Maggie Craddock: “Give yourself a break”

Never forget that, while the conversations you have with others matter, the most important conversations you have in life are always the conversations you have with yourself. In this interview series, we are exploring the subject of resilience among successful business leaders. Resilience is one characteristic that many successful leaders share in common, and in […]

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Never forget that, while the conversations you have with others matter, the most important conversations you have in life are always the conversations you have with yourself.

In this interview series, we are exploring the subject of resilience among successful business leaders. Resilience is one characteristic that many successful leaders share in common, and in many cases it is the most important trait necessary to survive and thrive in today’s complex market.

I had the pleasure of interviewing Maggie Craddock. Maggie Craddock is the founder of the executive coaching firm Workplace Relationships. She has worked with people from all levels of the professional spectrum — from people entering the workforce to Fortune 500 CEOs. Her work has been featured on CNBC, National Public Radio and referenced in national publications including the Wall Street Journal, The Harvard Business Review and Oprah Magazine.

Executive coaching is Maggie’s second career. She worked for over a decade on both the buy side and the sell side of the financial services industry before building her coaching business. As a lead portfolio manager for Scudder, Stevens and Clark, she won to Lipper Awards for top national fund performance. As a national director of consultant relations for Sanford C. Bernstein, she worked with top pension fund clients, boards of directors and industry consultants to keep them apprised of the firm’s strategy across asset classes.

A lifelong learner, when Maggie decided to make her own career transition, she did her homework. A graduate of Smith College and the London School of Economics, Maggie went back to school when she decided to transition from helping people manage their money to helping them manage their careers.

Realizing the magnitude of the emotional component involved in helping people clarify their genuine priorities and achieve authentic success, Maggie attended New York University where she received an MSW and then became an Ackerman certified family therapist.

Maggie is also passionate about her writing. Her latest book, Lifeboat: Navigating Unexpected Career Change and Disruption (New World Library, 2020) draws lessons from the stories of Titanic survivors and applies them to the challenges we are facing today. Her work addresses the human dimension of timeless questions such as: How long will this crisis last? How bad will it get? Who can I trust to help me survive, and how will living through this situation change me?

Thank you so much for joining us! Our readers would love to get to know you a bit better. Can you tell us a bit about your backstory?

Managing traders and research analysts in the 1990s taught me that the skills people draw from when it’s “business as usual” aren’t the same skills they needed to develop to operate effectively under extreme emotional pressure. On a fairly normal day, my team and I were cool, objective and hopefully strategic. However, under pressure, we all had to fight the tendency to succumb to snap judgement, polarized thinking and impulsive choices.

Years of navigating volatile markets taught me that trusting my decision making process was far more important than any single decision I made. After all, when conditions changed and things didn’t turn out as planned, sometimes the way our team course corrected ultimately prove more profitable than our original plan would have been.

Gradually, I began to realize that this simple truth about the importance of trusting my decision making process didn’t just apply to running money. It also applied to the way I navigated my life.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘take aways’ you learned from that?

In 1993, I found myself standing on the balcony at a spectacular resort in Laguna Beach during an investment conference. Our team had just won a Lipper Award for the best-performing short-term global bond fund in the nation. I’d been profiled on CNBC, was being quoted regularly in the national media and I’d even received an invitation from Michael Lipper who wanted to congratulate me on our fund’s success.

I should have been on top of the world!

However, as I watched the waves lap against the retaining wall underneath my balcony, I realized that something was missing.

I was experiencing a wake-up call from my authentic self.

While I was both humbled by and grateful for the success my team and I were enjoying, I also realized that one of the key skills I’d drawn on was mastering the art of being who other people wanted me to be. You could send me to a board meeting, and I could morph into who they wanted me to be. You could put me on the phone with an anxious client, and I’d become who they need me to be.

Where was I in all of this? Was this really the highest and best use of my talent and energy?

The conversation I had with myself in that rare moment of sacred silence in Laguna was when my ambitions shifted from helping people create profitable portfolios to helping them create profitable lives.

What do you think makes your company stand out? Can you share a story?

At Workplace relationships, we aren’t just focused on helping people think more strategically. We are focused on helping people cultivate the emotional agility they need to respond to unexpected changes and triggering situations that evoke such powerful feelings that they can barely think at all.

A person’s professional power style often mimics the power dynamics they experienced in the first system they navigated in life — the family system. By exploring the emotional and behavioral triggers developed in the family system, our process helps determine whether someone will react like a dictator or a doormat when he or she is under stress on the job.

