My weight has been a yo-yo my entire adult life. Up ten pounds. Down ten pounds. Up fifteen. Down fifteen. Up twenty. Down twenty.

Maybe because I’ve spent so much time on airplanes the last twenty-five years of my career. My closet has three sets of suit pants: 34inch, 35inch and 36inch. When I get to 36inch, I go on a crash diet to get back down to 34inch.

Been doing this for over two decades. I’ve done all the diets. Every one of them. South Beach, Atkins, Jenny Craig, Weight Watchers, Paleo and Ketogenic. They all work. Drop my 10, 15 or 20 pounds. And then I gain it all back. Hence, the yo-yo!

I’ve been coaching and teaching servant leadership for nearly twenty-five years. I’ve been blessed to have written a couple New York Times best-selling books on the subject. My clients refer to me as a leadership expert, but I blush when I hear that word… expert. I don’t believe in that word. I like to refer to myself as a full-time student of leadership. Every day I’m learning how I want to lead. And every day I’m learning how I don’t want to lead.

Each year my company hosts seven different Heart-Led Leader Retreats. Life changing – both personally and professionally. Been doing these three-day retreats for over a decade. Truly one of the most rewarding things I’m honored to be a part of… teaching heart-led leadership to hundreds of CEO’s, C-Suite and rising leaders from companies and organizations from all over the country.

Last year a gentleman from Omaha, Nebraska, named Kris, attended one of my Heart-Led Leader Retreats. I got to know his heart. And Kris’s heart is a good one. During the retreat I shared with Kris about my yo-yo weight problem. Told him all the diets I’ve been on. And off. And on. Told him about all the dang pant sizes in my closet.

Kris shared with me his success with losing (and keeping off) over fifty pounds. The guy is in amazing shape. So, I asked him what diet he recommends that I go on next? What foods should I be eating? What foods should I not be eating? He didn’t answer. He just listened.

A week later Kris called me. He told me that I’m asking all the wrong questions. The questions should not be what diet I should go on. Or what foods should I be eating. Or what foods should I not be eating. The question I should be asking myself is why I eat?

There was a long pause. I was trying to process his question. South Beach, Atkins, Jenny Craig, Weight Watchers, Paleo and Ketogenic all told me what to eat. And what not to eat. Kris asked me a completely different question…why do I eat?

Let me give you the punch line. Since that conversation with Kris, I’ve lost more weight than ever before…and have kept it off. No more yo-yo. I’ve ditched the 34, 35 and 36inch pants in my closet. Now proudly wear 32inch pants… on my way to 31inch pants. I haven’t worn 31inch pants since I came out of my mother’s womb forty-nine years ago!

Turns out Kris’s question changed my life. Perhaps even saved my life. Made me really think… why do I eat? The answer really scared me. I over-eat to mask my pain. The pain of feeling like I’m not good enough. Not smart enough. The pain of being betrayed by people that I trusted and cared about. The pain of being disappointed and let down by people that I love. The pain of bad people doing harmful things to me and my family.

The more pain, the more I eat. Kris’s why question made me fall in love with this guy’s heart. He cared enough to ask the hard questions. Got me thinking. Got me to work on myself.

We, as leaders, are sometimes afraid to ask the hard questions. Especially with those that choose to follow us. And with those that we love. What I learned from Kris is that Heart-Led Leaders are not afraid to ask the hard questions. In fact, the more we love and serve others… the harder our questions should be.I have a dear friend named Amy.

Probably one of my closest friends on the planet. And our friendship reflects the kind of questions Amy always asks me… the hard ones. And I’m better for it.

We don’t need to get rid of all the oversized clothes in our closet to be a Heart-Led Leader. But we do need to stop yo-yoing around and ditch the light, fluffy and softball questions we ask of those we love and lead. We need to ask the hard questions.

And like Kris & Amy, the harder the questions… the more we love and care.