10 Habits That Help Me as a Manager

Many years ago I was interviewing for a management job at a growing tech company. After a long day of meeting with engineers and product managers, I made it to the final boss, the VP of Engineering. He introduced himself, put his hands together at the fingertips, and said, "Tell me your top accomplishments for the last three and six months."

I froze up. It had been a very busy year. I’d worked on a wide variety of things. I stalled. "Hmm... Let me think about that." He quickly cut me off. “No. That's not a good answer. You should be able to answer that without hesitation. Communicating the value you bring to the organization is an important part of being a leader. My advice for you is to set a calendar reminder. Every three months write down the top achievements for your team and your personal ones."

I was not offered that job. But I appreciated the great advice! After the interview, I set a calendar reminder, and every quarter since that day I have written down my top accomplishments. It's a very helpful habit for reasons I describe below. Many things that help me succeed in my role as an engineering leader are simple habits, like that one. I developed a set of daily, weekly, quarterly and annual routines that I'll share in this post. Many were tips given to me by coworkers, some I read about in blogs and books.

These habits are all personal actions I would practice regardless of the type of project or team I’m working with. This is definitely not a comprehensive list of everything managers need to do to be effective. They’re just a few things I find helpful. Here are my habits:

Daily Habits

Identify Your Top Six Priorities

I use a to-do list in Evernote to record all my pending tasks. During the day I’ll agree to do some work and add a task to the bottom of my to-do list. The list gets long during busy periods, so I prioritize it daily using the Ivy Lee Method. Productivity consultant Ivy Lee recommended this method to Charles Schwab in 1918 as a way to help his company’s executives be more efficient. It’s very simple. At the end of work each day you rank your top six priorities in order of importance. When you start the next day, work on the tasks in priority order. That’s it! I typically set out to tackle three-to-six tasks per day, so the Ivy Lee number seems appropriate.

Write and Share Daily Intentions

Most software engineering teams start each day with a “standup” meeting where each member summarizes what they plan to focus on that day. The team I currently work on is distributed across US and EU time zones, so we do this asynchronously by writing that info into a Slack channel used for daily standup posts. I find it helpful to record my daily intentions as it motivates me to complete what I publicly said I’d do. Having those entries written down also helps me remember what I accomplished when I write my weekly status update.

Keep an Emotional Journal 

Since the COVID-19 pandemic started I’ve been trying to keep closer tabs on my emotions. After experiencing strong feelings like stress, irritation, fear, anger, or excitement, I jot down a brief note about the emotion and situation in a notebook I keep on my desk. Recognizing and naming your feelings is an important part of building emotional intelligence. My daily entries are useful to reflect on when I write my weekly impact journal entry. They often describe the emotional roller coaster I experience while encountering setbacks, pitfalls, and small wins.

Weekly Habits

Update My Calendar

It’s important to start your week with a good plan. As a manager in a medium-sized company, I usually have 2 to 4 hours of meetings per day. Many of those are recurring like 1-on-1’s and weekly staff meetings. Others are ad-hoc project meetings that I need to prepare for in advance. I take a few minutes each Monday morning to look at the week ahead, canceling or declining meetings I don’t need to attend, and adding blocks of personal time for accomplishing the tasks on my “top six priorities” list. This helps me spend my time intentionally.

Exercise

Exercise is an important tool I use to manage stress. I’ve been going to the gym twice a week for years and doing the same simple workout. It’s such a regular habit that, after years of repetition, it requires no will power or deliberate effort on my part. It has been tricky adapting my exercise habits during the pandemic, but I’ve made do with jogging, YouTube yoga, and buying a bench and a few free weights for my basement. Whatever routine I follow must be so easy that I have no excuse not to do it. I also listen to things I enjoy while exercising like music, podcasts, and audiobooks as a rewarding motivator.

