When Is it Time for a Career Coaching Conversation?

My wife, Margie, says managers have three roles—doing their own job, working with people to help them develop and accomplish their current goals, and talking with people about their career aspirations.

The third role Margie cites is one that is often either forgotten or squeezed in at the end of an annual performance review meeting. As a manager, why would you want to talk with your people about their career aspirations? It’s not necessarily because you have a promotion in your back pocket. It’s because you care about them and want to know where they see themselves in one, three, or five years—where they would like to be in their career.

Career coaching is an organizational strategy that retains high performers and increases bench strength over time. Why? Because people get energized when their manager wants to talk about their future—it shows them their manager is interested in them and it makes them more willing to share their thoughts and plans.

Several signals can indicate that it’s time to start having career conversations with a direct report:

  • When they continually exceed expectations
  • When they ask for more responsibility
  • When they bring up the topic of their career aspirations
  • When they have mastered the basics of their current role

Some managers are hesitant to have career coaching conversations with a valued team member because they fear losing the person to another department or organization. But consider this: research from world-renowned coaching expert Marshall Goldsmith shows that one of the most common reasons people leave a company is because nobody asked them to stay. Look at each coaching conversation as an opportunity to let your direct report know how much you appreciate them and their work.

Another reason managers are hesitant is because they don’t have a potential promotion to offer or a good idea of new opportunities in the organization.  The idea is to have the conversation without thinking either of you have an answer—yet.  One of the questions you could ask is What are two or three positions in this organization that might be of interest to you in the future?  The person’s reply may give you clues about their general interest or intent. It may even lead to a conversation about how they can find out more about those positions.

Managers, I urge you to sit down and discuss career aspirations at least two or three times a year with each of your direct reports. A regularly scheduled one-on-one meeting is a perfect time to bring up this topic.

People need their managers to be interested in their future as well as their present—and career coaching conversations are a great opportunity to show your direct reports you really care.

Ask Empowering Questions

Most of us—even millennials—have a history of working under guidance and control at school and in our workplaces. Therefore, we tend to think of authority as external rather than internal. The following questions are all too familiar to us:

At school: “What does the teacher want me to do to get good grades?”

At work: “What does my boss want me to do?”

While things are changing, we live and work in a culture predominated by top-down management and hierarchical thinking, so we’re far less likely to ask questions like these:

At school: “What do I want to learn from this class? How will I know I have learned something I can use?”

At work: “What do I need to do to help my company succeed?”

These are empowering questions. President Kennedy made a call for these kinds of questions when he challenged Americans: “Ask not what your country can do for you; ask what you can do for your country.”

Empowering questions open the possibility for us to become stronger and more competent. So why don’t we ask them more often?

It gets back to all those hard-earned parenting, teaching, and managing skills we learned from our hierarchical culture. Indeed, we feel it is our responsibility as parents, teachers, or managers to tell people what to do, how to do it, and why it needs to be done. We feel we’d be shirking our responsibilities to ask children, students, or direct reports empowering questions such as these:

“What do you think needs to be done, and why is it important?”

“What do you think your goals should be?”

“How do you think you should go about achieving your goals?”

Many of us are afraid to relinquish control to our direct reports because we’re concerned about outcomes. Yet organizations with a culture of empowerment almost always outperform their hierarchical competitors. Consider the following story from Ritz-Carlton, a company famous for its culture of empowerment.

A loss prevention officer at The Ritz-Carlton, Toronto, was called for the second time to a guest room after receiving a complaint of children playing hockey in the hallway. A typical response might have been to knock on the family’s door and ask them to be quiet. But Ritz-Carlton encourages its employees to think for themselves as they live by the company’s “Gold Standards.” These standards invite empowering questions such as:

  • How can I respond to the expressed and unexpressed wishes and needs of our guests?
  • How can I create unique, memorable, and personal experiences for our guests?

Rather than tell the parents to shush their hallway-hockey-playing kids, the loss prevention officer came up with a creative solution. He enlisted banquet employees to isolate space in one of the meeting rooms and create a hockey rink, using banquet tables as a frame. While the “rink” was being set up, he drove to a local sports store and bought two hockey nets, six sticks, and hockey balls. Finally, he delivered a written note to the family, inviting them to an impromptu hockey match against the Loss Prevention All-Stars.

