Leader Q&A

As chief strategy officer at Live Oak Bank, STEPHANIE MANN is responsible for strategic planning and investments and partnerships. She oversees the bank’s embedded banking business, Live Oak Private Wealth, and Live Oak Ventures, with eleven portfolio companies.

She is used to looking out at the horizon, both in her role in Wilmington and through her twenty-plus years of experience advising companies on capital structure and growth strategies.

“In my role, I can leverage my experience advising companies on transformational transactions and still have the benefit of opportunities to learn and grow,” Mann says.

She previously served as a managing director of investment banking at Citi, where she advised Fortune 500 technology companies and worked on more than $125 billion in M&A transactions.

Mann, a speaker about strategic thinking at WILMA’s Women to Watch Leadership Institute, shares how to get yourself out of the day-to-day grind and look at the big picture.

How do you think organizations can encourage a culture of strategic thinking? How do you as a leader promote it?

“Strategic thinking is a discipline of self-improvement, and we are all capable of participating in it. Organizations need to set aside time to think through their market, their customers, and their own strengths and weaknesses.

My job is to consolidate that thinking into a coherent framework, ensure that we continue to focus on realizing the long-term strategy, and communicate that to the organization. Everything an organization does is a choice to not do something else. By illuminating those choices, we can all be more intentional about our near-term and long-term objectives.”

What are some pitfalls leaders can make in this area?

“First, critical to a successful strategy is a clear vision, mission, and set of values.

We start every strategy conversation by grounding ourselves in our (Live Oak’s) goal to be America’s Small Business Bank, to treat every customer like the only customer, and to take care of our employees. Anything that doesn’t align with this is a distraction.

Second, strategic planning has to be collaborative. It is the ‘How’ of a company’s vision and mission and fundamentally requires the full support and shared commitment of the leadership team.

Lastly, don’t worry about precision. The future is uncertain, and the strategic plan serves to align the company directionally.

President Eisenhower once said, ‘In preparing for battle, I have always found plans are useless, but planning is indispensable.’”

What about personally? What have you learned or practice now to apply strategic planning in your own outlook?

“Both for Live Oak and for myself, feedback is an important part of strategic planning.

What are we/I doing well, what could be done better, what can I learn from what others are doing?

On a personal level, I seek feedback from my team, my colleagues, and my family, and I set annual goals for myself. I don’t want you to think I have it all together though. I don’t.

I have an amazing village that works with me, and some things just don’t get done. Give yourself some grace.”

Personal picks

Mann’s favorite podcast is NPR’s How I Built This. “Nothing fuels strategic thinking like hearing about the winding path to success that other leaders have taken. My kids love it, too!”

Asked who else we should know locally, Mann points to Katrina Knight, executive director of the Good Shepherd Center. “She is tackling one of the hardest problems we are facing today, with determination, creative thinking, and ambition,” Mann says. “Check out the work she is doing with Home for Good.”

Stephanie Mann’s strategy checklist

Be informed: Talk to your customers, your colleagues who work with your customers, and your competitors regularly.

Be reflective: Look back on what happened, what you did well, and where you want to be better.

Be aspirational: Set bold goals and use them to drive near-term plans.

Be data-driven: Measure the opportunity and your progress. Accountability matters.

Be disciplined: Know what you aren’t going to do. A good strategy acknowledges trade-offs. Place your bets and be ready to adapt.

To view more of photographer Terah Hoobler’s work, go to terahhoobler.com.

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