Chapter 2

Victoria is always prepared. The old saying, “It’s amazing how much luckier I became when I am prepared” is true, and it is one of the traits that served Victoria well throughout the book. Be prepared. Always. Full stop.

Understanding a person’s emotional motivation is important. Victoria’s emotional motivation was to please Moose; this was defensive. She wanted to keep the status quo and not change anything, living with Moose’s legacy.

Chapter 3

Scarlett was aggressive and smart. Her emotional motivation was revenge, fueled by a strong vengeful motive.

Positioning matters. Think about where Scarlett met Jeff at Rosewood. Be with the best (here in Silicon Valley) and surround yourself with the best—people better than you.

Build a strategic network. Scarlett built a network her whole career: Jeff Schmidt, venture capitalists, Heritage senior executives, ex-Googlers, etc. Do you actively and consciously do this?

Chapter 5

Like Victoria (Moose), Scarlett (childhood trauma and Victoria’s betrayal), and Lindsay (upbringing and doing right by others), motivation is important. Emotional motivation was different for each of them: Lindsay wanted to keep the town thriving, wanted it all to be robust. Victoria was disconnected, motivated by the past. For Victoria, the emotional disconnect between her and others caused, in part, the strategic failure of the company. The strategic and the personal, especially emotional motivation, are all intertwined. Always remember that.

Again, the importance of family: Lindsay had an emotional tie to not only her store but the impact it had on others. She also had a sounding board, Paul, two advantages that Victoria didn’t have. What about you?

Chapter 8

Corporate life, dedication to a small business, and business in general can take a toll on personal life. (Bill had a number of broken marriages.) Once again, the importance of family: Paul is not glass half full; it’s one hundred percent full. Support family. Don’t underestimate its importance in both your personal life and professional career. Balance is the eternal quest that many of us strive for but never quite achieve.

Chapter 10

Even for the most seasoned veterans, legacy “big shots” and “larger than life” personalities can be intimidating. George outlived his usefulness because Victoria could not overcome his legacy and ties to Moose.

Why did it take her that long to read the report?! It was more than Victoria being allostatic. She was also stubborn and obstinate in many ways, horrible traits for a leader and a CEO. We all have these traits to some degree. How strong are yours?

Chapter 12

It is interesting (perhaps ironic) that, in a way, Moose saved Victoria here (that is, if it weren’t already too late). It was Moose’s presence and Victoria’s fear of disappointing Moose that led her to a moment of self-doubt, something critical to her reexamining the business situation.

Note that Victoria was dismissive to everyone throughout the story until she saw it was Scarlett who was behind the disruption. That was her trigger. Remember that Paul had asked Lindsay what Victoria’s trigger was? Lindsay had this in her pocket all along but never realized it. It was unfortunate that it took this long to get to that point. Lindsay probably could’ve done this much earlier had she thought through what Paul had said. For every person you’re trying to influence, what is their trigger?

Chapter 13

Someone once said to us, “Strive for joy, not balance.” Well, there is certainly truth in this; life can change us for the better. Age can change us for the better as well. Always keep this in mind. Also remember that joy is short-lived; the effects of a lack of balance can take longer to manifest. It’s cumulative.

Notice how the entire executive team was energized once they were aligned for the right purpose. Also notice the reluctance of the Old Guard (George) to change. Alignment, especially alignment in emotional motivation, is crucial to organizational alignment.

Chapter 14

Be the first one at the meeting. Be prepared. This is true for senior executives but especially true for more junior people. A person close to us started as an investment banking intern at a large bank in New York, a bank that had “work from home” Fridays. The advice we gave him as a junior associate was to be there before everyone else was every day and leave after they left. “Work from home” Friday is an opportunity for you to be in the office working. It’s only a matter of time before a managing director (MD) or vice president sees you there when they happen to be in the office. In this case, one MD did indeed happen to stop by the office to pick something up one Friday and noticed that there was only one intern in the office and working hard that Friday. He was subsequently offered a permanent full-time investment banking position in the group that MD managed. That was not a coincidence. Be earnest as a junior associate or the CEO.

Chapter 15

Like Victoria, when you make work your life, be prepared and willing to accept the consequences, which are likely to come many years later. The rewards are often relatively quick to materialize, while the consequences are almost always a slow burn. You make a choice every day, consciously or without immediate thought of consequence, but you make a choice every day. The saying, “Work hard, play hard,” was never “Work hard, work hard.” Victoria was seeing this now.

On a more positive note, Victoria finally wised up and reached out to Lindsay to play a prominent role on the executive team. Many days late and many dollars short, but better late than never, as this may help in her next venture, something alluded to in the final few paragraphs of the book.

Lindsay does such a great job on many levels:

She had the presence, EQ, and humility to know that she was in their territory, as she presented in the meeting.

She demonstrated on-the-ground experience driven by data and specifics.

She was team-driven, giving credit to both Trish and Bill. How many times have you witnessed someone taking credit for a team’s work, and how has that left you feeling?

She displayed a candid and honest assessment of the company’s strengths and weaknesses.

Chapter 19

We talked (in the Leadership section) about the “New York Times test,” that is, don’t do something if you would not be happy having it exposed on the front page of the New York Times for the world to see. “Would you be OK if your family, your children, saw what you had done?” we asked. Here, where the leadership team failed in entirety was in thinking that putting together an inferior version of the AI system was a good idea. They should have thought about this being exposed and asked themselves, “What if the inferiority of the system we are launching is featured front and center in the New York Times? Would that help us?” Clearly, the answer was no, and that is indeed what happened. It also gave George the ammunition for the quote that was so damaging.

Chapter 20

People think leaders can’t evolve. A wise colleague once said that there is no standing still; if you’re not moving, you are essentially moving backward in relation to others. So, you either evolve forward or move backward. You must evolve.

There’s an old proverb about the frog and the scorpion. The short version of a long story is that the frog wanted to cross a pond and knew that he couldn’t swim the whole length. As he was standing there, a scorpion walked up and told him, “I’ll give you a ride to the other side of the pond.” The frog said in response, “No, if I let you give me a ride across the pond, you’ll just sting me, and I’ll die; you’re a scorpion.” The scorpion proceeded to promise not to sting the frog and did so apparently convincingly, so much so that the frog agreed to ride on the scorpion’s back across the pond. Halfway across, the scorpion stung the frog. While dying, the frog asked the scorpion, “Why did you sting me? You promised not to.” The scorpion responded abruptly, “I’m a scorpion. Why would you think I would do anything else?” Sometimes that’s true. For example, in game theory literature, we know that companies are incredibly consistent in the way they respond to competitive strategic moves. However, even in this example, there are exceptions. When a new leadership team is put into place or there’s exogenous shock in the marketplace, like an oil price spike or a recession, this consistency changes. Always be mindful of the past, but recognize that people, organizations, and situations evolve and change.