Working with Your Manager

In this chapter we’ve looked at the skills you’ll need to work with individuals: strong communication and the ability to delegate. However, there’s one important individual that you probably didn’t have in your mind while reading. That individual is your manager.

For many, their manager is the person that tells them what to do and judges their performance. But the relationship can be so much more if you focus on developing it by using the techniques that you’ll learn in this section. You can make your time with your manager a part of the week that you value and that you look forward to.

Let’s have a look at some of the techniques that you can use.

Pull, Don’t Push

The most important piece of advice is that you should pull on your manager, not wait for them to push to you. What this means is that it’s up to you to get the best out of the relationship that you have with your manager. Be proactive and don’t wait for them. Book that meeting, have that conversation with them, ask for that help. You’re not a marionette dangling from the strings that your manager holds, with them dictating exactly what you should do. Instead, you need to reframe the relationship that you have in your mind as one that encourages two-way empowerment through coaching, sharing of responsibilities, and support.

The techniques that follow all embody this principle. You need to understand how they view you and your team within the rest of the department and work out how best you can make it a better place. You need to remember, like you, your manager is probably busy and has a lot on their mind. They may be in a situation where they’re not getting the support they need from their own manager, so you can form a strong partnership by being on their side, with both of you supporting each other and getting meaningful work done.

Talk About Performance

At the beginning of your relationship with your manager, you should talk about performance. Notably, there are two areas to explore:

• What does your performance equate to in the eyes of your manager? Is it the retention and happiness of your staff, the amount of work that you get done on time, some strict uptime SLAs, or is it entirely subjective?

• What is their performance dependent upon? You can begin to get a view into the wider organization. Are they fundamentally accountable for everything that their teams ship, or are they accountable for more abstract business metrics? Do they even know?

You may even find that the answers are not clear to either of these questions. If they aren’t, then this is an excellent chance to define them. Perhaps your manager feels that good performance means that they need not worry about the internal workings of your team at all, and instead they only need focus on their relationship with you. Alternatively they could be accountable for ensuring that the department ships three major projects this year, that they retain 90% of their staff, and that a specific SLA is upheld.

If you’ve been a programmer before, then you may have thought about your performance and the performance of your colleagues. If you had to rate the performance of another programmer, then you may have considered:

• What level of technical expertise does this individual have? Are they able to take on large, ambiguous, and technically challenging problems and solve them in code? Or do they need others to help break down the problems so that they can implement each individual piece in isolation?

• How much do they increase the skill of the whole team? Are they a patient and skilled mentor who takes the time to teach others through conversation, demonstration, and collaboration?

• Do they have a positive effect on the team? Are they motivating and optimistic, and do they lead by example? Do others follow what they do?

• Do they understand the bigger picture of the software that they are building and the needs of the company?

I would advise that you work on framing your own role in the same manner with your manager. It’s also a good exercise for them to frame their role in the same way so you can see how your team fits into the bigger picture. Sometimes it can be difficult to define managerial performance because it’s more abstract and your output—as highlighted before—is the collective output of your team and those that you influence.

Later in Chapter 15, ​Dual Ladders​ we’ll be looking at defining career tracks for both individual contributors and managers. Feel free to skip ahead to that chapter if you’d like to have more material on hand for trying to frame how your performance is measured. However, if you’d like some inspiration for an initial conversation with your manager, then you could incorporate the following ideas:

• What traits does a high-performing manager have? What do they say and do regularly that make them so?

• How do you measure that a manager’s team is doing a good job? Is it simply through the output of their team, or is it through team happiness, retention, or all of these things?

• In the spaces between doing hands-on managerial activities, what is a successful manager doing? Are they getting stuck-in with coding, or are they working with their manager and peers on making the department a better place? If it’s the latter, then what sort of activities does that entail?

• How connected should a team’s manager be across the organization? Should they primarily be concerned about their team, or should they also be regularly talking to designers, product managers, and sales and customer success staff?

Getting both your input and your manager’s input on these themes—plus any others that you can think of—helps frame how you both think about performance. It also ensures that you talk about it from the start, which is a key part of a radically candid relationship.

Lifting the Lid on Their World

As you get to know your manager, you’ll want to begin to lift the lid on their world. If you wait for your manager to tell you what to do, or ask you for your input, you may be missing out on learning opportunities and career growth.

A simple technique is to ask questions during your one-to-one meetings. This has a number of benefits:

• It exposes you to the concerns that are going on at one level up in the org chart.

