Leaders today have all kinds of learning resources at their disposal—articles, videos, podcasts, and massive open online courses (MOOCs) to name a few. But a good old-fashioned book is still a great way to level up your leadership skills. So what are the best books on leadership?

Over the last few years, we’ve made learning a fundamental part of our company culture, sharing the best business books we can find.

There are many good leadership books out there. Here are a few of our employees’ favorites, with a little bit about why we think they are some of the top leadership books you can pick up and read to improve your skills, deepen your work relationships, and find more success on the job.

Start With Why

Simon Sinek’s best-selling 2009 book Start With Why presents a simple but powerful framework for organizing your organization around why you do what you do. For an introduction to the concept, check out this video, which happens to be one of the most popular TED talks ever.


The Golden Circle

Sinek describes a “golden circle”—really three concentric circles, like a bullseye.

The outer circle represents what you do. The middle circle is how you do it. And the inner circle is why you do what you do. Pretty simple, right? Yet Sinek says most organizations focus on the wrong parts.

Everyone knows what they do, he says, and most can explain how they do it. But most people don’t really understand why. And that, he argues, is the most important part of the golden circle. “Why does your organization exist?” he asks. “Why do you get out of bed in the morning? And why should anyone care?”

Inspired leaders and organizations think, act, and communicate from the inside of the golden circle out. In other words, they start with why. And your why, he says, isn’t to make a profit. It’s something more than that—a purpose, cause, or belief.


People don’t buy what you do

This, he says, is what separates companies like Apple from more ordinary computer makers. And it’s what lets revolutionary inventors like the Wright Brothers and transformational leaders like Martin Luther King, Jr. have such tremendous influence on the world.

That doesn’t mean you should forget about the necessity of winning customers to focus on your why. Sinek says knowing, and acting on, your why is what will make your business successful.

“People don’t buy what you do. They buy why you do it,” he says. “The goal is to do business with people who believe what you believe.”

So—what’s your why?


Radical Candor

Kim Scott, the author of Radical Candor, worked at Google and advised many other companies in Silicon Valley and elsewhere. In her book (and the podcast of the same name, co-hosted with Russ Laraway) she describes an approach to interpersonal communication called…Radical Candor.


What is Radical Candor?

Radical Candor is a way of communicating that Scott summarizes as “care personally, challenge directly.”

In other words, leaders can engage in radical candor by balancing two important things. On the one hand, they must show that they genuinely care about the person they’re talking to. And on the other hand, they must be unafraid to challenge those same people clearly when disagreements arise.


Care personally, challenge directly

Scott shares a helpful matrix to demonstrate how caring personally and challenging directly works to create productive communication.

If you do both, you’re in the Radical Candor zone. If you do neither, you’ve wandered into Manipulative Insincerity land, where you neither care about people nor tell them the things they need to hear.

Caring without challenging leads you to Ruinous Empathy, which may feel safe but doesn’t help people grow, because you aren’t calling them out when things need improvement. And if you challenge people but don’t let them know you care, you’re in Obnoxious Aggression territory—you may be speaking the truth, but your words won’t sink in because you’re coming off like a jerk and you’re not inspiring your team to get better.


How our team uses radical candor

Wendy, who leads one of our teams of virtual receptionists, says the Radical Candor approach resonated with her. “I have a similar style,” she says. “My team members know I am going to back them up, but I have a high expectation for them to be meeting stats. I will do everything I can to get them to that high level, and to have them challenge themselves daily.”

Sarah, who leads our recruiting team, says bi-weekly one-on-one meetings with her team members are a good opportunity to demonstrate both caring personally and challenging directly.

She makes these one-on-one meetings about the other person as much as she can—even letting them create the agenda.

But when Sara has something important to go over with a team member, she doesn’t wait for the one-on-one. “I try to get them right away,” she says, so that during the one-on-one she can focus on the person she’s meeting with. “I’ve already taken care of those things,” she says, “so I am able to just focus my attention on them rather than thinking of all the things I’ve saved up for this meeting.”


Turn the Ship Around

A former US Navy nuclear submarine captain, L. David Marquet wrote Turn the Ship Around to tell the story of his experience turning the USS Santa Fe around, taking it from “worst to first” in the Navy with a unique approach to leadership.

Marquet describes the culture on board a nuclear submarine as “very risk averse.” That’s understandable, given the high stakes of a military vessel’s mission. “When we get the risk wrong, we die,” he says.


Know all, tell all leadership

When Marquet got command of his first submarine, the USS Olympia, he spent 12 months training on that particular ship, studying every wire, every pipeline, and every control. “I was literally the smartest person on the planet when it came to that ship,” he says. “Why? Because as the captain, I wa going to give all the orders. We call it ‘know all, tell all leadership.’ The captain or the CEO knows all the answers and they’re going to give all the orders.

Though this kind of leadership is common in the military and the corporate world, Marquet says it often doesn’t really work that well. Leaders can’t actually control other people’s thoughts. “There are no Obi-Wan Kenobis in here,” he says.


Worst to first

Marquet discovered the limitations of “know all, tell all” leadership when he was assigned to take command of a different submarine, the USS Santa Fe. Not only was the Santa Fe considered the worst in the navy by various metrics, it was a different type of sub from the Olympia. All his study was irrelevant. He no longer knew everything about the ship. He found himself having to admit that he didn’t know things. “That was scary,” he says.

At one point, during a drill, he ordered the sub to travel at two-thirds power while on the battery—simulating what would happen if the reactor were inoperative. The problem? Unlike the Olympia, the Santa Fe didn’t have a two-thirds speed setting on battery power. But Marquet’s Executive Officer relayed his impossible command anyway, because the captain had ordered him to.

