How to Lead in Uncertainty: Interview with Terry Doloughty

A family member, who gained valuable insights from Terry’s coaching, said “Hey, I think you two should connect.” I jumped at the chance to chat with a new human since I miss people! Terry, Founder of B.O.S.S. Consulting, and I talked about facilitation, coaching, and leading in these fearful times…

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What things are bringing you joy right now?

I just wrapped up a Leadership Resiliency training cohort, and seeing how the attendees have built bonds and support one another feels fantastic. They really dove into the difficult emotional side of leadership and came out energized. That’s a real joy for me.

How do you define leadership?

There are so many different aspects of leadership. If I had to really narrow it down, I would define leadership as this: the choice to be actively present and thoughtful of the needs of others.

A leader is someone who has the ability to be patient, a good listener -- someone who can help others bring out their best.

What inspired you to coach developing leaders?

I was inspired by what wasn’t there. I’ve encountered many leaders who have developed their skills despite what they’ve experienced throughout their careers. They didn’t have someone to teach them how to be effective leaders. One of my main missions is to work with those existing leaders to help them create the support systems they need to succeed both personally and professionally.

What have been your biggest insights from doing this work?

Leaders in the nonprofit and business world all need the same support. Helping leaders work through anxiety, self worth challenges, and fear can have amazing results for the whole organization and help to initiate healthy culture shifts. As the leader heals and grows, the organization grows.

What are the most common challenges your clients face during these difficult times?

The pandemic has everyone operating in uncertainty -- the worst place for making decisions (especially if you want to feel confident in the choices you’re making). Some of the most common challenges that I’ve seen my clients face during this uncertain time include increased procrastination, a lot of self judgement, and damage to their self worth.

What practical advice would you give someone who is taking on a new leadership role like starting their own business or moving up within their organization?

Find a mentor or a coach. We all have negative experiences that impact our decision making and reactions -- invest in yourself and work through those challenges. Learn all you can about being an approachable and collaborative leader.


Since we love to talk about fears and following them, can you describe a time when you followed a fear or pushed yourself outside your comfort zone, and what you learned?

Sure, I’m glad to share. Starting B.O.S.S. Consulting was terrifying -- fear was one thing that was available to me in abundance. Why is that? I come from a background of scarcity. I didn’t just lack money, I also had a hard time with self worth and accepting validation. Working on those fears is a constant part of life (for me and my clients). So stepping out of my comfort zone to take the risk of starting B.O.S.S. was difficult, but I’m so glad I did it.

There’s no quick fix or two hour webinar that will change everything. Dedication, and the understanding that investing in yourself helps not only you but everyone around you, is key.

Leadership and fear are all part of the ecosystem we inhabit. Educate yourself, build a good support team, and be a part of supporting others.

What are a few articles/books/sites that you recommend to learn more about leadership development?

  • Primal Leadership by Daniel Goleman, Richard Boyatzis, & Annie Mckee has fantastic research and real world examples on how our brains operate and why we react the way we do.

  • Option B by Sheryl Sandberg takes a deep dive into building resiliency. It has a lot of practical advice for dealing with challenges.