Peter Dudley Of Gray Bear Coaching On The Five Things You Need To Be A Highly Effective Leader During Turbulent Times

An Interview With Sara Connell

Know who your allies are. When things are hard, it’s easy to feel isolated. The reality, however, is that we all have people who are eager to help if only we would give them an opportunity. Sometimes, those allies come from unlikely places.

As part of our series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times”, we had the pleasure of interviewing Peter Dudley.

Peter is an author and leadership coach with an extensive background in corporate responsibility, employee engagement, and nonprofit management. His career has taken him from aerospace to tech startups to financial services to healthcare. A dedicated writer since childhood, he’s published several novels and has been quoted or published in Money, Reader’s Digest, US News, and several tech and business journals and blogs. In his career, he’s worked on the first stealth aircraft (the B-2), the first PDAs (Casio “Zoomer”), and the first smart phones (Nokia 9000). He’s lived in the San Francisco Bay Area since graduating from UC Berkeley, and he’s the proud father of two grown children.

Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

My life and career have taken so many turns, it feels like I’m in a constant state of “getting started.” I grew up in New England but moved to California to study engineering at Berkeley. Pretty quickly I realized I would only be a mediocre engineer, but I had strong communication, marketing, and people skills. That launched me into tech writing, which morphed into marketing at tech startups. Then I kind of fell into a corporate responsibility role at Wells Fargo, where I grew the employee giving and volunteer programs to some of the largest in the country and built a national reputation for myself in employee engagement and community involvement. After a few years at a nonprofit, I’m now “getting started” again with my own leadership coaching practice, Gray Bear Coaching.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

I was about three weeks into my first job at Boeing, updating some outdated paperwork on an old project while I learned the company’s systems and processes and waited for my security clearance to come through. I had a question about the document, so I called the phone number of the person who originally wrote it. He was very polite and patient, and he did his best to answer my questions. Later, I found out that I had just called the direct line of the Air Force colonel in charge of the entire project — he’d been promoted several times since originally writing that document! My colleagues who had been on the project for years were mortified and couldn’t believe I’d done that. What I took away from that, and what I carry with me today, is the kindness and patience with which the colonel took my call and answered my questions. He surely did not expect that kind of call and probably did not have time for it. But instead of indignation and bluster, he gave me his time and attention. In hindsight, that’s a pretty powerful leadership lesson.

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?

This story is going to surprise some people, but I’m really grateful to my kids and my ex-wife. My oldest child realized she was transgender late in high school, and that led to several years of really difficult times for her. As a family, we’ve been open and relatively public about her gender struggles and her three years of deep depression and suicidal ideation. Fortunately, she is past that now. Those years were the hardest of my life, yet they were also the most transformative and educational. I’m grateful to my daughter for not only persevering and coming through those years, but also for her integrity and perspective. I’m grateful to my son, now about to graduate college, for being such a stalwart and unflappable, positive, supportive along the way. And I’m grateful to my ex-wife for partnering through such a turbulent, confusing, and terrifying time. Those years absolutely helped shape who each of us has become, and continues to become.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your organization started, what was its vision, what was its purpose?

Purpose in work, and purpose in a company’s mission, definitely drive better outcomes. I’ve been in the purpose business for two decades in CSR, employee engagement, and nonprofit work, and I left my last job few months ago to start Gray Bear Coaching with all that in mind. My goal is to use my experience, perspective, and accumulated wisdom to help guide the next generation into becoming the best leaders they can be. When someone is attuned to their values, the mission of their organization, and the purpose of their role, they can be a much more effective leader. Today’s leaders need to exhibit empathy and vulnerability, and those come from real self awareness. That’s why I am getting into coaching — I’ve managed programs, built teams, launched products, and a lot more. My purpose in this next (and probably final) stage of my career is to help the next generation do those things even more effectively. And, given the “great resignation” and all the other disruptions being precipitated by the pandemic, climate change, and global unrest, there is a lot of need for quality coaching and guidance right now.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you led your team during uncertain or difficult times?

