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Book Summary – Strategize to Win: The New Way to Start Out, Step Up, or Start Over in Your Career

Strategize to Win - Book summary

This book by Carla Harris is written to help professionals develop their career strategy, position themselves for their dream job, and figure out the next steps for their career progression. In this free Strategize to Win summary, you’ll learn how to start out with the right foundation, step up and grow your career, and start over with a right job/career.

Strategize to Win: An Overview

We face different challenges at different phases of our career. Fresh graduates may feel unsure about which career to pursue or what to focus on. After working for 5-10 years, professionals often find themselves struggling with changes and uncertainties, or to re-orientate themselves for personal and professional success. These difficulties are further compounded by dynamic environments and financial downturns.

This book was written in 3 parts, with strategies and tips for people who’re starting out, stepping up or starting over in their careers. We’ll start with an overview of your career strategy, then briefly introduce the key ideas in the 3 sections of the book.


Today, it’s no longer realistic to work for 1 company for life. In fact, staying too long in a single role or company can limit your growth, network, influence, compensation, and career success.

Most professionals will have multiple careers over a period of 30-50 years. Plan your career in 6-8 modules of about 5 years each. Have a rough idea of what you’d like to achieve in each phase.

  • Aim to work for at least 3-5 companies throughout your career. You can complete 2-3 modules in 1 company by (i) rotating to different roles within the same company, or (ii) moving to another company then returning to a more senior role in the original company.
  • To maximize your learning and exposure, work for the market leader and change companies as new market leaders emerge.

Strategize to win summary - career strategy

To position yourself for a job you want, you must first know what you want. On 3 separate sheets of paper, write down your answers to the 3 key questions below.

1. What type of content do I want in my job or career?

  • Identify the components or building blocks of a job that would motivate and engage you, including its domain, activities, people or environment. For example, are you passionate about sports, performing arts, or scientific explorations? Do you prefer to work alone or in teams, to solve problems or execute pre-defined solutions, to travel or stay in a fixed location?
  • Identify the activities that truly stimulate, intrigue and challenge you. Ask yourself: What would I be happy to do for free? What activities do I get so immersed in that I lose track of time? What type of work would I look forward to everyday?
  • Your ideal job may not exist yet, or you may not qualify for it yet. However, you can prepare yourself for your future dream job.

2. Which jobs have this content?

Explore as many options as possible to maximize your chances of finding a good fit.

  • Set aside about 100 hours a month to do your research and talk to people about what they do. Ask about the qualifications or experience required for their jobs, the pros and cons, and how they got to where they are. Make notes on possible career trajectories, and revisit this list throughout your career.
  • You can also immerse yourself in an environment that interests you, e.g. volunteer at a hospital. You may start to notice interesting combinations. For example, someone interested in technology and sports medicine may become an orthopedist or a technologist who invents orthopedic solutions.

3. What are the skills, experiences, or education I need to be considered for these roles?

  • You may need academic qualifications for certain jobs (e.g. a doctor or lawyer). However, in most cases, hirers are looking for generic traits such as self-motivation, people skills, or achievement-orientation.
  • Landing a job actually depends on your ability to understand what the hirer wants, and to convince them that you’re the right person for that role.

Strategize to Win in your Career

As mentioned, Carla Harris wrote this book in 3 parts. Besides the strategic picture (above), she goes into details for 3 major stages of your career: (i) starting out in the early stages of your career, (ii) moving up the career ladder and (iii) considering a job/career transition. Here’s a quick visual overview:

Strategize to win summary - positioning for career success

Starting Out with the Right Foundation

In our full Strategize to Win summary, we’ll elaborate on details and specific steps/tips for people in the early stages of their career, including:

  • How fresh graduates (or people who’ve just started working for a few years) can figure out the next step to take;
  • How to become a truly attractive candidate: do your research, catch the hiring manager’s attention, address the 3 things all hirers are looking for, prepare 10 common interview questions and position yourself to be the ideal candidate;
  • Position yourself with the right skills/exposure: know the best paths to upward mobility, the strategic skills to develop in the first 5 years of your career and how to handle rotational programs and negotiate for the market rate.

Stepping Up & Managing your Career

Once you know your career goals and what you’d like to achieve for each module, make sure that every step you take serves a career agenda, be it to acquire a specific skill, experience, network or title. In our complete Strategize to Win summary bundle, you can get details on:

  • Why/how to accumulate performance currency (through results and value), and get your ideas adopted by managing 4 types of stakeholders;
  • Why/how to accumulate relationship currency (through business and personal relationships);
  • How to master 2 parts to effective communication; and
  • How to manage your work profile: know the 5 work profiles, the environment you could thrive in, and the 6 traits of great leaders.

Starting over with a New Job or Career

Changes—be it voluntary or involuntary—come with both risks and opportunities. This last section is about:

  • Knowing when to change your job/career;
  • Managing involuntary changes, e.g. a new boss, losing a sponsor or even losing your job; and
  • Reposition yourself to leverage your unique strengths, skills and experience, at different phases of your career.

Getting the Most from Strategize to Win

This book is full of practical tips for people at different stages of their careers, and is especially useful for those who’re just starting out or are in the middle phase of their career. For details on each of the career strategies/tips outlined above, do check out the our full book summary bundle. This includes an infographic, 17-page text summary, and a 26-minute audio summary.

Strategize to Win summay - Book Summary Bundle

The book includes numerous examples to show how people in different industries and stages of their careers made decisions and positioned themselves for success. Harris also includes examples of scripts that you can use in your interviews and career discussions. You can purchase the book here or visit for more information.

Looking for more tips to stand out in your career? Do also check out our summary of So Good They Can’t Ignore You.

About the Author of Strategize to Win

Strategize to Win: The New Way to Start Out, Step Up, or Start Over in Your Career is written by Carla Harris–a Senior Client Advisor at Morgan Stanley, where she was previously also a Vice Chairman. She has extensive experience in technology, media, retail, telecommunications, transportation, industrial, and healthcare sectors, and was appointed by President Barack Obama to chair the National Women’s Business Council. She sits on several Boards and has received many awards and accolades. She was also named on numerous lists, including Fortune Magazine’s list of “The 50 Most Powerful Black Executives in Corporate America” and U.S. Bankers’ Top 25 Most Powerful Women in Finance. Harris is also an accomplished singer, an internationally renowned speaker and the author of several books.

Strategize to Win Quotes

“You will find the answers to your career questions not in knowing the job itself, but in defining the content of your job.”

“The key to… acquiring a job is actually highly dependent upon your understanding of what the buyer (the interviewer) is really buying and how well you sell it (your background and experience) to them.”

“Telling and selling your story is one of the most important components to successfully interviewing for any position.”

“It is up to you to get to know your role and its market rate, and to have a strong argument for why you deserve it.”

“Making mistakes is common in any workplace. What is important is how you recover.”

“What you say and how you say it has implications for how you are perceived in your environment.”

“You must know who you are and who you aspire to be.”

“The decision to change jobs, companies, or careers is among the most important you will ever make in your career.”

Click here to download the Strategize to Win summary & infographic

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