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Virtual Think IT Event: One on One with Kristofer O’Brien

Last Friday, we hosted a Virtual Think IT Event with Kristofer O’Brien, CEO, and Founder of Bluewater Leadership Academy, to discuss his experience with career coaching and his advice for leaders. A huge thank you to Kristofer and to everyone who joined the event and participated in the discussion!

Below you will find an overview of the most popular questions from our members and a summary of what was discussed.

What drew you to Leadership Coaching?

Kristofer has been in Leadership and Development for over 20 years in a variety of industries, and his passion for helping people has been the fuel that keeps him going every day. His goal is to help leaders view and approach situations and problems from a different perspective.

The tragic event of 9/11 was a pivotal moment in Kristofer’s career journey. At that point in his life, he was signing up to attend law school, a career path that he originally thought was the right one. When 9/11 happened, he took a step back and asked himself if that was really what he wanted to do with his life. He realized that law was not going to fulfill his passion for helping people the way he thought it would. His path started off in HR, which allowed him to work with leaders and understand their challenges and struggles in their roles. From there, he worked for multiple different companies, in multiple industries, gaining experience working with all sorts of people with very different duties and challenges. This ultimately lead to the birth of his own Leadership and Development company, Bluewater Leadership Academy.

What is Bluewater Leadership Academy?

Kristofer took a leap from the Medical Device industry, to fill a gap he saw in Leadership and Development. There are many companies that don’t have access to the proper leadership and development tools, which ends up acting as a barrier to their success. Bluewater Leadership Academy was created to break down those barriers and give companies an opportunity to utilize the tools needed for successful leadership practices.

What is your biggest challenge right now?

One of his biggest challenges is the fact that there is so much need for development in the world of work today. Due to the pandemic, businesses have been working hard to stay afloat, and have missed the opportunity to develop and adapt themselves to what leadership should look like in this new normal. The skills needed to be a leader in today’s world are drastically different than what they used to be, and the challenge is identifying those differences and finding a solution.

How has Leadership & Development changed since the Pandemic?

Since the pandemic, leading a team has become much more difficult than it used to be. In person, leaders were able to check in with their teams, build personal relationships, and be able to learn how people do their jobs. In a virtual world, there is a barrier between the leaders and their teams, making it much harder to communicate and manage.

Another struggle that current leaders are having is removing ego and bias from situations where they do not belong. There are many times when leaders are stuck on a problem because they are not willing to abandon the strategy that is not working because of ego and bias. If a leader removes their ego from the situation, it takes the pressure off of these teams and will not only help the leader grow, but it will help the team be successful.

What are the signs of a good leader?

Good leaders set a clear vision. They know what their intentions are for the next 6 months, 12 months, even 5 years. If they do not set those intentions, then it is hard to set goals, and without goals, there will be a failure somewhere along the way.

Good leaders show compassion, vulnerability, and empathy. If you cannot show compassion and empathy, your team will not follow you. Many leaders are reluctant to be vulnerable because they must admit and accept their mistakes. “There is no growth in your comfort zone and there is no comfort in your growth zone.” Leaders will learn the most from the negative experiences because they will be able to reflect on them, address their mistakes, and identify the solutions.

Why is it so important for leaders to be vulnerable?

It is important for leaders to be vulnerable when addressing failure so that they can demonstrate to others that is it okay to fail and create an environment where failure is celebrated as a success. When a team has a culture and an environment like this, it pushes them to step up and address their failure without fear of negative repercussions. This allows leaders and their teams to grow and gain confidence when it comes to taking on big challenges.

If you are interested in getting involved with Bluewater Leadership Academy, contact them at or visit their website for more information!