Six Leadership Lessons from Winston Churchill

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The greatest lesson in life is to know that even fools are right sometimes –Winston Churchill

As a student of leadership, I have much respect for Winston Churchill. As a student of history, I have an even greater appreciation for his leadership skills in a most turbulent time in world history. His strength and resolve during World War II gave the British people hope in their darkest hours. His courage and sense of purpose were the driving force that ultimately led the Allies to victory.

Step back in time with me and let Churchill’s own words teach us some time-tested leadership lessons that are applicable today. Here are six of my favorites.

Success is not final, failure is not fatal: it is the courage to continue that counts.

If you are going to last as a leader you have to let this truth resonate down deep. Every leader experiences failure. But failure does not define you- it shapes you. A failure is merely an event that happens on the road to success. What matters is not that you failed or even tasted the joy of success, but that you had the courage to continue.

We make a living by what we get, but we make a life by what we give.

This is such a valuable lesson to learn as a leader. Many have made the mistake of buying into the old notion that the one with the most toys wins. But true leadership is not about what you get but rather about what you give. The world will be a little better than you found it when you come to discover the joy of giving.

You have enemies? Good. That means you’ve stood up for something, sometime in your life.

Churchill was greatly admired but he also had plenty of enemies. While the consequences may not be as significant as what Churchill faced, you too will have your share of critics. But regardless of the challenges that you face and the enemies who would seek to harm you; hold true to your principles and hold true to your convictions. Stand up for what is right and do good by all men.

Attitude is a little thing that makes a big difference.

In the face of overwhelming odds and at times great calamity Churchill held on to what I would label his trump card. It’s what would give him the courage to move forward in the darkest hours of the war and is what would give his countrymen hope. Succinctly and truthfully put – Churchill’s attitude was a life saver. Never underestimate the power of a positive attitude. As a leader is will make you or break you.

I am an optimist. It does not seem too much use being anything else.

As a leader, you choose your attitude and you choose your state of mind. If there was ever a leader who could have chosen a different path and projected a totally different outlook it was Churchill. With the relentless bombing raids on London; the tremendous loss of life coupled with all of the sufferings that took place, Churchill could have fallen victim to despair. But his optimism would one day lead to victory. I don’t know the challenges you face today but I do know this much – being optimistic is a choice that will put you on the right path.

Lady Astor: “Winston, if I were your wife I’d put poison in your coffee.” Winston Churchill: “Nancy, if I were your husband I’d drink it.”

Humor was one of Churchill’s endearing qualities. His quick wit and sense of humor were a reflection of the total man who took his work seriously but knew the importance of enjoying a light moment. His humor was as much an integral part of his leadership style as any other trait. Your life in leadership will be marked by important decisions and things that will define your legacy. Churchill reminds us that having a sense of humor makes it all bearable. So remember this important principle in your leadership – it’s okay to smile, laugh; especially at yourself, and enjoy the journey.


© 2017 Doug Dickerson

  • This week’s column is courtesy of the vault. It was originally published in 2015.


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Are You Playing To Your Strengths?

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Focusing on our own strengths is what, in fact, makes us strong. – Simon Sinek

A recent story in the Gallup Business Journal revealed that only twenty percent of U.S. Workers think that their jobs use their strengths. It said, “Identifying strengths and fulfilling natural potential has never been more important for students and employees. In the United States alone, just 13% of workers say they find their work meaningful, and a mere 20% think they’re in jobs that use their talents”.

The fact that so many companies are failing to tap into the strengths of their employees is troubling. How can these companies expect to compete when the best that their employees have to offer is going unutilized? Is it any wonder then that only 13% of workers say that their work is not meaningful?

Bridging the gap between unsatisfied employees and those who actually do play to their strengths is a leadership challenge that must be tackled. Here are a few things that we, as leaders, need to do:

Know strengths before you hire

Knowing a potential employee’s strengths before hiring is just common sense. Why would you even consider someone for a position if that person does not possess the skill sets needed or without knowing whether or not that person would be playing to their strengths? Why set someone up to be unfulfilled, miserable, and ultimately fail? When hiring, don’t drop the ball; find out what strengths the candidate possesses and place them accordingly.

