Book notes & reflections: The Making of a Manager

Scott Brady
Scott Brady

In this article, I share my notes and reflections from the book “The Making of a Manager: What to Do When Everyone Looks to You” by Julie Zhou. This includes 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.

This article is a long one since the book really struck a chord with me. While I’m no longer in my first management role, I seemed to have picked this book up at the perfect time in my career to cause far too many reflections and eureka moments. As a result, this article also includes many thoughts about my career and, more often than not, my failings as a leader.

I’ve put my personal thoughts in a separate font from the book notes to make them easier to identify.


The Making of a Manager by Julie Zhou talks about what you should expect from your first management role. It focuses on that strange time when you start out as a manager with no idea what the job will really be like.

It’s a long-form book mainly focusing on advice suitable for new or potential managers. It gives some great insights into what the role entails, why you should and should not become a manager, and advice for being an effective manager. The book is broken down into the following chapters:

Each chapter starts with a Bojack Horseman-style cartoon showing a scenario to avoid and a scenario to aspire to, where the protagonist is a giraffe – major brownie points from me on that one.

A manager (who is a giraffe) being delivered by a stalk like a baby A manager (who is a giraffe) being created by a machine after lots of experience
Addressing the myth that managers are born rather than made.

Unfortunately, the majority of the author’s career has been at Facebook (they were one of their first employees). Some of the reviews on Goodreads do a good job detailing the hypocrisy of this. But, if you can weather the odd quote from the likes of Zuckerberg and Bezos, the author’s advice and views are worth reading. However, that being said, I did struggle with the later chapters of this book that talked about company culture.

I made a lot of notes from this book, despite initially not enjoying the audiobook. It took reviewing the paper copy, some reflection, and then reviewing my notes to find some common themes and interesting takeaways, much unlike The Art of Leadership, where the short-form essays allowed me to find the message without quite so much effort. This is probably due to my personality and background as much as the author’s ability to tell a concise story.

Book notes

For this article, I’ll share my key takeaways from each chapter. There are plenty of them, but once I started reviewing my notes, I began to see some common themes. As a result, I saw diminishing returns as the book went on, and the author started to labor the same points albeit in slightly different ways.

Great managers are made, not born

This introductory chapter echoes the message from The Art of Leadership: management is not a promotion. The author compares the initial offer to become a manager to Hagrid’s “You’re a Wizard, Harry!”, which again earns brownie points in my book.

The author also shares an interesting point on why they started writing about leadership & management. Initially, when someone asked them to share their thoughts on management or write on the topic, they said no, and that they’d share their stories in a memoir at the end of their career. But they realized, by that point, they’d have forgotten what it was actually like to become a manager. Those initial trials and mistakes are long in the past and what mattered to you at the time is most likely forgotten.

Removed from reality

This reminds me of an attitude I have unfortunately seen in many directors and CTOs, where they are so far removed from the original role of an engineer or engineering manager that they have forgotten what it was like when they started out.

Let’s use job titles, for example, something very important to an engineer, where an unsuitable job title may well disrupt their career and cause their CV to be ignored. Listening to some off-hand comments in all-hands/town halls from CTOs showed a complete disregard for this concern. I even saw one put on a whining voice, mimicking an employee about wanting a different job title. Obviously, this ridicule didn’t help; it only proved how far removed they were from the experiences of their engineers and the job market and alienated their engineers.

Sometimes these CTOs never even entered the management track; instead, they lucked out as a founding engineer or simply jumped straight in with their own company. As a result, I’ve found that some don’t understand or appreciate their circumstances and what actually worked for them, instead often devaluing other experiences. It reminds me of people who earned money in the early days of Bitcoin becoming financial advisors. I guess it’s a form of survival bias.

Anyway, I’m ranting. The important thing here is to remain grounded in reality. Remember what mattered at the time and write about leadership and management early while actually experiencing these things, reflecting on what is working well and not just if you are successful – waiting until your memoirs will likely not offer the same value or provide a realistic view of what truly happened.

What is management?

This chapter discusses what to expect as a manager and, interestingly, some wrong reasons to become one.

What does a manager do?

This is a really interesting question that I don’t think many of us would have a prepared answer for. Yes, it’s a job that changes daily, and you often find it hard to remember what you actually achieved by the end of the day, but the job is more than just a list of tasks.