Review Indicator Metrics

In the seminal management book “High Output Management”, Andy Grove recommends establishing indicators to help you understand how you’re progressing towards your goals. Pursuing metrics blindly can cause unintended problems, so Grove recommends using “paired metrics” that show both the positive effects of your teams’ focus as well as the negative consequences. An example is pairing Jira velocity (quantity) with the bug rate (quality). I’ve managed infrastructure owning teams over the last few years, so I’ve tracked metrics like:

• new platform adoption %

• weekly production incidents

• off-hours paged while on-call

• security tasks open past due date

Every Friday morning I add a new column in my “indicator metrics” spreadsheet then record 10 metrics for the week. This process helps me model how work flows through the system, and allows me to see if the team made progress or was interrupted by reactive tasks. It also produces data I use to create charts showing trends like the percentage of customers migrated to the new platform over the last six months.

Write in an Impact Journal 

During an all-hands meeting, a VP at my company mentioned they keep a work journal where they wrote down the impact they made each week and how they felt about it. I started doing this and found it’s a very useful way to reflect. After starting his habit, you can scan the weekly wins you recorded every three months to remember the highlights from the quarter. Writing down your impact is doubly useful because you can immediately copy-paste it into your weekly status report. I’ve also found it interesting to read through my emotions from the last three and six months. When I read about my greatest worries and fears months after a stressful situation has been resolved, it reminds me of the powerful emotions we experience during challenges, and that every crisis is eventually resolved one way or another.

Share a Weekly Update

Information flow within your organization is critical and it helps to have a planned, consistent approach. This often looks like a weekly email, shared doc, or internal blog post shared with your manager and ideally with your stakeholders. There’s great advice on how to do these including Laura Hogan's “Week in Review Leadership Comms” and my colleague Jade Rubick’s “How to be an information flow superhero”. Currently, my process is writing a “reflection” on Friday mornings in Koan, an OKR tracking tool. It's visible to leaders in my org and I also share it with the team I manage. The format of the update is: things the team accomplished, things I got done, after-hours on-call support issues, priorities for next week, and concerns I’d like to raise. I write this after reviewing indicator metrics and writing my impact journal entry, so it’s mainly a copy-and-paste exercise. As we’re all remote workers during the pandemic, this habit is even more valuable. Your manager and stakeholders need to know where your team is focused, what’s holding you back, what's finished, and what you’re working on next.

Quarterly Habit

Record My Quarterly Accomplishments

Every three months I write down my top achievements under these categories: 

• Team accomplishments

• Communications (internal blog posts) 

• Process work

• Helping other managers

• Hiring

I scan through my impact journal entries from the last 12 weeks and copy-paste the most impressive items into the quarterly accomplishment list. When it comes time for my performance review, which happens every six months at my company, I simply combine the lists from the last two quarters then share with my manager. Nice and easy.

It's great having a record from each quarter going back for years of the things I've helped my team do and other things I've done personally. If anyone asks what I've done over the last year, I know where to look to help jog my memory. Sometimes I go back through the lists during times of doubt and uncertainty to help me remember what is possible. Reflecting on how you overcame past struggles can provide insight into your current challenge.

Annual Habit

Create Personal OKRs

Each year on January 1st, I open a Google doc and create a list of personal OKRs (objectives and key results) for the year. I usually have three or four top objectives with about five measurable results under each one. After writing my list of new year’s resolutions, I set a biweekly calendar reminder to revisit and update my progress. Christina Wodtke, author of the book Radical Focus on OKRs, has some great tips about using personal OKRs here. 

Personal OKRs help me focus on my health, family, friendships, and things I aspire to do outside my 8-to-5 job. Life is not all about work. It can be easy to continue thinking about work challenges on nights and weekends. This habit helps remind me there are other important things in my life.

Any Suggestions?

Have you formed a productivity habit you find particularly useful? Is one missing from my list? I’m curious about what works for you. Feel free to share your favorite habit in the comments below. Thanks!

My Advice for New Managers

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:

1. 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. 

2. 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.

3. 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.

4. 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. 

5. 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.

