Strong leaders don’t play it safe.

There’s an old saying, “Nice guys finish last.”

If you know me, it won’t surprise you that the phrase has a baseball connection. The Brooklyn Dodgers’ outspoken manager, Leo Durocher, coined the phrase in 1946 to explain why the New York Giants were stuck in last place despite having good talent.

Known as “Leo the Lip,” Durocher was the kind of leader who would do anything to win, and he didn’t mince words. Talking to a reporter about the struggling Giants, he quipped, “Take a look at them. All nice guys. They’ll finish last. Nice guys finish last.”

Like most clichés, it’s not always the case, but there is some truth to it. Over the years, it’s come to mean that people who aren’t assertive, decisive, or self-assured may end up being used as a doormat by those who are more forceful, more insistent, and quite frankly, bolder.

Personally, I like leaders who are friendly, kind, and agreeable. Nobody admires execs who are abrasive or pushy. But—and it’s a big but—you do need to balance being a “nice guy” with being a “courageous guy.” If not, more aggressive competitors willing to take risks (or ruffle a few feathers) may outwit, outmaneuver and outsell your organization.

You could say these bolder leaders have chutzpah–-a Yiddish word meaning a confidence that can sometimes border on annoying. If you have chutzpah, you do and say what you think without worrying about stepping on toes, looking silly, or getting in trouble.

Leaders who have this kind of self-assuredness may be rough around the edges (like Leo Durocher), but they often inspire greatness in their teams.

Beware of the bland leading the bland.

“In a crowded marketplace, fitting in is failing. In a busy marketplace, not standing out is the same as being invisible.”

That’s Seth Godin from his book, Purple Cow: Transform Your Business by Being Remarkable. The danger of blending into the background is most obvious in the retail sector. In fact, the “power of the new” drives virtually all retail marketing—from food to fashion to furniture. But invisibility in any industry is deadly, whether it’s manufacturing, technology, financing, etc.

Even nonprofits can get stuck in a rut. That’s why millions of requests sent by charities to potential donors go in the wastebasket. Even though we may admire the sender, we don’t always bother opening their mail because we’re deluged by a flood of similar-looking generic appeals.

To offset this, leaders sometimes need to rock the boat, upset the apple cart, kick over the sacred cow—any metaphor you choose—to intentionally disturb the traditional, established routine of a company or organization.

As an executive coach, I’ve known well-meaning leaders with such an easygoing managerial style that they won’t disrupt the status quo unless absolutely necessary. (That’s a good reason to use a strategic planning consultant like myself. We bring a fresh, objective perspective.)

What’s the antidote to passivity?

A strong leader needs to embrace innovation, foster creativity, and inspire originality. Using these priorities, any group—even a legacy organization—can snap out of “sameness” and create a remarkable breakthrough that commands the attention of their target audience.

As Seth Godon says, “Something remarkable is worth talking about. Worth noticing. Exceptional. New. Interesting. It’s a purple cow. Boring stuff is invisible. It’s a brown cow.”

I’m not calling on leaders to abandon their current strategies or dump their best practices. But I am suggesting they encourage their teams to focus on creating truly exceptional products and unforgettable customer experiences—the kind that clients simply can’t help but talk about.

Let’s give ‘em something to talk about.

Bonnie Rait had it right. Do something that creates a buzz, ignites enthusiasm, and raises awareness of your brand. Something that will shake up your staff and your customers. Like never before, the “flat earth” marketplace is hyper-competitive and hyper-crowded. Fortunately, there are still unlimited opportunities for companies that innovate, disrupt, and surprise the market—if they have a strategic plan based on taking risks, prioritizing customer needs, and remaining adaptable.

Let’s consider three very well-known (but very different) companies who had one thing in common when they burst on the scene. Their common thread? They were not worried about flying in the face of conventional wisdom and standing out from the crowd.

In their own way, each of these innovators remind me of Robert F. Kennedy’s quote, “I dream of things that never were and ask, ‘Why not?’”

Sweet ideas attract a buzz.

For real donut lovers, there’s Krispy Kreme and then there’s everybody else. That’s why fans will drive for miles to get the real thing.

Granted, Krispy Kreme has a great product.

But what made them stand out in the beginning was their innovative methods of dominating a new market. They’ve recently updated their strategy, but it’s worth a look at their past tactics. Compared to the stodgy business norms of the day, their model was aggressive and exponential.

