Advice for new directors

I’m often asked about my advice for new directors. Here I lay out the ten things I wish I had known when I started as a manager of managers.

Being a director is a very different job

First of all, the move to being a director was a bigger change for me than I expected. I thought managing managers would be similar to managing engineers. That was naive.

The shift wasn’t quite as big as moving into management. But it was close.

Being a half director isn’t the preparation you may think it is

As a senior manager, I started to transition into a manager of managers role. But I did so in a hybrid way: managing a team directly, and managing another manager at the same time.

I thought this meant that I understood the job of managing another manager. I did learn a lot, but it wasn’t the preparation I thought it would be.

Why? The skills to manage that manager were new, so I did the job in a limited way. Only when my role switched to fully managing other managers did I have enough ability to focus on the job. It was then that I realized how little I actually knew about that work, and started to grow at a faster pace.

You’ll do most of your work through others

One of the larger shifts in the nature of your work is that Directors do most of their work through other people. You may think you’re doing work through other people when you’re managing engineers as a front-line manager. But Directors have to operate at a much higher level of indirection.

A consequence of this is that your weekly meeting with your managers, and your 1-1s with them, become your most important meetings of your week. Consider lengthening your 1-1s with them to an hour, and make them weekly. And spend serious time planning your management meetings and 1-1s. They are where you should be doing most of your work.

Operating with so much indirection can be an adjustment. Most successful managers have probably been successful largely through their direct efforts. They’ve managed projects well, or hired well, or made improvements on their team.

When you’re a Director, you’re usually working through someone else who is doing the work. Suddenly your success is based on how well your managers are running their projects. Your success is based on how well they hire. Your success is based on the improvements they make on their team.

This leads to a few common pitfalls. One is the overinvolved Director, who doesn’t make space for their managers to do the work themselves. One sign this is happening is if you’re in all the same meetings as your manager.

The second is the underinvolved Director, who views their role as hiring the right people and supporting them. This is similar to the shit shield school of management.

Instead, I encourage you to think about your level of involvement as something you flex depending on the circumstances. Your goal is to be less involved, but it should depend on the level of expertise of the manager in this particular area, and the complexity and challenge of the situation they’re facing.

When a situation is challenging for a manager, you might be more proscriptive, giving them a pattern to follow. You might review their plans and offer more feedback. You should interact more frequently, and talk through the actions they plan to take.

A lot of your job is training managers

This flexing of your level of attention is an important part of your role as Director. And it leads to the next thing to be aware of as a Director: your role is to train your management team.

Ideally, any of your managers should be able to step into your shoes, and do any part of your role. And even if they all can’t do so, your job is to prepare at least one of them to do so.

To understand this topic, I first recommend your read my post on Completed Staff Work. Pay special attention to the end, where I review Marquet’s Ladder of Leadership.

The way I like to look at my management team is that they all have varying levels of skills in different areas. Sometimes their skills will exceed my own in certain areas! But my role is to help them develop their skills as rapidly as possible.

Part of this is that the more skilled they are, the more autonomously they can operate. This is at the heart of a scalable organization. If all your managers rely on you for everything, you have an ineffective organization.

So your job is to create an increasingly autonomous and skilled organization. One that is able to produce good results independently. To do this, you need to be expanding their skill set, and creating the right environment for them to thrive. Coach and develop them to build their skills.

Biggest skill to learn: sensing your organization

The biggest surprise for me when I moved to a pure manager of managers role was how little I knew what was going on. It was like someone had turned off all the lights. I couldn’t see anything that was happening any more.

You may find the information vacuum unsettling. You’re simultaneously put in a position where your job is to make things better, but you have much worse information about where the problems are.

I see some Directors become destructive to their organizations at this point. They rely on their gut and pride themselves on making decisions without full information. This can work sometimes, but it can also result in problems. It’s like a doctor that doesn’t diagnose the disease, and instead starts filling you with random drugs, and starts surgery in random parts of your body. Correctly diagnosing and understanding the cause of things is essential.

You need to build a way to understand what is happening in your organization. You need to set up observability of your organization, so you’ll know if things are going off the rails. Pay a lot of attention to this. It gives you the ability to support your managers, and it provides opportunities for intervention.