The author breaks down each of their definitions based on their years of experience. Before they started management, they thought a manager’s job was to:

  • Have meetings with reports to help them solve their problems
  • Share feedback about what is or isn’t going well
  • Figure out who should be promoted and who should be fired.

After three years on the job, they thought a manager’s job was to:

  • Build a team that works well together
  • Support members in reaching their career goals
  • Create processes to get work done smoothly and efficiently.

But while a manager does all these things, they are just day-to-day activities. For example, if asked, “what is the job of a soccer 🤢 player?” you don’t say to attend practice, pass the ball to their teammates, and attempt to score goals. Instead, you say their job is to win games.

Therefore, a manager’s job is to get better outcomes from a group of people working together.

Why do you want to become a manager? Will I be a good manager?

Becoming a manager shouldn’t be a decision you take lightly. To help you, the author provides a list of likes that might suggest management is for you and, more importantly, some reasons that aren’t good enough for becoming a manager.

If the following describes you, then you may enjoy management:

  • Do you find it motivating to achieve an outcome or to play a specific role? Do you want to be an enabler (a manager) or to perform a specific task (an individual contributor)?
  • Do you like talking to people? As a manager, 70 percent of your time will be spent in meetings. You don’t have to be an extrovert, but the role may not be for you if you want a workday that has long, uninterrupted blocks of quiet focus time.
  • Can you provide stability for an emotionally challenging situation? Would someone describe you as empathetic or undramatic? Do you defuse situations rather than escalate them?
Context switching

Across all of my conversations with senior developers, the fear of context switching is usually the number one call-out about why they do not want to enter the management track. However, while adaptability is a great skill to have in a manager, I’m still working out whether this is a valid concern. There are many approaches to management; however, you often need to match your management style to the team, the organization, and the team’s current state (e.g., chaos mode, learning mode, etc.).

Does an aversion to context switching prevent you from being an effective manager? Or does it mean you would be too inflexible? Does it also prevent you from becoming an effective influencing contributor (e.g., staff or principal engineer)?

What about why you should become a manager? If the following is your reason, then you may want to rethink your decision:

“I want to progress my career”.

While all C-level execs lead teams, becoming a manager is not a promotion but rather a transition. The author offers the example of a heart surgeon not needing to become a hospital administrator to earn more money or to have more impact in their field.

If your organization’s framework does not have well-defined, separate tracks for individual contributors and managers, it’s a good idea to rectify this and dispel this myth. Of course, if your organization doesn’t even have a career framework, then that’s a whole other issue.

“I want the freedom to call the shots”.

To quote the author, “no leader free reign without accountability. If the decisions turn bad, they are held to task. Owners see their business flounder; CEOs of public companies get fired by their board. […] The best outcomes come from inspiring people, not telling them what to do”.

The ascension

You are not authoritative; your knowledge is not absolute. You don’t suddenly become omnipotent when you become a manager. Instead, you must allow yourself to be challenged and openly discuss the whys. If anything, I would say that the further up the chain you go, for both the management and individual contributor paths, the less power you have and the more you need to start selling rather than telling. I would say that this is the most common mistake I’ve seen in colleagues starting out in management.

“I was asked to be a manager”.

“I should” and “I can” are not sufficient reasons. Do you really want to?”. I think this book is a good start to understanding your answer.

Evaluating a manager

When you’re a manager, it can be hard to tell if you’re doing a good job and how your own manager might evaluate your performance. The author shares a framework that they use from Chris Cox, Facebook CPO:

  1. What are the team’s results? Did they achieve their goals? This looks at outcomes.
  2. What is the strength and satisfaction of the team? Did you do a good job of hiring and developing individuals? Is the team happy and working well together? This looks at outcomes for the future.

You are there to help your team achieve great outcomes. This framework asks if you are doing this now and if you are setting them up for the future. These are questions I’m starting to ask myself regularly.

Leader vs. Manager

The author offers a really interesting take on the leader vs. manager discussion:

“A manager is a specific role. Leadership [..] is the particular skill of being able to guide and influence other people.”

I prefer this over some of the derogatory definitions that conflate management with micromanagement. Instead, management is a career track with different expectations than an individual contributor’s. However, both tracks must use their leadership skills to be effective. Can you imagine a principal engineer who couldn’t lead? In my opinion, that would be just as bad for an organization as a micromanager.

