The Apprentice, The New Boss, The Successor and The Pioneer

The 4 paths to management

In “The Making of a Manager”,

Julie Zhuo

introduces 4 main ways people move to management roles:

1. Apprentice: Your manager’s team is growing, so you’ve been asked to manage a part of it going forward.

2. Successor: Your manager has decided to leave, and you are taking their place.

3. Pioneer: You are a founding member of a new group, and you’re now responsible for its growth.

4. New Boss: You’re coming in to manage an already established team, either within your existing organization or at a new one.

I’ve experienced 3 of the 4, and today I’m going to cover the main challenges each type will face and some tips to overcome them.

Most of the content in the article is from ‘The Making of a Manager’, so make sure to check out the book!

The Apprentice

This is the most common transition to management. Your organization is growing, and your manager is now managing 10 engineers. A decision is taken to split the team, and you are requested/offered to lead a new team.

Most often, your manager will move to a Director/Senior EM role, and will stay your manager, which is your biggest advantage! They know the team, they know you, they know the organization.

Still, there are some tough challenges:

Establishing a new dynamic with former peers

At first, it’ll be awkward (and even uncomfortable) asking a friend or former peer, “What do you want to be working toward in a year’s time?” or “What do you consider your strengths?”

Some people start to treat you differently or share less information with you. It’s less fun to gossip with the manager…

My tip: I became a manager of my former peers twice, and it was not easy. For me, the best way to minimize the awkwardness is to just talk about it. Putting it all on the table, and even laughing about it (as long as you know where to draw the line). It’s a tough balance at first, but the good news is it almost always just gets better with time.

Balancing writing code with management

Virtually every apprentice manager makes the mistake of continuing to write code past the point at which it is sustainable.

As an apprentice, you rarely start out with a big team. It’s more likely that you begin with 2-3 direct reports, and hire more people over time.

This makes it harder to balance IC and management work, as initially you are expected to code for the majority of your time. People are creatures of habit, so many apprentices are just stuck at that ‘too-much-coding’ phase.

My tip: been there, done that… I suggest setting time aside every 3-4 months to reflect on and adjust your coding workload.

I’ve started with 60-70% of a regular developer’s capacity, as I managed only 2-3 people for the first 6 months. Then I moved to 40% capacity, where I stayed for a year and a half, managing up to 5 engineers. Recently, with the promotion to director, I moved to 10-20% capacity.

The Successor

This transition is very similar to the ‘Apprentice’ one, but without the biggest advantage - your previous manager is no longer there to support you.

The 2 challenges above are relevant to you too, but there are 2 additional ones:

The increase in responsibility can feel overwhelming

Often, your previous manager just quits, so there is no smooth transition. One day you are a developer, the next you are a manager.

This can be a huge shock. From what I’ve seen, this transition has the lowest success rate, with many ‘successor’s giving up the management role after a while.

My tip: read ‘Why Team Leaders Give Up’ :)

Why Team Leaders Give Up

You are too influenced by the former manager

There are usually 2 extremes here:

1. You want to continue doing everything in exactly the same way.

2. You are tempted to change everything and do it ‘better’.

I’ve been in the 2nd category. As a developer, I had many ideas for improvements, and I felt I just needed the chance. Once it arrived, I found out it was much harder than I expected…

The reality is both options are bad:

Changing multiple things right when you start is not only very very hard to pull off, it can also alienate the team members.

On the other side, a manager transition is a great opportunity for a team to ‘refresh’, and reflect on what works and what can be improved. Don’t miss on it, just do it slowly :)

The Pioneer

You might be:

• A founding engineer at a startup.

• Someone who led a successful initiative that now requires a full-time team.

• An external hire who is tasked to lead a new initiative and build a team for it.

7 years ago, I experienced the 3rd option - I was tasked with building a new team, and creating a new solution in 2 months. It was crazy.

The biggest challenge in this transition:

You are alone

You might have people around you who can help, but YOU are the one responsible for that crucial initiative. There is no ‘set path’ you can just follow along, you need to create everything from scratch.

My tip: if you are in that situation, it means you know how to do it. Even if you feel it’s too much, you have the skills needed. Your main advantage is you can build the exact team you want - use it! Don’t hire out of desperation, be intentional on what kind of people you want on your team, and with which skills.

The New Boss

This is the only transition I experienced only from the employee side (my manager being replaced).

And let me tell you, it was a refreshing change.

Everyone starts with a blank page. Did you have a reputation for being indecisive or stubborn in your last role? Now you have a chance to form a new ‘identity’.

Same with your employees - some of them will appreciate the chance to build the kind of manager-report relationship that they’ve always wanted. Try to be open-minded, and form your own opinions about your new direct reports, no matter what other people in the organization tell you.

I had a bad relationship with my manager 6 years ago, which influenced my relationship with my peers. When a new manager replaced him, it gave everyone a ‘restart’ option, and we changed some problematic behaviors.

Still, there are some tough challenges in the transition:

Adjusting to the new norms

Even if you transitioned from inside your organization, and especially from outside, there are so many things you need to learn! Even things you thought were the same in all companies (like working in sprints) might be different.

It takes a while to adjust to a new organization, but you have a huge advantage! Unlike an internal promotion, you have a window of time (2-3 months) when everyone recognizes that you’re new, and cuts you some slack.

Use that time to listen and learn, and don’t push your opinions from day one.

Building new relationships

Before starting at my current job, I worked for ~6.5 years in the same company. I knew EVERYONE.

The move to suddenly being an outsider, can be very frustrating. So many new faces and names to learn. As a manager, it would have been even harder. New Product organization, new UX, new support team, new CS, a new manager - and all of that from day one.

Ryan Peterman

wrote a great ‘How to Onboard’ article, where he shared a golden tip from Meta’s CTO:

“The first step is to find someone on the team and ask for 30 minutes with them. In that meeting you have a simple agenda:

• For the first 25 minutes: ask them to tell you everything they think you should know. Take copious notes. Only stop them to ask about things you don’t understand. Always stop them to ask about things you don’t understand.

• For the next 3 minutes: ask about the biggest challenges the team has right now.

• In the final 2 minutes: ask who else you should talk to. Write down every name they give you.

Repeat the above process for every name you’re given. Don’t stop until there are no new names.”

Final words

Each transition to management is unique, and heavily influenced by the organization and the people involved.

Still, there are many common problems, even for managers outside the software world.

I was surprised about how relevant ‘The Making of a Manager’ was, considering Zhou was a designer, not a software engineer.

What I enjoyed reading this week

1. When is the Right Time to Quit by

   Akash Mukherjee

2. Secrets of Clear Thinking by

   Michał Poczwardowski

3. Stop Fighting Failure: Find Your Intrinsic Motivation by

   Akos