leadership philosophy

Leadership books that have impacted me greatly

This is intended to be a short list of books that really changed how I think, with a small blurb about how I think about each one.

The Top 3

Immunity to Change

This book unlocked something deep for me – a new attitude towards approaching challenge, change, growth, and knowledge at work. If you’re feeling stuck this book can and will help.

The Fifth Agreement

I read this book with discernment – there’s a lot of “woo woo, spirit-world” language here – to take what’s valuable to me personally while disregarding the rest. This book built on the concepts in Immunity to Change for me and showed me how to think about reality in a much clearer and more effective way.

The Five Dysfunctions of a Team

This is the #1 book I’d recommend to all new managers and aspiring leaders – it lays out an easy-to-understand and holistic framework any team can rally around to work toward results more effectively.

Honorable Mention

Extreme Ownership

This is a close 4th-place for me and introduced me to a clear mindset I could embrace to feel authorship of all the results in my world (while still working on a team!). If you’re feeling a little zany, listen to the audio book – it’s read by the authors, both of whom are former Navy Seals with awesome gravelly voices ✨

Nonviolent Communication

This book, despite its grandiose name, simply taught me to communicate in a way that is authentic and doesn’t trigger other people’s emotions – a super important and valuable skill to have in life and work.

Radical Candor

This book taught me why it’s mission-critical to be authentic, say what you mean, and reveal more of yourself to the people you’re working with? Read Radical Candor.

Start with Why

This book started me along a longer path oriented toward a new paradigm of leading – one where every single person on your team is a leader and decision-maker. Start with Why started me thinking about what my role could be in a world where it’s better if other people make most of the decisions.

An Everyone Culture: Becoming a Deliberately Developmental Organization

This book gave me a hard look at how to build teams and companies with growth and transparency as a #1 priority and convinced me that bold, growth-first companies are much more successful than traditional organizations.

Changing on the Job

This book is a great “chaser” book to Immunity to Change and dug me deeper into how I as a leader can work with individuals on my team to unblock them and help them grow by their own steam.

Good Strategy, Bad Strategy

Simply the authoritative read on how to think about strategy. For me this was a super pivotal book for my understanding of how businesses win in the market through bold strategic choices.

Drive: The Surprising Truth About What Motivates Us

This book brought a lot of things I had picked up in passing home for me into a concise framework around how we make meaning and find motivation in our work.

Tiny Habits

I love this book because it clearly gets into the psychology of how habits are formed – super applicable to my own behaviors and how I think about building software that changes how users work.

An Elegant Puzzle: Systems of Engineering Management

This book is a super prescriptive deep dive into one experienced leader’s mental models and tactical advice for running an engineering organization. I mostly agree with the author, but we’re not always in sync. If you’re looking for some concrete pieces of advise and are good at taking what’s valuable to you from a book and leaving the rest, look no further.

leadership philosophy

My Personal Vision Statement

My passion is in the exploration of what is true. I believe a higher well-being is available to every human being through courageous and curious self-reflection. I am dedicated to empowering as many people as possible to pursue, realize, and share their genuine selves.

leadership philosophy

A Guide to Working with Max

Here are some honest, unfiltered things about me:

  • I have a high tolerance for conflict, and I’m not easily offended. You can say pretty much anything to me and I’ll take it in stride.
  • If I’m working with you, I hold you in the highest positive regard, always. I trust by default and I know I need to give you respect to get it back. At core, I deeply believe in you and your potential.
  • I’m driven primarily by growth and I’m obsessive about discovering things I could do better. I’m constantly thinking about my blind spots, and if you let me know about an area I could improve I’ll appreciate it (really!).
  • I grew up with three parental figures who were entrepreneurs and I started my own business early on in my career, so I value an enterprising, scrappy attitude in the people I work with.
  • I have a terrible memory that’s only supported by my rigorous list-keeping. If I forget something we’ve talked about, it’s likely because I didn’t write it down.
  • I have a weird/dark/sarcastic sense of humor, which can rub people the wrong way. If that’s not your thing, just let me know and I’ll turn it down.
  • Forgiveness is a core strength of mine. I’ll always forgive and legitimately assume the best intentions from people I work with.

What makes me grumpy:

  • I get grumpy when people I work with are indecisive for a long time. I’m deeply oriented around the question “what do we do now?” and I start to feel stuck if we can’t make forward progress after a while.
  • I get grumpy when someone I’m talking to has trouble going from abstract ideas to concrete actions for similar reasons. I’ll do my best to steer the conversation into next steps when this happens.
  • I hate being interrupted. It makes me feel like you don’t respect what I have to say and I shut down if it happens frequently.

What I’m working on:

  • I’m working on being more patient. I can get impatient sometimes, which usually gets triggered when I perceive there’s a risk to something I really care about. If you see me start to get impatient, please call me out on it and I’ll take a breath so we can refocus on solving the problem (saying something like “can we take a breath for a second?” usually helps a lot).
  • I’m working on getting better at taking complements. If you say something nice about me I’ll probably grimace, but I’ll feel good about it later.

