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The paradox of proactive leadership

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Don’t be blinded by the short game. Learn how C-suite leaders are learning from past technology implementations and reinventing their organizations for the future.


Where were you the day the World Wide Web was invented?

While you might not remember exactly, there are a few things we know for sure: you weren’t scouring Facebook Marketplace, sending Slack messages to your colleagues, or pulling up your new favorite series on Netflix.

Much like the growing dot-com bubble of the late '90s, we’re experiencing a unique period of technological growth that will influence human behavior, jobs, and society as a whole, testing the ability of organizations to adapt. Companies like Microsoft and Amazon have embraced both rapid innovation and continuous change, allowing them to still be relevant and thriving.

Today’s executives are facing a similar dilemma: How do you keep up with the constant introduction of technological advancements while remaining focused and aligned to long-term strategy?

“We’re at that ‘internet just started’ moment, but already expecting quarterly returns,” says Slalom Managing Director Amalia Goodwin. “What is your organization going to be selling in three to five years? Because ‘long term’ is now five years instead of 10. So we have to think about what it really means to ‘move faster.’”

In our Q3 executive forums, we heard from 100+ senior leaders about how they’re navigating this paradox and building a future-proof enterprise. In these discussions, three key themes emerged:


1. Making the most of digital transformation investments

Most leaders have already completed a digital transformation in some form. But the challenge ahead is how to make the most of these multiyear technology investments.

How are you leveraging data and technology to enhance your customer experience across channels? Are you introducing new capabilities to differentiate your business? What are new revenue streams that can be introduced?

“Once your digital infrastructure is in place, meaningful business transformation can begin,” says Slalom Managing Director Michelle Page-Rivera, PhD. “Investing in digital technology simply lays a foundation and puts companies at the starting line. What these organizations actually do with that investment is what creates value and market differentiation.”

Taking digital transformations to the next level—and maximizing those investments—requires foresight, digital fluency, and rapid decision-making. It’s about using data to proactively predict buying behaviors and pave tailored pathways for customers through hyperfocus and hyper-personalization.

The next step? AI agents that can analyze data, answer queries, and perform repetitive tasks.

“We haven’t quite ‘productionized’ the new world of AI, workflow automation, and agents yet,” says Goodwin. “It’s still on the cusp, but it’s going to be the next stage of your digital transformation.”

2. Finding and communicating value in an AI-driven world

In spite of the hype, many organizations are struggling to translate AI into financial returns. Approximately 85% of leaders surveyed agree that there are still areas of their organization that aren’t yet prepared to integrate with AI. To avoid getting caught in the proof-of-concept loop, or with too much flowing into an innovation pipeline, organizations need to start moving beyond experimentation to measuring tangible value.

And—most importantly—how is that value being communicated to key stakeholders?

“Boards are starting to push their senior leaders on their AI roadmaps and differentiation,” says Slalom Chief Customer Officer Amy Loftus. “While last year it was more about what leaders are exploring and piloting, this year it’s about specifics. What are the levels of investment? Where is the return going to come from? And when?”

It’s not just about the ROI with AI, but continuously uncovering new areas to invest in and translating that value to decision makers across the organization so the right ideas can move to production quickly. This requires much tighter alignment between AI innovation, business strategy, and key stakeholders.


It’s a joint task force among business, technology, and product teams. This enables the organization to better move as one.

—CPO session participant

Grandfather and granddaughter Chicago Cubs fans.

3. Arming and enabling your enterprise for the future

In 1995—before kick-starting the popularization of online retail—Amazon was simply an online bookseller. Today, the company spans ecommerce, cloud computing, and digital streaming—and is considered one of the world’s most valuable brands.

The organizations of tomorrow will look vastly different from organizations today. And while the specifics are impossible to predict, it’s important for leaders to consider how their businesses may change to accommodate shifting consumer and internal talent needs—and adapt accordingly.

“To build your enterprise for the future, you have to lay a foundation of ongoing learning and skilling,” says Goodwin. Leaders need to be able to balance adaptive strategies with effective governance and long-term planning, she says. “Your teams are going to have to work with agents and other digital entities. You’re going to have to have cross-functional governance and a speed of decision-making you’ve never had before.”

With these rapid changes, there’s a need to go beyond AI technology and revisit your organization’s design: what work needs to be done, how that work gets done, and who does the work—digital or human.

“Shifting your strategy to incorporate AI also means shifting your ways of working,” says Page-Rivera. “We’re going see a wave of AI-first organizations built on an entirely new digital and human infrastructure, leaving behind companies mired by legacy technology and overengineered operating models.”

Today’s leaders have the opportunity to retool their workforce and take full advantage of emerging technologies, including AI and automation.


AI is generating buzz. However, pushing back on vendors can ensure the focus is right and the value is there.

—CDO session participant



Key takeaways

How can functional leaders balance adaptive strategies with effective governance and long-term planning?




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