Your first 30 days

This chapter is all about starting your management journey, the different types of start, and the advantages and disadvantages of each, including some questions to ask your manager to get you started in the right direction.

The author defines four manager starting types:

  • Apprentice – your manager’s team is growing, and you’ve been asked to step up
  • Pioneer – you are the founding member of a new team, responsible for its growth
  • New boss – you’re coming in to manage an established team
  • Successor – your manager left, and you are taking their place.

False starts

All four start types come with their own issues, but it’s the apprentice and new boss types that spoke to me, as I’ve gone through both twice.

As the apprentice, the first time around, I made it too big of a thing in my head; the director and I made it an us vs. them scenario when in reality, I was initially only the boss of one. The second time around, I was the only non-director on the management team, and my experience with my managers told me to take my foot off the pedal and play it by ear. Again, linking it back to this book, the question “what will be my scope to start, and how do you expect it to change over time?” was what I was trying to ask in order to avoid overstepping.

Thankfully, I didn’t face the issue of coaching & managing ex-colleagues due to being an existing leader in my niche and used to operating as a subject matter expert. However, things got tricky as I started to prioritize my management tasks. By reducing my individual contributions and increasing my management tasks, I got more from my teams than I ever could have contributed alone; however, some of my bosses didn’t like or understand this one bit. They wanted to continue judging me on my individual contributions and couldn’t accept that young Scott had any effect on the people he was managing when they had struggled to make changes for years.

For my first time as a new manager, I struggled with my mix of IC experience and leadership, finding myself stuck in an “everything is broken” mentality. My initial desire was to prove my IC knowledge; this was my niche, and I had been brought in to sort shit out. Obviously, this backfired. I fell into the trap the author describes as “it takes a while to adjust to the norms of a new environment”.

This led me to wildly swing the other way and give in to the urge to be quiet and not ask questions, which is your main task as a new manager. While there was an element of wanting to wait until I knew enough, in proper Scott fashion, it came down to holding myself apart from it, seeing it as rubbish, and therefore not wanting to involve myself or waste my brain capacity on it. This is not something you want from a leader.

Lessons learned. I think I’m doing better this time around.

Leading a small team

This chapter talks about leading your first team and mastering the fundamentals. After all, most of us begin with leading just a single team of just a few people.

Trust is the most important ingredient

A big part of this chapter is about building relationships with your team, and one quote really stood out:

“It’s human nature to want your manager to think well of you and not complain, but if you don’t share how you’re feeling, things will fester and become worse than they are.”

This is a big thing for my attitude toward my own managers (more on that later), but I’d never consciously considered it for my team towards me.

The author proposes that you review the following statements to see if that trust is there:

  • My reports regularly bring their biggest challenges to my attention - they come to you with their problems, with what keeps them up at night, rather than you hearing it through the grapevine. If they always answer, “everything is fine”, then this should be a sign to prod further
  • My report and I regularly give each other critical feedback, and we don’t take it personally - are you comfortable directly telling them when they have done work you weren’t happy with? Strive to make all of your 1-to-1s feel a little awkward by having hard conversations. Relationships cannot be created on pleasantries alone. Build a relationship so that you can be direct.
  • My reports would gladly work for me again - if someone wants to work for a manager again, this is the best sign of a great manager.
Friend vs. boss

That second one really sticks out for me. The easy path is to try and be everyone’s friend. It makes me think of the stereotype typically seen in smaller companies, the awful “we’re like a family!”. Unfortunately, I’ve seen this too many times, where the owner wants to take the easy path and be everyone’s friend while somehow also being the unquestionable “boss”. As a result, they struggle to feel the respect they crave and completely alienate their employees once they inevitably break and use their authority to get their way, breaking any trust they might have gained from being a “friend”.

Trying to be their friend by being insincere is unfair and selfish. Your team needs a leader and a manager to help them grow. Don’t deny them this by trying to have it both ways. Leave your ego at the door, start building trust, and do your job.

Invest time to help your report

Schedule 30-minute 1-to-1s every week. This is something I’ve seen echoed across all engineering management content I’ve come across so far. A weekly 1-to-1 to check in with each member of the team to find out what’s going on in their lives, how they are feeling about work, to share feedback, discuss priorities, and even to reflect on how things are going – it goes a long way to building trust and developing relationships.