A few things you might try:

• Look for meetings that give you signals that things are going well, or not going well. I found demos to be a particularly rich source of information, for example.
• Do skip level 1-1s, to get a random sense of how things are going, and to establish connections throughout your organization.
• Collect metrics from your managers, so you can have conversations about trends or things that seem to be going off track.
• Look at the information tools can give you. Stats on reliability, how often people are paged, product usage metrics, and analytics tools can help fill in your picture of how things are going.

One trap to be wary of is that your need for information may entice you to ask your managers for information. You’ll probably need information frequently enough that you can be a source of annoyance to them. Consider adding some structure around your information needs. Think about what you really need to know each week, and ask your managers to push it to you, instead of pulling it from them all the time.

You’ll need a new perspective

One question to ask yourself is where you can be helpful to the organization. What are things you can do that nobody else can do?

One thing you do more as a Director is to plan further into the future. You should have a higher-level perspective on how your organization’s work fits into the broader offering of the company. This perspective is something you can use to shape the direction your organization heads, and is something your managers cannot usually do.

The skill to learn here is outlined in my post: Leaders make their own problems. I recommend looking at that post carefully.

You can also look at this post on upstream thinking, as I think it outlines some of the mindset required as a Director.

You should focus on systems

A weird thing about being a Director is that you’re operating more at a meta level. What I mean by that is that instead of directly tinkering with a team, you’re working with a system of teams. Your focus should be shifting to be more about the patterns of things, than the details themselves.

This may come naturally to the rare people who tend to be systems thinkers. For everyone else, this is a skill to build. My suggestion is to always be operating at two levels: solving both the immediate problem, and looking at the level of abstraction above that.

For example, if there is a project that is going off the rails, you should be thinking both about how to help with that. But you should also think about what your playbook is for off-the-rails projects. Or how to notice these projects earlier. Or how to systematically reduce the prevalence of this type of project.

You also should think about ways you can influence the whole system. Your toolkit is different, because you’re operating at a systems level – at an organizational level.

A few suggestions:

• You are in a unique position to offer clarity. You can simplify things for people. You can allow them to focus on less things. This is almost always a helpful thing for you to be doing, so pay attention to how you can both simplify things in your own mind, but also how to communicate them.

• You’re also in a unique position to offer context. You will have a lot more context than you used to, because you’ll be interacting with higher levels of leadership than you did in the past. Think of that context sharing as a service you offer your organization.

• Constraints are a tool that you may wield more as a Director. For example, you can make simple rules for teams that help nudge them in the right direction. An example? Teams can only have a project or two they work on at a time. Don’t use over-use constraints as a tool, but sometimes it can be helpful to ask yourself: if I could only do one thing right now, what would have the biggest impact?

You should also familiarize yourself with the levers of coordination models. These are patterns in the way that humans work together in groups to be effective. You’ll need to learn how to organize groups of people, do reorganizations, and so on.

Some of your instincts may be untrustworthy. For example, when deciding whether to organize a team based on skillset or around a product area, you may have suspicions of the best way to do it. But most likely, you have no idea the kinds of tradeoffs you’re dealing with. Which leads to my next point.

Get support and mentorship

Many managers gradually reduce the amount of support and mentorship they receive as they go up the hierarchy. I think they do this because they’re expected to be experts.

This is foolish. As you change roles, and move through different parts of the organization, your skills will need to grow. So seek out people who can mentor you. Seek out peers that can give you feedback. Start your own Mini-M support group for Directors. Contact me or another experienced leader to advise or coach you. Read books and subscribe to newsletters that stretch your thinking (such as my newsletter for engineering leaders)

Beware the distortions of power

Another thing you need to be aware of is that the higher you go in an organization, the more there is an invisible distortion field around you. It affects how people interact with you, and the information you see from your environment.

This can have a harmful impact on your ability to understand the true situation in your organization. It requires a specific set of skills to counter. Without doing so, you’ll be operating in lala land, unaware of the problems you’re creating.

I wrote a whole post on this topic: Everyone Lies to Leaders. As a Director, you’re going to start getting the first tastes of this, so be on the lookout and start building your habits early.

You’re judged by the difference you make on your organization.

To close, I’d like to leave you with my mental model for how you can assess yourself as a Director.

You are judged by the output of your organization. And specifically, you’re judged by the difference you make on the organization. What do you make better? How do you improve things? What is the diff you apply to that organization?

Thank yous

The mental model for how to assess yourself as a Director comes pretty directly from the book High Output Management. It is one of the best books on engineering management.

Image by stokpic from Pixabay