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Lessons In Leadership: One On One With Major General Craig Whelden

I spoke to Major General Craig Whelden (U.S. Army, Retired) about his journey and his best advice on leadership

Adam: Thanks again for taking the time to share your thoughts on leadership. First things first, though, I am sure readers would love to learn more about you. What is something about you that would surprise people?

Craig: My time as a senior leader was split between TWO different military services:  seven years as an Army General Officer and another nine as a member of the Senior Executive Service (SES) for the United States Marine Corps.  Also, I lived 29 years outside the continental United States: 17 in Europe and another 12 in Hawaii.

Adam: How did you get here? What experiences have been most instrumental to your growth as a leader?

Craig: A key “fork in the road” for me was when I transitioned from an Army combat arms officer to becoming a base commander as a colonel. This “road less traveled” took me in a very different career direction, and ironically led to where I am today.  While I didn’t initially embrace this new direction – wondering why it was happening – it was the best thing to ever happen to me professionally as it made me discover new leadership techniques different from what I had used to date: requiring a leadership approach that worked equally well with civilians as with soldiers.

Adam: What failures, setbacks or challenges have been most impactful in developing your leadership skills?

Craig: A senior officer once helped me get through a failed marriage at a time when I was in a very dark place and this demonstration of caring for a subordinate – at a time when we had never even met – helped me to be more sympathetic and empathetic to other peoples’ life challenges.  I’ve never forgotten how he uplifted me when I thought no one cared. He did.

Later in life, my sister’s suicide made me reprioritize my life, and that tragedy became a factor in my decision to retire from the Army at the 30-year point so I could focus more time on my own family.  

Let me illustrate this point about priorities with another story:

A friend graduated from West Point and regularly attended reunions.  At one of these annual gatherings he saw a classmate sitting by himself at the bar.  Approaching him, he asked how he was. The classmate turned to him and was a bit misty-eyed.  My friend didn’t know whether this was from too much to drink or for some other reason.

The classmate – a retired General Officer – then said “I busted my butt for 35 years and the Army rewarded me with promotions and challenging assignments.  Along the way, my wife left me and now my kids won’t talk to me.”

One has to wonder whether this classmate had his life priorities in the right place and – as importantly – whether he encouraged others in his organizations to do the same.  

My own life experiences have taught me that you can’t be all things to all people; nor can you always “have it all.”  Long ago, I learned to prioritize what was most important in life, and I realized that everyone else needed to do the same.  Great leaders understand this challenge both for themselves and for those they lead.

Adam: In your experience, what are the defining qualities of an effective leader?

Craig: Without question, character is the basic building block for all great leaders.  Without it, leaders ultimately stumble. Character traits of great leaders include a healthy ambition, perseverance, self-awareness, empathy, humility, integrity, and always taking seriously the responsibility of being a leader… often while sacrificing their own personal welfare or gain.

Adam: How can leaders and aspiring leaders take their leadership skills to the next level?

Craig: Leadership is part nature, part nurture, and combining innate skills with world-class training often produces great results.  The U.S. military seeks the former and provides the latter. Aspiring leaders with these basic character building blocks should seek out such training and great leaders should provide it.  

Adam: What is the best advice you have on building, managing and leading teams?

Craig: I once worked for a 3-star general who was the consummate gentleman.  Very bright, extremely organized and competent, he never raised his voice. One day, a colonel on the staff told me the general was the “toughest guy he had ever worked for.” Perplexed, I asked him why.  He responded “Because I never wanted to disappoint him. I knew exactly what he meant. Inspire people to be their best and you’ll be amazed at what they will provide in return.

Adam: What are three leadership lessons from your time in the service that are applicable to a broad audience of leaders?

Craig: There are many more than three, but these come to mind:

1.) Loyalty: A two way-street.  Leaders need to demonstrate loyalty DOWN as well as up the chain.

2.) Trust: I often tell members of my organization that I trust them until that trust is violated.  This imposes a healthy kind of pressure on people because they don’t want to violate that trust.