This weekly 1-to-1 is something I’ve taken onboard and, thankfully, something that is expected from managers at ClearBank. This is certainly a big difference from the fortnightly or quarterly 1-to-1s I experienced in previous jobs.

Your team should not be wondering, “what does my manager think of me?”. Be honest and transparent about their performance. Don’t expect them to read between the lines or assume no news is good news. I’m crap at giving praise, so in my 1-to-1s, if I don’t have any feedback, I now at least explicitly say that I am happy with their performance.

Don’t let underperformers dominate your time while neglecting the rest of your team. A small improvement to a strong team member has greater returns than the same level of improvement for an under-performer. Remember to give some love to the rest of your team.

The “brilliant asshole”

The author presents the idea of a “brilliant asshole”. Someone who brings a lot of experience and ability to the team but is so wrapped up in their own opinions or just generally makes the rest of the team feel bad. Time is lost dealing with the fallout. Do not be fooled by their work as an individual. Removing this toxic individual allows the team to relax, bringing a different level of collaboration and honesty. The work of the team as a whole improves.

Unfortunately, I’ve fallen for this trap in the past. I got swept up in their stories about how bad things were, agonizing over past bad decisions and all of their ideas to fix them. Emboldened, they started making sweeping changes, picking fights on pull requests, and arguing with anyone who would listen. It soon became clear that they lacked the communication skills to work with others; they were just a bit of an asshole. Mediation turned into ignored messages; an ally turned into an enemy. While I eventually recovered the situation, it certainly damaged the trust amongst the team.

You don’t always have to make it work

It’s not your job to always “make it work”. Everyone doesn’t need to agree; you don’t have to make people get along or see things from each other’s perspective. You will often waste your time trying to make people get along, trying to solve the situation. Some situations are not solvable, and some people simply should not work together - they just have different values and working styles. If you try and force it, people will leave.

If someone’s not a good fit, no amount of extra work will solve this. Ask yourself:

“If this person were not already at the organization, would I recommend that another team hire them knowing what I know?”

This question cuts through it and reveals how you really feel.

The art of feedback

The author covers the usual importance of feedback, but they also encourage you to start giving feedback more often before even worrying about how to give it.

360-degree feedback

360-degree feedback is where you gather and aggregate feedback from multiple perspectives. It could be from all participants in a meeting, or it could be from peers across the business, as well as your manager and direct reports. If you do not have deep context into what your reports do day to day, 360 feedback can be a useful technique.

I’ve always hated the idea of 360-degree feedback. It seemed like proper manager drivel. But, as I find myself becoming further removed from the day-to-day of my team and their subject matter expertise and start to work alongside peers doing the exact same thing as myself, I am starting to see the benefits.

Every major disappointment is a failure to set expectations

A performance review should never be the first time your direct report hears that they are not meeting expectations. This will make them feel terrible.

This is the usual advice of giving feedback often and clearly; however, this book talks about their psychological response to rationalize your failure to provide feedback. The shock of your feedback will make them try to explain it away in their heads that the review wasn’t fair, that you, their manager, are being negligent, or that you are being dishonest.

“Every major disappointment is a failure to set expectations” – their shock and disappointment are on you.

Delegating challenging projects and the “swoop and poop”

Sometimes you’re going to need to delegate projects that you want to keep an eye on. However, if you frequently drop in and ask for an update or give unsolicited feedback, you will make them feel disempowered.

It’s best to set expectations at the beginning of the project about how you’d like to be involved. For example, be explicit about how frequently you’d like to review the work and talk through important problems together. Tell them which decisions you expect to make and which decisions they should make.

Managers who pop in out of the blue and throw down new requirements breed resentment in the team. This is known as the “swoop and poop”.

The "swoop and poop"

I love this term, as it perfectly sums up a couple of managers I’ve had in the past, who would infuriate developers with constant requirements changes or suddenly undermine a tech lead with unnecessary, opinionated changes that they’ve become fixated on, demanding they get actioned immediately, often calling out their disappointment with the whole team. This required a lot of upwards management to handle (I personally got very good at creating bait for them to focus on so that the real work could continue elsewhere), and it just made for demoralized engineers and stressed-out middle managers (ask my wife and hairline). Not fun.

