Change this Mindset to be a Better Leader

Jake Wilder
8 min readNov 17, 2018

5 Ways to be Influential in a Changing World

“If you’re drowning, you make a lousy lifeguard,” Seth Godin recently told Tim Ferriss. And while we’re quick to recognize this fact as it relates to beach safety, we’re less adept at recognizing the risk in our own companies. Too often we fail to see that as we push a a productivity-obsessed culture, it leaves a leadership vacuum in its wake.

Great leaders all have one thing in common: they help us to arrive at better places than we could reach on our own. Or as David Foster Wallace put it,

“A real leader is somebody who can help us overcome the limitations of our own individual laziness and selfishness and weakness and fear and get us to do better, harder things than we can get ourselves to do on our own.”

And yet most managers are rarely given this opportunity to lead. They’re drowned in daily tasks that focus on the imminent without a thought of moving in new directions. They’re time is consumed with unnecessarily babysitting people through their daily responsibilities and preserving today’s environment.

But that environment is changing. The target is no longer fixed. And in an unstable landscape we can no longer rely on preserving today’s version of ourselves or our companies.

In short, the job of a manager needs to change. The productivity-centric model is fast becoming obsolete. Instead, managers need to act less like employers. And start acting more like entrepreneurs.

Employers Solve Problems. Entrepreneurs Find Opportunities.

“Major breakthroughs come from the correct mind-set. It’s an attitude — an opportunistic attitude. People who make breakthroughs are always opportunity-focused. People who don’t, aren’t. It’s that simple.” — Jay Abraham, Getting Everything You Can Out of All You’ve Got: 21 Ways You Can Out-Think, Out-Perform, and Out-Earn the Competition

Employers focus their best people on solving problems. And in doing so, they donate their time and their best talent to restoring the equilibrium of yesterday.

Many managers spend the majority of their focus putting out fires. Yet entrepreneurs know that occasionally you need to let some fires burn so that you can make more important progress.

Entrepreneurs recognize that in order to move forward, they need to turn opportunities into results. They spend time reflecting on the future of the organization and looking for new and better ways to succeed. They look for these key opportunities throughout the company and align them to their best-performing people. And they gain a critical step on the competition in pushing towards new targets and changing the overall landscape.

Not only does this drive a more effective organization, it improves the overall morale. Would you rather work in a company that focused on maintaining today’s status quo or one that’s focused on meeting the opportunities of tomorrow? As the great management consultant Peter Drucker wrote,

“In every area of effectiveness within an organization, one feeds the opportunities and starves the problems… only strength produces results. Weakness only produces headaches — and the absence of weakness produces nothing.”

Employers Blame the Process. Entrepreneurs Blame Themselves.

“Extreme Ownership. Leaders must own everything in their world. There is no one else to blame.” — Jocko Willink, Extreme Ownership: How U.S. Navy SEALS Lead and Win

One of the best ways to differentiate between a leader and a follower is to watch what happens when something goes wrong. A follower will look around and say that it wasn’t his job. A leader takes ownership for every outcome — constantly looking for what she could have done differently to drive a better result.

I once had a supplier that failed to meet a critical delivery because of the weather. They couldn’t perform the necessary testing to complete delivery per our schedule. Their manager called me to say it wasn’t their fault — they can’t control the weather.

Here was someone who refused to take ownership — and his company was the worse off for it. True, he couldn’t control the weather. But he could have invested in an indoor testing facility so his company wasn’t dependent on sunshine for critical deliveries. He could have developed a schedule with more resiliency so that he wasn’t completely derailed by two days of rain. He could have resequenced the test procedure with more flexibility so they could take better advantage of good weather when it happened earlier.

He could have done any one of many things, none of which involved controlling the weather. Yet by refusing to acknowledge his role in this issue, he took no actions to prevent it going forward. And resigned his company for repeated struggles in the future.

Entrepreneurs recognize that it’s their job to ensure the business is successful regardless of external events. They never complain of outside forces. You never hear them say, “that’s not my job.”

When developing strategies, employers first account for outside forces and then decide what they can accomplish within these constraints. Entrepreneurs do the opposite. They first decide what they need to achieve and then manage the external environment to meet their goals. They recognize that while they may not control every constraint, they refuse to be deterred by them.

This ability to manage uncertainty is one of the biggest difference between employers and entrepreneurs — and one of the biggest changes managers need to make going forward into an uncertain future. As Dylan Evans wrote in his insightful book on risk intelligence,

“Our ability to cope with uncertainty is one of the most important requirements for success in life, yet also one of the most neglected. We may not appreciate just how often we’re required to exercise it, and how much impact our ability to do so can have on our lives, and even on the whole of society.”

