The scariest change in my career so far has been my transition from software engineer to manager. I wasn’t sure if I was ready and didn’t really know what to expect. People in my organization were unsure if I'd be good at the new job. Many engineers I worked with at different companies considered management to be an unpleasant and undesirable task. Was this career change a good idea? There were so many unknowns.
Most new managers have similar feelings of fear and uncertainty. Our industry has been expanding for decades as software eats the world, and all that growth leads to hiring new engineering teams, which creates demand for new managers. Engineers that show an aptitude for leadership, project management, or communication will likely be asked the inevitable question: “Are you interested in being a manager?” If you said yes, or are considering becoming a manager in the future, this post contains my advice for you. Some of this advice was given to me directly, and some of it are things I wish someone had told me when I was starting as a new manager.
Here’s my advice:
1. Don’t Freak Out
The day I was asked to become a manager, the CTO requested I meet him in the big conference room. It was eight years ago. I’d just returned from a sabbatical, which was a great perk the startup I worked for offered after five years. The timing for my sabbatical had been ideal. I’d just gotten married and completed grad school, and after the 5-week break, I was recharged and ready to take on new challenges. My grad program had been geared towards preparing software engineers for leadership positions, but I had assumed my move to management would happen 5 or 10 years down the road. When offered a management job, I said I wasn’t expecting it so soon, but I accepted.
I asked a few general questions about how to start. The CTO went through some logistics then said, “My main advice to you is: don’t freak out.” He was a direct communicator, which I appreciated. “Something will always be on fire at any given time. It’s normal. Don’t panic.” he added. This was the first management advice I’d received, so I pondered it over the next few days. Was everything always really going to be on fire?
In my experience, the answer to some degree is yes. There are always issues to deal with as a manager of varying urgency. Maybe your startup will go out of business if you don’t deliver new features customers will pay for soon. Maybe your SaaS app is experiencing massive usage growth, and the system is starting to melt down under the production load. Or maybe the new person you just hired is being rude and fighting with everyone. Previously, you may have been assigned a specific area to be responsible for and worry about. Now as a manager, you accumulate the concerns of everyone on your team, and it adds up.
Given that there are always urgent things to be concerned about, it’s important as a manager to consider the impact your reactions have on the team. People naturally want to consult the team leader when things aren’t going well. How will you react? In human group dynamics, teams look to their leader in a time of crisis, and it is pretty concerning when that leader is freaking out. It’s very unsettling. You in no way feel reassured that everything will be OK when that happens.
Part of becoming a manager is adapting to this new reality. You’re exposed to more emergencies, more interpersonal conflicts, more problems. And that’s OK! Eventually, you get used to the fact that triaging (perceived) emergencies is part of the job. You’ll build more skills and self-confidence around handling “emergencies” with practice. Eventually when someone pulls you aside to say “This thing is on fire! What are we going to do?”, you won’t freak out. You’ll think to yourself, “Great, it’s time to do my job. I got this.” Your calm, confident reaction will be much appreciated.
2. Negotiate for a Trial Period
Many wise authors in the blogosphere have written that management is not a promotion, it is a total career restart. It’s a different job that requires a new set of skills. You may discover you don’t particularly enjoy the role. If you’re being honest with yourself, you may decide you aren’t as effective as a manager and want to return to an individual contributor (IC) role where you were previously making a big impact. That’s OK! Trying out a management position then deciding it isn’t your preferred career path is a common scenario.
You won’t really know if you’ll enjoy or excel at being a manager until you try it. My advice is to negotiate for a trial period. Ask the person offering you the management job if you can try being a manager for a set period of time, then have the option of returning to your previous role if either of you decides it isn’t a great match. Give yourself enough time to learn the basics, fail at some things, try other approaches, and repeat a few times. Six to twelve months should be a sufficient trial period. It will take longer to develop your skills as a manager more fully, but you should be able to assess whether you like the job in that time frame.
It’s easiest to make this type of arrangement at a company where you've already proven your chops and are trusted as an IC. Starting as a first-time manager at a new company makes it harder to set up this type of arrangement, but it’s still worth exploring. Ideally, you work for a company that supports people moving between management and IC roles as your career goals and the business’s needs evolve. Some of the best contributors were once managers, and they have empathy for the things managers need from their team to succeed. It’s often in a company’s best interest to normalize the transition back into and out of management roles, as it’s better to retain valuable employees than to lose them because they determined a career in management wasn’t the best fit.
