News & Opinion

Inside the 2019 Longlist: Leadership & Strategy

Sally Haldorson

November 21, 2019


Porchlight General Manager and Chief Strategist, Sally Haldorson, takes us inside the best Leadership & Strategy books of 2019.

What is the purpose of any business? To what goal do we set our strategy? Most people will answer: to make a profit. Others may say, to beat the competition. Peter Drucker said it is to “create a customer.” Most recently, I’ve been thinking a business’s purpose might be to establish a legacy. Most of the time when we think about legacy, we rightly think about families, about the older generation creating opportunities for the younger generation to do better, have more. In business, we should want the same. Not just success and stability for the business owner or shareholders or folks in the C-Suite, but for every employee and every customer that comes into contact with the company, as well as their families, their children. Of course, a legacy isn’t limited to (but should necessarily include) the people in an organization. A legacy can also come in the form of ideas. In the same way that art and music are influenced by what came before, so too are business ideas. The trick is to build off the past with an eye to the future. Each of the finalists in this year’s Leadership & Strategy category instruct us on how to create just such a legacy. 


The Infinite Game by Simon Sinek, Portfolio | Simon Sinek declares business an “infinite game” that will continue to be played regardless of whether we participate and will continue on long after we’ve left the arena. Some companies may focus on beating the competition, or even the market, but that kind of finite strategy precipitates a finite lifespan. How we play the game when we are in it—are we responsible, ethical, adaptable?—is the only thing that matters, since winning is never achievable in an infinite game. 

It's How We Play the Game: Build a Business. Take a Stand. Make a Difference. by Ed Stack, Scribner | Ed Stack’s book is the literal application of Sinek’s theory. (#seetitle: It’s How We Play the Game.) Stack grew the company his entrepreneurial father started from a mere $300 from his mother’s cookie jar stash into a sports store behemoth that takes its civic duties as seriously as its business successes, focusing on supporting youth sports, especially in urban areas, to enrich young people’s lives, but also leveraging their market share to influence gun reform to save young people’s lives. 

Invisible Women: Data Bias in a World Designed for Men by Caroline Criado Perez, Abrams Press | In Invisible Women, Caroline Criado Perez identifies the myriad ways that data—notably, the data that influences business decisions—underrepresents women. Leaders must start, Perez nudges, by prioritizing the gathering of female-only data because we can’t change what we don’t know. But what we do know now via Perez is just how much our biases continue to risk women’s lives due to that underrepresentation. We can’t construct a true legacy when we devalue members of our human family. 

The Remix: How to Lead and Succeed in the Multigenerational Workplace by Lindsey Pollak, Harper Business | Neither can businesses dismiss the Millenial and Gen Z generations just entering the business world. Lindsay Pollak, in The Remix, asks that we cease the ‘whatever do we do about the young people and their screens and their demands?!’ hand-wringing so common now. Refreshingly, Pollak has respect for every generation, whether Boomer or Millenial, and catalogs the strengths and weakness of each, showing how companies and their employees can combine generational perspectives in the way popular music remixes combine the old and the new to create something that honors tradition but also pushes boundaries.

Seeing Around Corners: How to Spot Inflection Points in Business Before They Happen by Rita McGrath, Houghton Mifflin Harcourt | Rita McGrath would likely bump fists with Pollak in agreement. In Seeing Around Corners, McGrath suggests that one way to avoid being sideswiped by approaching change is to look to the behaviors and habits of the youth. Andy Grove warned us of inflection points back in 1988, and we have been afraid of them ever since, but McGrath lays out a common-sense practice in Seeing Around Corners that reveals the only thing to be afraid of in the future is our own unwillingness to change.


These five excellent books will guide you as you create your own leadership legacy. Here we learn that business isn’t about the score we keep. Instead, it is a journey that must pay tribute to the past while looking toward the future. By developing an ambitious but flexible vision, a willingness to trust and include others, and the courage to make tough decisions and take risks, you too can create something worth handing down. 

About Sally Haldorson

Sally’s mission as Porchlight’s Managing Director is to make Porchlight a great place to work for employees, and a consistently high-performing service organization for everyone in or orbiting the publishing industry. After 25 years working in book retail, she has developed a penchant for business strategy, both as a socio-economic force and a literary genre. Happy to put her English and Creative Writing degrees to work, she helped craft three editions of The 100 Best Business Books of All Time, and she reads, writes, and reviews for the company’s marketing team. Sally lives north of Milwaukee with her husband, son, and dog, and, in her spare time, rather doggedly works to perfect her writing skills and her tennis game, unsure which is the more Sisyphean endeavor.

Learn More

We have updated our privacy policy. Click here to read our full policy.