Needless to say, the family was wowed.

A tight match was played between the Loss Prevention All-Stars and Team Family, with Team Family emerging victorious. The game was recorded on the Loss Prevention in-house cameras and Team Family was sent photos of their epic game.

Double-wow.

My friend Tony Robbins often says, “Successful people ask better questions and as a result, they get better answers.” So, ask yourself some empowering questions, and encourage your people to do the same.

Unforgettable Herb Kelleher

Last Thursday, we lost probably the finest corporate leader I have known in my leadership development career: Herb Kelleher, cofounder and longtime CEO and president of Southwest Airlines. Not only was Herb the visionary who created the model for a low-fare, customer-first airline, he believed every executive is only as good as his or her people. And he walked his talk. More than anybody I’ve ever worked with, Herb Kelleher lived and breathed the philosophy that the number one customer of any organization is its people.

I first met Herb through Southwest’s president emeritus, Colleen Barrett. When Colleen ordered 30,000 copies of the book I coauthored with Barbara Glanz called The Simple Truths of Service: Inspired by Johnny the Bagger, I was so blown away by the size of the order that I flew to Dallas to meet her. Because Colleen and Herb had worked together since 1967 nurturing and grooming Southwest Airlines into one of the most admired companies in the world, meeting Colleen’s mentor and teammate was a foregone conclusion. From the moment I met him, I loved Herb’s big smile, tremendous sense of humor, and ability to bring insight and laughter to any situation.

I could tell many tales about my fun times with Herb, but my favorite story happened just after he had recorded his foreword for the audio version of Colleen’s and my coauthored book Lead with LUV: A Different Way to Create Real Success.

“Let’s go get a drink!” said Herb. He was always ready to do that. We went back to my hotel where my wife, Margie, would be meeting me later so we could go to dinner with the board of directors for Halftime, a faith-based ministry founded by the late Bob Buford. (Margie still serves on the Halftime board.)

At the hotel bar, Herb and I started drinking sidecars, one of his favorite drinks, made up of three ingredients: Cognac, orange liqueur, and lemon juice. By the time Margie arrived, let’s just say Herb and I were feeling no pain. Margie could easily tell I was not in any shape to go to dinner with a bunch of faith-based folks. When she began to give Herb a One Minute Reprimand, he held up his hands in surrender, saying, “Margie, this was all Ken’s idea! I’m usually a teetotaler!” We all had a good laugh about that.

Margie said, “Okay, Ken, you can come to dinner—just don’t say anything.”

Herb, now getting into the absurdity of the situation, said, “That would be something to see!”

So I went to the dinner. The seating was organized in a circle. When the waiter came around to take our appetizer order, I whispered, “I notice you have chocolate cake à la mode. Bring me that for my appetizer.” When the waiter put the cake in front of me, all conversation around the table stopped and all attention was focused on me and my appetizer/dessert. The cat was out of the bag—I was plastered.

When I called Herb the next day and told him what had happened, he roared. Suffice to say it cost me a lot of backrubs over the next few weeks to get Margie’s full forgiveness. After that incident, every time Margie and I saw Herb, the first thing out of his mouth was “Margie, that was not my fault!” and then we’d all laugh.

I’ll miss Herb—and not just because of the fun, fabulous human being he was. Herb taught me a lot about what it takes to be a pioneer, a maverick, an innovator, and a fabulous motivator of people. To Herb, the “business of business” was people.

A lot of folks are going to miss you, Herb, including the many thousands of employees of Southwest Airlines. You were the best in the business. Rest in peace and God bless.

New Year, New Goals: Don’t Go It Alone!

The New Year is fast approaching and here it comes again: New Year’s resolution time. Have you ever made New Year’s resolutions you didn’t keep? My experience is that all of us have had good intentions we didn’t follow through on over the years. We usually start out enthusiastic about the change but after a while our enthusiasm falls by the wayside. Why is that?

My friend Art Turock taught me that the problem stems from confusion between interest and commitment. For example, when interested walkers and joggers wake up and find it raining outside, they lie back down and think to themselves, “I’ll exercise tomorrow.” However, when committed exercisers wake up and find it’s raining, they get out of bed and think to themselves, “I’ll exercise inside today!” In other words:

They keep their commitment to their commitment.