Early in my career, I met a prominent investor who had developed such a terrifying reputation as a bully that his power style was becoming a liability for his firm’s culture.

I should have known things might get challenging when the HR representative assigned to introduce me to this investor gave me an anxious smile and bolted before saying a word.

When this prospective client finished his phone call, he hunched his shoulders and continued to purposefully ignore my presence.

Finally, I ventured into the threshold of his office and asked politely, “Excuse me, but I think we have a meeting. Is this a good time?”

My memory of what happened next is a little patchy. That’s what happens under stress.

I remember his face turning towards me with an expression of frustration mixed with fury. I remember hearing him launch into a tirade so loud that, out of the corner of my eye, I could see frightened subordinates sinking into their chairs. I even remember fragments of the phrases he was throwing out such as, “useless charm school…waste of my time…” and some choice expletives that honestly weren’t needed for emphasis, but I guess he threw them in for good measure.

Finally, he wound down. We all need to take a breath at some point.

I was still standing in the same spot which, in retrospect, may have surprised us both.

“WELL!??” he demanded.

Before he could get himself wound up for a second blast, I ventured a respectful response that I hoped would shift the tone.

“I hope you’ll forgive me,” I began as politely as I could manage, “but I’m afraid I didn’t catch everything you just said. It’s clear that based on your passion, and the fact that you repeated a few phrases, that’s there’s something urgent you are trying to get across. Unfortunately, I was so taken aback by your tone that I must confess that I can’t fully recall all of the words you used. While I hate subject you to further frustration, if you could take it from the top, I’m going to take notes this time.”

Then, he saw me.

This man was operating from the blind spots of what I refer to as the Commander power style. An emotional trigger for Commanders is impatience. Thus, under pressure, Commanders are prone to erupt when anything distracts them from what they see as their priorities in the moment.

However, the other side of this trigger is that Commanders often respond quite positively to people stand their ground with dignity.

“You can’t remember the words I used?” he asked with a trace of sarcasm laced with a growing hint respect.

“Sometimes,” I told him as calmly as possible, “people dissociate when they feel intimidated. I’m pretty sure that just happened to me. Do you think that ever happens with other people you work with?”

This client hired me on the spot, and we developed a rewarding relationship. Underneath his frustration, often born of a passion for excellence, this Commander turned out to be a caring and committed leader.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

The late, great Judy Tobias Davis was on the Dean’s Advisory Council for New York University’s School of Social Work with me. Judy was a tireless supporter of projects she believed in — both in her public and her private life.

We became fast friends from the moment we met. Fellow book lovers, Judy and I would spend glorious afternoons together in her apartment on Central Park South discussing writers who had inspired us.

What’s more, Judy eagerly poured over the manuscript for my first book, The Authentic Career. As any first-time writers knows, getting encouragement and emotionally honest feedback from a trusted source can be critical to writing your truth during moments of self-doubt.

Judy helped me tap into the resilience that comes from knowing you have the support of a true friend.

Ok thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the trait of resilience. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

To me, resilience is about embracing the relational lesson at the heart of any challenge we face. By embracing this lesson, we find ourselves tapping into a combination of purpose and passion that makes it possible to overcome obstacles that might otherwise hinder our progress.

Sometimes, the lesson we face invites us to strengthen our relationship with ourselves. This fortifies the resilience we need to chart our own course professionally and not have this dictated for us by outside forces.

Sometimes the relational lesson invites us to become more emotionally agile when we interact with others. This fortifies the resilience we need to negotiate conflict in a way that fortifies our personal integrity rather than diminishing it.

Often, the most powerful lessons we embrace play out in our relationships with the groups we join and the organizations we choose to support. When it comes to our careers, this strengthens the resilience we need to align ourselves with organizations that reinforce our core values and, when necessary, make a healthy break with those that don’t.

Resilient people don’t make snap judgments and they don’t harbor grudges. Resilient people bear in mind that, in a rapidly changing world, you can’t judge someone’s full potential until you have assessed their capacity to evolve.

When you think of resilience, which person comes to mind? Can you explain why you chose that person?

I’ve been thrilled by the press coverage of John Lewis lately, because these programs have showcased the resilience of an American hero who experienced others at their best — and at their worst.

