To Future Me, on Engineering Management, No Bull Included

Next week I’m moving from a manager role back into an individual contributor role as a software engineer at Trello. This career pendulum swing comes after four years of dedicating myself to learning the craft of engineering management.

I made this decision slowly and thoughtfully over the last 9 months. I love both roles deeply. I have proven to myself that I can be effective in either role. I expect I’ll end up back in management at some point in the future. 

However, as I enter the twelfth year of my career, I’m not ready to let go of the joy and fulfillment that I get from building software hands-on during my workday. It’s time to shake off the technical rust I can feel starting to accumulate.

One resource I visited repeatedly while making this decision was Charity Majors’ essay The Engineer/Manager Pendulum. That post is a recommended read for anyone considering crossing the engineer/manager bridge in either direction.

The following is an attempt to capture a “No Bull$#!@” list of notes for my future self when I’m inevitably jumping back into management. This list is not intended to be universal advice. It is specific to me, to my personality, and experience. I hope it will be insightful to someone considering taking the leap in either direction.

• Trust is the foundation and currency of management. Trust is required up, down, and sideways. Work hard to earn trust. Strive to keep it. Give trust to others quickly and freely.

• Shipping value feels good. Investing in a person and watching them grow and have an impact feels amazing.

• Building a team that is effective and healthy is immensely rewarding but has a long feedback loop. Patience is required.

• Performance management is a necessary part of the management role. I don’t personally derive much enjoyment from it.

• Flow state is far less frequent in a manager’s schedule. Make sure you have other sources for experiencing flow in order to maximize fulfillment.

• A manager’s schedule is often dominated by time spent talking to other human beings. As an introvert that means I have to be extra diligent about managing my energy and focus or I end up drained.

• Managing a medium to large size team (8+ direct reports) requires investing time and attention broadly across many simultaneous threads with frequent interruptions. I personally derive more enjoyment from working deep rather than wide. This means in order to succeed personally, I have to be deliberate about finding and blocking off time to allow myself to spend some time on deeper topics related to management.

• It took me a long time to learn how to delegate aggressively enough. Learning to delegate responsibility should be a top priority for new managers. Give away as much responsibility and hands-on involvement as you can. If it doesn’t feel unnatural and uncomfortable at first, you either aren’t delegating enough or you are a rare unicorn born to manage.

• The feeling of starting to lose the “sharp edge” of your technical skills is scary. It’s ok and expected, don’t stress. Consider either finding side projects to occasionally scratch that itch OR embrace a period of letting the skills fade knowing you can choose to dust them off later on. You are focused on developing your skills as a manager, not an engineer. You can’t do both well at the same time.

• Trust your intuition and experience. It’s critical to check your assumptions and biases but it’s also important to move with confidence and conviction rather than second-guess every signal you are picking up.

• Have hard conversations as soon as possible. When handled with grace and understanding, sooner = less painful. This is key when it comes to giving critical feedback. If you find yourself wondering if it’s time to have a hard conversation, you probably should have already had it.

• Management offers a lot of opportunities to speak. Remember that listening is often a more powerful leadership tool than speaking.

• Management is really fertile ground to apply systems thinking and that’s a lot of fun.

• Never sugarcoat your expectations of people. People appreciate clarity and will rise to the challenge of clear explicit expectations.

• It’s really hard to push people to grow in directions they don’t desire to grow. Open interesting doors, present challenging opportunities, and then follow their lead.

Make Promises, and Keep Them

“Did you come up with a solution for the customer renewal problem?”

The question gripped my suddenly overwhelmed and embarrassed heart. Two weeks prior, I had agreed to create a proposal for solving this particular issue. I had dropped the ball.

“Keep your word” is a core value I teach my children. It’s also a requirement for high performance in most jobs. When applied consistently, doing what you say you are going to do can be a professional superpower.

When someone tells me they will do something I expect them to follow through about 9 times out of 10. Unfortunately, keeping your word 90% of the time is not good enough!

Think about an app that you depend on almost every day like Gmail. If Gmail were only 90% reliable, it would be out of service for over a month every year. No one would use the app if that were the case. 

People are not expected to be as consistent as email software but we can learn a valuable lesson from Gmail. The reliability that an application, car, appliance, or human being offers us shapes the kind of relationship we have with it. If we feel like we can depend on something or someone, it frees us from having to make contingency plans. A high degree of reliability lowers the mental and emotional overhead of engaging in a relationship. People remember when they feel wronged. Sometimes all it takes is one broken promise to taint our reputation.

For that reason, some people go to great lengths to avoid commitment. This is impractical and undesirable. Studies have shown that making and fulfilling promises is a strong way to build trust and connection. We should look for opportunities to make promises and commitments that we can follow through on.

Why don’t we keep our promises and what can we do about it? 

Mistake #1: We over-promise

My wife and I recently did a full interior remodel of our house. Near the beginning of the project, the general contractor told us the rough plumbing would be completed in 3-4 weeks. It ended up taking 8 weeks! Similar timelines were communicated and inevitably missed again and again throughout the project. Despite the contractor delivering high-quality work, this pattern of over-promising and under-delivering drove us insane. It negatively complicated what would have otherwise been a happy customer relationship.

Over-promising is communicating an unachievable timeline or overstating confidence in the expected result. It can also be presenting your intentions as guarantees before they’ve come face to face with the unmoving contours of reality.

In order to stop over-promising, you have to train yourself to recognize when you are tempted to make someone happy by committing to something you can’t guarantee. Once we start to recognize when we are overpromising, we can chunk our promises into pieces that we can guarantee delivery on.

For example, instead of promising my co-worker a finished proposal in two weeks, I could have promised to schedule a time to begin work on the proposal and agreed to give a status update in the next meeting.

Mistake #2: We fail to create action plans for our commitments

My parents recently visited from out of town. At the start of their visit, my 10-year-old son asked if we could take my parents to his favorite park that has a goldfish pond. I figured we would have plenty of opportunities to hop in the car for a quick outing the following week so I said “yes” without hesitation. By the end of the week, we hadn’t made it to the park and I had broken a promise to my child. I can still feel the sting of disappointment in his voice.

In this case, my problem wasn’t overpromising. There was time to go to the park. My mistake was not following through on carving out space for my promise in the family's list of priorities.

I see the error of sloppy follow-up run rampant in many professional lives. A “yes” with no specific action plan, priority, or deadline is begging to get bumped by someone else’s plan, priority, or deadline. This mistake can be a fast track to a mediocre reputation.

The solution to sloppy follow-through is building a habit of writing down and scheduling a specific plan every time you make a promise. A goal with no game plan is a countdown clock to failure. Build this habit by deciding where you will write down your action plans and setting a daily reminder to take inventory of any promises you haven’t captured.

Every day is an opportunity to be more reliable

I could have avoided the mental anguish of disappointing my co-workers had I recognized the temptation to over-promise and instead made an achievable promise with a scheduled plan of action. Once you internalize how valuable reliability is, you will gain the clarity required to create habits that will make you a rock of trustworthiness. Use each day to cast a vote for becoming someone who makes promises and keeps them. It’s a sure-fire way to set yourself apart in a world of flakey people.