Book notes & reflections: The Art of Leadership

Scott Brady
Scott Brady
Leadership

In this article, I’m going to share my notes and reflections from the book “The Art of Leadership: Small Things, Done Well” by Michael Lopp (aka “Rands”). I’ll give an overview of the book itself and then some of my key takeaways, how they relate to my own experience, and what I am trying to implement as a result. I’ll finish with some career reflections that this book has helped clarify, including why I recently changed roles.

Overview

The Art of Leadership is a collection of essays from author Michael Lopp, offering insights into their time at Netscape, Apple, and Slack that corresponds to the different stages of their career.

The book cover for Michael Lopp's 'The Art of Leadership: Small Things, Done Well', published by O'Reilly. The cover includes a picture of a bee.

The book is broken into three acts corresponding to three stages of the author’s career: manager, director, and executive. As an experienced team lead looking to start managing managers in the next 1-2 years, most of my notes and head-nodding moments came from the manager and director sections.

It’s a small book, coming in at around 170 pages, but it is dense with anecdotes of lessons learned. In addition, each chapter is an essay focused on a single lesson. So, while it is something you can read cover to cover, each chapter is standalone, meaning you can pick and choose chapters based on your current dilemma.

As someone who struggles to concentrate on reading these days, I really like this approach. I read this book from start to finish; however, I found it hard to get through a few chapters at a time due to the amount of reflection it triggered, matching the anecdotes to my own experience. But this is a good problem to have! I listened to this book as an audiobook and then re-reviewed useful chapters in the physical book.

The writing style isn’t for everyone, as evidenced by some of the reviews on Amazon and Goodreads. It’s a very masculine voice with a conversational tone that relies on anecdotes. I saw one review call the author a “tech bro”, which I think is a tad unfair.

Storytelling and anecdotes are by far the author’s strong suit, and these are used throughout. But these are short stories used to illustrate a point, rather than the aimless stories you often find in management non-fiction, where you can often feel the author desperately trying to find a way to make it relevant.

Book notes

These are the chapters I found most useful and triggered some serious reflection. Where appropriate, I have linked to the original article on the author’s website, but I’m not entirely sure how much they differ between the blog and the book.

Management is a career restart

You do not need to become a manager to advance your software engineering career.

I had not really considered this until recently after a mentee mentioned that they aimed to become a manager to earn more money. They assumed that management is a promotion and the natural career progression for a software developer. Unfortunately, this assumption can lead to unsuitable managers, who find themselves burning out and leaving a role or becoming the main character in the “new manager death spiral”.

Unlike when you are promoted as an individual contributor, when you become a manager, you are not equipped for the job. Management is a career restart, and you will need to change how you do things.

Dispelling this assumption is also one of the reasons why having a well-defined career progression framework in your organization is so important, clearly showing the split career paths of individual contributors and managers. This is vital if you want to retain strong software leaders that do not want to manage.

The new manager death spiral

I recommend giving this one a read. The “new manager death spiral” is a story where every typical new manager failure happens one after another. Where the protagonist takes their skills and mindset from when they were an individual contributor (emphasis on the past tense) and apply them in their new management role.

If you’ve already started your leadership journey, then you’ll likely see yourself in different parts of this story. While this is a worst-case scenario, if you’re anything like me, you will still feel guilty when you see yourself reflected in some of the mistakes.

Blue tape – everything is broken

When everything around you changes, your ability to see imperfections rises dramatically. This can be true whether it’s with a new car or a new job.

After the honeymoon period of something new, you are going to start seeing everything that is wrong and enter a phase of despair. You will try and convince yourself that you made a terrible mistake and that everything here is broken. Most of us have experienced buyer’s remorse or felt that pang of regret when looking back through rose-tinted glasses.

When everything looks broken in your new job, the solution the author recommends is patience. Don’t ignore it or kick and scream. Instead, mark everything you see as broken (mark it with the blue painter’s tape) and sit on it.

  1. In a new context, you’re going to notice everything that feels off
  2. Make a list of everything that feels off, no matter how big or small
  3. Wait a bit, like a month, but address everything

You don’t commit to fixing everything, but you commit to addressing it. Addressing it might mean that you fix it or that you now understand it & can clearly explain why not fixing it is the right move. What seemed urgent at the time will likely become irrelevant after a month or two once you have developed some context and understanding.

This hit me hard in a recent hybrid role, where the individual contributor in me wouldn’t let go of this “everything is broken” mentality. More on this later, but in this instance, “Grumpy Scott” emerged and immediately started asking hard questions that often picked at old wounds. Unfortunately, while technically correct, “Grumpy Scott” isn’t the best leader or role model.

Act last, read the room, and taste the soup

One thing I’ve been struggling with recently is contributing to meetings when I don’t have any subject matter expertise. This is when the impostor syndrome really kicks in, and I can find myself becoming small and simply not saying anything, which is the complete opposite of what I want to achieve.

The author gives some good guidance on this. As the leader, it is your job to “taste the soup”. To get a sense of how the soup has been or will be made. As a leader, you likely have experience. You’ve seen things that have led to success or failure in the past; when it’s time to review something, it’s this experience that allows you to ask small and critical questions. This can help create an environment of helpful curiosity.

This is better than the opposite, a know-it-all micromanager who is looking to impose their will, noisily ignoring the room, and not letting others share their thoughts or allowing for debate and discussion.

Say the hard thing

The author echoes a similar sentiment to Radical Candor – not saying the hard thing only leads to disaster. Giving timely feedback is important and helps the team grow, which is a large part of a leader’s role. Not doing so is a mistake every leader will make multiple times before learning this difficult lesson.

Why and how to say the hard thing is a topic for another day, but in this book, the author offers some insight on how we rationalize delaying feedback (temporarily or indefinitely) and how we can receive hard feedback.

