10 Risky Questions for Leaders

I am always intrigued by what is said in commencement speeches. Steve Jobs’ famous 2005 commencement address at Stanford is one of the most Googled.  His “stay hungry, stay foolish” theme really resonated with listeners. If you never heard it, it is a real gem. You can watch it here.



This June, at my alma mater’s graduation ceremonies, Princeton’s departing President, Shirley Tilghman, referred to Jeff Bezos’ commencement address to graduates in 2010. Though not as memorable or as well-known as Jobs’ talk, Bezos offered a series of questions for leaders or at least what every leader should be asking.


Bezos is Founder and CEO of Amazon.com and is a Princeton Class of 1986 graduate.  His remarks challenged graduating seniors to consider 10 key questions.  Here they are for your consumption.


1)     Will inertia be your guide, or will you follow your passions?

2)     Will you follow dogma, or will you be original?

3)     Will you choose a life of ease, or a life of service and adventure?

4)     Will you wilt under criticism, or will you follow your convictions?

5)     Will you bluff it out when you are wrong, or will you apologize?

6)     Will you guard your heart against rejection, or will you act when you fall in love?

7)     Will you play it safe, or will you be a little bit swashbuckling?

8)     When it’s tough, will you give up, or will you be relentless?

9)     Will you be a cynic, or will you be a builder?

10)   Will you be clever at the expense of others, or will you be kind?


I certainly was challenge by almost all of these. I did not feel a sense of guilt or failure so much as new resolve to grow and risk in these areas. Numbers 1, 6, and 9 have particular meaning for me at this moment in life and leadership.


How about you? I suggest you reflect honestly on the list, and choose your top 2-3 questions for further investigation and focus. Leaders – especially those who share leadership or have collaborative styles – will have to take some risks that will cause discomfort and leave you vulnerable to failure or criticism.


But what other options are there? A life filled with woulda-coulda-shoulda regrets and a leadership legacy what-if’s and what-might-have-beens?


Not for me. And I hope not for you.

The School of Adversity

It’s compulsory education for every person on the planet. You simply must attend the School of Adversity.

School of Adversity Quote - There is no education like adversity

You need only meet 1 of 2 entrance requirements and you are automatically enrolled. No need to go online or show up at registration. If you 1) have a pulse or, 2) you can fog a mirror, you’re enrolled. Mandatory. There are no vouchers and no “school choice” options available. Once enrolled, classes begin immediately and might be held any day of the week, 365 days a year. There are no vacation days and no holidays (but there are LOTS of sick days).

It is likely each of us will take different classes in the School (Stomach Flu 101, My Teenager Hates Me 407, Chronic Unemployment 511- a graduate level course) and probably we’ll have different majors. NOTE: majors are assigned, rarely chosen. Some students will find themselves in the popular Financial Ruin Program or taking several courses in the Perpetual Pain Department. And almost everyone does a minor in Annoying Facebook Friends.

But no one gets a pass. Ever.

There are no strings you can pull. No Congressman or Senator can get you out or provide an appointment to a less rigorous program (like enrolling in the popular School of Rock – sorry, Jack Black).  There is no AP credit or credit transfers from other highly acclaimed, elite programs like the School of Hard Knocks (I spent a couple semesters there – it was hard…very, very hard).

Like it or not, you must enroll in the School of Adversity.

But don’t worry; no one can make you graduate. Actually, no one graduates. Ever. It’s like continuing education for CPA’s or required HR training classes on wellness management. Classes start and continue all the way to infinity… and beyond. Well, I suppose this is a graduation day. But you really do not want to hear about it.

Also, there are no online or virtual courses. Every class is live, has no official professor, and always takes place in the Experiential Learning Lab. All classes are on campus, but it is easy to get there. The campus address is: 5 Your Location, Anywhere, Earth.

Another bummer is cost. The School can be quite expensive. Actual costs may vary from student to student, and there are no scholarships or financial aid. Everyone pays full price regardless of how many classes you are taking, so you might as well load up early. Heck, I knew a guy who was carrying 42 hours one semester, and he almost died. Really, it almost killed him. He said he learned more that semester than in any other. But it was brutal. Made Med School and MIT look like kindergarten classes.

One thing you want to avoid at all costs – taking classes alone. As a matter of fact, going through the School of Adversity is a lot better if someone takes the classes with you. It is not only allowed, it is encouraged! (You can share answers, ask for help and solve the same problems using the same solutions others have already discovered! They are all cataloged in the Wisdom Library if you take the time to find them. That part is very cool.)