When Krispy Kreme rolled into a new town, they began by giving away carloads of free donuts. The lines on opening day were endless. Of course, the crowds most likely to show up had already bought into the legend of Krispy Kreme and were thrilled to finally have one close by. These “sneezers” quickly told their friends, shared samples with their friends, and best of all, dragged them along. And that’s where phase two kicked in. Krispy Kreme was obsessed with spreading their impact. In those early days, whenever they opened a flagship store, they rushed to partner with nearby coffee shops, gas stations, party stores and delis. The goal? To make it easy for the uninitiated to stumble across their product. What started with the true fanatics celebrating at a grand opening soon saturated the market by making converts out of the general public.

(What was so remarkable? Becoming the most coveted donut on earth.)

 It’s music to my ears.

In the summer of 1979, Sony introduced the Walkman, a 14-ounce, portable cassette player with cool buttons, tiny headphones and a leather case. It even had a second earphone jack so two people could listen in. That was a bold move and it changed the way we listened to music.

Fast forward to 2010, and the listening experience changed again. Today, the name Spotify is practically synonymous with listening to music. But this technology company didn’t rise to ubiquity by accident. Their success came from developing and executing a remarkable strategic plan that prioritized innovation and user experience. When leaders at Spotify recognized the music industry was ripe for disruption, they developed an intuitive platform that made it easier to discover, share, and listen to music.

Spotify’s “purple cow” success was built around its focus on innovation. They took the best ideas from iTunes and cleverly made them cheaper and better and more fun to use. They stuck their neck out by taking the best technology from illegal music platforms and making them 100 percent legal. In addition, they incorporated all-new social features, which allowed users to share playlists and music recommendations with friends.

(What was so remarkable? Revolutionizing the way we listen to music.)  

 Show me the money.

Ever hear of Fieldlink? How about Confinity? Me neither. They were the early names of a company that invented security software for hand-held devices. When that venture failed, they tried a new name and new focus—to create a totally unheard of “digital wallet.”

People had been writing checks to merchants for a thousand years. But with the advent of the internet, the world needed a better way. In 1998, Max Levchin, Peter Thiel, and Luke Nosek decided to rock the boat.

With a current market cap of $70 billion, PayPal is one of the most successful financial tech companies worldwide. It began with developing a way for people to beam money securely between Palm Pilots, but it didn’t take off. Rather than quit, the three founders pivoted their strategy towards an entirely new market—the online auction site eBay. At the time, using eBay involved physical checks and money orders. PayPal’s game-changing strategy focused on user experience and strategic partnerships with retailers by offering a platform that allowed anyone to send and receive payments online.

Their bold plan was obviously a winner, and to their credit, it’s continued to flex and expand with mobile payments, international transactions, and the payment transfer app Venmo.

(What was so remarkable? Totally transforming online money transactions.)  

Swing for the fences.

I began this blog with “Leo the Lip” Durocher. As a leader, he wasn’t always an ideal example. In fact, this celebrity manager was known for his clashes with the baseball commissioner, the press, and especially the umpires. He was ejected an unbelievable 95 times from games for debating the umps—but his players loved him for taking a stand on their behalf.

In spite of (or perhaps because of) creating so many altercations, Durocher was hugely successful as a player and a coach. This baseball icon won three World Series titles—as a player for the Yankees and Cardinals, then as manager of the Giants. Durocher retired in 1973 with an amazing 2,008 victories and was elected to the Baseball Hall of Fame in 1994.

As we saw earlier, he famously said, “Nice guys finish last.” But a truer maxim would’ve been, “Bold leaders finish first.” And that’s exactly what happened in 1954, when his New York Giants beat the odds by sweeping the World Series against the heavily favored Cleveland Indians.

Harvey Wineberg was Durocher’s business manager for three decades. He said, “Love him or hate him, but he was good at what he did. He knew how to get the most out of people. People followed him.”

Hmm. Good at what he did. Got the most out of people. Attracted followers. Isn’t that a legacy any leader would want?

Let’s play ball.

As a leader, you have to figure out how much risk is appropriate for your organization. Only you can decide how far you’re willing to go to stand out from the crowd and pull ahead. But I sincerely believe I can help.

If you’re interested in my advice on moving from “invisible” to “remarkable,” let’s set up a relaxed, informal conversation. Contact me to get started, and we’ll see if I’m the right business coach for your team.