The Engineering Manager

I’ve been thinking a lot about my energy levels at work this weekend, mostly because I’ve managed them badly over the last few weeks.

As a result, I am trying to be more mindful of habits or behaviours that I fall into in the hope that I can get better at managing them going forward.

In this article, I’ve tried to explore what I’ve observed in myself, in the hope that it might be of interest—or even of use—to those that read it.

Here’s what I’ve observed:: work generates energy and happiness for me, but only to a point, and I am very bad at identifying that point. I typically decide how much and how hard to work based on incorrect leading indicators, rather than the real, correct lagging ones.

Wonky predictions

Work is a core part of my life, much in the same way that my family is, and also my hobbies.

After all, why would I be spending part of my weekend writing this article? I am probably always going to be working in some way, shape or form, even if it isn’t for money. I just like making things.

I am also fortunate that I have a good job that I find meaningful and rewarding. When I am well-rested and in a good headspace, I know that my job is able to act as an energy flywheel: I do things, I feel good, and so I do more things to feel even better.

At the beginning of the working week—off of the back of a nice weekend—I know that I often work extremely hard, because there is a linear relationship between the effort that I put into my work and how good I feel about it.

It looks something like this.

This ideal represented by the graph is typically true for me on Monday through Wednesday.

Monday is always a flurry of activity as people get a jump on the week ahead, and most of my 1:1s happen then as I like to have all of us aligned. This makes me feel good.

Tuesday is scheduled as a blend of meetings and focus time. I typically make a dent in whatever my big personal task is for the week on this day, which also feels good and feeds the flywheel.

Wednesday is no-meeting day at Shopify, so that day is characterised by a flexible schedule and an intense focus: I don’t have any meetings to attend, so I can have a full day of intense deep work that almost always makes me feel really good. This is usually the day where I’ll write that long proposal, or go deep researching something in the product or in our technology.

But, as Wednesday turns to Thursday, there seems to be an inflection point for me in terms of my energy, but I am rarely able to perceive it at that time.

I’ve come to the conclusion that because, subconsciously, I experience three days where intensity is linearly correlated with feeling good, and I then ignore the fact that I am tiring because I have failed to pace myself, slow down and rest more on the preceding days.

The data from Monday to Wednesday produces a model like the graph above: linear and limitless. I am then using that model to justify ploughing on through the remainder of the week at the same high intensity.

However, not being more self-aware means that I typically seem to experience Thursdays and Fridays that look like this.

The issue is that I am making decisions in the present moment based on a model of how I am going to feel in the future that has been trained on data from the previous few days where my energy was high from the weekend.

But this model doesn’t take into account lack of ample rest, my cumulative tiredness, all of the usual curveballs that a usual working week and family week will bring.

On Thursday afternoon I know that I’m already starting to get a bit irritable and impatient, and by Friday I’m still working hard but I’m having to dig into my reserve tank of fuel, despite my best interests.

I write my weekly internal newsletter on Fridays, and I really enjoy writing, so it should—in theory—be a rewarding activity at the end of a long week. Instead, if I’ve managed my energy badly, I find myself bashing it out in haste just trying to get the damn thing done rather than taking any pleasure in it.

This isn’t a pattern that can sustain itself over long periods of time.

Something better in the long run

What I want to aim towards is something more like this:

In this model, my intensity is purposefully kept capped—much like the speed on powerful electric cars—to stop me attacking my work too hard, even if I feel like I want to.

This is because I think I’ve realised that my own subconscious mind can’t always be trusted to make the right long-term decisions when the short-term data suggests otherwise.

With that in mind, here’s a bunch of things that I’m going to be trying over the coming weeks.

Purposefully trying to work 10% slower. I have noticed that I have a habit of trying to work at breakneck speed. I think that this has something to do with my “Completer Finisher” personality (for what it’s worth, my Enneagram is type 3) and that I get a great feeling when a task is done, hence the intensity I generate to complete it. I’m going to try my best to mindfully work 10% slower to see whether treating the week like a marathon, rather than a race, leaves me feeling better and less stressed at the end of it. It’ll be interesting to see whether I get the same done, or more.
Being stricter with my input. I can’t deny that messaging applications feed the dopamine habit loop. There’s so much compelling discussion and information across countless Slack channels and mailing lists that it can become addictive to keep chasing inbox zero whenever there’s a spare moment. However I’m aware that context-switching can take its toll after several days in a row. I’m going to try to see whether I can limit checking messages to just a few intentional times every day, and then purposefully focus on input-free deep work—wherever possible—in between those times.
Limiting checking messages to within working hours. Related to the above, I’ve found myself falling into “busy waiting” behaviours with my input feeds because there is so much communication happening during the evening time in the UK (the critical mass of the company is in Canada). There’s no expectation for me to read any of it, but I tend to try to keep on top of it to “complete the task” of inbox zero. But this prevents me from recharging in my downtime.
Deferring non-essential requests and tasks into the following week. Another habit that I have is “cramming”, where I overestimate how much I can get done in a day, and underestimate how much I can get done in a week. This feeds a continual bin-packing loop where I try to clear as much as I can off my to-do list every single day to optimise all available time, even if some of those tasks could easily wait a little longer to get done with no ill effect. I’ll be trying to schedule less important things in the future using the Eisenhower matrix, giving myself more time to do the important work in a more considered manner.
Getting back on the tomatoes. When I was doing my Ph.D., I often used the Pomodoro Technique to make sure that I got enough breaks within my working day. It works by chunking your time into 25-minute sprints (pomodoros) with 5 minute breaks in between them, and then having longer breaks between contiguous blocks of pomodoros. I’m aware that often when I get deep into something I can work intensely for hours, but like the graphs above, too much intensity over too long a period can lead to irrecoverable energy drains. So I’ll try to pace myself more with some structure.

