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Bob Weiler of Brimstone Consulting: “

I prefer coaching to feedback; coaching is about advocating for optimal performance. It’s about the delivery — it’s not what you say, it’s how you say it. It’s important to not just outline what behavior needs improvement, for example, but it is also important to share what someone can do to improve. As a leader, I need […]

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I prefer coaching to feedback; coaching is about advocating for optimal performance. It’s about the delivery — it’s not what you say, it’s how you say it. It’s important to not just outline what behavior needs improvement, for example, but it is also important to share what someone can do to improve. As a leader, I need to coach on the how, and I need to make sure the person has what they need to be successful.


As a part of our series about “How To Give Honest Feedback without Being Hurtful”, 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.


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’ and how you got started?

Shortly after taking on the role of Executive Vice President of Hurricane Island Outward Bound, I went to Crotonville, GE’s management training center, and knocked on Noel Tichy’s door. Noel was the then-famous change management guru hired by Jack Welch to transform Crotonville into an engine for change. I invited Noel and his Crotonville teaching staff to Hurricane Island, a small island off the coast of Maine, to participate in a three-day action learning program. Noel initially said no, but I finally convinced him.

When Noel and his team of 24 arrived on the Island, I was off on a business development trip. When I returned, I found that the program had been a disaster, and Noel and his team had left. I immediately went to Crotonville, and I sat outside Noel’s door for close to seven hours. When he opened his door, the first thing he said was, “Where do we start?” My answer was, “With an apology.” For the next three years, I worked closely with Noel, Hiro Takeuchi, and the team at Crotonville. This experience was foundational.

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

Our people. Many of us have worked together for decades and in multiple contexts. We’ve hiked the wilderness together, traveled around the world together, and spent time everywhere from boardrooms to Bali.

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

Maybe not the most interesting, but something many leaders can relate to. Crammed for time, a CEO invited me to talk strategy with him on a flight to London. As I was boarding the plane, I got a call from another CEO asking to meet in Chicago the next day. I did some quick math and said yes. As soon as I landed at Heathrow, I said good-bye to the CEO I had traveled with and then raced across the airport and caught a direct flight to Chicago. No one was ever the wiser.

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 CEOs and business leaders to help their employees to thrive and avoid burnout?

Take time off. Taking time off not only gives you, as a leader, time to recharge, but it also demonstrates to the organization that taking time off is important. At the same time, encourage people to take time off. If someone should take time off and who is not, make them take the time. Even an afternoon or just a couple of hours can be helpful.

How do you define “Leadership”? Can you explain what you mean or give an example?

There are three components to leadership: getting results, aligning your team, and developing other leaders. A great leader needs to figure out how to make things happen (get results). They need to align their leadership team and their organization to help achieve the results or goals, and they need to develop the leaders in their organization.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

I take the time to learn and understand the meeting’s goal, the “owner” of the meeting, what everyone needs to be successful, and the roles of everyone in the meeting. Once I do this and any other preparation required, I typically go for a run or good physical workout.

Ok, let’s jump to the core of our interview. Can you briefly tell our readers about your experience with managing a team and giving feedback?

The most important thing for managing a team is being clear on goals and roles and understanding what needed to be successful as a team. We call this Goals, Roles, Process, and Interpersonal (GRPI).

I prefer coaching to feedback; coaching is about advocating for optimal performance. It’s about the delivery — it’s not what you say, it’s how you say it. It’s important to not just outline what behavior needs improvement, for example, but it is also important to share what someone can do to improve. As a leader, I need to coach on the how, and I need to make sure the person has what they need to be successful.

This might seem intuitive but it will be constructive to spell it out. Can you share with us a few reasons why giving honest and direct feedback is essential to being an effective leader?

Coaching helps one improve at a sport or a game. The same is true off the field. Coaching is a valuable tool to use to help develop your team and to help your people improve.

As we see in most professional sports, athletes are coached as they come off the field in real-time. The faster people can raise critical issues, highlight positive behaviors and actions, and give each other feedback, the faster the business will grow and deliver results.

One of the trickiest parts of managing a team is giving honest feedback, in a way that doesn’t come across as too harsh. Can you please share with us five suggestions about how to best give constructive criticism to a remote employee? Kindly share a story or example for each.

Be timely. I was recently working with one of our consultants on a client project, and I felt the consultant could have approached a situation differently than they did. I let schedules get in the way and didn’t share my feedback until a week later. Because so much time had passed, it was hard for that person to recall that situation, so I had to spend a chunk of time recreating the situation with them. What took me more than 30 minutes to get through then would have taken me five minutes if I had connected with them at our first break.

Be clear. I was recently talking with a client about how to engage a particular member of their leadership team. I shared the importance of communicating what success looks like; communicating expectations. I gave the example: “success is renewing the contract with X company.” Being clear on expectations makes it more likely that the expectation will be met.

Never used the words “we, others, etc.” I was recently giving feedback to a member of my organization, and I accidentally said, “a few of us.” As soon as I said that, I could tell the person I was talking to was trying to figure out who else had the same feedback instead of listening to me. My mistake was that I brought other people into a feedback conversation.

Focus on the why. Feedback needs to be helpful and focused on progress — it should not be based in anger. When you’re coaching or giving feedback to someone, you have to be clear on how you’re helping the person develop as a leader and helping them become more effective in their job. The challenge is to take something they did poorly, something that you may be disappointed with or upset about, and find a way to have that conversation in a helpful way for them and not negatively emotional for you. I believe that most everybody wakes up every day trying to do the right thing and therefore they were doing their best, which didn’t turn out to be the case, so you need to help them get better.

Take your time. Take your time when delivering feedback. If you don’t have time to devote to the discussion and developing an action plan, find another time.

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

I would only use email if there were no other options. I prefer to use an environment where there can be real-time discussion and back and forth. Zoom, Teams, WebEx, or even a simple phone call are preferred to email.

In your experience, is there a best time to give feedback or critique? Should it be immediately after an incident? Should it be at a different time? Should it be at set intervals? Can you explain what you mean?

The best time is immediately after the incident, as this ensures that the incident is top of mind. In many cases, feedback only needs to be delivered once. However, if required, regular intervals of communication can be established to help and support change. What is most important is making sure that the person receiving feedback creates a list of actions they will take on how they are going to fix the issue. And that you, as the leader, are aligned with these actions.

How would you define what it is to “be a great boss”? Can you share a story?

A great boss sets smart goals (specific, measurable, obtainable), helps to define clear roles, establishes a process around meetings, and then they let you do your job. They have an open-door policy, they inspire, provide accountability, and help you develop as a leader.

When I was a young broker with EF Hutton, I wanted to pursue commodities with a big client. I discussed the strategy with my boss, and he laid out all of the reasons he thought I shouldn’t pursue the strategy. At the end of the conversation, he said that while he wouldn’t do it, the decision was up to me at the end of the day. I pursued commodities and, just as my boss had said, it was a big mistake. The learnings from this experience were immense.

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?

One of my favorite quotes is “Come my friends, it is not too late to seek a newer world,” by Alfred Lord Tenneson. I grew up in a challenging family situation but had a very strong mother who taught us to overcome adversity and embrace change.

How can our readers further follow your work online?

People should follow Brimstone on Twitter, LinkedIn, Facebook, and via the articles written by Kate Lee and others in our organization.

Thank you for these great insights! We really appreciate the time you spent with this.

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