Is my feedback being heard?

This book talks about the other side of the Art of Leadership’s receiving feedback. How do you know if your feedback has been heard?

When giving critical feedback, the author recommends approaching it with curiosity, with a desire to understand their perspective. When you give the feedback, ask if it makes sense to them, if they think it is fair, and if it resonates with them. Ask why or why not. Always end with key takeaways and next steps.

Another interesting one is when receiving feedback about a report from someone else. Instead of trying to deliver it yourself, ask if they are comfortable sharing it directly. This can remove the go-between and any possibility of the message becoming distorted.

Delivering critical feedback and the scared manager

“I have a few questions about your latest work - do you have a moment to walk through it?” – this is the scared manager’s opener. You’re afraid of upsetting your report or unsure if your opinion is 100% right, so you phrase your concerns as questions.

At best, framing feedback as a question looks disingenuous. At worst, the feedback will be missed entirely. I’ve definitely fallen into this trap before.

This book recommends giving feedback directly and dispassionately. Say what you see the issue to be, what made you feel that way, and how you’d like to work together to resolve the concern.

“I’m concerned about the quality of the work I’ve been seeing from you recently”, or “your last few deliverables were not comprehensive enough to hit the mark”.

Try the template:

“When I [heard/observed/reflected on] your [action/behavior/output], I felt concerned because… I’d like to understand your perspective and talk about how we can resolve this.”

Don’t start with a preamble; don’t sugarcoat or pad it with softer points. And certainly, no poop sandwiches.

Own the decision

If you’ve made a decision about something and you are delivering bad news, own the decision.

“I’ve decided to go with someone else for this project…”

Don’t try and make it a decision you come to together. If nothing they can say could convince you to change your mind, it’s insincere to act as if they had a say. Some decisions are yours to make.

“I recognize that you may not agree with my decision, but I’m asking for your cooperation in moving forward.”

People are not fragile; no report wants you to treat them with kid gloves. On the contrary, they want your feedback to improve.

“You’ve been told since you learned to talk, “If you don’t have anything nice to say, don’t say anything at all.” Now all of a sudden, it’s your job to say it. You’ve got to undo a lifetime of training.” - Kim Scott, Radical Candor.

This is something I try and remind myself daily.

Managing yourself

This chapter focuses on self-care. Why you should look to your own skills and ways of thinking, as much as your team’s. You need to understand yourself to be the best leader you can be.

“Impostor syndrome is what makes you double, triple, or quadruple check your email before hitting Send so that nobody finds any mistakes and figures out you’re actually a fraud.”

Ouch. That one cuts deep.

Management constantly puts you in positions that you’ve never been in before:

“You can’t just snap your fingers and say, “I’m going to practice firing a lot of people this month.” You must actually go through the real thing in order to gain the experience you need.”

Strengths and weaknesses

Your strengths and weaknesses directly affect the people you manage. You need to understand yours.

While there are ways of reviewing your strengths and weaknesses, you should confront the truth of what you’re really like by asking others for their candid opinions.

Ask your manager to help you calibrate yourself:

  1. What opportunities do you see for me to do more of what I do well? What do you think are the biggest things holding me back from having a greater impact?
  2. What skills do you think a hypothetical perfect person in my role would have? For each skill, how would you rate me against that ideal on a scale of one to five?

Understand yourself at your best and your worst

Building upon this idea of self-understanding, the author suggests understanding what habits you have that work well for you and what your environment brings out the best in you, the conditions that enabled your best moments to happen.

On the flip side, what triggers you but not other people? Reflect on when you’ve behaved irrationally in the eyes of others. Understanding this is a good step towards catching yourself in the moment before you get too upset. Besides that, getting a handle on your prejudices is a damn good idea.

It’s good to share your triggers and learn what other peoples are.

  • When was the last time someone said something that annoyed me more than it did others around me? Why did I feel so strongly about it?
  • What would my closest friends say my pet peeves are?
  • Who have I met that I’ve immediately been wary of? What made me feel that way?
  • What’s an example of a time when I overreacted and later regretted it? What made me so worked up in that moment?

When stressed, write down what is bothering you on a post-it note. Acknowledge it and then focus on what you need to do that day, not the stress.