From the physical blows he survived marching for civil rights to the tireless years of service he gave to our government, John Lewis exemplified that inspirational combination of courage and humility that is the hallmark of a resilient leader in the service of a cause that’s greater than any one individual — or any one generation.

Has there ever been a time that someone told you something was impossible, but you did it anyway? Can you share the story with us?

I struggled with a lot of emotional backlash as the dream of developing my coaching methodology formed inside of me. In fact, there were moments when my inner doubts threatened to paralyze me.

One reason was that, in the 1990s, the industries of consulting, counseling and personal growth were well-established but often poorly integrated disciplines. How dare I, as a beginner, attempt to cross boundaries in multiple disciplines simultaneously?

Once I started to take action, the years that I spent developing the inner resilience to trust my decision making process and live my own truth were integral to my success. My work involved digging deep into myself and finding the courage to put my beliefs into practice. I was acting on the faith that helping people listen to their inner voice would not only make it possible for them to identify what they wanted to do, it would also help them find a way to get paid to do it.

While many people have been enthusiastic supporters of my approach to integrating previously disparate disciplines over the years, there have also been “experts” who sought to discourage my efforts when they threatened the boundaries of previously established methodologies. The inner resolve that I had cultivated by staying aware of the conversations I was having with myself, and the ways that emotional triggers could impact my thought process under pressure gave me the courage I needed to negotiate with and learn from others when my convictions were on the line.

Did you have a time in your life where you had one of your greatest setbacks, but you bounced back from it stronger than ever? Can you share that story with us?

As an only child, my priorities abruptly shifted from my career to my family during my parents’ final years. Fortunately, the resilience required to meet the challenges of this chapter of life were reinforced by the blessing of being married to my best friend.

My husband Charles and I settled into a routine of ending the work week by heading to the Philadelphia airport, boarding an 8pm flight for Fort Worth Texas and arriving at our hotel around 1am. We spent the balance of our weekends during those stressful years visiting with my parents, taking care of chores and paperwork for them and crashing in our hotel room to replenish our energy.

What took my breath away was the kindness of the people we encountered everywhere we turned during this challenging time.

By the time my father passed, the hotel staff not only helped me print out the eulogy I wrote for his funeral — they laminated it. As I raced to the nursing home during my mother’s final days, I found that head of the nursing unit had literally moved her desk in to my mother’s room to make sure mom wasn’t left alone before I could reach her side. Years later, people we worked with to help settle their legal affairs, keep their home repaired and even store their possessions still reach out to stay connected with us.

This challenge taught me that, when it comes to resilience, people matter in a very human way during a crisis. There are some things you simply can’t do alone. Without the emotional support of my husband and our friends, I’m not sure how I would have balanced my duty to my parents with my professional responsibilities.

Did you have any experiences growing up that have contributed to building your resiliency? Can you share a story?

From my earliest memories, my parents were tireless supporters of getting me the best education possible. As a result, I took some aptitude tests and ended up receiving a scholarship that made it possible for me to attend an exclusive private high school in Fort Worth.

What my parents didn’t anticipate was the social challenges I faced integrating into a student body where many of the other kids came from extremely wealthy families. While I grew up in a comfortable middle class suburb, compared to the wealthy lifestyles of many of my peers, it often felt like I was from the wrong side of the tracks.

I’ll never forget the day that I was late to class because a group of girls were clustered around my locker chatting gaily. Because of the way they were standing, I couldn’t get to my books. I politely asked them to move. One of them looked down at my shoes, rolled her eyes, the group continued their conversation as if I were invisible.

It felt awful.

As the years progressed, I learned that the way these young women had reacted had very little to do with how they felt about me. It had much more to do with how they felt about themselves. In spite of their expensive cars and fancy shoes, many of them came from homes where they received little genuine validation or emotional support.

Some of the girls who blocked me from my locker that day ended up becoming friends of mine by the time we all graduated. I think this is because, in spite of the stressful social moments we all weathered, they watched me stay focused on my studies, my painting (I love art work!) and my long term plan of getting the education I needed to make my mark in the world.

Decades later, one of them invited me to vacation with her at her family’s vacation home. Over dinner as we watched the sun go down, she turned to me with tears in her eyes and confessed, “I’ve always admired your career. I wish I could figure out some way to have a meaningful job too.”

I remember telling her that one of the gifts I started my life with was the realization that I had to make my career work. Then, I shared one of my favorite Eleanor Roosevelt quotes with her: “It’s never too late to be what you might have been.”