I really appreciate it when my teammates do this:

  • Are open and honest with me about how you’re feeling. I see deep, two-way communication as the way we can learn to work together. Just try me.
  • If you hear me say something that sounds odd or wrong, give me the benefit of the doubt. Say, “When you say X, I hear Y. Is that what you meant to say?”. A lot of the time there’s a communication problem in a way I hadn’t anticipated and I’ll be able to rephrase in a better way.

Qualities I particularly value in people who work with me:

  • A deep commitment to openness and honesty in our work relationship.
  • The ability to break down large, ambiguous problems into chunks and display them visually. I’m a very visual person and this helps me understand solutions!
  • An entrepreneurial attitude of ownership of results, not just for your personal work or your team, but for the company’s success as a whole. The desire and ability to fix things when they’re wrong, even if it’s outside your normal work purview.

Some things that people might misunderstand about me that I should clarify:

  • I have an exploratory brainstorming style and I like to throw ideas out there and see what sticks. Sometimes people take these half-formed ideas as something I strongly believe in, but that’s usually not the case. I’m interested in your opinion and pushback regarding what I’m saying because I’m legitimately interested in working with you to find the best solution to whatever problem we’re discussing!

How I encourage people to do their best work and develop their talents:

  • I encourage ownership over all the results in your world.
  • I listen intently to where you want to grow and try my best to open up opportunities for you in those areas.
  • I try to strike the balance of getting you the right amount of ambiguity and autonomy for the things you work on. I want for you to feel challenged, creative, and empowered while we’re working together.

The best way to communicate with me:

  • I’m an extremely visual person. Charts, graphs, pictures, and lists are my preferred methods of communication. If we’re having trouble communicating, taking it to a whiteboard will help me a lot.

The best way to get to a shared understanding of something with me:

  • Start by listening to me and understanding where I’m coming from. Try to re-express my position so clearly, vividly, and fairly that I say, “Thanks, I wish I’d thought of putting it that way.” I’ll do the same for you! (For more on this idea I’d recommend checking out Rappoport’s Rules)
  • I have a strong aversion to Arguments from Authority – if you take the time to walk me through your decision-making journey from start to finish I’m extremely likely to engage constructively with your idea!

How I like to give feedback:

  • I like to give feedback in-person and as soon as possible. I like to get your unfiltered reaction to what I’m saying because it’s my goal that feedback I give you shouldn’t be a surprise. If I’m surprising you with feedback then that’s a flag to me that I need to do a better job of being open and honest with you.

How I like to get feedback:

  • I like to get feedback in-person and as soon as possible. There’s one exception to this rule: if you don’t have time to dive into the feedback with me at the time, please wait until we have the time to break it down together.

code philosophy

How we build at Textio

When’s the last time you had a chill-inducing, unforgettable idea? Ideas are fragile things, and good ones are incredibly rare. Ideas also have power – the right idea can be the catalyst to change our lives, our company, and our world.

At Textio, our teammates bring unique, fresh ideas to their work every single day. A big part of what we do on the engineering team is build out those ideas, collaborate across the company, and create something that’s as true as possible to each idea’s spirit. Here are some of the principles we believe make Textio one of the best places to build as an an engineer.

We value people over process

Processes exist to serve people. At Textio, we work diligently to ensure all our processes are both valuable and flexible. If a process is tedious, dehumanizing, or is taking more time that it’s worth (see: granular time tracking) we replace it with something lighter that gets us a similar benefit. We believe that no process can replace human conversation, and we build our processes to encourage more discussion and collaboration in-person.

We know small, empowered teams build better

At Textio we hire people who are great at something, give them hard problems to work on, and trust them to be outstanding. To facilitate this, work at Textio is done in Squads. Squads are small teams of fewer than 9 people from across the organization that are empowered to solve a hard problem. Each squad starts with a specific idea that grows and evolves as the squad builds. Squads decide on a meeting cadence and a tracking system that works for them internally, which varies quite a bit based on the size and scale of their idea. Each squad has ownership of the results of their idea across the company, and they work to create the best overall results together.

Every week on Fridays, we give Squad Updates (or “squpdates”). Each squad takes the time to write a short summary of their week, which goals they’ve completed, and what they’re planning on starting next week. This lightweight process helps the entire company understand what’s being worked on and where we are along each idea’s journey.

We get lots of perspectives early

Ideas at Textio start small. Usually they’ll look something like a thumbnail and a few bullet points. This is the perfect time to get varied perspectives: when there’s still lots of ambiguity and things are easily moldable. At this early stage we start with a meeting between a business advocate, who is the person who knows the most about the spirit of the idea, and the technical lead of the squad, who can be any developer. These two collaborators work together to discover what kinds of people they’ll need to make the idea a reality. Who can help them see more viewpoints on the idea? What does the architecture of the solution likely look like? How can they execute in a way that plays well with how the rest of our offering works? What development talents will be particularly useful in building the idea? The technical lead and the business advocate work together to answer these questions and more.

As the solution for the idea comes into focus, more people join the squad according to what its members determine it needs to grow and thrive. Textio’s managers work hard to ensure all running squads have the people they need (and to give everyone the growth opportunities they’re looking for in their career). In this way, squads grow organically and develop in as broad a frame of reference as possible.

