The Art of Leadership: Small Things, Done Well by Michael Lopp

Date Added
Feb 17, 2022 9:31 AM

The book is presented as a series of practices for leaders that will provide a compounding effect into helping us be better leaders.

What are the key highlights?

Part I: For Managers

Meeting blur: We all know that feeling, you have been all day in meetings. By the end of the day you find your self struggling to get the context out of them. This is a sign that you are over committing above your capacity to process that much information. As a leader you need to assure that you are able to deliver high quality throughput and that you are able to meet to all of your commitments. This is leading by example.


The situation: As a leader you will be often in the need to face with the situation. Situations are those things that happen that need a strategic approach to manage it and the team will look at you for managing it. As a leader there are a few questions that you should ask yourself before bringing your perspective to it.

  1. Am I the right person to handle this Situation? Find who that person is.
  2. Do I have complete context? If not, look for it.
  3. What is the track record of my sources of information? Can it be trusted?
  4. Do I understand the nature of those inconsistencies? Find that common ground
  5. Do I understand my biases relative to the Situation? Acknowledge them so you can take action to overcome them.
  6. Do I understand my emotional state relative to the issue at hand? Take your time to cool down if you need to or find a neutral party to help you.
  7. Can I coherently explain multiple perspectives of the Situation? This will help you acknowledge the complexity of the situation.

Act Last: As a leader there are two main reasons to be the last to share your ideas in a discussion, first it will give you enough context to evolve your thinking and provide better input. Second if you are the first to provide your ideas you will be setting the tone for the conversation and probably shy away people from sharing their own thought to do not contradict you. Your job as a leader is to enable debate so the best ideas arise from confronting multiple perspectives.


Read the room:


When you are part of any meeting you should be able to read the mood of the room. By reading the room you will gain context and insights about “What mood is this particular set of humans in?” which will give you the tools to best approach for you to take to maximize the value of the conversation.

Taste the soup: Your job as a leader is not to prescribe how to do things. Your job is to “taste the soup”. Based on your acquired experience you have developed the ability to identify what are the main components that build an idea. Your primary resource as a leader is your ability to ask critical questions to understand the ideas being discussed and the decisions made. This is the opportunity to exercise your curiosity. Which is the ingredient? Why did you choose A over B? Where is C? Why is it missing? etc.


Spidey-sense: As a leader you probably have built wisdom based on your experience, these experiences have helped you create your own judgment, opinions and learnings. You will probably experience similar situations again and you will be able to detect patterns from them. When you inevitably start seeing these patterns flashing saying that something might be “off” thats your “Spidey-sense” kicking in, “trust it”. Take your time, collect information, connect the dots and eventually you will be able take actions if needed.


Performance: Remember this, “It’s always performance season” for yourself or for your team. As a leader you need to have frequent touch points through the year with your team, identifying the aspects that where you can provide the necessary feedback, suggests alternative approaches and give and actionable insights. You should not wait for “Performance Season” to do so. Your primary job as a leader is to continuously ask yourself “How can I make this human better?”


Part II: For Directors (Managers of Managers)

The Blue Tape List


When landing in a new leadership role it’s normal that you find that there are multiple things that you think need to be fixed. You are able to do so because your brain is adjusting to the new context and it’s in high alert mode. You begin noticing things that people that have been in the same place for a while aren’t able to detect. Here is when you need “the blue tape” to identify all those things that might feel off.

As soon as you start gaining context you’ll notice that when you go back to the blue tape list you will be better positioned to handle the items on that list. Some of these items will require attention be indeed fixed but others will have a good reasoning to that way or might feel less urgent. The important thing here is not to rush to go and try to fix everything on day one until you have gained the enough context.

Delegate Until it Hurts


Delegation is probably the most important thing you need to learn to do as a leader no matter the level. But delegation must come with trusting your teams to do the job. Your role now is the one of a coach, we know that you know how to do the work but avoiding micromanaging is the one thing that will help you grow as a leader.

How to Recruit


Always be hiring, even when you don’t have open positions. Some times you will need to be in discovery mode by looking for people that will be a perfect fit for your company, use your network of people that you will love to work with again.

Once candidates have entered the pipeline. The goal is to understand if the candidate has the right set of skills for the job and for the candidate to understand your company’s mission, culture and values. And optimise for the best candidate experience.

Finally when you are ready to make an offer you need to make sure that what you are offering to the candidate is a delightful experience, compensation, perks, understanding of the job, what projects will they be working on, and what is the expected growth path from day one, overall a holistic onboarding process.

Gossip, Rumours and Lies


Chances are that if you are in a senior leadership position where you are a manager of managers you will need a staff meeting. This meeting is a flexible setting where you make sure that your multiple teams are in sync.

In the staff meeting you keep track of key metrics that tell you a story of whats going on in the company. In this meeting you open the conversation for a rolling agenda and leave space for spontaneous side conversations that otherwise wouldn’t happen.

Finally this is the place were your staff can raise any issue, ask questions or discuss those gossips, rumours and lies happening so you are able to articulate a healthy response.

Rainbows and Unicorns


Celebrate your team wins, celebrate work well done. We should not underestimate the impact of continuously recognising the work done by our teams, even for the simplest things.