Mega Book Report (Part 1)

I love books, but am not a particularly fast reader. Because of my slow pace, I’m picky about which books I read, relying on advice from peers, Goodreads ratings, and annual “best book” lists. Earlier this year I saw Jeff Marten’s post “My 2016 year in books”, and ended up reading Shoe Dog based on his recommendation. It was so good! To pay it forward, I compiled this list of books I read and enjoyed over the last two years.

Career Path Books

I found these book helpful in my role as a software development team leader. We read the first three in New Relic's management book club.

High Output Management by Andy Grove

This was on my “to read” list for a while. It’s widely considered a seminal work in the category tech management literature, and for good reason. Grove's writing is very persuasive. Written in the 80’s, some of the examples are a bit dated ("email will be huge!”), but I found the historical context interesting. Human nature is surprisingly consistent through the decades, despite the endless waves of tech innovation. Grove’s advice on tracking team indicator metrics and conducting performance reviews were two tips I immediately put into practice. This question from the book resonated with me: “Are you trying new ideas, new techniques, and new technologies, and I mean personally trying them, not just reading about them?"

Good Strategy Bad Strategy by Richard Rumelt

I discovered that I was fascinated by business strategy while reading this book. It explains ways to critique your company’s annual strategy, if you’re lucky enough to have one. Rumelt teaches strategy at UCLA’s school of management, but also has decades of experience consulting in the private sector. The case studies in the book are great business history. They illustrate how difficult it is to understand your competitive landscape in the moment (everything is clearer in hindsight) and design a focused, effective strategy. I found it both entertaining and educational to read about companies whose strategies achieved “success" (e.g. Starbucks, NVidia, IKEA, Cisco) as well those that didn’t pan out (WorldCom, Enron, GM). It’s a solid intro to strategy, providing a vocabulary for discussing the subject. Spoiler: good strategy includes a diagnosis, guiding policies, and a set of coherent actions to carry out.

Managing Humans by Michael Lopp

Michael Lopp made a name for himself by blogging about engineering management under the pseudonym "Rands”. The book is more of a packaging of his best blog posts than a cohesive narrative. In our management book club, some people disagreed with Lopp’s opinions and conclusions, but we appreciated his efforts to answer “What does a software engineering manager do? What should they do?” Despite my initial objection, I found some of his descriptions of diametrically-opposed engineering personality archetypes (e.g. Completionists vs. Incrementalists, Mechanics vs. Organics, Old Guard vs. New Guard) to be helpful in understanding the behaviors and motives of my co-workers. This book is recommended reading, especially for new managers living through start-up drama.

Work Rules! by Laszlo Bock

Google built a reputation for being a great place to work, and that is no accident. Laszlo Bock, who led Google’s PeopleOps team for 10 years, describes their journey of innovation in this space and the rationale behind their approach. After becoming a big company, Google hired data scientists to run experiments testing the effectiveness of their employee perks and management approaches. They open sourced their findings on re:Work, a site describing best practices for managers. Bock makes a good case for a career path in PeopleOps, and the benefits of caring about your workforce.

Influence: The Psychology of Persuasion by Robert Cialdini

This book details six techniques used by sales folks, or “compliance professionals” as Cialdini calls them. These tactics leverage, or you could say exploit, universal principles of human psychology such as seeking approval from an authority, and the desire to be consistent with our past statements. The book opens a window into the black magic of marketing, and why certain ads are effective. I’m now better at identifying tactics salespeople use on me. I notice the theory of reciprocity used frequently, which is when you give people something (often of small value), then ask for something in return (often of large value). These approaches can be used for evil, or just to boost your persuasive communication at work.

Honorable Mention:  The First 90 Days by Michael Watkins (read this one prior to starting a new job)

Business Stories

I discovered this genre recently, and am now a devoted fan. These are often told chronologically like fictional stories, a great format for info-tainment.

