The Toughest Choices a Leader Must Make

By Ray Blunt

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When you achieve a position of leadership for the first time, things change in your daily world. Maybe you notice the size of your paycheck is bigger, or maybe you notice subtle changes in personal relationships—with your peers especially. Or maybe your office is bigger, it’s better appointed, and even has a window. Perhaps your self-esteem goes up a notch or two. With all that (and more) you may also get some nagging worries as you feel the weight of responsibility settling in on your shoulders and a sense of aloneness creeps in. These are all things you likely noticed during your early days in the new position. While there is much focus on developing the competencies to take on this new role, there is less said about something that is more important to your initial and long-term effectiveness. They are the three toughest daily choices a leader must make.

Unavoidable Choices

They are choices that you must make because you cannot avoid any of these. They are choices you will make one way or the other anyway, and perhaps not even consciously. Yet, if there are right and good choices to make consciously, choices that make a difference, why not make them from the start? It could make all the difference not only in your life but even moreso in the mission and in the lives of those you serve.

And, when you look back on your career and your time as a leader, you will better be able to do so without regret. As Soren Kierkegaard has rightly observed, “You live your life forward and understand it backward.”

Looking Backwards

An interesting commentary on just that perspective is provided by Richard Leider1 who spent nearly 20 years interviewing older adults—people over 65—asking them deep questions about life. One question he consistently asked was this: “If you could live your life over again, what would you do differently?” Strikingly, three themes were repeated over and over:

  • I would be more reflective, take time to think because life passes so quickly and I was too busy doing to think adequately;

  • I would be more courageous, take more risks; I played it too close to the vest; and finally,

  • I would be clear, far earlier, on what my purpose was in life.

Your First Toughest Choice

This latter point he makes is your first choice—what is your purpose in life and how will it guide you each day? Do you have a clear life mission statement?

To paraphrase the words of Jim Collins, if this nation is going to be built to last, you will have to preserve the core values and beliefs and the core purpose on which we were founded. That is your choice to make.

Perhaps the most important choice you will make as a leader is what will be your telos, your enduring purpose—who and what will you follow--what will be at your core; what will you place before the people you lead as the purpose that gets them out of bed each morning. It is the task of a leader to connect people with purpose.

There is no better place to go for perspective on this than the place both Lincoln and Martin Luther King went for the core beliefs that drove them to keep the Republic intact and to reach the dream that all people live together as created equals. It was not the Constitution that energized their calling, but the Declaration of Independence.

We hold these truths to be self evident, that all men were created equal. That they were endowed by their creator with certain inalienable rights . . .
. . . that in order to secure these rights governments were instituted among men deriving their just powers from the consent of the governed.

Our power and authority as leaders is not of self or of position. It is conferred by those we serve. Our mission is to secure the rights to life, liberty and the pursuit of happiness by serving others. This is often a choice that comes at a cost—to keep that focus true in the face of self-interest and conflicting visions of others.

The Second Choice

The second choice that you will be making as leaders is how you will use your most precious resource: time. If you are clear on your purpose, it makes it much easier to begin to focus the way you use your time. Sometimes we focus so much on competencies in leaders we forget that the daily reality on the ground is one of time priority. Look at your calendar if you want to know where your priorities lie in reality—maybe it’s meetings or e-mail or phone calls. These are all things that eat our lunch if we let them.

How we spend our time directly impacts on what we ultimately accomplish with others; how we spend our time depends on what we use as our purpose for living. If I could somewhat shift the balance of how you spend your time, I’d suggest two things:

  1. Focus on defining reality. What do I mean? Max De Pree says the first task of a leader is to define reality—what is true. Speak the truth to power, speak the truth to those who work for you, and be transparent about yourself. Don’t leave it to others to tell you that you are naked. I have yet to work with an organization that does not have what Annette Simmons calls “dangerous truths” that need to be spoken. Sometimes it requires what Thomas More did for Henry VIII—speak the truth to power. Sometimes it requires what we all hate to do, give someone honest feedback about their performance. And sometimes it means opening ourselves to honest feedback from our folks or saying “I screwed up.” But these “dangerous truths” require courage and they require that we devote time to talking honestly and openly to people and encouraging the same for ourselves. Truth helps in driving fear out of the organization by making it a safe place for truth telling. It is one of the most productive uses of your time you will ever experience. And it’s hard. As Solzhenitsyn said, “One word of truth outweighs the whole world.”

  2. Focus on developing your most valuable assets. Max De Pree goes on to say that if the first task is to define reality, “the last is to say thank you and in between a leader becomes a servant and a debtor—the measure of your effectiveness is found in the lives of those that follow you—are they growing, adapting, being creative?” The coin of the realm in today’s organizations is resolutely human capital (an awkward term)—people--because the assets of an organization reside primarily between the ears and in the hearts of those who are in the organization. That’s why serving those who are in your organization, focusing on their development and their careers is such a good choice. It not only helps in building the real assets of an organization, it is transformative—it changes people and organizations helping them become places of grace (and truth). And particularly I would add growing the next generation of leaders behind you—leaders of competence and character. Some call that servant leadership and it’s a soft skill that pays hard dividends. But that’s your choice.

The Third Choice

The third choice you make is where your energies take you at the end of each day. Consider this poem for a minute:

By Percy Bysshe Shelley

I met a traveler from an antique land
Who said: Two vast and trunkless legs of stone
Stand in the desert. Near them, on the sand,
Half sunk, a shattered visage lies, whose frown,
And wrinkled lip, and sneer of cold command,
Tell that its sculptor well those passions read,
Which yet survive, stamped on these lifeless things,
The hand that mocked them, and the heart that fed,
And on the pedestal these words appear:
"My name is Ozymandias, King of Kings:
Look upon my works, ye Mighty, and despair!"
Nothing beside remains. Round the decay
Of that colossal wreck, boundless and bare
The lone and level sands stretch far away.

Are we building monuments to ourselves or are we building something into the purpose and people of the organization that will endure? It’s a good question for reflection at the end of the week.


In closing, what I’d like to encourage you to do in these times of such difficulty for our Nation is to be open-eyed about the choices before you as leaders. Don’t simply stumble along letting your in-box or your too-full calendar guide you.

Choose the humble purpose of public service over pragmatism and personal gain.

Choose courageous truth over self-deception and fear.

Choose to serve others rather than to be served.

Grow the next generation of servant leaders behind you. Build a great and safe place for people to work and find their purpose and calling. Leave your legacy in the lives of others.

It is in such a life that you will meet a true servant leader down the road one day and that leader will be you: grown much larger in the ways that matter--perhaps forever.


  • 1. Richard Leider, The Power of Purpose: Creating Meaning in Your Life and Work, (San Francisco: Berrett Koehler, 1997).

Ray Blunt currently teaches philosophy and theology to juniors and seniors at Ad Fontes Academy, a classical Christian school in Centreville, VA. He is the author of Crossed Lives, Crossed Purposes: Why Thomas Jefferson Failed and William Wilberforce Persisted in Leading an End to Slavery, an historical leadership exploration, and a contributor to The Jossey-Bass Reader on Non-Profit and Public Leadership. Ray has long served as a leadership consultant, teacher, and speaker for many government and non-profit organizations after spending 35 years in public service in the US Air Force and the US Department of Veterans Affairs as a Senior Executive. He is B.J.'s husband of 50 years and the father of two grown children, and grandfather of five aspiring servant leaders.

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