Let’s see how it goes.

How about you? What sort of ways do you try to control your energy as the week goes by?

Do you start strong, but fade towards the end of it? Are you checking your Slack messages on your phone whilst trying to relax in the evening because you think it helps you out tomorrow, or have you mastered a separation (or integration) of your work and your recreational time?

I know I’ve still got a long way to go, so I’d love to hear your tools and tips if you have any.

If there’s one thing as sure as death and taxes, it’s the fact that you’re going to have many managers over the course of your career. Even if you stay at the same company for decades, it’s unlikely that your manager is going to as well.

What’s more likely is that you may find yourself with a new manager every few years, due to one or more of the following reasons:

You change jobs.
You move to another team, either by choice or because priorities have changed.
Your manager leaves.
Your manager moves to another team, for the same reasons as above. You get the picture.

So, this week, we’ll look at the following question:

Q: How do I deal with my manager changing?

Change isn’t all bad

I think it’s important to begin by addressing the elephant in the room: changing managers shouldn’t be avoided at all costs.

In fact, it can be good for you. Sometimes getting too comfortable under someone can hold your development back, compared to someone that could push you outside of your comfort zone, help you work on something new, and make you see sides of yourself that you hadn’t been made aware of before.

If you really want to work on something different, but you pass because it means changing managers, then you’ll eventually regret missing that opportunity just for keeping the familiarity of your current relationship.

However, the reason that people avoid changing is completely understandable: we’ve all had our share of experiences with our managers, from the good to the bad. Reporting to a good manager is a joy. And when you’re reporting into a bad manager, work can really suck. So why take that risk?

After all, your manager is responsible for your performance reviews, finding opportunities for you to grow and progress, and for making sure that you’re happy and productive day to day, week to week.

Even if you try your best to stay with the same manager, much is outside of your control. They may leave. You might get moved to another team. So, with time, it only becomes more likely that you’ll be reporting to someone else.

Therefore the question remains: how can you get things off on the right foot when you make the switch?

We’ll break this into three different parts that represent the past, present and future at the point of changing. But first, let’s look at some general advice.

Own your own development: push, don’t pull

Actors in a system can only affect what they can fully control. Everything else is up to the altruism of others or just pure luck. This holds for your career as well.

If you give complete control of your growth to your manager, then you may get lucky with someone that truly dedicates their time and attention into finding opportunities for you, lays out clear goals for you to reach, and ensures that you’re always progressing at all costs. However, the likelihood that you’re going to find a manager that does this consistently is low.

Why? Well, not only does it take a huge amount of time for any manager to plan development for each of their direct reports, fundamentally you are the one that best knows yourself and where you want to go, not your manager.

Instead of seeing your manager as the pilot and yourself as the passenger, you need to work that relationship differently with yourself as the pilot and your manager as the copilot.

You need to know where you want to go, and you need to steer in that direction with their help.

Think about it: if you were managing someone and they were able to take the lead on suggesting their goals, asking you for more work, and encouraging you to delegate things to them, wouldn’t that be wonderful?

Being proactive with your development ensures that you get what you want since you know yourself best, and it makes your manager’s life easier because they can be the copilot, rather than the pilot. Yes, you can ask for advice. But you take control of planning your direction of travel.

And, if you have managers that you don’t really gel with—as we all have had in the past and will in the future—then having them occupy a position where you can set the direction and then mostly get out of your way can be liberating for both of you.

So always own your own development and push towards it, rather than waiting for your manager to find you opportunities and to pull you along. The latter rarely ever yields optimal results.

The past: the handoff and your audit trail

Let’s now look at the switching point.

When you change managers, they won’t know your past. They might have access to your previous performance reviews, but they weren’t written by you, nor do they represent your whole self.

