The new leadership playbook for unpredictable times — Dispatch #5
͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌     ͏ ‌    ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­ ­
Dispatches from the Collective

This fall, leaders are mulling more than just cider. The coming new year brings growth mandates against a backdrop of uncertainty and unpredictability. While no one is daring to predict the future in this environment, everyone is willing to predict that some tradeoffs are on the horizon.  

Here’s what’s top of mind from conversations with executives, thought leaders, and others on the ground.

#5

Planning for unpredictability, bracing for contact

HUMANITY & PERFORMANCE

“Organizations are navigating the tension between humanity and performance, rather than seeing the two as vital parts of a virtuous cycle,” says the Chief Learning Officer of a large national healthcare company.

The shift to AI has intensified the spotlight on performance, overshadowing the very real human needs in the workplace. The conversations on results and what people need to deliver are increasingly happening in two separate rooms, a worrying trend.

How can leaders bridge the gap between what they want and what employees need?
“Cultures that focus solely on process and efficiency will become hollow, while those that thrive will remember that attending to their people also happens to be the best way of attending to their business,” says Jason Baer, SYP’s Chief Client Officer.

SHORT-TERM THINKING

“I’m being asked, for every new hire, to justify that AI can’t do the task, and that we actually need a person,” says one senior executive at an entertainment company. “But I’m also a parent who wants success for my child, so I feel it acutely from both sides.”

The great replacement fear with AI is nuanced, especially when it comes to  entry-level positions. Leaders faced with short-term pressures from boards and shareholders understand that AI can show short-term results, such as expense reduction. But in the long term, these entry-level positions are vital for training the next generation of leaders, creatives, and apprentices.

How will the next generation become high performers if there’s no longer a place for training, for making mistakes, and learning from them?
“It’s getting very real. What we’re hearing on a personal level is very different from what these short-term pressures force on a fiduciary level,” says Jessica Orkin, CEO at SYP.

UNLEASHING CURIOSITY

“I want to feel like an intern,” says Cedric Wilmotte, former CEO of Michael Kors. “I want to get beyond the obvious and expand my horizons to understand what’s possible.”

Whether the AI bubble bursts or continues to grow next year, one thing for certain is that proficiency and literacy of the technology will need to expand beyond the CTO/CDO and across the C-suite. The sheer size of the investment in AI will drive greater accountability and pressure to get results throughout the organization.

How do you ignite greater hunger for learning among senior leadership?
“This is the moment to lean into building organizational curiosity and it needs to be modeled from the top,” says Venture Partner Marc Winter. “The neuroscience is clear—our brain rewards us for acquiring knowledge. Start with a beautiful question that unlocks something from within. Share it openly and invite others to help you find the answer.”

DEEP LISTENING

“I've been on this deep listening tour, going around and talking to everybody, and you know what? There's so much that is working. Part of our strategy is actually about raising up what is working, and then figuring out what can scale,” says a new CEO in the civil society space.

Given the rapid advancement in technology, world-shaking political events, and massive short-term financial pressures, it’s easy for organizations to go into next-year planning with change as the top priority. But we’ve also been hearing that some savvy leaders are leaning into stability and being careful not to overlook or undervalue what’s currently working.

How do you best elevate what’s working to keep employees engaged?
“Take a grassroots approach vs. top-down,” says Venture Partner Marc Winter. “People want authenticity in this moment. Spot the bright spots in the field and equip your people to make the win their own.”

A peek into SYP

Signals of the future of AI adoption. Over the past two years, we’ve been exploring how organizations are adopting GenAI. In 2024, we synthesized six practices any company can undertake to build a strong AI culture. Since then, we’ve conducted several in-depth interviews and surveys, collaborated with clients on AI initiatives, and led workshops at Columbia University and the Stanford d.school. From this research, we’ve identified five emerging signals—each offering a glimpse into what’s next.

AI, a challenge 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, before the end of the year we’ll be 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 previous 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.

Illustration by Brian Rea

Go here to see other issues