November: Leadership Insights, a fresh podcast and a free course!
From comfort to challenge. Change hurts.
Leadership transformation has been front and center of the client challenges we’ve been thrown this month and there’s one theme that keeps coming up: the step change. Many of the organizations I’ve been working with are realizing that their “comfortable” ways of operating aren’t cutting it anymore. To get to the next level, leaders are having to shift—not just how they operate, but also what they tolerate.
At a recent offsite, I guided a team through a tough but exciting process:
• Defining the culture they need to achieve their strategy.
• Reflecting on (their own) behaviours that were unintentionally creating the comfort and diluting their own impact.
• Creating a realistic action plan to adopt new behaviours which will be more conducive to transformation and growth and,
most importantly, how they can hold each other accountable.
It felt doable, and it is—but consistent behavior change is harder than most expect.
Here’s my advice: if you’re shifting how you lead (being firmer, for example), communicate the “why” to your team before you set off on a completely new style. Let them know it’s part of the strategy for growth, not a personal critique. Every challenge, and how you respond to it, is an opportunity to reinforce your narrative and inspire alignment.
Great leadership isn’t just visible actions. It’s about controlling the invisible—shaping the culture through consistent behaviours. It’s challenging, yes, but also incredibly rewarding when done with intention.
You got this,
G
In practice
We recently concluded a 14-week leadership program with Dexory, focusing on equipping their engineering leaders with practical tools to enhance their leadership impact. Initially met with some skepticism (cause we’ve all been one of those programs), it quickly gained traction as participants saw the tangible value of the strategies we introduced.
Key takeaways included:
• Structured 1:1s: Building trust and alignment through regular, purposeful conversations.
• Giving More Feedback: Creating a culture of growth and accountability by making feedback a regular practice.
• Listening, Not Fixing: Shifting from solving problems immediately to creating space for their teams to lead the thinking.
• Peer Support: Turning to lateral peers for venting or advice, keeping negative energy away from teams to not hinder collaboration.
By grounding these concepts in Dexory’s highly technical context, we enabled leaders to foster better collaboration and drive cultural shifts critical for their innovation-driven environment.
November’s Feature: Katie Lee on Matrix Leadership
This month, I spoke with Katie Lee, COO of Wavemaker, about the challenges of leading in a matrix organization and how we’ve worked together to make it succeed. From building trust across peer groups to clarifying accountability, Katie shared how leadership behaviors can make or break collaboration in complex environments.
🎙️ Watch the full episode here.
Top Tip
Actually listening.
Psychological safety drives collaboration and innovation—but only if leaders create space for ideas to emerge.
At this time of year, stress can make a leader rush to answers, but remember: you’ve hired smart people. Give them room to contribute.
The key? Active listening and embracing silence. Instead of seeing silence as uncomfortable, recognize it as valuable processing time. When you’ve asked a great question, resist the urge to rush or fill the gap. Let the silence do its work—it’s where deep thinking happens. It’s also a great signal to the team that they are invited and empowered to contribute to the solution.
And if you’re struggling to stay present, calm your internal dialogue (try pressing your tongue to the roof of your mouth for a few seconds) and focus fully on what’s being said. These small shifts foster trust, spark ideation, and unlock innovation.
*News* Launching the ScaleUp Leadership Program
We’re thrilled to announce the launch of our ScaleUp Leadership Program—a comprehensive course designed to help leaders at all levels develop high-performing, adaptable leadership strategies.
This program distills ten years of our best work into practical, targeted exercises that deliver real impact.
What You’ll Learn:
• Aligning Leadership with Strategy: Use tools like the strategy pyramid and leadership wheel to hone your leadership style.
• Navigating Change: Lead your team through uncertainty with the Minimum Viable Change (MVC) approach.
• Building High Performance: Set goals, deliver feedback, and cultivate a thriving culture.
• Strengthening Team Dynamics: Foster psychological safety, resolve conflicts, build cohesive teams—and more!
Who is this course for?
Whether you’re a founder, a seasoned executive, or an individual contributor (IC), this program is designed for leaders committed to growth and ready to meet today’s challenges.
Time for change?
Leadership isn’t just about managing change—it’s about designing it.
At OverTime Leader, we equip teams with the tools and strategies to navigate pivotal moments, align around shared goals, and deliver focused impact.
From leadership development to cultural transformation, we help unlock potential at every level of your organization.
If you’re ready to create lasting change, we’re ready to partner with you.