The 6 Decades Of Leadership And How To Win In Each

Photo: John Moeses Bauan/Unsplash

Photo: John Moeses Bauan/Unsplash

Leaders are never stagnant.

As leaders grow up and mature, their leadership evolves. As experience and skill continue to grow and maturate, new opportunities and new responsibilities emerge.

Although leadership is never the same journey, there are enough great leaders who have gone before who have left us traces of what that a leader’s path truly looks like.

Every leader begins as nothing more than an explorer. They learn along the way, often by hands-on experience.

As they go, eventually they turn the corner from exploration to refinement. The measure of a leader in this stage is no longer the ability to amass great hordes of information or experiences, but rather to distill the vague into the specific.

Refinement leads to mastery. Mastery leads to wisdom. Wisdom leads to stewardship and stewardship leads to storytelling. Great leaders know that each season of leadership is characterized by a different skill. These skills build on one another and are the culmination of a life lived well.

For every level of leadership, there are core pieces of advice or lessons that highlight the main points of focus during that season. I’ve built this list from dozens of conversations with leaders in every one of these seasons.

While this is not an exhaustive list, you will not find a great leader who doesn’t practice most of these pieces of advice in their corresponding season of leadership.

20’s — Explorer

  • Diversify your inputs of learning: an ocean is never sourced by a single stream.

  • Fuel your curiosity by learning how to ask really great questions.

  • If you find a shortcut, don’t take it; you never hear the story of someone you admire characterized by the shortcuts they have taken.

  • A good mentor is worth 10 average friends.

  • What seems costly to you now will seem cheap to you later; don’t put off something just because it hurts.

  • Everything you start doesn’t have to be finished, but if you finish nothing, you’ll never grow.

30’s — Refiner

  • The young leader speaks many words of little weight while the mature leader speaks a few words of great gravity.

  • Luck almost always follows after hard work, not the other way around.

  • A King who lives in a cave has no power; you can be the best in the world at your craft but if you aren’t willing to lead people, you’ve only got a title.

  • You can’t care about everything equally; it is a recipe for isolation and a critical spirit.

  • There is a purity of passion and performance that is only achievable through the furnace of challenging circumstances.

40’s — Master

  • Achieving greatness is when you can make the difficult look simple.

  • Learning to control your emotions is far more valuable than learning to control your circumstances; the storm inside of you is always more deadly than the storm surrounding you.

  • Once you’ve built the rocket, the most important adjustments are the seemingly minute course corrections done consistently over time.

  • There is never a level of mastery that makes you impervious to the temptations of small disastrous mistakes.

  • No man has ever reached a mountaintop and been truly satisfied for no one lives on top of mountains but they always come back down.

50’s — Sage

  • Wisdom is the most enduring currency and will be the last to depreciate.

  • Don’t just tell people how to do things but tell them why they must do them. As Antoine de Saint-Exupéry said, “If you want to build a ship, don’t drum up the men to gather wood, divide the work, and give orders. Instead, teach them to yearn for the vast and endless sea.”

  • There comes a time where your counsel is worth more than your hands but it is later in life than most leaders originally believe.

  • Quick advice is often more dangerous than silence; you more you grow in leadership, the more you realize how little you are actually qualified to give advice on.

  • Aim to be full of grace and truth; don’t compromise your hard-won truths, but you must learn to communicate them in ways that people are able to hear and understand.

60’s — Steward

  • You can win no better award than to see someone you’ve invested in carrying your leadership beyond you.

  • Purposefully slowing down is not a sign of failure but of ensuring that you can give your best to a reduced number of commitments.

  • There is rarely a good time to release control; if you wait for the perfect time to release your leadership you likely never will.

  • If you invest in too many people you end up investing in no one — choose carefully and be intentionally narrow in your mentorship.

  • The burden of leadership rarely gets lighter over time. Throughout your growth, you must focus on developing two core strengths: deep roots and broad shoulders. The best stewards can shoulder the most weight.

70’s — Storyteller

  • Your story is yours to tell, and yet, others will try to tell it for you. Great leaders know that once a story is accepted, it is very difficult to change.

  • Most if not all stories are embellished or will become proportionally more embellished over time. Develop and embellishment filter so that you can both tell and hear stories a bit more realistically.

  • Not every story needs to be told.

  • Great fires are started by small sparks. Great ships are sunk by small leaks. Great movements, organizations, and leaders are birthed from small stories.

  • A brilliant story can change the world. It can captivate the heart, educate the mind, and motivate the will.

The culmination of a great leader

The most common mistake the young leaders of today make is assuming that leadership is a title to be earned rather than a lifestyle to be embraced. If leadership is a title, then once you reach that status, you’ll stop reaching further.

Rather, leadership is ever-changing. When you feel like you have figured leadership out, you are likely right on the cusp of breaking through into a whole new dimension of leadership.

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