Employers Issue Orders. Entrepreneurs Provide a Vision.

“Leaders never start with what needs to be done. Leaders start with WHY we need to do things. Leaders inspire action.” — Simon Sinek, Start with Why

Anyone who’s tried to motivate people through direction know it leads to dismal results. People check out, stop thinking, and resign themselves to minimum compliance.

Employers operate on the delusion that if they just tell people what to do, they’ll do it. And so they write policies and fill rulebooks. And then are surprised when behavior falls short of their expectations.

Authoritarianism may gain results in the short-term. It works when you want immediate compliance. But it comes with a heavy long-term price.

Policies and rules don’t develop people. And they don’t inspire them to go beyond the rules and develop a better method. As a result, the majority of the organization stops looking for new ideas and opportunities. And a major source of innovation is lost.

Entrepreneurs recognize that people are rarely motivated by orders. They know you can’t demand loyalty and excellence. So instead, they focus on giving people meaningful challenges and personal choice. They surround themselves with high quality people, give them a vision and trust them to come up with the best way of achieving it. As French WWII pilot and author of Le Petit Prince Antoine de Saint-Exupery put it,

“If you want to build a ship, don’t drum up the men to go to the forest to gather wood, saw it, and nail the planks together. Instead, teach them the desire for the sea.”

Employers Look for Consistency. Entrepreneurs Look for Change.

“Whenever you find yourself on the side of the majority, it is time to pause and reflect.” — Mark Twain

One of the most dangerous terms you’ll ever hear is “if it’s not broke, don’t fix it.”

Many managers strive for predictability. They try to implement systems that smooth out the rough edges and drive a repeatable product.

And in many ways this is a positive. Companies can’t survive without reliable systems that they can trust to deliver quality products.

Yet this push into predictability often leads to a bureaucratic inward focus. Employers become driven to maintain the current system — creating significant sources of complacency throughout the organization.

The primary reason that most change efforts fail is they do not create a strong sense of urgency throughout the organization. They fail to shake people out of the complacency of today’s status quo and convince them of the need to move forward.

And for people who’ve been consistently asked to maintain the current system, there’s little urgency to break into new areas when everything’s going okay.

Entrepreneurs actively work to avoid this complacency. They cultivate curiosity and push for new ideas and improvements, even when there’s no driving need. As Idris Mootee, CEO of Idea Couture put it,

“The biggest challenge is advising successful companies to think about change. When a company is expanding, when a manager starts saying “our firm is doing great”, or when a business is featured on the cover of a national magazine — that’s when its time to start thinking. When companies are under the gun and things are falling apart it is not hard to find compelling reasons to change. Companies need to learn that their successes should not distract them from innovation. The best time to innovate is all the time.”

Employers Focus on the Imminent. Entrepreneurs Focus on Impact.

“Companies must strive for 10x better because merely incremental improvements often end up meaning no improvement at all for the end user.” — Peter Thiel, Zero to One

My friend had a manager who read all of his emails. Not just his, but everyone in their section. She’d routinely spend several hours every day going through their emails looking for who knows what.

An extreme example perhaps, but how many managers spend their days needlessly monitoring peoples’ work?

There are few fates worse for a leader than going through a career and realizing that instead of leading people to achieve great things, you merely joined them in a trip they would have taken anyways.

And yet this is often the result of people who fill their days checking minor boxes and chaperoning employees through their daily tasks.

Ultimately, these tasks are easy. It doesn’t take a lot of skill to watch someone else do the hard work, requesting updates and offering minor suggestions as they go. Or attend meetings all day and throw out a bunch of opinions without the need to execute any of them.

And therein lies the appeal to many employers. Easy. Safe. Comfortable.

The alternative is to lead into a new direction. One that risks failure. And brings vulnerability. And ultimately is a much more difficult path.

Yet entrepreneurs know that thinking small is a self-fulfilling prophecy. They’d prefer to risk failure and embrace vulnerability than commit to a career of irrelevance.

And so they create bold visions. And think differently. And inspire others to do the same. In the wise words of Debbie Millman,

“If you imagine less, less will be what you undoubtedly deserve. Do what you love, and don’t stop until you get what you love. Work as hard as you can, imagine immensities, don’t compromise, and don’t waste time. Start now. Not 20 years from now, not two weeks from now. Now.”

Thanks, as always, for reading. If you enjoyed this or have any suggestions, please let me know your thoughts. I’d love to hear from you. And if you found this helpful, I’d appreciate if you could clap it up👏 and help me share with more people. Cheers!



Jake Wilder

I don’t know where I’m going. But at least I know how to get there.