The story in your head is probably irrational

If you’ve been left out of a meeting, you might think you weren’t invited because your teammates don’t like you or don’t think you are useful. If you feel this way, then ask why! They likely didn’t want to waste your time or make you feel obliged, they didn’t realize you cared about the meeting topic, or it was just an honest mistake. It is rarely because they didn’t want you there.

How can you be twice as good?

Ask for feedback all the time. The more concrete you are about what you want to know, the better; otherwise, you’ll be met with “I think it went well”. Consider: “I’m working on making sure my key point comes across clearly in the first three minutes. Did that come across? How can I make it clearer next time?”.

Always thank people for feedback. Even if you don’t agree with it.

Okay, thank you anyway
Always be thankful, even when they are clearly lying

Something I’m starting to do is write down any feedback I receive, who I received it from, how it was delivered, and how it made me feel.

Treat your manager as a coach

Your growth is in your hands; it is up to you to make sure you are learning from people, including your manager. However, people shy away from asking their managers for help. When a manager has to step in, it makes you feel like you have failed and cannot do your job. However, a manager’s job is to help their team get better results. They are on your side and will want to help you.

You do not hire a personal trainer and then say, “oh, I’m pretty fit; I’ve got this under control”. You instead ask for coaching. You do not hide your weaknesses.

Engage your manager for feedback. Ask, “what skills do you think I should work on in order to have more impact?” or share your personal goals with “I want to learn to be a better presenter. Can you keep an eye out for opportunities where I can get in front of others?”, or ask them to work with you with “I’m struggling to choose between two candidates. Can I walk you through my thinking and get your advice?”.

Come up with open-ended questions to ask your manager in 1-to-1s. For example, “how do you decide which meetings to attend?”.

Asking for help

Asking for help is something I’ve struggled with this ever since school, where my feedback was always, “Scott needs to learn to ask for help”. I was viewing asking for help to be a weakness. The reasoning for this is deeply personal, and I won’t go into it any further, but that mentality found its way into my professional career, where I found pride in getting shit done without managerial assistance. While this brought some success, it also made learning harder (it prevented any mentorship or coaching) and could lead to issues that would otherwise have been avoided if I had just asked for a little help. I’m still working on this one.

Make a mentor out of everyone

Explicitly asking someone to be your mentor won’t work. It sounds needy and time-consuming. Instead, ask for specific advice.

Try the template:

“Hey, I was really impressed with the way you [handled x]. I’d love to learn from you. Would you be willing to meet up with me and share your approach?”

Keep in mind that you are asking for a favor. It’s well within their rights to say no. Thank them anyway.

Set aside time to reflect and set goals

Studies show that people who choose to reflect outperform those who just constantly look for new experiences to learn. Which is exactly what I’m doing right now!

Amazing meetings

Giving a meeting a purpose isn’t enough. Instead, ask yourself, “what does a great outcome look like?”.

Use your answer to understand who should be invited. Who needs to be there to make the outcomes happen? If people disagree and want to be there, consider a different meeting to communicate this rather than the full discussion.

Always send an agenda and always confirm next steps, who owns what action item, and when the next check-in will be.

Making a decision

If two sides disagree, whatever your decision, you are going to make someone unhappy. The author wants you to challenge this. Everyone in the team is ultimately working towards the same goals. However, sometimes you have to “disagree and commit”.

A good decision-making meeting:

  • Includes the people directly affected by the decision and a clearly designated decision maker
  • Presents all credible options objectively and with relevant background information, including team recommendations
  • Gives equal airtime to dissenting opinions and makes people feel that they are heard.

Bad outcomes to avoid:

  • People feel their side wasn’t heard and therefore do not trust the resulting decision
  • Decisions take a long time to make, delaying progress. Be careful doing this for small, easy-to-reverse decisions
  • Too much time is spent trying to get a group consensus rather than escalating quickly to a decision-maker.
  • Time is wasted on rehashing the same argument in twenty different ways
Selective memory

That last one reminds me of a boss and a few engineers I’ve known in the past. If they ever “lost” an argument, they would pretend to accept the decision but then rehash the same argument a week later as if it had never been discussed before. Often, this would catch their victim unprepared, the original points and reasons behind the decision already out of mind. As a result, they’d win the argument by wearing the victim down, often resulting in an unnecessary change, a week of wasted work, and a demoralized team. Protecting the team from this was hard and sometimes impossible without managerial authority.