The obvious and most recent situation was when the pandemic hit and a regional shelter-in-place was declared on March 16, 2020 for most of the Bay Area. Due to good planning on the part of those who came before me, Cancer Support Community San Francisco Bay Area was ready to go fully online with nearly all our services that same day. But I was the only one on the staff who’d ever worked remotely or even worked extensively from home. Complicating matters, the CEO who had been there 14 years was retiring, so we had to hire and onboard a new CEO during those first few months. The staff definitely had a lot of uncertainty and felt a bit adrift during that time. Our executive team kept calm, focused on what we could control, made safety and employee engagement our top priorities, and looked for novel ways to ensure the entire staff felt connected, valued, and valuable. On the fundraising team, we turned very quickly away from in-person meetings and events to a lot of phone calls to our donors to make sure they were all doing okay, and also to virtual events. I saw many of my peers at other organizations beginning to panic — what would fundraising look like during a pandemic? What would happen to the economy? Would donations dry up? How could we hold galas or charity walks? Leadership in those moments comes down to keeping calm, staying focused on the mission, making an extra effort to connect individually and as a team, and listening to your team members. (I actually wrote about this for the CHC: Creating Healthier Communities blog back in 2020.) Since I’d managed virtual teams before, I was able to maintain the team’s focus, though there was definitely a period of adjustment. The biggest change perhaps was putting our major fundraising events online, which took considerable imagination and learning since none of us had ever done that before.

Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?

I am not really sure what “giving up” means. Certainly, there are times when you need to change course. None of us ever thought of giving up when it came to our fundraising events. In fact, in September of 2021 when the omicron variant was surging and we had to cancel the in-person portion of our online film festival, we found a unique and innovative way to turn that setback into a really meaningful event: Instead of simply canceling the dinner, we delivered meals to oncology nurses along with a personal thank-you. Not only did it generate tremendous goodwill and support our organization’s mission, but it got on the evening news and gave the organization a boost. That said, there have been times in my life when I stepped away from a project when it became obvious that there was no future in it. For example, a friend and I had built a fairly solid business plan for a startup in the 1990s, but we decided to shelve it when two competitors we were watching both got significant funding and were already pretty far ahead of us. Even though this validated our concept, we decided we’d rather move on to other pursuits than spend all our time and energy trying to catch up to them. I don’t consider that giving up; I think of it as an intentional change to a more productive and enjoyable course when circumstances changed.

I’m an author and I believe that books have the power to change lives. Do you have a book in your life that impacted you and inspired you to be an effective leader? Can you share a story?

When I was younger, I read a lot of business books. Not too much of that sticks with me today, to be honest, but anyone who knows me well has heard me cite concepts I read in a book first published in 1987 called Peopleware, by DeMarco and Lister. That book has made me think differently about a lot of trends that have swept through business over the last three decades. One example is the fad of creating “open” office spaces in order to spur creative interaction. I hate open office spaces because in reality all they do is destroy concentration by creating a constant flow of interruption. A story I’ll share happened with a coaching client this week — he had always been a super individual performer, but as a new manager he was struggling during a particularly busy time. He didn’t want his own stress to affect the rest of his team negatively. When we got into the details, it became clear that he was in a constant state of being interrupted by email, instant messages, and texts. This not only made it nearly impossible for him to concentrate on his own work, but by always being available at a moment’s notice to everyone, he was never fully available to anyone. While that revelation didn’t come from the book I mentioned, I would credit that book with giving me a much more skeptical attitude toward new trends that sweep through business culture without any real research to back them up. Like, having your company’s instant message channel open in front of you all the time because it “improves communication.”

What would you say is the most critical role of a leader during challenging times?

It’s the same as in regular times — ensure employees feel valued and valuable. It used to be that leadership meant projecting an air of unerring authority even when you had no idea what was going on. Today, employees want to know that their leaders have integrity, empathy, and a desire to do right (as opposed to be right). Good leaders do this by knowing their teams, ensuring that everyone on the team feels connected to both the organization’s mission and their workgroup’s role, and recognizing both the challenges facing the team and their successes. A good leader will make sure their employees feel both valued (both as people and as members of the team) and valuable (that their work contributes to a worthwhile outcome and is valued by someone, whether that’s a customer, a manager, or a teammate).

When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?

Certainly there are the trappings of recognition and engagement, like giving everyone a company branded water bottle or sending everyone a gift card to a coffee shop. Those things are like engagement jelly beans — a quick sugar rush without creating genuine, lasting engagement. As with so many things, the way to motivate and engage a team is to stick to the fundamentals. Provide good compensation. Act with integrity and good ethics. Actually care about people and show it through language, regular interaction, and active listening. Make sure people feel purpose in their roles by ensuring that they know how their work contributes to fulfilling the company’s mission, helping customers, or solving problems. As a manager, you can’t hope to overcome anxiety or insecurity caused by a pandemic, climate change, or global unrest. Employees shouldn’t expect you to, either. They expect you to be able to acknowledge those things, talk about them in real and rational terms, and focus on what you can control. The fundamentals matter during difficult times more than ever; it’s easy to rationalize painting over big cracks in the foundation during easy times, but it’s impossible to fix those big cracks when an earthquake is shaking the building apart.

What is the best way to communicate difficult news to one’s team and customers?