Reevaluate strengths on a regular basis

Our hope is that our employees are continually growing and improving. It is important that you reevaluate employees’ strengths on a regular basis. Are they ready for more responsibility? Would they benefit from gaining experience in a new area? Is the position where they serve still a good fit? Make sure your knowledge on where employees’ strength lie is always up-to-date. Make ongoing training a part of their empowering process.

Don’t allow the position to define the person, let the person define the position

A cookie-cutter approach to filling positions within your organization typically centers around the “duties” of the job. While that is important to understand, the position must not define the person. In the final analysis, you are hiring a person, not a position. A person will only be fulfilled when he or she plays to their strengths. This is what matters most. Hire qualified employees, put them in positions where they can best utilize their strengths, and then get out of the way and allow them to make the position their own.

People will thrive when they play to their strengths

People find their work meaningful when they are playing to their strengths. When they feel they are contributing in meaningful ways they will produce at higher levels and everyone wins.The right people in wrong positions will only lead to low morale and poor performance. Make sure you know where your employees’ strengths lie and then give them the opportunity to utilize those strengths in defining their position and contribution to the organization.

The fact that only 20% of employees are in jobs where they believe that their talents are being used is a sign of deficient leadership. This trend can be reversed but it has to start with a fresh approach to your leadership and recognition and respect for what employee strengths can contribute to the organization.

Employee engagement can be a challenge on good days. Don’t complicate things from an organizational standpoint by not allowing people to play to their strengths. Unleash their potential to be their best.

© 2017 Doug Dickerson & Liz Stincelli


Learn more about Liz by visiting her website, and connect with her on Twitter @infinitestin, Google+, and LinkedIn. You can contact her by email at


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Death By A Thousand Titles

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Success is not a function of the size of your title but the richness of your contribution. – Robin S. Sharma

I’m sure if you’ve been in leadership circles long enough you’ve heard the adage, “People don’t leave jobs, they leave managers”. And it happens for good reason. A person with a title gets a position and then suddenly they think they know it all. Instead of growing into their leadership potential they fall back on their title to push their agenda and ideas.

A must-read for all leaders is John Maxwell’s book The Five Levels of Leadership. It should be required reading for all organizations and their leaders.

In the book, Maxwell walks the reader through the five levels beginning with level one, the lowest level – position. While it is a starting place for leaders it’s not where you want to stay. One of the main problems, as Maxwell points out, with positional leaders is that they want to “focus on control instead contribution.” And this is why people don’t leave jobs, they leave managers.

Positional thinking for any organization is like death by a thousand cuts (titles). It’s not necessarily one thing that is the deal breaker for people, but the culmination of bad leadership behaviors over time that seals the deal. It’s management by decree in place of leadership by example. It’s painful to watch, and horrible to experience. But what do those mindsets and thinking sound like? I will highlight a few that Maxwell describes.

Top down – “I’m over you”

The person with a title can either be humble or arrogant. They can take advantage of the opportunity they now have to learn, mature, grow, and develop into a good leader. Or they can be arrogant and think they are important because they have a title. When a leader relies on a position rather than influence to get things done it’s death by a thousand titles.

Power – “I determine your future”

Positional leaders on power trips will kill your organization. This mindset is counterproductive to any that wants to move forward. Sadly, the good people working for this type of positional leader will soon move on. Leaders who like to wield this kind of power soon find that there’s no one left to control. It’s death by a thousand titles.

Selfishness – “You’re here to help me”

For the positional leader, it’s all about them. You will fall into their good graces of leadership so long as you understand that is your role. Not the other way around.The antithesis of this, of course, is servant leadership. As you mature as a leader you learn that it is not about you and that the best way to lead is by serving others. A selfish leader is only thinking about his or her self-preservation. Everything else and everyone else is subservient to that end. Organizationally, it’s death by a thousand titles.

Rules – “The manual says”

Positional leaders are big fans of the rule book and the manual. This, of course, kills morale, stifles creativity, and otherwise makes life unbearable for those actually trying to make a difference. Howard Behar described it best when he said that what organizations need is not a rulebook but a playbook. Unfortunately, the positional leader doesn’t yet have the skill and foresight to lead any other way than by the book, not realizing that much of leadership is by the heart. Organizationally, it’s death by a thousand titles.

