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Engineering Management Pearls

Points of wisdom, learned the hard way.

Relationship with Your Team

🦪 A 1:1 has a 10-minute decompression zone.

The first ten minutes of a weekly 1:1 meeting should be spent building rapport. Ask your direct report about something in their personal life, and just let them talk. After that, they will be warm enough to get into a more honest conversation about work.

🦪 Present a high-quality quarterly kickoff deck, every single quarter.

The information you convey in this deck is important, but not as important as the effort you put into making it look good. This shows your team that you care about what they are doing enough to spend the time to present it cleanly.

🦪 Stay for at most two drinks, then leave.

When going out to a bar with your team, stay for one drink, two at most, then leave. No matter how good a rapport you have with your direct reports, they need time together without the boss around.

🦪 Don't drink alcohol with co-workers.

You need to be completely above reproach as a people manager. Stay sober and keep your wits about you when in the company of the company. This is not contradictory to the previous pearl: when you are out drinking with co-workers, order a club soda with lime. It looks like a vodka tonic, and nobody will be any the wiser.

Performance

🦪 When there is always an excuse, there is always a problem.

An IC who always has an empathy-provoking excuse about why they are not meeting their goals is simply an under-performer. If it happens once, that's just life. Twice is a string of bad luck. Three times is not a coincidence.

🦪 You will never regret firing somebody too soon.

Firing people sucks. It is one of the worst parts of being a manager, unless you're a psychopath. When you start thinking that someone is underperforming, start gathering the evidence. The longer you keep them around out of guilt or uncertainty, the longer the rest of the team learns that this is an acceptable standard.

🦪 Your team is high-performing if it is constantly expanding its scope.

To expand its scope, your team needs strong technical skills and strong internal leaders. If you are developing both of these, then your team is in the top 10% of performance.

Politics

🦪 People will support you if they don't like you, but they'll never support you if they think you don't like them.

You can't control whether or not people like you, but you can control your outward opinion of others. When someone believes you dislike them, they will avoid you, for fear that you will use any influence you have to harm them.

🦪 Always try to make your manager look good.

Brown-nosing is telling your manager how great they are. Smart relationship-building is finding out what success looks like for your manager, then delivering on that, in a way that your manager's manager can see.

🦪 Name identification is a valuable asset.

Similar to electoral politics, people can't have an opinion of you if they don't know who you are. This is different from self-promotion (i.e. "I am Ted and I do amazing things, the most amazing things, bigly, all the time.") There is no valence attached to name ID. Make sure your leadership-track direct reports understand this.

Developing and Maintaining Software

🦪 (number_of_subtasks + 1) is a strikigly effective method of estimating story points.

For a junior team, or a team that is just getting started with an Agile-like methodology, this helps them learn to break down stories into manageable chunks, and the pointing falls out of the decomposition exercise. It will get you off the ground quickly.

🦪 Jira always wins.

Jira is one of many pieces of software that tries to be everything to everyone, but one of the few that actually succeeds at it. Engineers all know it. They are comfortable with its warts. Other task trackers aren't worth the trouble.

🦪 If your team doesn't have enough to do, you have weak product management.

You should be able to explain what your team is doing for the next year in 30 seconds. If your team is looking for projects to fill their quarterly dance card, then the product managers that support you are not feeding you.

🦪 Look for common on-call trends quarterly at most.

Your team is smart enough to find the small fixes that yield fewer pages, but the work necessary to solve larger trends is almost always a quarter-plus scoped project. Analyzing trends at the end of every rotation is unlikely to yield useful results, and is not a good use of time.

Hiring

🦪 When interviewing other managers, look for situations that don't work out cleanly.

A weak manager will not admit to you that they "failed". A strong manager will tell you what they learned. My favorite question for this is: "Tell me about a time that you performance-managed an IC". Weak managers will tell you about an IC recovering after a PIP or coaching. Strong managers will tell you about someone they fired, and how they made the call. This profession is all about solving problems that don't have great solutions, so look for managers who understand that.

🦪 LinkedIn is becoming asymptotically less useful for recruiting.

LinkedIn suffers from the Tragedy of the Commons, whereby an influx of rational actors, all acting in their own self-interest, dilute the value of the resource. This applies to both applicants and recruiters. The more labor who joins LinkedIn and tries to stand out with cringeposting, the less useful it becomes for recruiters. Conversely, the more recruiters who only use LinkedIn as a discovery channel, the more top talent ignores LinkedIn solicitations. There is a non-zero lower bound to LinkedIn's utility, so don't write it off entirely, but the channel is saturated.

Remote

🦪 Use a dynamic microphone.

A high-quality dynamic microphone like the Shure SM7B gives you the "smooth podcast voice". This is a way to stand out and project authority in video calls. Condenser microphones, which are the majority of inexpensive microphones sold, pick up a lot of background noise and do not give enough depth to your voice. Don't use Apple AirPods, or any other Bluetooth headset. The Bluetooth channel is highly compressed, and your voice will sound tinny.

🦪 Have a recording device on-hand, just in case.

Reasonably advanced podcasting mixing decks like the Rodecaster Pro II can record the entire audio stream to an SD card by pressing a single button. There is no beep or other notification to other members of the video call, so you can record without their knowledge. This can be useful in a CYA situation, for example, if you are being disciplined for reporting suspected illegal activity. There are some jurisdictions where it is illegal to record people without their consent.

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Wisdom from a career of managing software engineers

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