Rachel Pacheco - Bringing Up the Boss

Contents

PRAISE FOR BRINGING UP THE BOSS

I only wish that Bringing Up the Boss had been around when I got my first promotion to manager. The tools in this book are accessible and easy-to-useI immediately put them into practice on my own teams. This is required reading for first-time and senior managers.

Fiona Greig, President, JP Morgan Chase Institute

In fast-growing start-ups, its up to managers to help guide their teams through constant change. Yet there are also many first-time managers who are often thrust into leadership roles with very little training and are unprepared for the new responsibilities that they will face. Rachel Pacheco expertly helps new managers learn the ropes with bite-sized lessons on how to effectively manage, lead, and inspire through change, particularly in high-growth start-ups.

Katherine Ryder, Founder & CEO, Maven Clinic

Behind any great organization are strong managers who can motivate and inspire their teams. Over the course of my career, Ive realized that the ability to do so is not innate, but learned. Bringing Up the Boss helps new and established managers quickly gain these skills and immediately apply them to their day-to-day.

Stephan Jacob, Cofounder & COO, Cotopaxi

Start-ups are inherently crazy. Bringing Up the Boss is a great guide to help make them a little more sane by focusing on what managers in these high-growth companies need to do to succeed.

Andrew Savage, Founding Team & Head of Sustainability, Lime

The lessons in Bringing Up the Boss are not unique to start-ups. Managers and leaders in the nonprofit world have needed an accessible book like this for years. Any person in a position of management will gain new insights and wisdom from this book.

Janet Dalziell, former International Director of People and Culture, Greenpeace

When I started Wellthy, I quickly realized how challengingand crucialit is to train up new managers in a fast-growing environment. Bringing Up the Boss is required reading for leaders and managers alike, and especially for a person managing in a fast-growing company.

Lindsay Jurist-Rosner, Founder & CEO, Wellthy

Over the course of my career, Ive learned the key to any great ensemble is open communication and honest, thoughtful feedback. Bringing Up the Boss acts as my conductors scoreinstructing me how to do both and so much more. Its full of easily digestible nuggets of wisdom for real-world application on and off the stage.

Joseph Conyers, Bassist, The Philadelphia Orchestra & Faculty, The Juilliard School

Whether youre managing dozens, a handful or just one employee, Bringing Up the Boss will help you sharpen the skills you need to build and maintain a strong, happy team.

Erin Lowry, author of the three-part BROKE MILLENNIAL series

Bringing Up the Boss copyright 2021 by Rachel Pacheco

All rights reserved. No part of this book may be used or reproduced in any manner whatsoever without written permission of the publisher, except in the case of brief quotations embodied in critical articles or reviews.

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First E-Book Edition: August 2021

Library of Congress Control Number: 2021905263

ISBN 9781953295019 (print)

ISBN 9781953295408 (electronic)

Editing by Vy Tran

Copyediting by Ginny Glass

Proofreading by Lisa Story and Cape Cod Compositors, Inc.

Text design and composition by Katie Hollister

Cover design by Heather Butterfield

Special discounts for bulk sales are available.

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To my mom and dad.

Thanks for everything youve done to bring up this boss.

CONTENTS

A number of years ago, I joined a small and growing start-up as the chief people officer. During my first week of work, I had coffee with Sandy, an employee who had joined the company two years earlier when it was only five people. She was poised, knowledgeable about the business, phenomenal at the work she was hired to do... and totally freaking out. Sandy came on board fresh out of college, and now two years in, she was managing four new employees, some older than she. Earlier that day, shed received her first upward performance review from her team, and the jury was in: Sandy was a terrible manager. Over oat-milk lattes, Sandy read me the litany of sins she had committed as a managermost of them unbeknownst to her.

But was this a surprise? Sandy didnt have any work experience outside of our company, and she definitely had never managed before. Moreover, Sandy didnt have a skilled manager managing her, so she didnt have anyone to emulate. And our little boot-strapped start-up didnt exactly have tons and tons of money to send Sandy to a fancy management training or run a whole bunch of internal training programs. Sandy was desperately trying to keep her head above water as a manager and absolutely suffering in doing so. And even worse, Sandys team members were suffering as she staggered in the dark trying to manage them.

Sandys challenge is not unique.

Often, we are put into positions of managementespecially in small and growing organizationsbefore were actually ready. Our organizations grow quickly, and we are expected to grow in our roles with just as much speed. We end up stumbling along and doing our best, but our best may make our teams miserable. In the start-ups and other organizations Ive worked for over the years, Ive seen this cycle repeated over and over again: Top performer gets promoted to manager, has no idea what to do, team members become unhappy and leave, and the new manager becomes unhappy and feels terrible about themselves and their job. Repeat cycle.

Being a manager is a huge responsibility. For better or worse, we play outsized roles in how our teams experience their days and their jobs. We have the power to help someone grow, develop, and thrive; we also have the power to overburden, confuse, and wreak havoc. Many of us have personally had the experience of a terrible boss. And many of us have left jobsjobs that otherwise were fulfillingbecause weve had a manager who was not just awful but also unbearable.

We have the power to help someone grow, develop, and thrive; we also have the power to overburden, confuse, and wreak havoc.

For the last fifteen years in my coaching, advising, and teaching, Ive collected stories, experiences, and challenges that new managers face. In particular, Ive focused on new managers in small and growing organizations who dont have the resources of a large company. These organizations may not be able to train their managers, send their employees to courses, or hire fancy business-school graduates (not that a diploma from a business school means youre a great managertrust me). From these stories and challenges, Ive developed a set of tools and best practices to help make the new managers job a little easier.