Rethinking Digital Transformation: Insights from the Frontline

I recently dipped a toe back into digital transformation, but not because I’ve changed my mind about the concept. Instead, I found somebody else who shares a similar perspective to mine: Jen Swanson , a seasoned consultant who believes, like me, that digital transformation isn’t as snazzy as the buzzword title suggests.

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With extensive experience in customer advocacy, marketing technology, and service channel operations across multiple industries, Swanson has been in the digital transformation game before any of us started calling it that.

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Ready for a deep dive into what it means to stay on top of your business? Here’s what we talked about on a bonus episode of The Business of Tech.

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Transformational v Transactional Leadership

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We began our conversation by revisiting the idea of digital transformation as it pertains to leadership. What’s the difference between transformational leadership and transactional leadership?

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Swanson pointed out that in the last 10-20 years, the constant acceleration of technology means that for the people leading companies today, very little about what got them to this point is equipping them to deal with what’s coming at them tomorrow.

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Across the board, Swanson believes that leaders are struggling to understand how to keep up. So a transformational leadership approach means assessing what needs to fall away within yourself to know what to focus on next.

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“The idea of transformational leadership really is about checking your skills, checking your capabilities, checking your tool belt, and figuring out, okay, what have I got here that's going to equip me for this absolutely breakneck speed change that we are seeing in technology and the workforce?” she said.

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Less Digital Transformation, More Keeping Up With Technology

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I’ve come to believe that digital transformation is often just code for “keeping up with technology.” And when someone announces their intent to digitally transform, they’re really just admitting that they haven’t been paying attention and have fallen behind.

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I ran this by Swanson, and she agreed that I’m not wrong. In her own words:

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“When people ask me what I do, I always start with digital transformation. Some people’s eyes glaze over because they're not working in the space at all. Other people will lean in and say, oh, what part? Do you implement software? And that's when I say, actually, I don't do digital transformation. I do operating model transformation.”

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In fact, she sees technology as a very small part of her job.

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“I actually don't care what the technology is. Technology is totally irrelevant. What I care about is how organizations are evolving around technology. How are they leading their teams differently? How are they transforming their organizations structurally, emotionally, and spiritually? The technology piece doesn't matter because it's going to change tomorrow anyway,” she said.

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In Swanson’s experience, the companies that struggle with digital transformation most are the ones who think they can slap technology on an old structure and stop worrying about the rest of it. They’re the ones who stop paying attention to team structures, leadership competencies, or how they articulate strategy.

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“How you think about results and success is totally different than saying hey, let’s go make more money this year than we did last year. That’s not meaningful. How are we going to do it? Who are we serving? What do we want to, what do we want to stand for? And what do we mean when we say we want to grow? Those are very different ways of leading today, and technology becomes the enabler of it,” she said.

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The Service Retirement Dilemma

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How can companies apply Swanson’s advice here? In an oversimplified sense, it seemed to me that it could just be a matter of regularly reviewing their service offerings, retiring some, and launching new ones.

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I asked Swanson if this was accurate, and the answer was an enthusiastic yes. Getting companies to retire services is a never-ending battle in her field. Too many people layer and add instead of simply retiring something, which, in her view, becomes baggage.

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This felt to me like the innovator's dilemma – that leaders feel the need to hold onto something because it generates money, but they don’t invest enough in new sources of revenue. But isn’t it easier to retire things the more often you do it? If you’re constantly slicing at the back end of your offerings, it seems to me that it would be easier to walk away from the old stuff.

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Swanson agreed with my instincts here, explaining that it’s a muscle the whole organization needs to have.

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“The whole organization, top to bottom, left to right has to be good at it. And especially the C-suite,” she said. “Because it's very easy at the top of the house to get really comfortable with that recurring revenue with old systems that are getting older and older and older and harder and harder and harder to move away from. But it's about diversification of revenue streams.”

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This goes back to one of the core tenants of product management and agile software development: small bets placed often.

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So when her customers are scared they’ll cannibalize themselves by retiring something, her response is better us than somebody else. It’s better to learn that lesson yourself than have somebody else come in, disrupt the old ways, and take the money outside your company.

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Unexpected Successes

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You might be surprised to know that in Swanson’s experience, the companies that are best at this transformative way of thinking are flyover companies in legacy industries – the ones that Silicon Valley forgot about a long time ago.

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Swanson believes they’re successful with digital transformation because they have the padding to experiment, place small bets, and carve out space to try something new. More modern companies, on the other hand, are almost too efficient. They’ve trimmed too much fat to have room for opportunity. She loves working with these people because they’re always asking, what if? How might we?

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Swanson’s MSP Relationships

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Another group of people Swanson loves working with is MSPs. While she tends to ruffle feathers with business partners, she knows that IT is capable of more than just ticket fulfillment, and isn’t afraid to tap them for their strategic and creative chops.

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When Swanson is helping clients push into a new space and doesn’t have the internal skillset to move as quickly as she wants to, she leverages her external MSP network and staff org teams. The relationship is symbiotic, too; she sometimes helps business partners connect with their IT leaders to help them on the strategic side of things.

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Interested in learning more or getting in touch with Swanson? You can reach her via the Tuckoint Advisory Group on LinkedIn, and her LinkedIn DMs are always open. You can also visit www.TuckPoint.com.

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That’s it for this week! As always, my inbox is also open for questions, stories, reactions, or whatever else is on your mind.