Make it safe for people to contribute

“Early in my career, I was the quiet person whose contributions in meetings were inversely proportional to how many people were in the room. Which meant that in 1:1s, I’d say a lot, but in groups over seven, I’d make like a ninja and stay as inconspicuous as possible.”

You will get better results if you get everyone in the meeting to contribute. Ask someone for their opinion. Be explicit about the norms you want to set (e.g. Q&A expectations, hard questions, silly questions).

An unstructured group discussion might not work for a set of introverts.

Consider a round-robin approach, where every person gets a say on what option they prefer and why. This ensures no perspectives are left unsaid.

Consider a retrospective style approach, where everyone submits post-it notes ahead of time, you group similar proposals/topics, and then discuss from there.

  • Do not allow people to talk over one another
  • Call out fidgeters - give them an opening - “X looks like they might have something to say”
  • “X, you look puzzled - what do you think we should do?”
  • “X, we haven’t heard from you yet. What’s your opinion?”
  • Nip over talkers in the bud – they obviously feel strongly about the topic but make space for other opinions.

I think some of these are worth experimenting with. Hopefully, they can improve my otherwise unstructured group discussions.

Hiring well

This book echoes The Art of Leadership: you, the manager, are also a recruiter. However, this time there’s a focus on hiring the right person for your team. You are looking for an attitude and perspective that will improve your team. Someone that will add something this is missing from your current team. This is something a recruiter will never be able to do for you.

Look for passionate advocates rather than consensus

The author makes an interesting point: you should never hire to fill the role. A lot of weak hires are from when a candidate doesn’t have any obvious issues. They seem pleasant enough, and people don’t see any reason why they shouldn’t hire them. But they didn’t wow anyone.

The author recommends that you reject weak hires. While they likely won’t bomb, they’re also unlikely to add much.

Mediocre hires

Unfortunately, this does match my experience. Hiring someone who was just “okay” or even taking the “best of a bad bunch” due to limited applicants often led to, at best, mediocre hires. These individuals often didn’t fit the company culture and just didn’t add anything new to the team. They got the job done, but not to the same standard as the rest of the team, and required much more management at the expense of others.

Prepare interview questions ahead of time

The author shares some interesting open-ended interview questions:

  • What kinds of challenges are interesting to you and why? Can you describe your favorite project? Find what they are passionate about.
  • What do you consider your greatest strengths? What would your peers agree are your areas of growth? Get an idea about their self-awareness and their real strengths & weaknesses.
  • Imagine yourself in three years. What do you hope will be different about you then compared to now? Understand their ambitions and how goal-oriented and self-reflective they are.
  • What was the hardest conflict you’ve had in the past year? How did it end, and what did you learn from the experience? Understand how they work with other people and how they approach conflict.
  • What’s something that’s inspired you in your work recently? Get some idea of what they think is interesting or valuable.

Aim to deliver an amazing interview experience. Have them accept an offer because the interview process was so good (attentive, focused, and fast). Even if they turn you down this time, they will be back! Use interviews to build relationships and play the long game.

Interviewer nerves

The author also talks about interviewer nerves. Even though you are ultimately in a position of control and power (you are the hiring manager), that fear of being seen as a fraud, competing with the desire to do a good job, can set off your impostor syndrome. This is something I still struggle with. While I’m comfortable in my nice and cozy identity niche, I’ve still got a hefty case of impostor syndrome when it comes to my core software engineering skills. Unfortunately, this is something that stems from a particularly critical boss from my past, but I’m working through it by running as many interviews as I can.

Reject anyone who exhibits toxic behavior

The author suggests being on the lookout for red flags during the interview process, such as:

  • “My last manager was terrible” - bad-mouthing past employers
  • “The reason my last project didn’t succeed was because of internal politics” - blaming others for failures they were associated with
  • “The sales team were bozos” - insulting groups of people. Strong use of the b-word.
  • “It feels like a step up for my career” - asking only about what the company can do for them
  • “I was attracted to this position because it seems like you need someone really senior” - arrogant or no self-awareness
What really happened?