“A compliment is a selfless, timely, and well-articulated recognition of achievement.”

Compliments should come in the form of recognition that celebrates and encourages certain behaviours. They should be done in a timely manner, on the spot, the closer to the event that triggered the better. It should be well articulated, a “good job!” is not enough. Be specific on what was the act, the value and the impact it generated. And above all it should be selfless and sincere.

Say (and listen) the Hard Thing


We all hesitate when its time of giving critical feedback to someone because inevitably we can emphasise with the person receiving it. But the thing we need to acknowledge is that giving (and receiving) feedback is actually a gift. A gift that will help us be better.

When we receive or give feedback its important to understand that what we are we are being given is additional context of the impact of our actions that we were unable to perceive.

“Feedback is about building trust

The way we react when we are giving or receiving feedback is what will help us build trust with each other. As time goes and the trust strengthens you open the door better, more complex and harder feedback. Embrace it and use it to grow yourself and your team.

Everything Breaks


As the company grows the need of “A clear explanation of the rules” gets more and more important. Human relationships are complicated and without these rules things can get very chaotic. One thing we need to acknowledge is that the rules need to evolve as the company grows. The rules that were fit when you were only two people wont apply when you are 8 or 100.

Onboarding is another critical scenario where you will need to have this rules in place. Every new person added to the team should be able to understand the company’s vision, values and practices that define how it operates.

Finally you should use failures as the best tool at your disposal to grow your business. Take advantage of every failure and extract the most important lessons that address the root cause of it. Your company should have the mechanisms that allow comprehensive and blameless post-mortems where the most important thing is to learn and adapt so no failure happens twice.

The Org Chart Test


Org charts are a resource to effectively describe how your company operates, how the product is developed, who is responsible for what. These charts need to be easily discoverable and shared across the organisation. Anyone from the company should be able to draw from scratch (without adding any person’s name) describing from any perspective how the company builds its products, how the business units are split or how the reporting chain is structured. This chart should be constantly refreshed to reflect the current state of the company.

Part III: For Executives

This third act of the book is dedicated to emerging executives and the challenges it has, these kinds of positions are one step upper on the latter demand something extra from the leader, it’s no longer about managing a group of managers in a small organization, now you are responsible for an entire business or an organization. You are far away from the teams but at the same time, you are accountable for their outcomes. Usually, when fires fail to be handled up the chain they will escalate to you. As an executive, you will find yourself using your executive role to assign the right people to be on the front lines to put it out. But that's not your primary role, your role is to set the company for success and prevent the fires from starting in the first place.

Allergic to Wisdom


Startup companies as they grow create unique ways of doing things. And the people in it will firmly believe they can apply their uniqueness in all aspects of the organization, this can probably be justified as this was what made them successful in the first place. This usually translates into spending a lot of resources on innovating in areas where existing knowledge can be applied. In the book, this is referred to as “allergic to wisdom”.

But the truth is that not all aspects of the organization are the subject of innovation. And your job is to manage the resources of the organization as efficiently and effectively as possible to help your teams to move forward and keep innovating in the core areas where your company stands out from the crowd.

So, what do you do as an executive? You act, you don’t ask; you use your experience to identify those aspects where you can generate impact and just act upon it. You’ll share the vision and explain in detail where do we want to go next. You don’t say “back in <company name> we did it this way”, you just push the changes necessary to move the organization forward saving time and resources, even if they are not perfect at first. Then you’ll iterate.

The Guard


If you are an executive that joins a start-up company that has been running for a while and starts to scale you will find that usually two groups of people can be identified; The Old Guard, and the New Guard.

The Old Guard is formed by the early employees of the company who have been there since the beginning of the times, they have been long enough to remember how and why things are the way they are. These people have built over time bonding as a result of building together and failing together. They look up to each and seem to have a superpower ability to fix things really fast when they break.

The New Guard is everyone else that arrives at the company after the first group. You can find them both in an awe state and a helpless state. They are inspired by the work done so far by the old guard but also can feel overwhelmed by not fully understanding how things work and why they were done that way.

Old Guard: “I feel empowered to fix everything”

New Guard: “I don’t know how to fix anything”

Now, these two groups don’t know each other well enough. They don’t have shared experiences and haven’t built the same level of trust that the old guard did.

As a leader, you will have a mission to help build that new layer of trust. Your focus should be to create the environment and context where you can get these individuals to join their forces and use the first group's experience and the latter's fresh eyes to build The Guard.

The Guard: A team who works together while learning better ways of building things and trust with each other.

The Culture Creek


What is the company culture? It’s not a set of sentences or words someone decided to paint on the walls and in a set of slides. The culture is formed like a creek, parting from an initial set of conditions where the water starts flowing.

Everything that happens afterward is a result of its beginnings and it evolves from there. When you put together a group of people the culture is formed by the stories that mattered to them, the stories that are told when similar situations arise.

As a leader, your mission is to be a guardian of the culture, to pay attention to and remove obstacles that prevent the water from flowing its course. You won’t be able to change the course of how the culture is defined but you can help to keep it clean.