Leadership Spotlight

Courtney Hamilton, Senior Managing Director, The Miles Group (TMG)

As part of our new leadership spotlight series, we’re sitting down with leaders across Council Advisors—including our colleagues at SSA & Company, The Miles Group, and High Lantern Group—to share insights on leadership, execution, and what it takes to drive results in today’s business environment.

 

In the private equity landscape, what leadership challenges and opportunities are you seeing most often right now?

Leadership profiles are shifting. Sponsors still need efficient operators, but they also need leaders with technical fluency, learning agility, and the ability to execute in rapidly changing environments. Business models are evolving mid-flight, which forces a real-time reevaluation of talent models and team composition.

 

A second theme is exit readiness. In the past, focus on leadership was front-loaded. Today, many of our clients are seeing equal value in using leadership assessment to prepare the team and the narrative for a sale. Longer hold periods raise the bar. Buyers want world-class operators who can also articulate the commercial story. I am seeing more interest in building a clear, strategic narrative about the team as part of the value creation story at exit.

 

What do you see boards and CEOs underestimate most often during leadership transitions?

New leader, new team. Even one change alters the chemistry. Organizations often over-rotate on selection and underinvest in team formation. The basics matter: when someone new joins the team, reset communication, meeting, and alignment norms. Then commit to a cadence across year one and beyond. Quarterly work on team effectiveness, with measurement at 6 and 12 months, keeps the team aligned. 

 

From a board perspective, set explicit expectations for CEO-board engagement at the outset. Define the role of the chair, outline the flow of information, and describe what good performance looks like. In some cases, formal chair support in the first quarters helps a new leader close knowledge gaps without losing face with the team. Boards should also ask to see the CEO’s onboarding plan. They don’t need to own the plan, but they should confirm that one is in place.

 

How has your experience across industries and markets shaped the way you advise executives today?

Context is everything. There is no universal model that works across companies. What works at a tech company might get you fired at a financial institution. Some foundations, such as communication skills, travel well. Things like engagement style, pace, and expectations often do not.

 

Working in different environments over the course of my career has taught me to read the room, adapt, and know when to plant a flag. In my current work, interview-based 360s provide thousands of data points on how leaders actually interact with others. No one gets it right every time. The strongest executives notice signals, recalibrate, and close the loop. Humility, curiosity, and the willingness to correct course are durable advantages.

We use data collected by cookies to analyze traffic on this website. By clicking “Yes,” you agree to our use of cookies as described in our Privacy Policy