Are you applying an analog leadership style to your digital transformation projects? Deborah Reuben and Jen Swanson discuss how to evolve your leadership style to achieve success in a digital world.

Too often digital transformation initiatives fail to deliver their intended value. Digital transformation is an industry imperative; however, some analog world leadership styles don’t directly translate to digital success. How might leaders evolve to succeed with digital transformation?

To learn more, I sat down with Jen Swanson, digital transformation expert and CEO of Tuckpoint Advisory Group. We explored the project to product mindset shift, the critical role of customer focus and the nuances of empowering teams and leading digital transformations within regulated industries. The following is our interview condensed and rephrased for conciseness.

DEBORAH REUBEN: What are the highlights of your journey leading to what you do today?

JEN SWANSON: My journey to Tuckpoint Advisory Group started in higher education, where I initially worked in counseling. This background might seem far removed from technology and digital transformation, but that’s where my technology fascination began. As my career progressed, I moved through roles in healthcare and eventually into consulting, always with a technology focus.

My technology interest was sparked early on, when I worked on a project involving email communication between a higher education institution and its alumni. This experience underscored the transformative potential of digital tools in communication and operations across various sectors.

Throughout my career, I’ve navigated through heavily regulated industries — the trifecta — from education, to healthcare and, now, financial services. Regulatory constraints have never deterred me. Within these boundaries, I’ve focused on leveraging digital technologies to enhance experiences and operations, leading to my current role in guiding digital transformations.

REUBEN: How are you helping guide companies through digital transformation?

SWANSON: We specialize in guiding companies through digital transformation with a focus on reshaping their operating models. Essentially, we restructure how teams are formed, financed and managed to ensure efficiency and
governance within digital transformation efforts.

The first wave of digital transformation focused primarily on integrating new technology across all business aspects, from operations to marketing. However, many companies simply layered these new technologies over outdated
structures, expecting transformative results without altering the underlying organizational framework. This approach often fell short of delivering the desired outcomes.

Our approach is to drive the second wave of digital transformation, which involves a fundamental shift in the organization. We help leaders develop strategies that prioritize clear, outcome-driven objectives. This second wave demands a laser focus on a few key initiatives, with the willingness to defer other opportunities.

To achieve this, we believe in an organizational transformation combining shifts in both mindset and methodology. This includes coaching in change management, leadership development and transitioning from project-based to product-based thinking. Our role is to provide the tools and guidance necessary for companies to not only adapt to the changing digital landscape but to thrive in it.

REUBEN: What is the role of coaching in digital transformation projects?

SWANSON: Coaching is crucial for leaders facing digital transformation for the first time. The reality is most executives are accustomed to a leadership model that is becoming obsolete in the modern, digital world. They’ve climbed the ladder through control and precise planning, but today’s tech-driven environment requires a more adaptive approach.

We advocate for what we call ‘contextual leadership.’ Instead of micromanaging, it’s about setting a clear vision, defining outcomes and then empowering teams to execute. It’s leading from the front, like the leading goose in a V-formation, and letting the team draft off your momentum.

A coach can be a guide in this new territory, providing the experience and support leaders need to shift their leadership style. It’s not just about giving them a playbook; it’s about walking beside them, showing them the ropes and helping them navigate the transition. That’s where we come in — we’re the seasoned partners who have been through the process and can mentor leaders through the same journey.

REUBEN: How can leaders struggle with a do-it-yourself approach to complex digital transformations?

SWANSON: There’s a real danger in the DIY mindset when it comes to digital transformation. Many leaders watch success stories and think, “I can do that,” much like viewers watch cooking shows and attempt elaborate recipes. But without the proper skills and experience, they often end up with their version of a ‘cake fail’ in the transformation process.

It’s critical for leaders to understand that digital transformation is more than just following a recipe or software installation. It requires a blend of skills, a shift in mindset, and experience to apply the right ingredients for success.

Leaders might be tempted to think they’ll ace their initiative on the first try, akin to whipping up a perfect dish on the first attempt. But like Martha Stewart, it takes practice, and early attempts might not turn out as expected. This is where psychological safety comes into play — creating an environment where it’s okay to have those initial messy attempts and learn from them.

Having a coach or advisor is like having an experienced chef in the kitchen with you, guiding you through the process. They provide the reassurance that discomfort and initial setbacks are part of the learning process. With time
and coaching, leaders and their teams will refine their methods and outcomes, moving from messy first attempts to well-executed strategies. This support is invaluable for leaders to not just survive but thrive in their digital transformation journey.

REUBEN: Could you explain the product mindset for us?

SWANSON: The product mindset is a fundamental shift from the project-based focus on time, scope and budget, which often lacks customer involvement. In a product mindset, we center on delivering value to the customer with a product that is usable, valuable and viable.

We pivot from an internal viewpoint to asking if we’re building the right thing in the right way for the customer. This means continuously validating the customer’s needs and expectations, even as they evolve during the product development cycle.

The product mindset emphasizes real-time feedback and adaptation. It’s not just about delivering a project but ensuring that it’s sustainable for the company and solves a real problem for the customer. It’s a shift outward to focus on customer needs while maintaining the integrity and sustainability of the product for the business.

REUBEN: How can leaders shift their strategy frame to a more outcome-based approach?

SWANSON: To embrace outcome- based thinking, leaders should reevaluate their current strategies and objectives. Rather than focusing on outputs, which are often binary and internally focused, leaders should aim for outcomes that directly impact customers or users. This means setting goals that are not about just completing tasks but are about creating value — whether that’s improving employee experiences, increasing customer satisfaction or attracting new business.

Ask yourself, are your goals about doing something or achieving a particular effect? For instance, instead of aiming to ‘launch product X’ or ‘complete project Y,’ reframe your goals to ‘increase user engagement’ or ‘improve 40 monitor operational efficiency.’ If your goal is to ‘increase revenue,’ dig deeper and define how — through new customers, enhanced services or perhaps re-engaging former clients.

By shifting to a mindset that’s focused on improving, increasing or decreasing something significant for your customers or teams, you’re taking a significant step toward a more outcome-oriented, customer-focused approach. This
is the start of moving towards a product-led strategy, and it’s a crucial step for leaders looking to create a future-ready organization.

REUBEN: What can leaders do today to shape a better tomorrow?

SWANSON: Focus on your people. Consider how your teams feel about their work and their collaboration with others. While there’s much debate on finding meaning or passion in work, the simple fact remains: we spend considerable time at our jobs. By fostering autonomous and empowered teams, recognizing their talents and leveraging their intelligence and experiences, you set the stage for success. I’ve witnessed incredible results from such environments, and that’s why I do this work. Make it your daily mission to enhance your team’s empowerment, no matter the scale, and you’ll see significant positive changes. •

Jen Swanson is CEO and founder of Tuckpoint Advisory Group and a sought-after Transformation Advisor and Strategic Consultant. She brings more than 25 years in customer advocacy, marketing technology and service channel
operations in higher education and healthcare organizations, including the University of Minnesota, Capella University, Children’s Minnesota and UnitedHealth Group. Learn more at

Deborah Reuben, CLFP is CEO and founder of TomorrowZone, an innovative consulting firm bringing forward-thinking insights and original ideas to help companies adopt digital, gain efficiencies and design roadmaps for the future. She holds many industry leadership positions and authored The Certified Lease & Finance Professionals’ Handbook 6th- 9th editions. Learn more at