Marquet realized he had a problem. And he settled on a surprising solution. “I decided I’m never going to give another order on this ship,” Marquet says.


The power of “I don’t know”

“I now think these words ‘I don’t know’ are the most important words any leader can say. Because those are the words that open the door to learning,” Marquet says. “All learning starts with the assumption that we don’t know. And when the leader says ‘I don’t know,’ it makes it safe for the whole team to say ‘I don’t know.’ I don’t know, let’s find out.”

Rather than give orders like he used to, Marquet empowered his submarine crew to make decisions. They would keep him apprised of their actions by telling him and other officers what they intended to do. “When you say that, you own it,” he says.


You can’t order people to think

The most important thing in a company, Marquet says, is “the creativity, the passion, and the thinking of your people. You can’t order people to do those things.” Instead, he says, you have to “create an environment where they can just do what they need to do without being told.”

For Steven, who leads one of our virtual receptionist teams from his home office in Boise, Turn the Ship Around is all all-time favorite. “The ability to empower people is largely significant in a remote model,” he says.


Crucial Conversations

Another one of our picks for best leadership books is Crucial Conversations:Tools for Talking When Stakes are High, by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler.

The authors maintain that “…the root cause of many—if not most—human problems lies in how people behave when others disagree with them about high-stakes, emotional issues.”


What is a crucial conversation?

In response, the four authors developed the concept of “crucial conversations,” defined as a situation in which opinions vary, stakes are high, and emotions run strong. Sound familiar? Crucial conversations come up (or maybe more often, are avoided) in many contexts, including the workplace.

Over twenty years of research involving more than 100,000 people, the authors of Crucial Conversations have concluded that “the key skill of effective leaders, teammates, parents, and loved ones is the capacity to skillfully address emotionally and politically risky issues. Period.”


Why mastering crucial conversations matters

The authors have identified some real benefits to improving how we handle these crucial conversations. Companies whose employees master this skill respond five times faster to financial downturns. They’re two-thirds more likely to avoid injury or death due to unsafe conditions. And they save over $1500 and an eight-hour workday for each crucial conversation they hold rather than skip.


Crucial conversations on a remote team

Getting better at handling crucial conversations has benefits that touch every part of life, from business to personal. But for remote teams, these conversations might be even more important.

Virtual teams need trust, and handling crucial conversations well helps build and maintain that trust. That’s a big reason why Letty, who leads one of our teams of virtual receptionists, named Crucial Conversations as one of her best management books.


The 5 Levels of Leadership

Our fifth pick for best leadership books for managers of remote teams (or any team) is John Maxwell’sThe 5 Levels of Leadership.

In the book, Maxwell shares his framework for five stages a person goes through on the lifelong journey of mastering leadership.


Level 1: Position

At Maxwell’s first level of leadership, people follow you because of your position. They follow you, in other words, because they have to. For Maxwell, this level is an opportunity to work on ourselves as leaders. But it’s just the beginning, and people who follow you only because of your job title, he says, will give you as little effort and energy as they can get away with.


Level 2: Permission

At this level, people follow you because they want to. They follow you because you’ve done the work to form good relationships. This kind of leader, Maxwell says, has learned to listen and observe, and often has an attitude of servanthood.


Level 3: Production

At level 3, you start to get results for your company’s bottom line. You are effective as a leader, Maxwell says, because you produce.

The level 3 leader builds credibility by setting a good example, and is able to attract other productive people to create even more value. A level 3 leader builds momentum for your organization.


Level 4: People development

At level 4, a leader commits him or herself to developing people, having realized that people are the most appreciable asset in a company or other organization.

The level 4 leader, Maxwell says, understands that 80% of your success is in who you bring in the front door, and in positioning those people for success.

“Successful people,” he says, “discover what they’re good at. Successful leaders discover what other people are good at.”


Level 5: Pinnacle

Maxwell’s top level of leadership is all about respect. Here, people follow you because of who you are and what you have done.

Maxwell warns that reaching this level is a lifelong pursuit. “Leadership is an always ongoing, always learning, growing process,” he says.

In addition, your level of leadership may vary depending on which relationship you’re considering. You may be a level 3 leader with one report, while still at level 1 with someone else who is new to the team.


Discovering your leadership level

For Rebecca, who leads one of our teams of dedicated agents, the book “put into perspective what kind of leader I was. That book helped me get to that level with more people, and maybe go up a level or two.”

She followed Maxwell’s advice to use the framework to identify where she was as a leader with each of her team members. “You can’t force someone to follow you,” she says. “It’s about connecting with them and also having humility. You have to look into yourself, and identify things in yourself. I think a lot of people don’t do that a lot. It was an eye-opener for me.”


More books about leadership we love

Leadership is a big topic, and one that can take a lifetime of experience to master. A short list can’t possibly cover all the good leadership books out there. Here are a few more that our team recommends.

Good Leaders Ask Great Questions by John Maxwell

How to Win Friends and Influence People by Dale Carnegie

Who Moved My Cheese? By Spencer Johnson, MD

Lead Simply by Sam Parker

Stepping: How Taking Responsibility Changes Everything by John Izzo

The Charisma Myth by Olivia Fox Cabane

Disney U by Doug Lipp

The Future of Management by Gary Hamel

The Toyota Way to Lean Leadership by Jeffrey K. Liker and Gary L. Convis


What are your top leadership books?

We’ve had our say. Now we want to hear from you! What great books on leadership did we miss? Is there a book that changed the way you approach leading your team or company? Let us know in the comments! And if you’re wondering what kind of leader you are, here’s a quick roundup of several types of leadership.


Photo by Tamarcus Brown on Unsplash