Actually, large families, small groups, neighborhood communities, and sometimes – this is hard to imagine – entire countries have gone through a class together! It makes the School of Hard Knocks look easy by comparison.

There is something about doing it together that not only makes it better, but each class seems to get a little easier to handle; the surprise quizzes are not so surprising, the tests require less preparation and study, and you tend to get higher grades. Did I mention that grades matter?

How you perform prepares you for the next class, though it might be in a different department. For example, I did well some years ago in the introductory Facing Your Fears 101 class because I had already taken Working in a High-Crime Area 201. Facing Your Fears is usually a pre-requisite for all 200-level classes, but for some reason I was forced to take WHCA 201 first. That happens quite often. Classes are rarely offered in logical order. (Very annoying. But there is an elective to help with that now: Annoyances and Petty Frustrations 001 is available whenever you plan a vacation or prepare for Christmas.)

And, surprisingly at first, many students report a sense of joy and gratitude after completing a particularly difficult class! Kind of counter-intuitive  to say the least, though I confess I understand.

Well, I am off to class. Right now I am just beginning Character Growth 204 with a group of friends. There is no syllabus so we do not know what will happen. But we are told by the Administration that we will have the choice to “become bitter or better” as a result of what we experience. Not sure I am looking forward to all of it, but I hear they do have recess and a snack!

Since Christmas I have been enrolled in several courses of moderate but annoying difficulty: Your Wife Broke Her Leg at Christmas 305, Daughter Badly Sprained Ankle in Championship Game 208, I Threw My Back Out Sunday 401 (an intensive 3-day seminar), Son’s Car Needs 3rd Repair in Two Weeks 510, and The Water Pump for Your Home Broke 211.

I am discovering that the School of Adversity while not always a fun place to visit is a great place to learn.

I am getting better at responding with joy in the struggle of pain, listening more carefully to God and others when trials come crashing down, and building up some tolerance to the dozens of small annoyances that pester me like sand flies on the beach of life.

And I continue to gain empathy and respect for the awful circumstances and challenges others face worldwide (in doctoral-level courses I dare not even name and, thankfully, will hopefully never have to take.)

Like you, I am a full-time student in the School of Adversity. So off to class I go. Oh no, my car won’t start…That’s just great…I’ll be late for class.

Oh, wait a minute. This IS my class. Here we go. Hope I pass. Wanna join me?


What Courses are you taking in the School of Adversity? What are you learning? How can you and others get through it together?


We would like to encourage your feedback as it helps us to identify the issues that are important to you. It also helps others who are searching to develop new creative ways of leading. Thank you in advance for your comments.

Looking in the Leadership Mirror

Looking in the Leadership Mirror ImageGood leadership coaches utilize a 360-degree feedback tool to provide input from peers, subordinates and supervisors. But self-leadership is also necessary and that requires self-evaluation “Looking in the Leadership Mirror.”  If you are coaching or leading other leaders, how do you evaluate your growth and performance?

Leaders of Christian groups and organizations tend to shy away from evaluation and feedback – it is not “spiritual” enough. Or we harbor fears that negative feedback will create mistrust or relational breakdown.

But we must do it and be honest with ourselves especially as we are called to evaluate others. Here is a chart Greg Bowman and I put together in our newest addition of Coaching Life-changing Leaders, page 38. How might you rate yourself as a leadership coach, developing the leaders in your area of responsibility?

This is essential. I met with a leader recently who said he was concerned about a top staff member who excelled in personal performance, but was not developing their team. Leading others – particularly leading other leaders – is serious business. Are we coaching our leaders (staff, volunteers, etc.) well?


Take a moment to Look in the Leadership Mirror.

Rate yourself as you reflect on these questions below.

Up Arrow

If you feel your growth has been positive.


Down ArrowIf you feel your growth has been negative.


Minus signIf you feel you have not changed.


  Live with personal integrityAm I living acting according to the values, beliefs and principles I claim to hold?
  Passionate about developing leaders Am I consistently investing in existing and emerging leaders?
  Spiritually attunedAm I leaning into the wisdom of God’s Word and the power of the Holy Spirit as I Coach?
  Self-starterAm I coaching with initiative, adaptability, and trustworthiness?
  Intellectually curiousAm I consistently searching for the core idea or issue to achieve the best outcome?
  Others-focusedAm I working to discern what God may be doing in each leader’s life?
  Relationally awareAm I aware of when to challenge and when to encourage my leaders?
  Effective communicatorsAm I listening well and communicating clearly with my leaders?
  Truth-tellerAm I conveying what needs to be said without being hurtful?
  InspiringAm I helping leaders make a direct connection between the leadership tasks and the broader vision for community?


