavior communication management

Simple Product Management Tricks

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

Delegation: How to Delegate Meeting Attendance

Wrapping up my series on delegation with an example: how to delegate meeting attendance.
October 6th, 2021 • delegation management meetings

Delegation: Briefing a Delegate

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.
September 27th, 2021 • delegation management

People- vs Results-Oriented Management: Both Work!

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.
September 22nd, 2021 • management management style

Delegation: Delegate Outcomes, Not Methods

To make delegation most effective, tell people the results you want, but let them decide on how to achieve those results.
July 21st, 2021 • delegation management

Delegation: Make Failure A (Safe) Option

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: “Give Away Your Toys”

My foundational principle of delegation: “give away your toys”. Look to delegate the work you love, not the stuff you dislike or dread.
July 19th, 2021 • delegation management

Delegation: What's delegation?

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?
July 19th, 2021 • delegation management

Book Review: Team Topologies

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.

The VPP/VPE Relationship

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.

Positive feedback is different from praise

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.
May 12th, 2021 • feedback management praise

The Mass Email Mistake

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

Three Feedback Models

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.
April 22nd, 2021 • feedback management models

The Fundamental Purpose of Middle Management: Context Down, Information Up

On the fundamental purpose of middle management: context down, information up.
April 19th, 2021 • communication management

“Fair” Doesn't Mean “Equal”

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.

How managers should respond to defensiveness after feedback

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?

How to Give a Status Update To Executives

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.

Unpacking Interview Questions: Types of Interview Questions

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.
March 1st, 2021 • hiring interviewing management

Effective Organizations Value Autonomy

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: Interview Question Series Wrap Up

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.
February 15th, 2021 • hiring interviewing management

Unpacking Interview Questions: The Weakness Question

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.
February 12th, 2021 • hiring interviewing management

Unpacking Interview Questions: “Tell Me About a Disagreement…”

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: Diversity, Equity, and Inclusion

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 Project You Led…”

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.
February 9th, 2021 • hiring interviewing management

Unpacking Interview Questions: “Explain a Topic At Multiple Levels…”

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.
February 8th, 2021 • hiring interviewing management

SOCCR: the framework I use for decision briefs

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!

How to gather consensus before a big decision

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.
January 18th, 2021 • decisions leadership management strategy

Designing Engineering Organizations

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.

Measuring Hiring Manager Effectiveness

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:
September 14th, 2020 • hiring management measurement

My questions for prospective employers (Director/VP roles)

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. You may have a lower risk tolerance and want to scale some of these back.

Goals aren't enough; you have to talk about performance, too

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). This can leave staff and management with wildly different views on what “good” looks like, which can cause all sorts of problems. Even if you’re totally aligned on goals, if your team doesn’t understand what good performance is, you might never hit those goals. As a manager, you have to talk about performance. Any tool you use is fine. OKRs, like Craig says, are heavyweight. But heck, if that’s what you need to force a conversation about performance, then fine.

April 1st, 2019 • management performance

My interview kickoff script, annotated

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

November 29th, 2018 • hiring interviewing management script

A reading list for new engineering managers

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. It’s organized roughly in the order that I’d want to have read them. If you’re a new engineering manager: I hope this list helps you succeed.