I think these red flags are useful to consider, but some require more discussion. If you poke at these and get them to open up about what really happened, it can reveal a lot about the interviewee. If they show some genuine introspection, lessons learned, and how they would or have done things differently since, then that sounds like a decent attitude to me. If they double down and just mouth off without any self-awareness, then yes, toxic behavior.

Making things happen

This is quite an interesting chapter, deconstructing the iterative design that led to the creation of Instagram and disputing the idea of the sudden “Eureka!” inspirational idea that will change the world.

“It’s not about suddenly having the single, brilliant, lightning-flash insight that suddenly wins the game. Instead, it’s about consistent planning and execution - you try what seems like a good idea. You do it quickly. You keep your mind open and curious. You learn. Then you scrap what failed and double down on what’s working.”

The author talks about creating a vision and building a game plan for your team. The guidance boils down to the following:

  • Focus on doing a few things well
  • Define who is responsible for what
  • Break down a big goal into smaller pieces
  • Talk about how everything relates to the vision. Keep talking about the goal and link deliverables to the goal.

One thing at a time

Focusing on doing a few things well has been a big thing for me recently. I’ve found myself getting spread too thin and often becoming paralyzed due to too many competing important tasks. Instead, I now try to focus on a single or a select few tasks at a time, accepting that the others can wait. I even do this if I know that some issues will become worse as a result. Instead of trying to keep every plate spinning, I abandon a few and focus on the most important ones. If they are still spinning when I get back to them, great. If they fell on the floor, oh well, I saved the others at least. Besides, plates aren’t that expensive to replace. Okay, maybe this analogy is starting to break down.

In the sometimes-wise words of Ron Swanson, “Never half-ass two things. Whole ass one thing”.

Ron Swanson from the TV series Parks and Recreation, saying 'Never half-ass two things. Whole ass one thing

Perfect execution over perfect strategy

In a similar vein, the author also warns you not to spend too long creating the perfect strategy. While you could spend weeks debating which idea is best, instead, choose to learn as quickly as possible by doing. Build simple tests that help you understand which options you should double down on and which things you should. However, this does require that you make each task short enough so that you don’t waste too much time if one idea fails.

The portfolio approach

The author suggests taking a portfolio approach, where you balance short, mid, and long-term deliverables. For example, a third of the team is working on quick wins (delivered within weeks), a third is working on medium-term projects (delivered in months), and a third is working on innovative, early-stage ideas whose impacts won’t be known for years.

I want to look into this more as I start understanding my approach to tackling the backlog and tech debt and appreciate alternative approaches now that I have a team that is not in chaos mode.

Leading a growing team

This chapter was mainly about managing managers. While I did read this chapter, I didn’t find as much use from it as the others. To be fair, this is something that isn’t top of mind for me just yet, but it is something I plan to revisit within the next 12 months.

Nurturing culture

This chapter was a little hard to swallow, considering the author’s history of working at Facebook. The quote “nothing at Facebook is somebody else’s problem” was a bit of a shocker.

But there were still some insights to be gained from this chapter; particularly some questions to ask yourself and others about your culture:

  • What moment made you feel most proud to be part of your team? Why?
  • Imagine a journalist scrutinizing your team. What would they say your team does well or not well?

Another key point was to never stop talking about what’s important to you and the culture you’re trying to create. Keep reinforcing your message and values over time & consistently.

Closing thoughts

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

I ended up really enjoying this book and, after a few reads, ended up making way too many notes, around 50% of which found their way into this article.

I’m currently recommending this book to anyone considering switching to the management track; the first few chapters alone are worth the price of entry. If you’re already in a management role and starting to reflect on your approach and upping your game, this is a decent read; however, you may need to give it a few reads to distill the value. In fact, I’ve already found myself recommending this book to colleagues, albeit with a warning about the Zuckerburg & Bezos quotes.

Final reflections

Looking back through my personal notes on this one, I realize I’ve taken quite a negative tone. Unfortunately, it seems I have seen some bad managers in my time and made my own fair share of mistakes.

Trying to become one is tough if you’ve never had a good manager. As a result, we often end up emulating flawed individuals, just like we did as children with our parents. But, just like growing up, you can overcome this lack of a role model by making your own mistakes, reflecting on them, and welcoming a diverse range of opinions.