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  • Writer's pictureDawn Burkett

Book Review: Bringing Up The Boss

Reaction and takeaways from my recent read: Bringing Up The Boss by Rachel Pacheco. In this article, I will share why this book is great, the pages I dog-eared, and a few of my favorite moments in the book.


What's it about?

Bringing Up The Boss by Rachel Pacheco is a book that explores areas a first-time manager will face in a practical and thoughtful way. The book is divided into three main sections:

1. Managing an Individual

2. Managing a Team

3. Managing Yourself

Within each section, chapters provide micro-lessons on specific topics ranging from holding people accountable to building a team that trusts each other. With quirky titles ("The Heavyweight Title Fight"), captivating illustrations (created with The Noun Project) and self-deprecating stories, Pacheco offers real world advice that is supported with theory and data.

Why I chose this book...

I cannot tell you how many times I have had a conversation with someone new to management about how completely unprepared they felt about being an effective manager. With so many articles and books to choose from, I was looking for something fresh and fun to read about being a first-time manager. This book definitely checked that box.

Who this book is for...

Obviously, this book is targeted to those brand new to leadership or those looking to move into a leadership role. However, as simple as some of the chapters seem, there are so many nuggets that anyone in leadership can apply. I especially think it is important to read this book before assigning/recommending to a new leader as there are methods and concepts that make you ponder your current processes as a leader.

Why it's great...

  • The author, Rachel Pacheco, is funny and authentic. Her personality comes out through her experience and stories which make her lessons so relatable. Her humor (although a little over-the-top at times) makes this book not feel like a "business book" or a required reading.

  • Pacheco comes from the start-up world and caters her message to new managers that will be responsible for everything. I love this because we often teach new managers only what they will be directly involved in and skip important lessons on topics like compensation plans, job design, and performance management cycles. When new leaders understand the basics of how pay, bonuses, job titles, and promotions are determined they can be more supportive of the processes that are in place.

  • There is a great mix of real world scenarios and data that support each chapter. Regardless of preference, the reader will find value in how the information is delivered. Chapters are extremely bite-sized, which makes it easy to read a chapter or two on a 10-minute break.

  • The appendix is legit! As a new leader, having templates and examples make a world of difference. Whether it is a performance improvement plan template or a motivation intake form, the author provides tangible tools that can immediately be applied. She also shares these tools on her website,

The pages I dog-eared and why...

Disclaimer: This is not comprehensive, nor is a complete summary. Just a few learnings that I immediately found helpful/interesting when reading this book. I honestly could have dog-eared each chapter as there was value everywhere!

Page 53 - The dangers of confirmation bias.

  • Confirmation bias happens when we have a theory about someone and we seek out examples that confirm our theory. This is dangerous because we ignore situations when someone behaves in a way that negates our theory.

  • For example, we believe our co-worker is unreliable because they come to an important meeting late. We begin to make note of all the times they come in late or are not at their desk while ignoring the 15 meetings over the last two weeks that they have been on time.

  • Understanding that this bias exists allows managers to step back and take in the full picture before making a reactive decision.

Page 74 - A well-intentioned goal can create shady practices.

  • When the goal becomes more important than the process, extreme measures can be taken to achieve the goal.

  • Although goals should be challenging, Pacheco discusses the importance of setting the right goal.

  • New managers will not only be responsible for setting goals, but also executing goals. Managers must ensure that their work environment is set up in a way that ethically supports the goal and that the processes are well defined.

Page 100 - Great managers support learning.

  • Obviously, this is an area that I am passionate about. I love the practical advice that Pacheco shares on how managers can support employee learning.

  • So much learning takes place in the regular day-to-day activities. Using those opportunities in a more intentional way to support employee growth is a win/win for leaders and their team.

  • For example, staying on the line 10 minutes after a virtual meeting to discuss reactions/discoveries can be such a valuable learning experience for a new employee.

Page 178 - Illustration of how transitions impact teams.

  • Pacheco discusses what happens to productivity during a transition (endings > exploration > new beginnings).

  • I love that the illustration addresses what happens to productivity when people are in the middle of a transition.

  • Spoiler: productivity suffers. However, it is in that lost productivity that individuals are most creative and come up with a new normal.

