As we leap toward the end of an unprecedented year of uncertainty, many leaders are facing a reality check. They are finding themselves in the spotlight, navigating a turbulent global environment while confronting unexpected gaps ahead of them. Our sense is that this isn't something you can simply wait out. As the London Underground so famously reminds us: "Mind the gap."

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Mind the gap: bridging what matters in uncertain times

THE KNOWLEDGE GAP

"For organizations running especially complex businesses, I'd love to ask leadership: 'How many of your most senior people will retire in one, three, or even five years?'"

This provocation from Global Advisor Martin Jetter (now Chairman of the Board at Scion Organization) emerged as we explored how AI might capture institutionalized wisdom in super innovative ways as a new generation of workers enters the workforce. There is a sense of urgency for some in our collective around the topic, especially on the manufacturing side, and we're seeing a variety of experiments at play from basic conversation capture to building CEO avatars.

How might you best preserve institutional memory?
"Imagine as a CEO, you could prompt—'What would my founder say about X or Y decision?'—as a way of stress-testing strategy and alignment to purpose/values," wonders Venture Partner Marc Winter. "Following the answer blindly has obvious risks, but asking the question unearths interesting untapped opportunities for scalability, knowledge retention, and consistency."

THE CULTURE GAP

"We've been making a lot of withdrawals from the culture this year; it's now time to make some deposits."

So quipped an HR executive at a major technology company. We are 75% through a year of unprecedented uncertainty that has contributed to layoffs, return-to-office mandates, and increased scrutiny in performance. Few in the collective have felt untouched by change.  

How can you start to restore goodwill after a rough year?
"People want two things: to be seen and to be inspired," says Managing Partner Sabrina Clark. "Seen for their efforts and impact—which means pausing for recognition, even with your foot on the accelerator. And inspired by the future they're building—which takes creativity, vision, and, above all, real belief that it's possible."

THE REALITY GAP

"I see my clients (CEOs) telling the markets stuff like 'We're all in on AI', when I know for a fact no one deep down inside their organization knows what that means."

A head of product at a large social media company observed this over an informal gathering of technology leaders. This, in the season of designing next year's annual budget, where leaders fight for a smaller pool of dollars and AI investments continue without proven ROI. We're seeing internal frustration growing as the promise-reality gap widens.

How do you manage expectations when they are through the roof?
"With any major technology disruption, people tend to overestimate the short-term changes and underestimate the long-term shifts on the horizon," says Managing Partner Nicolas Maitret. "Leaders should be both more pragmatic about what can be achieved right now and more imaginative about what can be unlocked five years out."

THE SOUL GAP

"We issued our RTO and delivered our ultimatums, the expected pushback came, and we're still pushing through. And it has all felt a bit soulless throughout."

A frustrated CHRO of a major technology company shared this shortly after their return-to-office announcement. The theme continues to surface—in headlines, in our client work, and therefore this newsletter. Just last week The Wall Street Journal reported on a nationwide stall, despite highly publicized mandates. The data doesn't tell a clear story for either side, and many (particularly engineers) are making their case as they see fit. For most organizations, though, the decision has already been made. The focus is on the big welcome back.

Now that you made your RTO announcement, what comes next?
"A useful reframe: think of this as an invitation," says Partner Laura Gordon. "You've made your announcement, set the date, and now you have to design the experience. What are you inviting your people back to?"

THE JUDGEMENT GAP

"Our CTO is making the big decisions, because we're in uncharted territory."

The CHRO of a large industrial manufacturer shared this observation. Lack of experience with new technologies is creating unprecedented judgment gaps in the C-suite and beyond. It's not only about AI. Traditional decision-making frameworks are being surpassed by the rapid pace of change.  

What is the modern way to make decisions?
"Transformational decisions require commitment to the journey, not just the outcome," says Partner Andy Chern. "It's about being willing to discover what your organization can become—by building structures, processes, and rewards that incentivize risk-taking, learning, and iteration."

A peek into SYP

Why nimbleness matters more in an AI era. SYPartners 's partner Kendra Cooke reflects on two decades of Agile, highlighting its impact on digital transformation—and its limits in the era of AI in this article. She argues that today's essential mindset isn't rigid methodology, but "nimbleness": the ability to adapt quickly, align across the enterprise, and scale responsibly to build trust and design a sustainable AI future.

An Enterprise Strategy for Ideas. Over the past few years, we've had the honor of working with the leadership and board of the Aspen Institute as it has embarked on an enterprise transformation to help ensure the organization sustains its mission in the world. This Harvard Business Review case study (subscription required) explores the evolution of the institute in depth and highlights the role we played in this process.

An event for CTOs and CHROs. If your organization is pushing for AI adoption, you're probably feeling some friction in your culture—and a lack of collaboration between your People and Technology functions. To address this, we're hosting a virtual event exclusively for CTOs and CHROs—where successful practices will be shared and meaningful conversations can begin. If you'd like to attend, please reach out to request an invitation.

About us

Dispatches from the Collective delivers insights from SYPartner's work through human anecdotes, practical tips, and beautiful questions designed to help C-suite leaders navigate the unknown and act with purpose—shared in the spirit of helping all of us lead in a better way. Click here to subscribe and see all issues.

SYPartners is a consultancy that partners with clients at their critical turning points to design new possibilities for impact, create paths for long-term value, and build cultures of competitive advantage. For more than 30 years, we've helped transform some of the world's most iconic organizations by fusing strategy and design.