3.) Setting organizational expectations:  With over four decades of experience in the military, I’ve learned the value of setting expectations early on so people don’t waste time trying to figure out what the new boss thinks is important.  Do this soon after your arrival and often thereafter.

Adam: Who are the greatest leaders you have been around and why do you admire them? What did you learn from them?

Craig: Broadly speaking, I most admire those who demonstrate the elements of character described in my earlier response; especially humility and integrity.  It’s important for leaders to never forget their roots and to remember that it is those who work for them that are largely responsible for the success of both the leader and the organization.  I’d rather see these traits in a leader rather than just intelligence or raw talent.

Adam: What is the biggest misconception people have about the military, the Army and military leaders?

Craig: Perhaps the greatest misconception is that military leadership varies greatly from the corporate world and that the approaches are different.  While it’s true that the military lives in a very structured and disciplined environment, the best performance and results are generated from leadership traits that are universal and applicable across society in general.   

Adam: What do you believe are the three most important issues facing the country and the world? Are you optimistic about our ability to address them?

Craig: Our Country:

1.) Rabid partisanship currently infects the discord in our capitol and is unhealthy and unproductive.  Logical solutions can only be achieved through great leaders stepping up to bridge differences rather than exacerbate them.

2.) Addressing our national debt requires leaders to make tough choices in order to find solutions.  We cannot continue to wish it away to follow-on generations or they will rightly blame us for the result. Unless addressed, burgeoning entitlements will eventually strangle us.  This requires tough choice that only great leaders can make.

The World

3.) Whether man-made or the result of natural evolution, most agree that global warming requires both our attention – and some action – so that we don’t go past the point of no return, irreversibly damaging our world.

I’m normally an optimist, but I’ve not seen the strength of character in our leaders to address any of these… yet.  At least not in sufficient strength to matter.

Adam: What is the single best piece of advice you have ever received?

Craig: When I received my first star, I asked a mentor what was different about being a general.  I felt the same as I did the day before when I was a colonel. After thinking a moment, he replied: “Your jokes don’t get any funnier; you aren’t any better looking; and if it tastes good, spit it out.”  

While humorous at first, this advice has a deeper meaning about humility and integrity and I’ve passed it on every year to others who have arrived at that same professional milestone – in both the Army and the Marine Corps.

Adam: What is one thing everyone should be doing to pay it forward?

Craig: I often tell people that their greatest legacy should be to pass on to others the leadership lessons they’ve learned along their own life journey.  Great leaders don’t patent their behavior; they freely pass it on.

Nelson Henderson once said “The true meaning of life is to plant trees under whose shade you do not expect to sit.”

That kind of selfless giving is the true test of a leader motives.

Adam: What are your hobbies and how have they shaped you as a leader?

Craig: My family is my hobby, and by extension, the young people I’ve been able to help through teaching, mentoring, or passing on what I’ve learned in life.  This gives me the greatest satisfaction and is the one legacy I’d like to leave behind.

Adam: Is there anything you’d like to share?

Craig: Earlier I spoke of the importance of prioritizing what’s important in life.  I’m reminded of the story of a professor who makes that point by placing a glass jar on the table and then placing rocks in the jar.  

Once the rocks reached the top, he asked “Is the jar full?” The class answered “Yes.”

He then pulled out a bag of pebbles and poured them in the jar.  They fell through the larger rocks and eventually filled the jar.  He then asked again “Is the jar full?” A bit embarrassed, the class answered “We think so.”  

He then pulled out a pitcher of water and poured it in the jar until the water reached the top.  He then asked “Is the jar full?” Again, the class had been fooled once before and now wasn’t sure how to respond.  

The professor then suggested that the rocks represent what’s most important in life.  Put those in the jar first. If you put the pebbles and water in the jar first, all the rocks will not fit and you will be leaving out something that’s important.  

Figure out what rocks to put in your jar and put those in first.

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