  • Managers must learn to embrace the discomfort and lack of productivity.

Page 186 - Understanding our past.

  • One of my favorite tools that Pacheco introduces for building trust is the "Journey Line".

  • Each person on the team maps out their journey of highs and lows over the past year. Included on this line is professional and personal moments that are discussed with the group.

  • Sometimes new managers may feel as though it is not "professional" to share personal stuff with their team. Crazy, right? There is a line, but it is so important for teams to know each other.

  • As a new manager, developing a team that trusts each other can be extremely difficult. When we know others more, we develop empathy and understanding.

Page 200 - Where does conflict come from?

  • This is a great chapter as it relates to conflict. Being able to determine if a conflict is occurring due to a relationship, task, or process can help a new manager come to a resolution sooner.

  • Relationship conflict can be the toughest to deal with and will not go away on its own.

  • New managers must be aware of team dynamics and tension as a relationship conflict can create discomfort for everyone on the team.

Page 227 - How power changes you.

  • Pacheco explains what happens when you gain power. I will not even attempt to summarize this because I think her individual bullets are so important. To put it simply, those with power (big or small) will act different.

Page 236 - The Manager-Expert Inflection Point

  • As managers move up, there comes a point when they will work for a boss who does not share their expertise.

  • Often, managers are not prepared for this scenario and struggle to find value in the relationship. Pacheco's advice on "managing up" is so relevant and helpful for those who find themselves in that situation.

  • Won't get in the weeds here but she challenges the reader to take ownership of the relationship and adapt to their leader's style.

  • This struck a chord with me and is on my list as a deeper dive topic.

Page 247 - Knowing what to love.

  • What a great way to wrap up the book. Pacheco reminds readers that the job cannot love us back.

  • As a manager, especially a new manager, it can be quite tempting to live and breathe the job. Keeping things that are important in check is absolutely necessary for the long haul.

  • We can all run for a small period of time, but what happens when we stop? Managers must ensure that they are pacing themselves and reserving their full selves for the things in their life that can love them back.

Favorite quote...

I intended for this to be a quote, but this illustration was just too good!

If you read just one chapter, read this one...

I firmly believe that each reader will get something completely different out of this book depending on where they are in their leadership journey. But for me, it is Chapter 22 titled: Confidence and Vulnerability. In this chapter, Pacheco discusses her management nugget, "Show confidence up and vulnerability down." This means that your boss must be confident in your ability to produce and lead your team. You do this by taking initiative and ownership of your job and your relationship with your boss.

And you know what your team needs? Vulnerability. They need to see you as a human being that does not know the answer to every question. When you show them that some things are hard and some situations create fear for you, they begin to connect with you.

Here's the part that I really liked....

Do not mistake vulnerability with incompetence.

When you "try too hard" to be vulnerable, you end up looking like you don't know what you are doing. Here's an example:

Let's say you have been asked to lead a meeting that includes senior-level leadership. You are nervous and have spent tons of time preparing. During a check in meeting with your team, you share your afternoon plans.

  • Option 1: You try to be vulnerable by saying, "I've been asked to lead the meeting this afternoon. I'm not prepared because I don't have any real power. I'm not sure why I was chosen, but I'll wing it."

  • Option 2: What you could have said that is more truthful and shows vulnerability is, "I am leading the meeting this afternoon and am feeling a little intimidated by some of the people in the room. I would like to talk through my agenda with you all to work out my nerves and get your feedback on the content."

Such a powerful lesson. I see this a lot, especially with people that are afraid and uncomfortable with being "the boss" and overcompensate by appearing to be weaker than they are. You can be totally competent and vulnerable at the same time!

Random note...

At the end of every chapter, Pacheco summarizes using "TL;DR" as the end-of-chapter title. You guys... I read the WHOLE BOOK with complete confusion as to what these letters mean. How embarrassing! I feel like I should have known this! I am sure that you probably know, but in case you don't … the abbreviation is for "too long, didn't read" and is essentially a summary of her key takeaways from the chapter. Duh!


About the Author

Dawn Burkett is the Founder & Principal at DRIVE Talent Development. She is all about developing people to make meaningful impact at work. Learn more about Dawn and her work here.


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