Management, Two Years Later — Values (Pt. 2)

Note: This is part 2 of a series of posts talking about my experiences and learnings the last two years. You can find the rest of the series here.

Early in my management career, I remember being in a planning meeting with another person and that person started raising his voice at me. I remember feeling upset but also really torn. Looking back my mind was torn between two competing thoughts. On one hand, I wanted to tell that person that yelling is unacceptable and that if it ever happened again I’d walk straight out of the room. On the other hand, I also believed in team success above all else. We couldn’t afford to lose that person at that time and I felt I should somehow figure out how to work with this person first. Also, the general perception in Silicon Valley is that sometimes it’s OK to deal with difficult people, especially when you see companies succeed despite difficult leaders (Apple with Steve Jobs, Uber with TK).

I talked with a lot of people in my company to try and get perspective. There were some people who had similar experiences. Still, some wanted to give the person a benefit of the doubt and see if the person can improve. It took me long, long time before I refined my personal values: team success is entirely dependent on having a safe environment first and any kind of hostility is unacceptable under all circumstances. With a better understanding of my values, I decided that not only will I refuse to work with people like that in the future, but that I’d also snuff out that kind of behavior in any team I’m responsible for.

This situation was a pivotal moment in my career. Before, I thought there were at least two truths: 1) that when people join your company they will immediately share your values and 2) that all values are created equal. This situation, however, actually pitted two values I held against each other. This experience forced me to further clarify my values which ultimately gave me clarity on what next action to take.

Defining your personal values is extremely valuable in both the business world and personal life. Values enable you to make quicker decisions when faced with huge uncertainty. As a technical leader, you’ll encounter many situations where it’s unclear which course of action will lead to the optimal result. How do you ensure a project is delivered on time: do you jump in and write code yourself or do avoid playing hero for the team? If the project does go behind schedule, do you tell the PMs that it’s their fault for introducing too much scope or do you tell your scrum team that they should have pushed back? When mistakes are made, do you deliver feedback sternly to get your point across, or do you go with the gentler way to make people feel supported? Knowing your own values will help you navigate through these situations.

Additionally, defining your personal values helps create richer relationships with other people. It sets expectations with other people, especially with direct reports. In the manager-to-direct-report relationship, there is a power dynamic such that the manager is looked upon for measuring employee’s performance (Side note: I hate using the word “performance” because it makes it sound like people can be tuned like machines! But I’m going to continue using this since it’s a common term in the management/HR space). Because of this power dynamic, it’s imperative that clear expectations are set between the manager and direct report so that a strong foundation is established and the working relationship can be genuine and mutually beneficial. This can have the profound impact of influencing how people behave when you’re not around.

Defining your personal values is a tough task because it’s entirely a personal journey. Your experiences, your upbringing, your friends and family all collectively shape who you are today and will continue influencing you in the future. However, there is a process to understanding your own values, and I hope that sharing my process can enable you to refine your values so that you can make better, faster decisions and build richer relationships with others.

1. Start off by putting your values into words.

It’s simple, but writing down your values forces you to break down complex thoughts and feelings and condense it into a set of concrete words. To start off, think about the most critical situations that you’ll face as a technical leader and what you believe is best course of action. Drawing common themes will lead you to your values.

For example, here’s a series of questions that revolves around operational excellence. Note that each question ties values relating to ownership, communication, and teamwork.

• Should everyone be on-call for production site issues, only the team leads, or just be the managers (aka just you)?
• Do you believe that every person on the team should be empowered to have direct production access, or do you believe that security policies are absolutely critical?
• Do you believe that every app should have an SLA (e.g. availability, response times, etc)? If so, what kind of SLA do you think is appropriate for the application? Also, what kind of additional effects you hope to create by defining an SLA?
• Who should be responsible for deployments?

Here’s a set of topics that you can use to help jump start additional situational questions:

• Code quality (relatedly, tech debt)
• Team dynamics and culture
• Ownership for an individual/team/organization
• Employee happiness
• Giving/receiving feedback
• Engineering/Product prioritization
• Learning/development
• Inter/intra-team communication

(Side note: doing this exercise is also super helpful in preparing you for interviews as a team lead or manager!)

2. Recognize that nearly all your values define are simply guiding principles…

If you tried answering the questions I posed above, your answers probably start with “Well, it depends...” To be rigid with ALL your values means that you can’t adapt to new, ambiguous situations. If you were dropped in a different team where the software’s business requirements and the tools are completely different with different people and you bring in strong opinions, the team will quickly tune you out. You also run the risk of potentially making suboptimal decisions. For example, let’s suppose that you believe high availability and performance trumps everything else when it comes to prioritizing technical tasks. But let’s suppose your project is to build a simple internal tool with a minimal feature set, and it’s only used by a very small number of people at any given time. It probably makes more sense to optimize for simplicity and ease of maintenance (e.g. Heroku, Postgres, Ruby/JS/Python) and not over engineer it (e.g. AWS/Kubernetes, Cassandra, C). Obviously, this doesn’t preclude you from tackling some low-hanging fruit scalability, but being flexible when it makes sense leads to the optimal solution.