Having a title doesn’t make you a leader. It simply means as Maxwell points out, that you have leadership potential. Your growth as a leader will be accelerated as you stop relying on your title and use your people skills. This begins by practicing servant leadership. As a leader you must come to know, it’s not about you.


© 2017 Doug Dickerson

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On The Other Side Of Fear

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We must build dikes of courage to hold back the flood of fear. – Dr. Martin Luther King, Jr.

In his book Intentional Living, John Maxwell describes the faith factor as it relates to connecting us with like-minded people. In a more personal way, he relates the role fear plays in preventing us from reaching our goals and dreams. Maxwell states, “Fear is the most prevalent reason why people stop. Faith is what makes people start.” Over the years I’ve had my fill of fears. I reckon it’s possible you have as well.

If you’re like me, you possess no shortage of ideas or goals you’d like to achieve. I’ll admit some ideas were perhaps conceived too soon, some a little too late, while others just died a slow death due to the restraints of time. Can you relate?

Yet there are some dreams and goals that died a slow death for another reason- fear. We’ve all wrestled with fears. I remember in Little Leagues it was always the fear of striking out. In school, I had test anxiety. Fear would get the best of me that I would fail. Even today I struggle with another fear- arachnophobia- the fear of spiders. What are yours?

Thankfully, Maxwell’s depiction of fear and the struggles we all face didn’t stop there. He went on to point how faith makes up for our fear and when applied in our lives can turn the tide in our favor. Maxwell said, “Faith does not make things easy, but it makes things possible because it puts everything, including fear, into the right perspective. So, if you want to learn, to grow, to achieve your dreams of significance to make a difference, have faith”.

How different would your life look if the decisions you made, whether those decisions are personal or professional, look if they were made through the lens of faith rather than through the lens of fear? How would things look on the other side of fear? Here’s my challenge to you.

Lead on the other side of fear

Imagine the kind of influence you could have as a leader if you opted for faith over fear? Fear will paralyze you as a leader and hinder you from becoming all God created you to be. When you lead with faith it will bury your fears and you will lead on a new level. Living on the other side of fear doesn’t mean you don’t have doubts or have questions, it just means that it’s a burden that doesn’t rest entirely on your shoulders anymore. Faith takes the weight off, fear puts it on.

Dream on the other side of fear

I know all too well what happens to dreams when fear sets in. They die. How many dreams of yours have suffered an untimely death because of fear? Fear will keep your dreams small. But I’d rather fail on the other side of fear with a God-inspired dream than succeed knowing I didn’t need God’s help. As Mark Batterson says, “If your dream doesn’t scare you, it’s too small.”

Serve on the other side of fear

When you live your life free from fear you live a life that is a peace. You are at peace knowing that you don’t have to worry about what other people think about you, say about you, or otherwise interfere with your life’s purpose. You are free to lead with your heart and serve causes greater than yourself. Fear is a speed-bump on the road to being a blessing to others. Get rid of the fear.

Grow on the other side of fear

Fear stunts your growth on many levels. It can rob you of your dreams, goals, creativity, and productivity to name a few. But when you feed your faith and starve your fears you position yourself for unprecedented personal and professional growth.

I am in no way suggesting here to throw caution to the wind and chase your dreams on blind faith. It pays to be prudent and listen to wise counsel. But well-meaning people along the way will fuel your faith or they will fuel your fears. You must not allow fear to win. Faith is hard because of the unknown. But with fear, the unseen and unattained dreams and goals will always be that–unseen and unfulfilled.

A wonderful life in leadership awaits you. It’s on the other side of fear.

© 2017 Doug Dickerson

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Growing Big, Staying Small

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Thinking is the hardest work there is, which is probably the reason why so few engage in it. – Henry Ford

In his book, It’s Not About the Coffee, Howard Behar, former president of Starbucks International, recounts a fascinating story about attaining the kind of culture every company wants. Behar says one concept that he learned and developed from Howard Schultz was, “The fundamental task is to achieve smallness while growing big”.

It almost sounds like a contradiction upon first glance. How does one actually go about achieving smallness? What does it look and how can it improve the culture of any company? How could it improve yours?

Behar relates one custom that became part of Starbucks culture. The writing of cards. Each month he would write birthday and anniversary cards to everyone in the organization. It started with about sixty cards a month. Behar says that by the time he retired he was sending out more than five hundred a month.

