Strategic Advisor Profile: Annette Mason — Creating Purposeful Work

Curiosity can save us all…being curious is a game-changer.”  ~ Annette Mason 

Annette Mason is the founder of Trilogy Design Works, a leadership development firm that uses design thinking techniques and ROI (return on investment/ripple of impact/ripple of influence) metrics to “build creative leadership muscles” for leaders of purposeful organizations. 

One of the tools Annette uses is facilitating immersive travel experiences to help leaders foster curiosity around different cultures and learn to navigate the contemporary complexity and chaos of our times. The day after we talked, she was scheduled to lead a group to Morrocco. 

From Subject Matter Expert to Strategic Advisor

Annette spent about 20 years in fiance management and strategy for geospatial intelligence firms, whose clients were primarily federal government agencies. During that time she led teams responsible for pricing and rate development, and merger and acquisition strategy. Basically, she provided analytical support to senior, C-suite level executives.

She became intimately familiar with the pitfalls and politics of large corporations. She also saw the potential and opportunities for creating more people-centered leadership models. 

In 2019, Annette took a “purpose-seeking sabbatical” to determine the next phase of her career.  Four months into her sabbatical, she had an “AHA  moment” that she needed to pivot her leadership development practice to take people on immersive travel journeys, which could have a social impact on corporate executives as well as under-served students. While she “could see it,” she didn’t yet have a clear path to execute. Then the pandemic hit. While the pandemic devastated travel, it created new opportunities for advising corporate leaders on how they can do “purposeful work” and have positive social impacts.

We talked last week about her experiences moving from a corporate subject matter expert (finance, strategy, M&A) to a strategic advisor to purpose driven organizaitons. Our conversation has been edited for brevity and clarity.

How Does Being a Consultant Differ From Your Role as an Employee?

“The autonomy is incredible,” Annette noted. “The choices of what work I do and who I work with are all mine. I get to collaborate with clients to design the scope of our work, so that it works for the business” — and her schedule. 

She likes the fact that she’s no longer “pulling all nighters.” In her corporate career, Annette would travel with the CEO, and have the “opportunity” to fly first class. Of course that meant she worked on presentations en route; and when they arrived at their destination (typically Washington, DC), she worked through the night revising pitchbooks for meetings the next morning. It was exhausting and eventually led to burnout. 

Now she works with organizations to “design for better,” using innovation tools, like journey maps, to bring people into the design process and minimize the speed bumps that lead to interruptions, revisions, and all nighters.

As an independent, she can test for organizational culture fit. It’s especially helpful that most of her work comes from former colleagues or referrals from them.

What’s Most Rewarding About Your Current Role?

Annette’s face just lit up at this question: “Doing work that I love” that synthesizes her  operational experiences in finance, strategy, and M&A. 

“In any business, it’s all about the people. I have a lot of learning experience in my career…I understand how corporate politics can work. I understand how business structures can get into a rut. They’re organized for scale, but need to know when and how to adapt.”

“I love using my ability and experience to help others…quickly getting to the essence of people’s challenges, and asking questions that help them see a path forward.”

Annette noted that we’re still trying to understand what truly drives people. Organizations need to incorporate a “line of sight” for their employees, where they understand the direction of the organization and they understand their role in moving in that direction. “That kind of clarity creates amazing alignment” and helps to enhance employees’ curiosity.  

What Do You Miss Most About the SME/Operational Part of Your Career?

“Knowing where my rock stars are…I miss the relationships with my teams where I knew who my ‘go-to’ people were.” 

What Aspects of Your Operational Roles Prepared You for Your Role as a Strategic Advisor? 

“My curiousity about people, let me quickly build high-trust relationships — both within my teams and with the executive leadership. As a result, I was invited to participate in special projects that were often beyond the initial scope of my responsibilities.”

If You Could Change One Thing About What You’re Doing Now, What Would It Be? 

Annette noted that she really struggles with where to go to share her knowledge and information with others. As a solo entrepreneur, it’s hard to find the appropriate “watering hole” where information and experiences can be shared; where she can collaborate with like-minded folks; where others can leverage her experiences. It’s one of the reasons she’s writing a book, which is slated for publication later this year.

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