What can you do?

If you can, try to arrange a manager handoff with your previous manager and your new manager. This is a 1:1:1 (read: one-to-one-to-one) where all of the important information is passed from your old manager to your new manager whilst you are there.

This is important because that transfer is transparent to you, ensuring that you have the opportunity to know that it’s happened, can hear what is being said and therefore reduce the friction in the process.

The agenda of the meeting is as follows, mostly driven by the former manager:

Details from your most recent review cycle.
Your recent feedback, current projects and other relevant information.
Your goals, growth areas and any important things for the new manager to know.

Read Lara Hogan’s post in detail to see exactly how to structure the meeting and ensure that all parties leave satisfied.

Also, in the spirit of pushing, rather than pulling, we wrote last week about how you can ensure that your work is visible. Check it out if you haven’t already.

The core of the practice is creating a habit of writing “brag docs” at regular intervals—say, weekly or fortnightly—that detail everything that you’ve been working on, from the tangible (e.g. shipping a feature) to the less tangible (e.g. that you made a decision, or mentored a colleague).

If you get into the habit of writing these and sharing them with your manager, then the archive can come along with you when you switch, giving your new manager the ability to read through what you’ve been up to for the last weeks, months, and years if they wish.

By lining up a manager handoff, and by having a past audit trail of your work as written by you, not only have you given your new manager plenty of opportunities and material to understand where you’ve been and where you want to go, you’ve also been present and have had complete control of the process and information.

The present: contracting

Now, let’s move on to the present. You’ve had your manager handoff and you’re about to have your first one-to-one meeting. What do you do?

I always recommend an exercise called contracting, which I learned a long time ago from a workshop with Conscious Business People in my early management days.

The idea is that you’re starting a brand new relationship and your first meeting together is an opportunity for both you and your new manager to make it really clear as to what you both need from each other in the relationship.

The contracting exercise is just a few simple questions that you prepare beforehand. You then come to the meeting to talk through your answers with each other and to discuss how you feel about them.

The questions are as follows. They’re two-way, as a direct report supports a manager by helping their team succeed.

What are the areas that you’d like my support with? This can range from technical challenges, performance management, visibility into other areas of the company, and so on.
How would you like to receive feedback and support from me? This is about working out how the other person likes to operate. Do they prefer written or verbal feedback? Do they prefer synchronous or asynchronous communication? Everyone’s personalities and preferences are different, so this gives an opportunity to uncover that.
What could be a challenge in us working together? As before, everyone’s personalities and preferences are different, so that can cause some clashes, and these can be explored. Additionally, are there big skill set gaps that might make the relationship harder because one person doesn’t have in-depth knowledge of the other’s world and vice versa?
How might we know if the support I’m offering isn’t going well? If there are occasional flashpoints, or if the relationship really starts to go downhill, how will both parties know? Do they feel comfortable just saying so, or are there particular behavioural signs that each other can look out for such as quietness, frustration, or lack of responses to messages?
How confidential is the content of our meetings? Since one-to-ones are private, sensitive topics can arise. Should those topics stay completely private, or are there circumstances where that information could generate some actions? If so, how should permission be granted to share private information if it needs acting upon?

Contracting is a great exercise to get relationships off on the right foot, and it doesn’t have to be used exclusively between managers and direct reports. It works between any two people. It’s also a neat tool that you can use to reset relationships as time and circumstances change them.

The future: your goals

With the relationship with your new manager grounded, you should also take ownership of coming up with your goals and trying to achieve them. I’ve always been a big fan of the 30-60-90 day plan when moving into a new role, but it also works really well when starting out with a new manager.

The reason is that when you start with a new manager, you want to build two-way confidence in that relationship from the start to show that you’re someone that they can rely upon to get your job done.

By starting with this short time frame of three months with a check-in every month, you get plenty of opportunity to start building a goal-centric relationship with your manager, which will frame the rest of the relationship that you have with them.

Doing so is simple: you just come up with some objectives to achieve within each of those time periods. The goals themselves don’t need to be ostentatious: they should just be your usual job, and the kinds of things that you’d be writing about in your brag documents.

However, you’ll find that by being able to show your new manager that you’re actively planning and achieving, they’ll more quickly give you autonomy and think of stretchier and more interesting goals that you can achieve.

Resets are good

With these tools, changing managers can be a great opportunity for a reset and a chance to shape a future relationship exactly how you want it.

You can use a manager handoff accompanied by your brag docs to cover the past, contracting to cover the present, and a 30-60-90 day plan to move you into the future.

Even if you’re not changing managers, why not give these tools a go as a way of rebooting your current relationship? Try it out.

If this article was right up your street, then there’s plenty more ideas and tools in my book, Become an Effective Software Engineering Manager.

Until next time.