In a time when company culture and employee engagement are the buzzwords and people are trying to figure out what it means, is it possible that we are simply over thinking it?

Maybe it has nothing to do with how big we are thinking and the grand schemes and plans of making improvements. Is it possible that employee engagement and company culture is not working as it should because we are not thinking small enough?

At the end of the day here is what we must remember: it’s all about people. Call it company culture, employee engagement, call it whatever you wish- but it all boils down to people and how you make them feel. Do they feel appreciated? Do they feel valued? How are you showing it?

An article in Talent Culture revealed that employees who “feel valued by their employer are significantly more likely to be motivated to do their very best (93 percent vs. 33 percent).” In addition, it said that “those who do not feel valued are significantly more likely to seek new employment within 12 months (50 percent vs. 21 percent)”. Look within your organization. How many people are motivated to perform at their very best? How many people do you suppose are looking for new jobs?

Growing big and thinking small is not a mutually exclusive goal. But it will require intentional thinking and action on your part as a leader. Here are a few ways you will have to do it.

Think small relationally

It makes no difference if your vision or goals are big or small, it only comes into existence through the dedication and hard work of your people. Every leader should take the advice of John Maxwell who said, “Always touch a person’s heart before you ask for a hand.” You must connect relationally before you can ask people to help you reach your goals.They must first buy-in to you before you can expect them to buy-in to your vision.

Think small serving

It was a brilliant quote I still remember from the late Sam Walton who said, “The bigger we get the smaller we have to think, customers still walk in one at a time”. Whether it’s your employees whom you are serving or the customer base your organization caters to, the way you treat each individual makes a world of difference. Too often we worry about pleasing the masses and forget we still serve our employees and customers one at a time. If you do right by one, you will do right with many.

Think small growing

Intentional smallness is what Behar modeled by writing hundreds of cards a month. It happens with random acts of kindness in recognizing your people. It’s being intentional about building relationships. It’s about ensuring that your people feel valued, respected, empowered, and trusted. It’s about writing that card.

Growth begins to happens when you take care of building a powerful culture of smallness that gives you the momentum to become a big organization that held true to its most sacred values along the way.

Are you thinking small enough?


© 2017 Doug Dickerson

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Taking ‘No’ Out of Your Playbook and Why it Matters

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Nothing will ever be attempted if all possible objections must first be overcome – Samuel Johnson

Leaders understand that obstacles are a part of the landscape on the road to success. But how many leaders are self-aware enough to realize that some of the obstacles blocking their desired success are self-inflicted?

When what stands between your employees or volunteers and potential success is a constant drumbeat of “no” or the good ole standby of, “We’ve never done it this way before,” then you are capping your talent and are hindering your chances of success.

In his book, It’s Not About the Coffee, past Starbucks International president Howard Behar writes of the necessity of taking ‘no’ out of your playbook. His thought was that we can grow so accustomed to saying no to our customers or employees that soon these roadblocks take on a life of their own and become the unspoken rules, the No Book, that stands between you and your potential success.

One example Behar shared about Starbucks turning an everyday ‘no’ into a ‘yes’ was by opening the door early in the morning. Customers would come by ten minutes before the store opened and were routinely turned away. The message the prospective customer would get was, “No, we’re not open yet.” When they realized they could say yes they began to open ten minutes before the posted opening to serve their customers.

To be sure, not every yes will guarantee success and not every no will deny it. But what you must realize is that until you release the power of possibilities in your people they will never have a chance to find out. Taking ‘no’ out of your playbook will unlock their potential and give them much-needed freedom to grow. That is critical to your success. Here is why taking ‘no’ out of your playbook matters to you as a leader.

It empowers your people.

There is no better way to empower your people than to release their creative ingenuity with a ‘yes’ attitude. It signals that you believe in them and want them to reach their full potential. Empowered people are driven people and are more invested in the product and outcomes. When you remove ‘no’ from the playbook and replace it with a yes then you elevate everyone to a new level.

It puts the focus where it belongs.