So, let’s get real. What have you been wanting to do for a long time but just haven’t been able to get done? Maybe it has to do with your health and fitness. Or maybe it’s learning a new language, or getting organized, or cleaning out your garage. Whatever it is, that’s great. You’ve got your commitment. Now, how are you going to keep your commitment to your commitment?

First, don’t go it alone. The heroic legend of the lone wolf who succeeds at lofty goals through willpower alone is strong with many people. This “John Wayne myth” isn’t dead—it’s just not effective.  I should know. For years I could not keep my commitment to good health and wellness. I needed help.

That help eventually came from Tim Kearin, the health and fitness coach who had been patient with me for many years. Each year Tim listened to me announce my New Year’s resolution to improve my health and fitness—and each year he watched me not keep my commitment. Year after year we went through the same routine: Tim would receive a call from me early in the year to begin a fitness program. I would get underway with enthusiasm, but after a month or so I would gradually become too busy to keep my commitment to my commitment. The process would start again at the beginning of the following year.

The way I broke this ineffective cycle—and the way you can, too—was to follow the six principles outlined in Fit at Last, the book Tim and I wrote to document my fitness journey:

  1. Have Compelling Reasons and a Purpose
  2. Establish a Mutual Commitment to Success
  3. Apply SLII® (in other words, get the coaching and support that matches your development level)
  4. Develop Age-Appropriate Goals
  5. Set Up a Support System to Hold You Accountable
  6. Have Measurable Milestones to Stay Motivated

While these six principles were developed to accompany a fitness program, they can be adapted to any kind of goal accomplishment.  I’m happy to say that by applying these six principles, I’ve managed to maintain my health and fitness goals for the past five years.

You, too, can keep your commitment to your commitment. Just don’t be a lone wolf. Set yourself up to succeed by finding the coaching and support you need.

What’s Your Leadership Point of View?

Margie and I recently spent a wonderful weekend teaching our “Determining Your Leadership Point of View” class at the University of San Diego. It’s part of the Master of Science in Executive Leadership (MSEL) degree program offered by USD in partnership with our company.

I often start off training sessions with managers by asking: “How many of you consider yourself a leader?” Amazingly, only about 20 percent raise their hands. I think a lot of people believe that to be a leader you have to have a certain amount of power or an executive position—and for some reason they don’t think they have enough power or the right title yet. The second thing I say is: “Tell me about one or two people who have impacted your life the most.” Almost no one names a manager or supervisor; they all identify a parent, grandparent, their spouse or significant other, or a relative, coach, friend, or neighbor.

In life, everyone has the opportunity to lead. In fact, we all are leaders right now. Why do I say that? Because there are two different kinds of leadership roles: life (as a spouse, parent, or friend) and organizational (as a manager, supervisor, etc.). So everyone is a leader in some aspect of their life—even if they are a follower! In fact, my wife, Margie, wrote an article titled “In Praise of Followership” for the book Servant Leadership in Action. It’s all about how followers are also leaders.

Research proves that effective leaders exemplify and communicate to their followers a clear and consistent Leadership Point of View. The students in our MSEL class develop their own unique Leadership Point of View that they will be able to demonstrate to people who work with them. So often in organizations, people can’t figure out what’s important to their boss—what “makes them tick.” When direct reports are aware of their manager’s Leadership Point of View, that mystery is solved.

We tell our students that figuring out their unique Leadership Point of View is like writing a course on themselves. After they identify the people and events that have impacted their life the most, we ask them to think about what they learned from those people and experiences. How did those parts of their life influence their leadership style? What values did they instill? Then, based on those reflections, what do they expect of people who report to them now—and what can their people expect from them as a leader?

It is a fascinating process. As students unearth these thoughts and memories, they write their Leadership Point of View in a story format. Why? It’s a more authentic and personal way of communicating. Stories paint a picture that allows others to see the consistency between values, words, and actions. As students progress in their writing, they share their work in small groups of their classmates. At the end of the course, each student stands in front of the class and tells their leadership point of view story as if their fellow students were their team members at work. They get feedback from their classmates as well as from Margie and me.

What values have you developed through the important people and experiences in your life? Based on those reflections, what do you expect from your people and what can they expect from you as their boss? I’d love to hear your thoughts about the Leadership Point of View process in the comments below.