The Innovators: How a Group of Hackers, Geniuses and Geeks Created the Digital Revolution by Walter Isaacson

This book should be required reading for computer science and electrical engineering students. Weighing in at 560 pages, it covers a lot of territory, from Ada Lovelace's notes describing an analytical engine, to the traitorous eight forming Fairchild Semiconductor populating the Silicon Valley with their “Fairchildren” spin-off companies. As technologists, we stand on the shoulders of giants, and this book is the story of those giants. Isaacson has a gift for humanizing the legendary innovators by detailing their feelings of failure, struggle, and self-doubt. He also works to dispel the myth of the lone genius by describing innovators that found success by teaming up with collaborators with drastically different skills and personalities. I was surprised about how many of these stories I didn’t know, like the long and unlikely partnership between government and academia that created the internet, and the fierce competition among scientists to invent the transistor. Amazing, and inspiring.

Shoe Dog: A Memoir by the Creator of Nike by Phil Knight

Being a native Oregonian, it was fun to read about Nike’s humble beginnings in Portland. Phil grew up in the Eastmoreland neighborhood, and Portland is the backdrop to many events in Nike’s history. Phil begged for loans at banks downtown and taught accounting classes at PSU. He is very humble, self-deprecating, and honest in his memoirs. I was impressed by his search for purpose as a young man as he traveled around the world learning about other cultures. It's inspiring to hear very “successful" people describe their feelings of intense uncertainty, doubt, and fear. Without knowing that, we might assume their path to success was easy.

The Everything Store: Jeff Bezos and the Age of Amazon by Brad Stone

My personal and professional lives were increasingly impacted by Amazon’s services (Prime & AWS) this year, but I didn’t know much about the 23-year-old company. Author and former NY Times journalist, Brad Stone, covers Jeff Bezos’s background as a gifted youth raised by his Cuban immigrant stepfather and self-sufficient Texan grandparents. After reading about Amazon.com’s fast and furious startup days in the 90’s, I was exhausted. The book includes several great anecdotes, like employees so busy that they forgot where they’d parked their car days before, and Jeff’s biological father’s career as a traveling unicycling polo player. I’d recommend it for people trying to understand Jeff Bezos and Amazon’s history, motives, and ambitions.

The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Change the World by Brad Stone

After enjoying Brad Stone's journalistic style of narrative storytelling in “The Everything Store", I read his follow-up business book chronicling these “sharing economy” companies. Uber and Airbnb started eight years ago, while I was worrying about being laid-off during the great recession. Obviously, their story isn’t done yet, and they continue to create major controversies. Some of the most interesting topics to me were how they tackled rapid international growth, the history of Lyft, and the two CEO's (Travis Kalanick & Brian Chesky) frequent meetings to discuss strategies for disrupting their respective industries (hotels and taxis). In retrospect, Uber’s story is a cautionary tale about fostering an aggressive company culture for too long.

Honorable mention: The Phoenix Project by Gene Kim (fictional story, but it feels real) 

Next Time

Wow, that’s a lot of reviews. I’ll stop there and add my favorite “leisure reading” books from the last two years in a follow-up post. Do you have a favorite book you read recently? I’d love to hear about it!

How to Select Software Engineering Tools without Inciting Team Rebellion

Lately I've been thinking a lot about how we choose the tools we use to build software, and how important those choices are. I figured it might help others if I wrote down my own thought process for selecting development tools, so I published this post on Medium: "Choose Your Weapon: How to Select Software Engineering Tools without Inciting Team Rebellion".

This was my first post on Medium where I received help from others using their editing tools. Reviewers can add private comments using the same mechanism that reader use to make public comments. I received some great ideas from Tyler Fitch, and wording advice from my wife. The collaboration features worked great, although my wife missed the power-tools for tracking changes offered by Microsoft Word. This is also the first time I wrote the whole post in Medium, instead of saving drafts elsewhere then pasting it in, so I must really trust their editor.

Thus concludes my obligatory annual blog post. At this point I'm just writing on Medium and using my blog for editorial. Am I doing it wrong? Also, if you have any thoughts about selecting development tools, I'd love to hear them :)