3 Things I Learned in 3 Months of Career Coaching with BetterUp

Maggie A. Whatley
Upside Team Blog
Published in
3 min readJan 31, 2020

Three Things I learned in Three Months of Career Coaching with BetterUp

I’ve never worked with a coach (athletic, professional, etc) before — I was a reader growing up, and had access to thoughtful managers and generous mentors early in my career. When Upside Business Travel offered me space in the company’s BetterUp pilot program, I was excited to participate. The goal of the pilot program was to explore the benefits of supporting multiple employees across Upside through professional coaching.

We could have left it there, but Sarah offered two new tools as part of that conversation. The first was a new framework for me — if I think something will create conflict, I’m likely going to try to avoid it. To challenge that avoidance, I now think through alternative outcomes and best case scenarios, which allows me to be more open to what is possible if I do have that conversation or ask that question. And, Sarah shared with me her favorite Brené Brown quote “Clear is kind.” I left that session with a new way of approaching conversations and appreciating conflict.

A coach looks to the future, but can talk through immediate challenges

My sessions with Sarah covered a lot of ground — from immediate meetings and conversations to upcoming presentations and projects. We decided to start off 2020 with a new focus on big-picture, strategic thinking. I shared with Sarah a thought exercise that my manager Jason has offered before: If I gave you $100,000 right now, would you know how to use it? Previously, my answers were focused on short-term solutions — I’d access this tool or run this incentive. This time, we used this exercise to think 6 months or a year out. I asked myself ”Who would I hire?”, ”How would we expand?”, and ”What are team-level changes I’d introduce?” It was a powerful mental pivot from what’s in front of me to what’s ahead for my team.

In our most recent session, I asked Sarah if we could spend some time talking about the far future — ten years out from here, what that looks like for me. We talked about how I build my schedule now, including where I put my energy, find joy, and experience conflict. We talked about how each of those answers could help shape a career path — or at least help me pick areas for development and growth along the way.

Sarah was a wonderful resource for shaping my strategic thinking around my team and my career, and she gave me tools and frameworks I can apply today. I looked forward to our sessions each week, and I’m proud of my progress. I’m grateful Upside offers BetterUp coaching, and I hope you get the opportunity to experience a career coach, as well.

Have you ever worked with a career coach? Did they offer you tools you still use today?

Sarah’s been a wonderful resource for shaping my strategic thinking around my team and my career, and she’s given me tools and frameworks I can apply today. I look forward to our sessions each week, and I’m proud of my progress. I’m grateful Upside offers BetterUp coaching, and I hope you get the opportunity to experience a career coach, as well.

Have you ever worked with a career coach? Did they offer you tools you still use today?

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Maggie A. Whatley
Upside Team Blog

I am a systems thinker energized by new challenges and innovative solutions. Washington, DC -> Columbus, GA