• It can expose additional things you can help your manager with. For example, they may mention another team is having difficulties with a particular project or technology, and you may be able to offer some advice.

• It shows that you’re interested in career progression and growing outside of the confines of your role.

• It strengthens your relationship because you are taking an active interest in their world.

The questions themselves can be straightforward and worked into your conversation:

• “So what’s been on your mind this week?”
• “What’s your biggest worry at the moment?”
• “How are your other staff doing?”
• “What are your peers working on?”

Although simple, having this active interest can unlock a number of career growth opportunities for you. You may get to assist with hiring in other teams, expanding your influence. You might get a chance to meet others in the organization that you can form a relationship with. Maybe you’ll even get asked to assist with performing technical due diligence on a startup that your company is thinking of acquiring. You never know. But it starts with questions and an active interest. With time, you may see your relationship with your manager feeling more like a meeting of peers rather than a boss and their subordinate. You both get real value from each other.

The Power of Summaries

In the same way that you can ask questions to get an insight into your manager’s world, there’s also a way that can open up yours to your manager while also helping you pause, reflect, and plan. That technique is the simple regular written summary. Every week, take thirty minutes to note down the main activities that you and your team have been involved in, how you feel about them, and what decisions you’ve taken or need to take. Write down how your staff are getting on and how they are feeling about their work. Is anything becoming a blocker? Do you see trouble ahead? Is everything actually just going really well? Note it down.

The simple act of taking time for yourself every week to summarize how things are can be extremely therapeutic. It can help you abstract away from the problems that you are facing and work them through with yourself on paper. Often you’ll find that they’re not so important or challenging once you’ve spent some time with them. Studies have shown that journaling in one’s personal life can have a positive effect on mood and well-being. I’ve found the same to be true about weekly journaling at work.

If you struggle with what to write, then perhaps you could try an approach based on four Ps:

• Progress: What has happened since last time you wrote?
• Problems: What issues have occurred and what needs addressing?
• Plans: How are you going to approach those issues going forward?
• People: How are the individuals on the team? Are they doing well or are they having a hard time? What could be improved?

Rubber Ducking

In The Pragmatic Programmer [HT00] there’s a story of a developer who would use a rubber duck to help debug their code by talking to it while they unpicked the problem. Often explaining the steps to someone else helps you solve a problem yourself, even if it happens to be an inanimate object. Writing weekly summaries is the closest thing that I have found to rubber ducking in a managerial role. Often when I’ve had multiple issues whirring around my brain, the act of committing them to paper has enabled me to be more logical and clearer in my thinking, thus unlocking the solution. Sending them to my manager weekly holds me accountable, so I always perform this summarization exercise. Better still, it gives us a lot to talk about.

Here’s what you can do to build these summaries into your week. Before you start doing this with your manager, let them know that you’re going to do it. You can tell them that you don’t necessarily need a reply, but you’re interested in showing them weekly what is going on in your world. They are, of course, totally welcome to comment, debate, or challenge anything that you write. In fact, that makes excellent material for your one-to-ones.

• Pick a suitable time to do it and make it a recurring to-do. Perhaps you find that finishing off Friday afternoon by writing is a good place to pause and reflect on the week that has just ended. Perhaps it’s more useful to do it the day before you have your one-to-one with your manager so you can talk about the issues in greater depth when you next meet.

• Dedicate thirty uninterrupted minutes to writing. Make some high-level bullet points on the areas that you’ve been focusing on, whether those are elements of the project, interactions that you’ve had with your staff or outside the team, concerns you have about what’s coming next, or any progress toward your goals.

• Write as you think in a continual flow. Don’t worry about formality. Write as if you were speaking to a good friend. How have you felt about each item on your list? Have you worked through any problems, or are you stuck on something in particular? You may find that you make progress on your problems as you write.

• Give it a quick proofread. No more than a couple of minutes. Don’t worry about it being perfect.

• Send it to your manager. I recommend using a shared document that allows commenting. That way, you and your manager can continue the discussion asynchronously.

This technique is especially useful if you have a remote—or extremely busy—manager and don’t have the opportunity to walk over to their desk each day to have a conversation. However, I have used this technique identically when I’ve had my manager sitting on the desk next to me and when they’ve been on the other side of the Atlantic Ocean. The ability to perform an exercise that benefits both you and them is a high-leverage activity and it comes fully recommended.