Three Questions for the Gray Areas in Leadership

I love the gray areas, but I like the gray areas as considered by bright, educated, courageous people. – Alan Furst

A story is told of Lord Halifax, a former foreign secretary of Great Britain, who once shared a railway compartment with two prim-looking spinsters. A few moments before reaching his destination the train passed through a tunnel. In the utter darkness Halifax kissed the back of his hand noisily several times.

When the train drew into the station, he rose, lifted his hat, and in a gentlemanly way said, “May I thank whichever one of you two ladies I am indebted to for the charming incident in the tunnel.” He then beat a hasty retreat, leaving the two ladies glaring at each other.

I can just imagine the reaction of the two ladies when Lord Halifax left the compartment. Do you think they ever figured out that they had both been played? What lingering doubts did they leave with?

As leaders we pride ourselves in our values, missional statements, and principles that we subscribe to personally and professionally. But sooner or later our beliefs and assumptions will be challenged. Gray areas will emerge. What we once thought of in strict black and white terms become clouded. Now what?

Here are three guiding questions worth asking when the answers aren’t so clear.

1. What does my head say?

When faced with gray areas in your leadership you can use your cognitive skills to walk through all available options. Not every circumstance you face as a leader is going to have an answer readily available in some employee manual collecting dust on a shelf somewhere. There will be situations thrown at you that you didn’t prepare for nor did you see coming.

The key for you as a leader is to think through the situation and in a level-headed way in order to chart a path forward. One simple way to navigate through the gray area is to ask how your decision will either uphold or take away from your values.

2. What does my heart say?

Gray areas compel us to think different. We wrestle with the gray areas because intuitively we know that life is not always predictable. Stuff happens. Our cognitive skills are important, but there does come a time we have to think with our hearts. Some situations call for emotional intelligence to find the answers we need.

The key for you as a leader is striking a balance between what you know in your heart and what you know in your head. How do you reconcile the two in gray areas to arrive at the best solution?

3. What does my history say?

As a leader no doubt you’ve struggled with gray areas. Beliefs that you once thought were “settled” some time ago suddenly resurface and challenge your beliefs today. I’ve been there many times. Your growth as a leader is always evolving. The challenges you faced five, ten, twenty years ago are going to look different from the challenges you face today. And they should.

The key to dealing with gray areas in your leadership is to utilize all three questions in your approach. Welcome gray areas as an opportunity to grow and develop as a leader. In the end; trust your head, trust your heart, and lean on your history. This is where your judgment in dealing with the gray areas has been formed.

© 2016 Doug Dickerson Doug Dickerson is an internationally recognized leadership speaker, columnist, and author. A Lowcountry resident, Doug is available to speak for your civic, business, or church group. To learn more visit or email him at

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