Bob Weiler of Brimstone Consulting: “Encourage your team to take time off to recharge”

Encourage your team to take time off to recharge. As a leader, it is important to model this behavior — to let people know that not only is taking time off OK, but also that it is a priority. As a part of our series about the five things you need to successfully manage a remote team, […]

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Encourage your team to take time off to recharge. As a leader, it is important to model this behavior — to let people know that not only is taking time off OK, but also that it is a priority.


As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Bob Weiler.

Bob Weiler, Managing Founder of Brimstone Consulting, partners with CEOs and their leadership teams on accelerating business results and large-scale change initiatives. Much of his work focuses on advising CEOs and C-suite executives on methods to achieve short- and long-term results, while simultaneously achieving alignment, developing leaders, and energizing the organization.

Before launching Brimstone, Bob served as: President and COO of Grand Circle Travel, an industry leader in direct marketing of travel to mature Americans; Associate Director of the Global Leadership Program, a renowned executive development program at the Ross School of Business at the University of Michigan; and EVP of Hurricane Island Outward Bound School, the largest Outward Bound School in North America. Working with leadership expert Noel Tichy at General Electric’s Crotonville management training center, Bob designed key modules for developing high-performing teams and individuals.

Bob has competed in the Hawaii Ironman World Championships, the Spartan Peak to Peak 50-mile race, and the Leadville 100 MTB. He has also participated in expeditions in Nepal and the Swiss Alps.


Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

When I was in high school, I took an Outward Bound program at Hurricane Island. Then, as a college freshman, I applied to be an Outward Bound instructor. I soon found myself teaching winter courses in the White Mountains of New Hampshire and summer courses on Hurricane Island in Maine.

In the early days of the Hurricane Island Sea Program, a qualified US Coast Guard licensed captain was required to be aboard the boats. As I was still in the process of getting my license, I needed someone who had a license to sail with me. The person who sailed with me was Peter Willauer, the Founder and President of Hurricane Island Outward Bound. I spent many, many days at sea with Peter. This unique opportunity enabled me to lead at other Outward Bound sites, within other programs, and eventually return to Hurricane Island as the Executive Vice President.

Working with Peter, a visionary, and watching him navigate challenging and tricky operational and political situations with the board was foundational. I use much of what I learned today.

Can you share the most interesting story that happened to you since you started your career?

Change management guru Noel Tichy was hired by Jack Welch to transform Crotonville, General Electric’s (GE) management training center, into an engine for change. Noel brought together GE’s Hong Kong Executive team for a workshop. In pain due to a bad back, Noel decided, at the very last minute, I should run the workshop instead of him. I had just graduated with my master’s degree. Young and fearless, I jumped in and did it.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

We were in the final stages of negotiating a 1 million dollars contract when the power went out and stayed out. In the dark and unable to use the phone or fax, we could not continue contract negotiations. The prospect thought we flaked and awarded the contract to another company.

Just months before, I had gotten quotes to install a generator because I knew power outages were frequent in the winter in what was at the time, a fairly rural part of Maine. Rather than pay 10,000 dollars for the generator, I decided to take the gamble — and I lost.

That experience taught me that small investments can have huge returns and to always have a back-up plan.

What advice would you give to other business leaders to help their employees to thrive and avoid burnout?

Encourage your team to take time off to recharge. As a leader, it is important to model this behavior — to let people know that not only is taking time off ok, but also that it is a priority.

Change can also help people thrive and prevent burnout. Mix up teams, pair people who enjoy working together to tackle a new project, switch things up.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

In 2001, we closed our offices in Boston and Chicago and moved to a remote model. So, for the past 20 years, I have led and managed a remote organization and remote teams.

Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each?

Not being able to read body language. Seeing a face on the screen is only a small part and doesn’t tell the whole story. People can be doing many things and still look like they are paying attention to a video or audio call.

Rethinking what works. I like to use flip charts as I believe a picture can speak 1,000 words. However, a flip chart doesn’t work well when you aren’t in the same room. It means rethinking and adapting.

Spontaneity. Rather than walking down the hall and asking people to jump into a meeting, coordination needs to happen to bring people together.

Loss of the “watercooler.” When people aren’t together in an office, you lose the hallway chats and the ability to pop into someone’s office for a quick check-in.

Onboarding and developing people. This can be challenging because you need to be much more planful.

Based on your experience, what can one do to address or redress each of those challenges?

Continually raise the issues with your team and ask questions: “What can we do better?” What do you need from me as a leader?” How can we be more effective as a team?” Communication is critical.

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote employee?

I prefer to use the word coaching and make the conversation a two-way street. Focus the conversation on the future. A great leader will identify (and take ownership) if there was a lack of clarity on goals and expectations and then work with the person to develop an action plan for success — including clear goals and expectations.

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

My recommendation is to avoid using email. Zoom, Team, WebEx, and even a simple phone call is preferred to email.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic. Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

The biggest mistake leaders can make right now is not meeting with their team regularly and not communicating enough.

What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?

Find some time every month to have some fun and build in virtual team-building exercises. And steer clear of repetition. Add to your meetings, personal shares, tech shares, or anything that creates a little bit different of a conversation and laughter.

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. 🙂

The number of children who are homeless and who do not have enough to eat is staggering. If I could start any movement, it would be to ensure that every child has food and shelter.

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

Robert Frost’s poem, “The Road Not Taken,” resonates with me. Unlike my peers, I decided to become an Outward Bound instructor prior to going to graduate school. I took the road less traveled by, and that has made all the difference.

Thank you for these great insights!

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