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The Top Five Questions of Leadership

Written by Chuck Olson

Making Frozen Yogurt With Chocolate Chips And Sprinkles At The Buffet

The Top Five Questions of Leadership

We must have been out of our minds!

A few years ago, when our grandkids were younger, Pattie and I took all six of them (aka The SixPack) to Yogurtland. What an adventure! Step 1: Choose your favorite frozen yogurt (NTF: Pistachio was the front runner). Step 2: Choose your favorite toppings. Oreo cookies. M&Ms. Chocolate malted balls. Gummie bears (BTW: Which food group do gummie bears belong to?). Watching them choose their toppings was hilarious. Some were decisive. Some had to mull it over a bit. And others wanted to test drive the options, putting Yougurtland’s “A” rating in certain jeopardy.

Yogurtland is full of choices. So is leadership.

As a leader, you understand well the significance of the choices you make, because ultimately they serve as the scoreboard of your leadership effectiveness.

Through the years, as a leadership coach, invariably the topic will surface about how to choose the best ways to leverage your time as a leader. To that end, I have developed a set of questions that serve as an evaluative filter.

1. What must I do to remain faithful to the stewardship of my role?

There are certain responsibilities etched deeply into your job profile that if given away would be an abdication of your ultimate assignment. For example, if you occupy the top box of the O-chart, you own the vision/directional issues of your organization.

Insightfully, to this point, legendary management expert Peter Drucker contends that shortly after their establishment, most organizations lose sight of their purpose and begin to focus on efficiency (doing things right) at the expense of effectiveness (doing the right things).

2. What is my unique contribution?

You are a composite, a customized package of strengths and gifts and talents and experiences. Your highest level of influence will show up when you bring your distinct sweet spot to the endeavors of the organization. Be you. Bring you.

Your highest level of influence will show up when you bring your distinct sweet spot to the endeavors of the organization.

3. What empowers others to develop further/faster?

In leadership, ultimate contributions are measured on the scale of how well you invest in others. At times, this will include giving away responsibilities that you personally enjoy simply because it will create space for team members to rise to their next level of effectiveness.

In leadership, ultimate contributions are measured on the scale of how well you invest in others.

4. What will yield the greatest return?

In view of the mission of your organization, having scanned the list of available options, your job is to select the one(s) that you believe will bring the highest ROI. This is a battle you will continually fight…and must win. Work hard at downsizing the focus of your organization to a limited number of initiatives. Do a few things well.

5. What is God asking me to do?

With this final question, a line is drawn between everyday leadership and spiritual leadership. In your quiet moments of solitude, as you seek to discern God’s guidance, what is He saying to you? This is the question that eclipses all others. There will be times when conventional wisdom will collide with divine direction. This is the true test of Kingdom leadership: walking in obedience to the God who throughout the Scriptures often calls audibles that make little human sense. But it is in following God’s audibles that we learn how to accomplish His purpose. In His way.

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Chuck Olson
Founder | Lead With Your Life

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Chuck Olson

As founder and president of Lead With Your Life, Dr. Chuck Olson is passionate about inspiring, resourcing and equipping Kingdom leaders to lead from the inside out.  To lead, not with the external shell of positions, achievements or titles, but from an internal commitment to a deep, abiding and transparent relationship with Jesus. Serving as a pastor and leadership coach for over forty years, Chuck has a track record of building these truths deep into the lives of both ministry and marketplace leaders.

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