Ideally, difficult news is never truly a surprise and you’ve been preparing for it. If, however, something suddenly happens that you have to announce unexpectedly, the best way is to approach the topic directly with candor, compassion, and vulnerability. People don’t like bad news, but by and large they can handle it. What they won’t forgive is being lied to, and with the speed and availability of information these days, it’s best to be above board.

How can a leader make plans when the future is so unpredictable?

The future has always been unpredictable. There have always been times of unrest, upheaval, and disruption. It’s been shown throughout history that times of great change are also times of great opportunity. To take advantage of that opportunity, you need to approach these times with an attitude of curiosity and an intentionality of will. I go back to the surge of omicron in the fall of 2021. At Cancer Support Community, we didn’t simply shut down all our events; we planned for flexibility, and then we came up with ideas of how to make the most of the situation when we did have to cancel our in-person dinner. When things are uncertain, you plan with the knowledge and tools you have, but you also think through contingencies and likely scenarios. Then, if you’re forced to change your plans, you’re ready and able to do so. You don’t throw up your hands and say “we don’t know what will happen, so we won’t plan anything.”

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

Sure… turbulent times will come. Look to your fundamentals and prepare for them during the good times. Compensate your people properly. Keep the foundation of your brand strong. Have strong principals and ethics, and live to those. When times get hard or especially unpredictable, do right by the people who rely on you, and they will do right by you. If you live in an area where there are earthquakes, you prepare for earthquakes. The more prepared you are before the disaster hits, the more likely you are to get through it and the more quickly you recover.

Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?

Mistakes happen when leaders allow themselves to be driven by fear, making decisions that feel right in the short term but which sacrifice long term stability. Cutting costs to hit a target profit margin can damage trust among employees and customers, prioritizing short term shareholder value over long term business health. Holding back information from employees and middle managers might feel like you’re trying to avoid panic, but in reality, it creates distrust and uncertainty among the people you most need on your side. On the other end, I’ve seen managers panic and go into a mode of “the sky is falling, all hands on deck” which leads to irrational decision making. In one case, that panic turned what was a difficult but solvable problem into a spectacular disaster. The way to avoid these things is to build a foundation of trust, to stick to rational decision making, and to not give in to the hasty decision-making that fear creates.

Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.

Good leaders are trustworthy, have integrity, embody a growth mindset, and care about their team members. This is true in easy times and difficult times. Here are five things I focus on when helping people become better leaders.

1. Know who your allies are. When things are hard, it’s easy to feel isolated. The reality, however, is that we all have people who are eager to help if only we would give them an opportunity. Sometimes, those allies come from unlikely places.
2. Embrace vulnerability. Too often, leaders are afraid to let others know that they’re struggling, just like everyone else. Social media especially encourages us to keep up a front of strength, but doing so can actually create even worse feelings of isolation and inadequacy. The more that leaders project an inhuman level of capability in tough times, the more their employees will feel they’re not able to measure up. Modeling fake perfection doesn’t actually serve anyone, and breaks down trust.
3. Build infrastructure during good times. The best way to recover quickly from disaster is to prepare for the disaster. You can’t fix a leaky roof in the middle of a hurricane. When times are good, nurture and strengthen your professional network. Set aside reserve funds. Plan for contingencies. That way, when the “rainy day” hits, you’ll be able to weather the storm and rebuild more quickly.
4. Remember what’s truly important. I have learned from cancer patients that “the gift of cancer” is a more meaningful, complete, and fulfilling connection to the things that truly matter in life. These things aren’t the same for everyone, but identifying and focusing on your personal values will keep everything in perspective and help you avoid making decisions from a place of fear.
5. Engage a coach. In my 30-plus years in business, I’ve witnessed the profound benefit of having someone to help you see things a different way, connect to your values, and find ways through uncertainty and indecision. Even if you already have that in a colleague or a friend, there can be great value in talking regularly with an impartial, experienced, nonjudgmental professional.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

When I was nine years old, my 15-year-old brother was trying to teach me how to ski. He got frustrated because I was too cautious and slow. Finally, he said, “If you don’t fall down, you’re not having enough fun.” Of course, we’ve all heard the old saw, if you don’t fall down you’re not trying hard enough, but I like my brother’s version better. The idea that you should be working so hard that you risk injury seems pretty cynical, but I can get behind the idea that we might push the envelope in pursuit of joy. I frequently think of that whenever I find myself retreating into a cautious mindset.

How can our readers further follow your work?

If anyone is interested in coaching, they can find me at https://graybearcoaching.com. If I’m not the right coach for you, I might know someone you’d like better. You can also connect with me on LinkedIn or at my personal author website, https://peterdudley.com. That’s where you can learn about my novels and other creative writing.

Thank you so much for sharing these important insights. We wish you continued success and good health!