Dave Habiger on Hiring, Judgement and What Leaders Do When No One’s Watching

Dave Habiger has built a career inside industries that reinvent themselves every few years. He led Sonic Solutions as digital media took shape, helped guide NDS through its $5 billion sale to Cisco, ran Textura before its sale to Oracle, and has served as CEO and Vice Chair of Thoma Bravo-backed JD Power. Alongside these roles, he spent time working with leading growth equity firms, including Silver Lake Partners and the Pritzker Group, giving him a front-row view into how investors select leaders and how companies navigate transformational moments.

Today, he brings that breadth of experience to several major boardrooms, serving as a director at Boston Scientific, the Federal Reserve Bank of Chicago, and Reddit.

But the most compelling part of a conversation with Habiger isn’t the scale of the companies he has led. It’s how consistently he returns to human tells, the small signals that reveal how someone behaves when they’re not performing. 

For him, leadership isn’t defined by bravado or pedigree. It’s defined by judgment, character, and the way people show up in the small, forgettable moments.

Leadership Reveals Itself in the Small Moments

When interviewing a new hire, Habiger prefers to break out of the formal structure. His goal isn’t to unsettle candidates, but to observe them as they really are. 

He likes to walk with people, share a meal, and even take their car to the restaurant, if available, just to get a glimpse into the real person. These moments reveal things a conference-room interview never can.

He shares one story with clear hesitation, not wanting to be misunderstood. Before interviews, he sometimes asked the receptionist to leave a candy wrapper visible on the floor of the lobby. Some candidates walk past it. Others pick it up without thinking.

“That says a lot about people,” he explains. “Do they own the problem?” His hesitation to share isn’t because he doubts the insight, but because he knows some might interpret it as a trick. He doesn’t see it that way. The wrapper isn’t a test; it’s a window into instinct. Into whether a leader takes responsibility for their environment and for improving the world immediately around them.

This same instinct shows up at the front desk. As CEO, he always gave the receptionist a real vote on the candidate. How someone treats the first person they meet — respectfully, dismissively, or indifferently — signals something deeper about how they lead.

For Habiger, character isn’t theoretical. It’s observable. And it shows up long before someone talks about their accomplishments.

Why Revenue Doesn’t Predict Leadership Ability

Habiger has run companies ranging from 200-person growth-stage teams to 10,000-person global organizations. Across that range, one misconception that frequently surfaces is the belief that bigger companies require better or more complex leaders.

“People think revenue correlates to complexity,” he says. “I’ve never found that… the correlation isn’t high.”

He explains that running a massive division inside a global conglomerate often demands less hands-on leadership than running a mid-market business fighting for growth. In established companies, infrastructure and momentum do much of the heavy lifting. In smaller or mid-sized companies, the CEO must make sharper decisions, prioritize ruthlessly, and absorb volatility directly.

Yet hiring committees, particularly in private equity, often default to candidates with marquee names on their résumés. Habiger believes this can be a major blind spot. In his experience, someone who has run a $300–$500M business through hard conditions is often far more “battle tested” than a divisional executive from a Fortune 50 company.

The lesson is simple but rarely followed: the reality of the work matters more than the size of the logo.

Hiring for Disruption: Focus Over Flash

Much of Habiger’s operating career unfolded in industries where the playbook didn’t exist yet — digital media, streaming, data analytics, and other emergent sectors. In those environments, he learned not to overvalue candidates who rely on buzzwords or who lead with their network.

“When I hear someone say they know everyone, that’s a red flag,” he says.

He believes the leaders who succeed in disruptive environments share three traits:

• They hire exceptionally well.
  
• They focus intensely on what actually matters.
  
• They avoid unnecessary bureaucracy, structure, and layers.
  

He’s particularly wary of candidates who sell themselves on expertise that’s hard to validate. When the conversation turned to fields where true experience is still relatively rare — like AI —he agreed that companies may tend to overemphasize credentials that may not be meaningful. 

Depth is limited, and claiming mastery can be misleading. What matters far more, he emphasized, is whether a leader can hire strong people, focus on what moves the business, and keep a team aligned on outcomes rather than buzzwords or noise.

He also notes that he much prefers flatter structures. Functional leaders should genuinely run their functions. Marketing in charge of marketing, sales built like a commercial engine, legal built like a law firm. A mismatch or mis-hire in a critical seat “filters all the way through the org,” he says.

Clarity, not flash, is what lets disruptive organizations move.

Boards, Alignment, and the Art of Good Judgment

In boardrooms today, Habiger brings the same attention to nuance that shaped his operating career. He believes smaller boards work better because real relationships form and decisions move faster. He prefers directors who are operators — people who’ve held accountability and understand how businesses function beneath the surface.

He’s direct when asked to share advice to first-time board members: spend your first year listening. Most of your influence will come from a few pivotal decisions, often concerning leadership. You’re not there to run the company, even the CEO can’t fully know every layer of the business.

For CEOs, he distills the work with boards to one core requirement:

“Make sure the board knows the long-term vision and is aligned with the risk–reward ratio you want to achieve.”

In his opinion, misalignment, not strategy, is what derails most CEO–board relationships.

This clarity shapes how he thinks about private-equity partnerships as well. Before accepting a CEO role, leaders should understand the business realities, investor expectations, and timelines. “You’re interviewing them,” he says of PE firms. The relationship lasts years. It needs to be right. And, he jokes, it’s worth seeing if they pick up the Snickers wrapper.

Leadership as a Physical, Human Job

Despite decades at the top of organizations, Habiger talks about leadership not as a prestige role but as a physically demanding one.

“You see people five years later and they look like they’ve aged 10 or 15 years,” he says. “That’s the physical nature of it.”

He stays grounded by running every day, eating well, and sleeping whenever possible. He’s even been known to take a meeting while out for a jog. To him, CEO work is something done on your feet: meeting customers, spending time with employees, staying close to where the real work happens.

“Plan on travelling to where your customers and your employees are,” he says. “That’s where the work happens.”

Across his stories, one theme threads through everything: leadership isn’t a title you grow into. It’s a pattern you’ve already lived.

Long before someone steps into the role, it shows up in their judgment, their instincts, and the small, human choices they make when they don’t think anyone is watching. Those moments, he suggests, are what determine whether a leader can carry the weight that comes later.