We aren’t afraid to change our minds

Despite our best efforts, sometimes we make a decision or build something that doesn’t work out. It can be as blatant as the code we’ve written not being flexible enough to fully realize the idea. It can also be subtle – sometimes we’ll build something and it doesn’t feel right yet. There’ll be too much friction in our user’s experience or what we’ve built won’t solve people’s problems as fully as we’d hoped. In these situations it’s important to be able to take a step back, rethink, rework, and rebuild.

Making the decision to scrap work, go back and rethink is incredibly hard. It’s hard because everyone believed we were doing the right thing – everyone was bought in and excited about what we were doing, and acknowledging we were wrong isn’t something that comes easily. Ultimately it takes everyone on the squad having the ability to set aside their ego and break through the sunk cost fallacy in order to value creating something awesome for our customers. I’ve witnessed squads do this again and again at Textio, and the level of patience, grit, and dedication to quality displayed by my teammates is a constant source of inspriation to me.

We make tradeoffs together

At Textio we talk a lot about tradeoffs. What can we deliver to our customers if we simplify this feature? What would it take to add an extra flourish to an experience? Could we take on some responsible tech debt to ship this idea faster and pay it down afterward? Questions like these are asked throughout the product lifecycle here, and we answer them as a team.

We use dates as a tool to help drive tradeoffs as we build. I’ve worked at organizations that use deadlines as a means to pressure developers to get more done or work overtime. This is an incorrect and incredibly harmful use of dates not just because our teammates get burned out but because the focus of deadlines is on the date instead of the idea. We think about dates much differently here.

We’ll start with a thought experiment asking, “what would it mean to deliver this idea by this date?”. Usually the answer involves a lot of collaboration between everyone on the squad, business advocates and developers alike. Are there features our customers don’t need immediately? Are there ways of building that might be faster? What would we be able to likely deliver by the proposed date? This thought experiment around dates isn’t a strict deadline but rather a way to focus us around delivering the most value quickly. No one needs to burn themselves out, and if we discover something we didn’t take into account initially we’ll just do the exercise again. We know estimates are difficult and by their nature can’t take into account everything that’s needed to deliver a project! Our ultimate focus is on quality, and we treat dates as a way to help us deliver the high-value pieces sooner.

Summing up

I love being an engineer at Textio. Building here is infused with cross-functional collaboration, focus on realizing an idea, and treating people like human beings. I believe our principles for how we build show up directly in the quality of our product. I’m incredibly proud of what we build every day, and how we work together to bring our best ideas to life.

leadership philosophy

Why I Work for Startups

In the tech industry, a “unicorn” is a company that has raised a round of funding that values the company at over a billion dollars. Every ambitious techie with an entrepreneurial spirit looks to these companies with a gleam of respect and envy in their eyes. In Y Combinator’s How to Start a Startup series, founders of unicorn tech companies warn potential founders against joining a startup for the wrong reasons. Movies like “The Social Network” represent startups as glamorous vessels of infinite potential and success, but in reality working for a startup usually boils down to a lot of hard work and stress.

Dustin Moskovitz, a co-founder at Facebook, lists four misconceptions about working for startups:

  • It’s glamorous
  • You’ll be the boss
  • You’ll make a lot of money and have more global impact
  • You’ll have more work flexibility

Dustin then moves on to dismantle the validity of these ideas one at a time (I’d highly recommend watching the video for the full explanation). Basically, if you’re looking for any combination of these ideas you’d be better off working for an established company. In the end, Dustin concludes that the best reason to join a startup is because there’s an idea so compelling, so utterly fascinating to you that you must work on it. To use Moskovitz’ words, the idea has to be “beating itself out of [your] chest, forcing itself into the world”.

While Dustin is absolutely right, I believe there are other good reasons to work at a startup. Many of these reasons are the same reasons someone would decide against taking the plunge, but they’re exactly what I’m looking for in my career.

Influence Over the Company’s Direction

While working for a larger company might net me more influence on the direction of the world, I can’t beat the direct influence I have on the direction of my startup. At a startup, things are in general much more fluid and open to change, from technological tools to the sales process. I crave responsibility in my work and having a significant effect on the success or failure of my company matters a lot to me.

Lots of Ownership

Working for a startup makes me feel responsible for the success of not only the projects I’m working on, but the company as a whole. At a startup I can craft (and take pride in) something I believe in. Realizing that no one’s going to make things work if I don’t rise to the challenge motivates me to push myself every day.

You Matter a Lot to Your Teammates

In a startup, I rely heavily on the dedication of my team, and vice versa. In larger companies it’s acceptable to have people who aren’t contributing or who aren’t a good fit. In a startup there is simply no room for anything other than a collaborative, ego-less, “leave nothing behind” attitude, and I can see that attitude reflected in everyone I’m working with. The feedback loop of passion and energy I get from my teammates at a startup is incredible.

It’s Hard

Simply put – I want to be challenged, and there’s no challenge quite like joining a startup. Living a comfortable life is not my goal. I want to be constantly striving to be better in everything I do. For me, working for a startup provides a strong impetus to improve myself and my company every day.