There’s a saying that applies here: have strong opinions, but weakly held. It’s important to recognize that the world does not operate in black and white and neither should you. If you only operate in black and white, then you’re going to be consistently disappointed for the rest of your life.

3. … But sometimes, you’ll realize “absolute truths” and that’s OK too.

While 99.9% of the time you should be flexible with your values, if you do enough introspection and reflection you’re going to realize some “absolute truths”, or values that will you’ll never compromise on. Drawing clear lines in the sand for what’s acceptable (and inversely what is unacceptable) is key to something that’s so crucial and basic when dealing through uncertainty and adversity: confidence and self-respect.

Some of you may ask, “Well you just said that I shouldn’t operate in black and white, so aren’t you contradicting yourself?!” So to clarify, nearly all your values should be guiding principles so that you can adapt in a multitude of situations, but(!) as human beings it’s imperative to have a solid moral foundation. For example, you may believe in fundamental truths through your religion, or you may believe in ideas like free speech and equal rights are unequivocal. As human beings, it’s in our very nature to hold absolute truths dear to our hearts; to completely reject that is to deny our very nature. (Side note: I feel like I’m just re-packaging ideas from Westworld like core drive and reveries. I swear this blog post didn’t come from just watching Westworld all day long!). Having zero absolute truths can be perceived as not having a backbone, which undermines anyone’s ability to lead. So to conclude: we should be as flexible as possible, but it’s OK to hold some absolute truths as long as we’re open to re-assessing them when presented with new data points. Which leads to my last point…

4. ABR — Always Be Reflecting

Everyday is a gift because you will receive additional data points about what works well and what doesn’t. To never reflect is a missed opportunity to refine think about the things that you have learned and apply them in refining your values (which, if I haven’t made clear, will impact your ability to make optimal decisions and build meaningful relationships). Create a habit of asking yourself the question, “What did I learn today, and does this change how I view the world?”

While introspection is critical, this entire process isn’t done in isolation. It’s also crucial to find a group of people that you really trust in sharing your thoughts and exposing yourself to different perspectives. Reflection in isolation is worst case an extremely frustrating/lonely experience and best case leads you to sub-optimal or incomplete conclusions of the world. Data points to validate (or disprove) your values aren’t just pushed to you in life; you should also pull data points from other sources. Reading many different blogs and books is another source to help widen your perspective. All this follows the same principles as machine learning: the more data points you have to feed into your mental model of the world, the more accurate your mental model will be.

Another personal story

At the core of it all is that this process is really about exploring and learning about yourself. So I’d like to to end this post with a personal story about some of my absolute truths and what I’ve learned through my experience.

So near the end of my tenure at Teespring, the company wasn’t hitting its numbers and there were legitimate concerns throughout the company about its financial viability. In a meeting with all the managers, we were asked to not only work more hours ourselves, but that we need to demand the same from our direct reports. There’s a lot I didn’t like about the message, but the thing that bothered me the most was that directive that I had to demand my team to work more hours.

This pitted me against two of my absolute truths. The first is that I only ask people to do something if it’s something I’m willing to do myself. I believe that as leaders, our biggest vehicle to inspire is through action, not words. For example, when I ask my team members to participate in an on-call schedule, I make sure I’m the first person in that schedule. This helps highlight to my team that they’re not alone in this. I don’t do this because I’m trying to manipulate people to do what I want them to do; I do this because I believe that being on-call is critical to the health of the business, and I believe that people will follow if you lead by example.

Throughout my time at Teespring, I put in a ton of extra hours because I believed in the startup. But in that meeting with all the managers, I was already feeling burnt out and I knew I myself just couldn’t give anymore to the company. And it also broke my heart imagining delivering that message to my teams. Some people had families, and they didn’t have much skin in the game (i.e. equity). Most people joined Teespring because they thought working with t-shirts was going to be cool and fun; but the reward for working more was not something that they would (nor should) make huge personal sacrifices for.

The second absolute truth is that I believe people can only be motivated through inspiration and togetherness, not through fear and competition. In this situation, I totally understand why we were being asked to put in extra hours. Everyone knew this was a precarious time. A lot of people really, really still believed in the company’s mission. However, in that meeting with all the managers the message was delivered with an defiant, dismissive tone. Some people brought up morale concerns. The response was that people who wanted to work extra hours are the true believers. Those who didn’t are irredeemable and should simply leave the company.

These absolute truths are core to who I was (and still am). That night, I asked myself if there’s anything I can do to help steer the company to a better place. I had already been through a startup’s downturn before (Fundly), so I felt that our teams had already tried everything. The next day I put in my notice. But before my last day, I learned that Teespring wouldn’t institute the longer work hours policy.

I never regretted my decision to leave Teespring. It was a liberating experience; it felt like I honored something deep within myself and freed me to pursue my next opportunity that was going to rejuvenate me. I recognize that there were probably a lot of factors that went into Teespring not instituting the longer work hour policy. But I’d like to think that my leaving had some impact in that decision. And while I may not know full truth of what could have happened with Teespring had I stayed, I feel reassured knowing my absolute truths that I live my life by.