The Headwinds Of Leadership

When everything seems to be going against you, remember the airplane takes off against the wind, not with it.

~Henry Ford

I came across a humorous story about a captain and three sailors who were left on a sinking ship. The captain spoke first, “Men, this business about a captain going down with the ship is nonsense. There’s a three-man life raft on board and I’m going to be on it. To see who will come with me, I will ask you each one question. The one who can’t answer it will stay behind.”

The captain asked the first question: “What unsinkable ship went down when it hit an iceberg?” The first sailor answered, “The Titanic, sir.” On to the next question, the captain asked, “How many people perished?” The second sailor said, “One thousand five hundred and seventeen, sir.” “Now for the third question,” the captain turned to sailor number three. “What were their names?” There are times in leadership that you might identify with the captain- asking all the questions. Some days you might feel like the third sailor in the story- up against impossible odds- facing those inevitable headwinds of leadership.

If you hang around in leadership long enough you will encounter headwinds – challenges to your leadership that may at times cause you to second guess yourself. Don’t worry, most all of us have been there at one time or another.

Instead of making the focus here about specific headwinds that we face- and we could make a long list of adversities, I’d rather focus on our responses to them because it’s in our responses that we earn our leadership stripes. (I wrote here about specific threats leaders face). Here are three self-evaluations worth considering when you face the headwinds in your leadership.

What does my response say about my values?

When facing your headwinds in leadership how you respond makes all the difference. What’s foremost on your mind when going through a struggle? Is your reputation? Is it your pride? Could it be you are trying to protect your own interests? As much as I hate to admit it, I can look back at times early on in my leadership when I was out to protect my own image and it was detrimental in many ways.

When uppermost in your response to adversity is the protection of your values over your ego then what you go through won’t be a waste of time. Your values- your core beliefs, will be what sustains you long after the storm has passed.

What does my response say about  my attitude?

I’ve yet to meet a leader who enjoys the headwinds of adversity and challenges. But make no mistake – we all go through it. We may not choose the adversity, but we do choose our response. So what is the tipping point between a headwind that stops us or one that causes us to take flight like the airplane? In a word- attitude.

Your attitude will lift you up or tear you down. It will inspire those around you or it will be a source of discouragement. It’s your lifeline when the headwinds are strong, and it’s the the predictor of how you will respond when the chips are down. (I wrote here about hope for discouraged leaders). It won’t always be easy to have a good attitude. Life happens and circumstances can wear you down, but developing a strong attitude will carry you further than you could go otherwise.

What does my response say about my future?

You are never more than one response away from a headwind of adversity that is going to shape the future of your leadership. Be it the wrong decision about your ego over your values, or a bad attitude that does more harm than good in your organizational structure- attitudes are contagious after all- your response to headwinds is a game changer.

It’s in the daily decisions of your leadership and the headwinds you face that your future is being decided. Be clear about your values and be mindful of your attitude because it’s in these things that your future is being shaped.

Your adversity will last but for a while but you will carry with you the consequence of your response for a long time. Choose wisely.


Doug Dickerson
Doug Dickerson
DOUG has been speaking to audiences in the U.S. and overseas for more than 30 years. Doug knows how to spin a story, make you laugh, and how to challenge your traditional ways of thinking about leadership. Most of all, Doug is committed to helping you grow as a leader. Doug is a graduate of Southeastern University in Lakeland, Florida and studied Clinical Pastoral Education at Palmetto Baptist Medical Center in Columbia, South Carolina. While his leadership expertise has its roots in ministry and teaching. His background also includes public relations and business. Doug understands the necessity of leadership development and why creating a leadership culture in your organization is critical to your success. He is the author of four leadership books including: Leaders Without Borders, 9 Essentials for Everyday Leaders, Great Leaders Wanted, It Only Takes a Minute: Daily Inspiration for Leaders on the Move, and Leadership by the Numbers. As a speaker, Doug delivers practical and applicable leadership insights with a dose of humor and authenticity that endears him to a wide range of audiences. Doug is a John Maxwell Team member.

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