3. Get Support
Being a manager will often be emotionally difficult. People will ask you for help with their toughest personal challenges. You’ll need to make difficult hiring and firing decisions that will have a major impact on people's lives. There will be a sense of pressure and high expectations coming from your company’s leadership. You’ll encounter new problems that weren’t your responsibility to fix before, like mediating conflict and addressing performance issues. On top of all this, you won't always be able to ask your teammates for help in the way you did when you were their peer, as it will now seem inappropriate in some situations.
Some new managers put on a brave face and try to handle everything on their own. This approach is not recommended and won’t set you up for success. You need to ask for help. Find a mentor that will be able to spend a few minutes with you every week or two, listen to your problems, and offer you advice. It can be another manager in your company or somewhere you worked before, or maybe another manager you met at a networking event. You may not be as comfortable sharing all your fears, concerns, and anxiety with your direct manager, so getting an additional person to confide in is helpful. Sometimes just hearing someone say, “Oh, that’s normal. I’ve been in that same situation several times” can be very reassuring.
One of the most useful support tools for managers at my current company is our “Mini-Manager Group”. Basically, new managers are placed into a group of random managers from different parts of the organization that meets every week or two to discuss challenges. It’s a great way to share tips and best practices, and I highly recommend setting up something similar if you’re at a medium or large-sized company.
What if you’re at a smaller company and there are only one or two managers? You can join an online community like the Rands Leadership Slack. If you live in a metro area, there are probably leadership meetups like the PDX Engineering Managers meetup in my city. If you can’t find an experienced manager in your field, expand your search to anyone that has managed people.
4. Read Management Books
Learning lessons as a manager takes time. You'll try various approaches with different teams on numerous projects, and slowly learn what works for you. You will not be prepared on day one. To fast track your learning process it’s important to read some books about leadership and management. This may sound obvious, but it’s still important.
Reading advice from experienced managers helps prepare you for the many common situations you'll encounter when you're supporting and managing people. Some management tasks like facilitating a reorg or delivering performance reviews may only happen once or twice a year, so you won’t have frequent opportunities to learn by trial and error. It's much faster to learn by reading about the successes and epic mistakes of others.
Here are the five management books that I found the most helpful:
The Manager’s Path - This book describes the roles of technical leads, engineering managers, and higher levels of management. It’s a great primer for understanding the expectations and challenges of each role of the management career path.
High Output Management - Andy Grove is a great writer and very persuasive. Written in the 80’s, some of the examples are a bit dated ("email will be huge!”), but much of the advice is timeless as human nature and the role of a manager remain fairly consistent over the decades. Groves describes how the performance of a manager should be evaluated and what successful management looks like in practice.
Radical Candor - Personally, I have a deep-rooted desire to make people happy and to shy away from conflict. That tendency can be problematic as a manager. Sometimes the most important thing we can do to help people is to give them uncomfortable, honest feedback. This book provides great strategies about how to have tough conversations with people to discuss the things that matter most.
The Five Dysfunctions of a Team - This book will resonate if you’ve been on a team that was struggling and the group dynamics became toxic. It helped me understand the behaviors and emotions I felt and observed when I’ve been on dysfunctional teams and projects. This book will help you recognize problematic behaviors and provides tips for reestablishing trust and team alignment.
How to Win Friends and Influence People - Don’t let the clickbait title fool you. This is one of the first books I read after becoming a manager and it helped me start thinking more about my own emotional intelligence. As an introvert, I've felt "socially challenged” for much of my life. This book helped me see that some aspects of human nature are fairly universal and that social etiquette can be learned and improved just like any other skill.
If you want some shorter management advice in addition to books, here are some blogs to check out:
Ask A Manager - Answers reader questions about management topics.
Lara Hogan’s Blog - Management advice from Lara, formerly a VP of Engineering at Kickstarter and Engineering Director at Etsy
Rand in Repose - The blog of Michael Lopp, author of “Managing Humans” and VP of Product Engineering at Slack
The Year of the Looking Glass - Essays about management by Julie Zhou, a Product Design VP at Facebook.
Final Thoughts
If you’re considering the move to management, I hope I didn’t scare you off! Being a manager is a role I’ve found very fulfilling. It’s rewarding to help your direct reports develop their careers and to find ways to help teams thrive. Management isn’t an innate talent, it’s a job with skills that can be learned, and our industry definitely needs the help of people who are willing to give it a try.
If you’re an experienced manager, what’s your advice for people just getting started? Is there something you typically tell new managers, or a favorite management book you’d recommend? I’d love to hear your thoughts. Feel free to add some tips in the comments.
