What I'm Hearing From Leaders
Every month I have the opportunity to speak with founders, CEOs, executive coaches, marketers, AI strategists, product leaders, designers, and entrepreneurs navigating growth and transformation.
While their industries and challenges may differ, I am always fascinated by the patterns that emerge across these conversations.
This month, discussions repeatedly returned to organizational design, leadership adaptability, artificial intelligence, decision-making, and the growing importance of human judgment in an increasingly automated world.
Below are a few leaders whose insights stood out during my conversations this month.
Founder, Spark Catalyst | CEO & Chief Strategy Officer, CTR Inc.
Growth often comes from adding people, resources, and complexity. Scale requires the leadership structures, decision-making processes, and organizational design necessary to support sustainable growth.
— Yasmin Glanville
Our conversation quickly moved beyond organizational design and into leadership psychology, founder evolution, and the future of work.
Yasmin spoke about helping organizations become future-ready rather than simply solving today's problems. Through scenario planning, AI-enabled foresight, and executive coaching, she works with leadership teams to anticipate change before it arrives.
One insight that resonated was her distinction between growing and scaling. Many organizations add people and resources in pursuit of growth but fail to redesign decision-making structures, leadership accountability, and operating models along the way.
We also discussed the challenges founders face as organizations mature. The instincts that help build a company are not always the same instincts required to scale it.
My Takeaway
In executive search, we often see organizations attempting to solve structural challenges through hiring. Sometimes the answer is a new leader. Sometimes the answer is redesigning the organization itself.
HCD-AI Transformation | Agentic CX | Speaker & Educator | Nucleations
Organizations need to understand and redesign how work gets done before determining where AI can create meaningful value. AI should not simply be layered onto existing workflows.
— Vanessa Rementilla
Our conversation centered on AI transformation and the misconceptions many organizations have about implementation.
Vanessa challenged the idea that AI adoption begins with selecting technology. Instead, she emphasized understanding workflows, decision points, information flow, and organizational friction before deciding where AI belongs.
One particularly interesting discussion focused on the difference between automation and transformation. Many organizations attempt to use AI to improve existing processes rather than reimagining entirely new ways of working.
We also explored the implications for leadership roles, product management, and knowledge work. As AI automates more executional tasks, strategic thinking, judgment, and cross-functional leadership become increasingly valuable.
My Takeaway
The companies creating the greatest value from AI aren't necessarily adopting more tools. They're redesigning how work gets done. AI is not replacing leadership. It is forcing leaders to rethink how organizations operate.
VP, Marketing | WestJet Group
AI is making marketing more efficient, but often less transparent. Leaders are increasingly being asked to trust systems and algorithms they cannot fully see or explain.
— Stephanie Ng
Stephanie offered one of the most practical leadership perspectives on AI that I've heard recently.
While AI-powered platforms continue to improve campaign performance and efficiency, marketers are increasingly operating within systems that are difficult to fully understand. The result is a growing tension between automation and accountability.
Our discussion also explored the evolution of the marketing leadership role itself. Today's marketing executives are expected to understand customer behaviour, brand, growth, technology, analytics, and business strategy simultaneously.
Marketing has become significantly more interdisciplinary, requiring leaders who can connect multiple functions and translate data into business decisions.
My Takeaway
The challenge is no longer access to information. It's understanding what the machine is doing with it. As AI takes on more executional work, strategic judgment becomes increasingly important.
Transformation, UX, Service Design & Digital Products Leader | Director, Sun Life
The most effective organizations align around outcomes rather than functions. Today's business challenges require leaders who can work across disciplines rather than within silos.
— Karri Ojanen
Karri and I spent time discussing the changing role of design leadership inside organizations.
What stood out was the shift away from viewing design as a standalone function and toward seeing it as a catalyst for alignment, innovation, and business transformation.
Our conversation explored how organizations often struggle because teams optimize for departmental goals rather than shared outcomes. The leaders creating the greatest impact are increasingly those who can bring different perspectives together around a common objective.
As business challenges become more interconnected, the ability to work across product, technology, customer experience, operations, and strategy becomes increasingly valuable.
My Takeaway
The leadership profiles I see most in demand today are increasingly difficult to place into a single category. The future belongs to leaders who can connect functions rather than optimize them independently.
Co-Founder & CEO | Walnut Insurance
The leaders who thrive in the future won't necessarily be the deepest specialists. They will be adaptable learners who can combine multiple disciplines and evolve alongside technology.
— Derek Szeto
Derek brought a founder's perspective to many of the themes emerging around AI and organizational change.
We discussed how technology is rapidly reshaping the skills organizations need and how traditional job definitions may continue to evolve.
One particularly interesting observation centered on the rise of hybrid skill sets. Increasingly, organizations are seeking leaders who combine expertise across multiple domains rather than remaining confined to a single specialty.
Our conversation also touched on curiosity, continuous learning, and the importance of remaining adaptable in an environment where technology and business models continue to change at an unprecedented pace.
My Takeaway
For decades, organizations hired primarily for experience. Increasingly, I believe adaptability may become just as important. Learning agility is quickly becoming a competitive advantage.
Founder & CEO | Singularity Group
Technology will continue to evolve, but meaningful engagement and human connection remain at the center of creating valuable experiences.
— Oren Berkovich
Oren brought an interesting perspective rooted in experience design, community engagement, and human behaviour.
While much of today's business conversation focuses on technology, automation, and AI, Oren emphasized the enduring importance of participation, connection, and shared experiences.
We discussed how organizations often become consumed by efficiency and optimization while overlooking the human elements that drive engagement, loyalty, and trust.
Whether the audience is customers, employees, partners, or communities, meaningful relationships continue to sit at the centre of long-term success.
My Takeaway
Almost every leadership conversation today eventually arrives at AI. Yet most end with people. Technology may change how work gets done, but people remain at the centre of every successful organization.
My Overall Takeaway
Despite operating in different industries, these leaders were wrestling with remarkably similar questions. How do we build organizations that can adapt?
How do we leverage AI without losing visibility and judgment?
How do we scale without creating unnecessary complexity?
How do we develop leaders capable of thriving in a rapidly changing environment?
As an executive search partner working with startups, scaleups, founder-led businesses, and organizations navigating growth, these are the same themes we are hearing from clients across North America.
The conversation is no longer simply about hiring talent.
It is about building organizations that are prepared for what's next.
The organizations that succeed over the next decade may not be the ones that adopt AI the fastest.
They may be the ones that combine technology with thoughtful leadership, strong organizational design, adaptability, and a relentless focus on people.
What themes are you hearing inside your organization?