One thing that really stuck is that while it is empathetic to put yourself in the recipient’s shoes and feel their reaction, by not giving the feedback or by watering it down too much, you are not doing your job properly.

“[…] the work you should value the most, is the growth of your team. Compliments and recognition are one way to highlight exceptional work but saying the hard thing always gets their attention.”

Another interesting point is that when we fail, we protectively rationalize, creating a story in our head that is acceptable to us and doesn’t keep us up at night. After all, we are the main character in our heads. I think this is important to remember not only when receiving feedback and understanding our reactions (short-term and long-term) but also when a colleague fails to show any meaningful progression after a mistake.

Hearing the hard thing

“Do you have any feedback for me” – Scott Brady in every 1-to-1 ever after.

This book breaks feedback into three types:

  • no big deal feedback – easy to accept and easy to action. This is the ideal kind of feedback, but not always possible
  • slow burn feedback – feedback that seems like no big deal feedback until you’re in the car on the way home and realize that it was just hard feedback or possibly even untrue. I knew a serial offender of this kind of feedback, and it just hurts
  • plain hard feedback – critical feedback that makes the room go cold.

When receiving critical feedback, do not get defensive; instead, follow these steps:

  1. No matter how critical the feedback, listen and search for just a glimpse of understanding. Ask yourself, “why are they choosing to give me this feedback right now?”. There is always something of use in the feedback. Even if it’s an outright lie, why are they telling you the lie?
  2. Repeat what you heard. Prevent yourself from building your own narrative. Find clarity and acknowledge the feedback.

The author gives an excellent example of step 2, revealing clarity from the feedback: “You weren’t prepared for that all hands.”

Me: “Just so I’m clear what you’re saying, you’re saying that I didn’t perform well at the all hands?”

Them: “No, I didn’t say that. You’re a delight to watch speak, but you weren’t prepared. The narrative didn’t hold up and I think you think being eloquent is making up for the fact that your thesis wasn’t sound.”

Me: “Oh.”

I wish I’d been able to apply these steps in conversations in my previous roles. Taking a step back and asking myself, “why are they telling me this now?” would likely have changed the course of my career.

Everything else

Other key snippets and quotes that I found helpful.

Always assume they have something to teach you

There are going to be meetings that offer you little to no value. You can’t get away from this. So, to increase the value of a meeting, assume that they have something to teach you.

A performance question

Before putting some on performance management, ask yourself or their manager:

“Have you had multiple face-to-face conversations over multiple months with the employee where you have clearly explained and agreed there is a gap in performance, and where you have agreed to specific measurable actions to address that gap?”

It’s a big question, but if you break it down, it makes it super clear what needs to happen to prevent the employee from being caught unaware.

Look for the stories

Look for the stories in an organization. The ones that get told fondly over beers. While these stories may not be entirely true, how they are told often reflects the company’s real values and culture. For example, a story of failure and compassion is one of the reasons I decided to join ClearBank.

A precious hour

Take an hour out of every day to build something – you won’t be getting “in the zone” as a manager. Instead, scratch that itch and find that inspiration by aiming to take an hour to build something. For example, I take time to tweak my website, work on one of my crappy OSS projects, or write a hopefully not-so-crappy article.

How to recruit

Recruitment isn’t just down to the recruiter; it’s also your responsibility. Build a list of people that you must work with again. When you have an opening, try reaching out to suitable people on this list and ask them out for coffee. Even if they’re not interested in moving jobs, you get to meet up with an old friend.

Gossip, rumors, and lies

“In the absence of information, humans fill the gap with the worst possible version of the truth”. I just really liked this quote.

Allergic to wisdom

Every start-up has a “unique culture” and is “doing things no one else has done before”. This is both true and false. Don’t take away their wins; they have actually built something and created a successful company. But also remember that you were hired for a reason; your past experience and wins have been brought in to fix a problem or improve this “unique” culture.

Closing thoughts

Rating: 5 out of 5 stars star star star star star

Overall, I highly recommend this book. While it was one of the first leadership books that really spoke to me, I do think its combination of anecdotes and lessons learned offers some great insight.

Career reflections and why I am taking a break from identity

Some of the above lessons have certainly come at the right time in my career and have helped me make sense of what has been working for me and what has not. It has also shown me the importance of discussing leadership experiences and mistakes and even documenting them, as I have here. It can feel a bit pretentious, but it’s helping me to understand my approach and what I value.

I fell into leadership twice by naturally accepting more and more responsibilities, as you do, but I never understood the reasons behind my early successes or failures. So far, I’ve found success in hybrid leadership roles, automatically creating a technical-focused team lead role for myself without understanding why it worked for me. It wasn’t by my own design, and it certainly wasn’t by the design of my bosses.

Last year, when I started looking for a new role, I faced the dilemma: where do I fit in the identity world? I didn’t want to work for one of the large identity vendors, and I didn’t want to go back to being a big fish in a small pond with an architect or principal engineering role; it just wasn’t working for me, and I was stagnating. Only my leadership skills were improving.

Moving into another hybrid role, but moving the slider slightly more towards leadership, didn’t really help. On paper, the role was a subset of my previous responsibilities, but with an established team and a much better paycheck. However, I hadn’t moved the slider far enough towards leadership, and I hadn’t learned the blue tape lesson yet. As a result, the “everything is broken” stage hit me way harder than it should have.

For my newest role, I’ve decided to go all in on this leadership thing, moving into a management role and leaving behind identity, removing the temptation to act as an individual contributor. While I still write about identity and provide identity consultancy, it’s not something I want to do in my day job right now.

Reflecting on this and some of the lessons in this book, it all seems a bit obvious now. Isn’t hindsight fun?

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