When ‘no’ is replaced with a ‘yes’ then the playbook becomes a different document. The paradigm shifts. You go from playing defense to playing offense. Now, instead of the focus being inward it’s outward. Where once it was all about you, now it’s about those you serve. When your purpose revolves around a “yes we can” mentality then there is no room for “no we can’t” detractors. When your people are free to focus on what they can do instead of what they can’t do it will make a world of difference.

It creates momentum.

Some leaders exert a lot of energy and waste a lot of time trying to figure out the secret to creating a culture of momentum. Sadly, what some do not realize is that they are the reason why it’s lacking. Why? They haven’t taken ‘no’ out of their playbooks and consequently their much-needed momentum lies dormant.

What would it take to motivate you? Former Miami Dolphin’s great Bob Kuechenberg shares how he got his. He tells the story of his father and uncle who were human cannonballs in carnivals. His father told him, “go to college or be a cannonball,” said Kuechenberg. Then one day his uncle came out of the cannon and missed the net and hit the Ferris wheel. It was then that Kuechenberg decided to go to college.

As a leader, you can either take ‘no’ out of your playbook and put in a resounding ‘yes’, or be shot out of a cannon. Why not release the potential of your people, focus on those you serve, and generate the momentum you need? Say yes!


© 2017 Doug Dickerson

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It’s Your Time to Soar

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Photo Credit: Google Images

Eagles don’t flock, you have to find them one at a time. – Ross Perot

“While walking through the forest one day, a man found a young eagle who had fallen out of its nest. He took it home and put it in his barnyard where it soon learned to eat and behave like the chickens.

One day a naturalist passed by the farm and asked why it was that the king of all birds should be confined to live in a barnyard with the chickens. The farmer replied that since he had given it chicken feed and trained it to be a chicken, it had never learned to fly. Since it now behaved as the chickens, it was no longer an eagle.

“Still it has the heart of an eagle,” replied the naturalist, “and can surely be taught to fly.” He lifted the eagle toward the sky and said, “You belong to the sky and not to the earth. Stretch forth your wings and fly.” The eagle, however, was confused. He did not know who he was, and seeing the chickens eating their feed, he jumped down to be with them again.

The naturalists took the bird to the roof of the house and urged him again, saying, “You are an eagle. Stretch forth your wings and fly.” but the eagle was afraid of his unknown world and jumped down once more for the chicken feed.

Finally, the naturalist took the eagle out of the barnyard to a high mountain. There he held the king of the birds high above him and encouraged him again, saying, “You are an eagle, you belong to the sky. Stretch forth your wings and fly.” The eagle looked around, back towards the barnyard and up to the sky. Then the naturalist lifted him straight towards the sun and it happened that eagle began to tremble. Slowly he stretched his wings, and with a triumphant cry, soared away into the heavens. ” (Source)

In leadership, as in life, you will have competing voices that will cause you to walk with the chickens or soar with the eagles. Here are a  few truths worth remembering.

Not everyone who picks you up will lift you up

The man who found the young eagle might have meant well in bringing the young eagle to his barn. But over time, his good deed turned the majestic bird, full of so much potential, into a common barnyard chicken.

If you want to soar as a leader you must break free from the good intentions of people who do not bring out the best in you.

Your worth is not defined by those holding you back

As the young eagle grew its identity was shaped by the company that it kept. Instead of realizing its full potential to soar the heavens, it was grounded with the chickens. The eagle was being labeled as something it wasn’t. His future was being cast. And the man could not be more wrong.

If you want to soar as a leader you must never let the people who are holding you back to define your worth. When you have the heart of an eagle, don’t allow the mindset of a chicken hold you back.

You can only soar like an eagle when you start acting like one

Over time, the young eagle was persuaded by the naturalist that he was more than a chicken as led to believe. It was when the eagle embraced everything that was great about him that he took his rightful place soaring to the heavens.

If you want to soar as a leader you will have to shake off the labels of your critics and stop hanging out with the chickens. Surround yourself with those who bring out the best in you.

Those who believe in you the most will insist that you fly

The naturalist saw the eagle for the grand and majestic bird that it was. He knew that as long as it was confined to the barnyard it would never live up to its potential. He saw the eagles’ potential and he didn’t give up until it flew.

If you want to soar as a leader you will need people in your life who believe in you, people who will call out the best in you, and people who will never rest until you fly.

This is your time to soar!


© 2017 Doug Dickerson

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