Now, if you really want some engagement, hand this same chart to some people you lead and compare their responses with yours.

I confess self-evaluation is sometimes painful, or even brutal. But we can be shaped by the process of looking in the leadership mirror. As I write this I can tell you I have “down arrows” in the areas of personal integrity, effective communication, and inspiring others. I am not feeling good about it – but that is the truth.

I do a lot of teaching and too often am not practicing what I preach – leading to an integrity crisis. Also I find myself making assumptions and drawing fast conclusions, which is no substitute for clear two-way communication. And keeping leaders motivated and inspired has been too far down my coaching list.

I met with a great senior leader today who has navigated difficult changes in the organization. He said, “Every year I realize I know less than the year before.” We talked about what that meant, the hard realities of leadership, and the loss of idealism from his younger leadership days 30 years ago.

It was a great conversation. We talked about how this reality sets in, what his team is feeling, the strength of his core staff, and so on. But I missed the opportunity to inspire him. I affirmed him – but I did not motivate him.  Big difference.

So I am aware of at least three areas of focus and growth.


This is a powerful evaluation “Looking in the Leadership Mirror” …. how many of you took the time to do it??


Care to share what you learned?




How Did You Read Your Bible Today?

In the book To Know as We Are Known: Education as a Spiritual Journey, Parker Palmer notes that two primary sources of knowledge we use are curiosity and control. Curiosity is “pure speculative knowledge.” But Palmer notes, “We are also creatures attracted by power; we want knowledge to control our environment, each other, ourselves. Since many of the boxes we have opened contained secrets that have given us more mastery over life, curiosity and control are joined as the passion behind our knowing.”

Palmer goes on to say that compassion should be the primary use for knowledge. But how can we develop this as we read Scripture? M. Robert Mulholland has been a great help in this area, teaching the difference from pure informational use of the Bible to a more transformational engagement.

Here is a summary chart of how we use the Bible in Groups influenced by teaching from Mulholland in his book Shaped by the Word and compares Informational versus Transformational reading.

Focus Quantity Quality
Approach Linear Holistic
Attitude Critical/Analytical Humble
Objective Master the Text Mastered by Text
Result Study Jesus Know Jesus
Method Observe, Interpret, Apply Listen, Meditate, Respond

None of us would debate the essential nature of information — but when we approach the Bible we are encountering mystery, relationship and the author Himself! Our approach should create a different experience than we have discovered in classic Western, scientific analyses of texts in the university classroom.

Questions: Which method do you tend to use? What resistance do you anticipate from others as you prompt them to engage the Bible differently than they have in the past?

And most importantly, is knowledge being used for compassion?


Many years ago I became a big Parker Palmer fan– his book “To Know as We are Known: Education as a Spiritual Journey” rocked my world. However, in recent years his writing has drifted considerably theologically. And although he was mentored in some ways by Henri Nouwen and other more centrist biblical thinkers, he has forsaken the need for Christ and his atoning work for salvation, becoming increasingly universalist. All this aside (and these are no small matters) his book “The Courage to Teach” has been a favorite that I re-read from time to time. His classic definition of teaching from To Know as we are Known, “To teach is to create a place/space where obedience to truth can be practiced,” is further elaborated on here. It is as much a statement on the role of community in education as it is about the art of teaching.

Here are few keen insights for discussion, reflection and integration from The Courage to Teach.

1. We Teach Who We Are. Intellectual, emotional, spiritual– all that we are is really what we teach.

2. Integrity and Identity lie at the Core of Teaching. So we ask, “Who am I and what gives me life?”

3. Connect your Soul with Students’ Souls. Teaching is a soulish work, not just an intellectual transfer of data.

4. Power comes from Outside; Authority comes from Within. Power can be conferred or acquired by position, role in the food-chain. But real authority comes from within (re: Jesus who startled audiences because he spoke with authority).

5. Have Fear, but do not BE Afraid. You identity is not fear and you do not have to teach from it or with it.

6. Objectivism = Sterility; Subjectivism = Community. We must have contact with the subject, not simply treat it/him/her as an object to dissect.

7. All Real Knowledge is Communal. This can always be debated but he argues for engagement and “knowing” in the biblical sense, much as he did in “To Know as We are Known.”

8. Do not Separate

The Head from the Heart

Facts from Feelings

Theory from Practice

Teaching from Learning

Questions are obvious: how does this apply to our preaching and teaching? To group leaders who lead Bible discussions and formation groups? Some powerful reminders and ideas. Thoughts?