At the beginning of 2021, I put on my Instagram stories that I wanted to read more ~business~ books this year and I opened it up for others to join me. I chose Carla Harris’ book “Expect To Win: 10 Proven Strategies for Thriving in the Workplace” because I saw her speak at a virtual conference in 2020 and thought she had a lot to offer. A few friends agreed to join me on this journey and we’ve been meeting once a week since.

In these book club meetings, we’ve been discussing a chapter each week and speaking to our experiences in our current job as well as growth opportunities. We’ve all come to realize that 2020 going the way that it did, we were all just fighting to survive but we want more for and from ourselves in 2021.

Each week I’ve been compiling discussion questions to help guide us in conversation so that we’re able to touch on as many of the major points Expect To Win addresses. They’ve been beneficial to our discussions so I wanted to share them with you!

There will be a few parts of these posts (will be linked here once posted), but I wanted to get the first chunk out so you can read along if you’d like.

Chapter 1.   Authenticity: The Power Is You

• Was there a specific story or situation that Carla mentioned this chapter that you resonated most with? Why?
• How do you define authenticity? How does that differ from how Carla defines authenticity?
• Which tasks or other parts of your job make you feel the most “authentically you?” Which tasks or other parts of your job do not?
• What are some actions, mindsets, qualities, or experiences that highlight how you are a great fit for what you do (your competitive advantage)?
• Where do you think you need to add more authenticity at work? What are things you can/need to change to be more authentic?
• When is a time that you’ve felt, acted, or been inauthentic at work (or outside of work)?
• What holds you back from being authentic at work?

Chapter 2.   Be the Architect of Your Own Agenda: Have a Flexible Strategy and Don’t Be Distracted by Mistakes 

• Was there a specific story or situation that Carla mentioned this chapter that you resonated most with? Why?
• What is your agenda?
• Do you find yourself comparing yourself to the Joneses and their careers? Who are you most likely to do that with? What is usually the item/quality/experience you fixate on?
• What are you flexible on in regards to your career? What are you less likely to be flexible on?
• What are examples of things you’re looking to add to your repertoire? Clients, events, sectors, etc.
• Do you forgive your own failures easily? What are some ways you can be better about this?
• Have you ever had a “naked short” scenario, where you were too afraid to ask for help? What did you learn from that experience?
• Are you more of a “political maniac” or a “workhorse”? What is your boss? Your direct reports/colleagues?

Chapter 3.   You Are the Captain of Your Career: The Ninety-Day Rule

• Was there a specific story or situation that Carla mentioned this chapter that you resonated most with? Why?
• What was the most important thing you learned in your first 90 days?
• What is something you wish you’d learned in your first 90 days?
• Who is someone (name or position) you want to build a relationship with at work? Outside of work?
• What are some of the unspoken rules at your company?
• What are skills you need to teach yourself to make up for skills others should have taught you in the first 60 days?
• What training opportunities are open to you? Where else can you look for training opportunities?

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Have any other questions for these three chapters? Have suggestions for what we should read next? Leave them in the comments below!

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*Link to Carla Harris’ book “Expect To Win” is an affiliate link. I receive a kickback from this link, but this doesn’t affect my opinions of the book.

*Cover image from Amazon.