Resilience is like a muscle that can be strengthened. In your opinion, what are 5 steps that someone can take to become more resilient? Please share a story or an example for each.

1.) Never forget that, while the conversations you have with others matter, the most important conversations you have in life are always the conversations you have with yourself.

Because my methodology encourages clients reflect on the values, approaches to conflict and even the definition of success they internalized in their early family system, I’ve had the privilege of hearing a wide range of formative stories. These early stories often form the narrative that shapes people’s beliefs about their own potential and the range of possibilities open to them during changing times.

It’s important to clarify how the experiences in your early family system have shaped your thinking. This is because, through becoming aware of how other people have trained you to define yourself, you tap into the resilience you need to rewrite this definition in a way that feels authentic and genuinely fulfilling.

2.) Accept your feelings with as little judgement as possible — don’t waste valuable energy suppressing them.

When we judge ourselves for experiencing flashes of envy, resentment or even anger under pressure — we undermine our resilience.

Give yourself a break. Learn to acknowledge and accept your feelings with humor and gentleness. You need to be aware of what you are feeling during rapidly changing times, as your feelings may be vital clues about what you need to change in your work and life to stay true to yourself.

3.) Don’t get so wrapped up in how you are coming across that you lose sight of how other’s feel about themselves in your presence.

What motivates others to open up and support you, and what causes them to shut down and avoid you, doesn’t always stem from how they feel about you. It often stems from how being around you causes them to feel about themselves.

After someone has had a conversation with you, how do they feel about themselves? Do they feel validated and supported? Do they feel anxious or emotionally erased?

Learning the art of establishing sustainable rapport with others is vital to creating relationships that fortify our resilience under pressure.

4.) Aligning your thoughts, feelings and actions in the present moment trumps trying to think yourself through a thorny situation every time.

Resilient people get centered under pressure. They look at what’s right in front of them, check in with what they are feeling and carefully observe what’s going on with others in the moment. Establishing this inner alignment often reveals hidden resources, taps into latent strengths and creates potential solutions that might otherwise elude you if you were trapped in a thought loop.

5. ) Look for opportunities to do for others without stopping to calculate what’s in it for you.

When my team and I worked on a trading floor, we learned the art of taking action before the market moved away from us.

In life, it’s powerful to train yourself to act on opportunities to be helpful and supportive of others before you stop to calculate what’s in it for you. This is because, if you take time to do an internal cost-benefit analysis, the moment may pass.

Stop and give directions — even if you are in a hurry. Buy that box of cookies or whatever the hopeful young student is selling. Give the coupons you aren’t using to someone who has that item in their cart.

How will this help you?

Well, for starters, you never know whose watching. I had a client who gave a young woman in a hurry the cup of coffee that he’d just paid for so she could make it to the office on time. Fifteen minutes later he discovered that this same woman turned out to be the receptionist at the firm he was visiting to apply for a job.

Yep — he got the position.

But more to the point, when it comes to resilience, the one person who is always watching you is you.

Cultivating habits that systematically enhance your respect for yourself is foundational to your resilience in work and in life.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Making a shift from the Self-help mindset to what I call the Us-help mindset.

What I mean by the Self-help mindset is a perspective on life where you are primarily focused on your personal security and advancement. While this approach is understandable, particularly under stress, when a large group of people are operating from this mindset they all end up feeling alone together.

In contrast, the Us-help mindset is where you balance your individual goals and needs with an appreciation for the overall well-being of the group. This approach to work and life breaks the chains of isolation and encourages you to prioritize the value you bring to others as well as the individual accolades you may enjoy along the way.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them 🙂

Rachel Maddow — and, by the way, I’d be thrilled with a brief phone call.

Rachel’s penchant for helping her viewers put current political developments into context by giving us brief history lessons is, in my opinion, extremely valuable to our cultural conversation. I’d love to learn more about the thought process she goes through to inspire her audience to think more broadly about what they are witnessing while she updates them on current event.

Also, I’d welcome the chance to thank her for the tone of humor she occasionally injects into her work. There have been nights during this challenging time where her approach to delivering dire news has reset my sanity by helping me laugh.

How can our readers follow you on social media?

My website is

You can also find me on LinkedIn, Instagram and Facebook under Maggie Craddock and on Twitter at @MaggieCraddock

This was very inspiring. Thank you so much for joining us!

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