Assessing Future-Ready Leaders: An Interview with Mark McClain

Hear an experienced director’s perspective on why boards must rethink succession planning and leadership evaluation in an era defined by disruption and rapid change.

How can boards avoid relying on backward-looking performance metrics when evaluating senior leaders for an uncertain future?

Mark McClain, CEO and founder of SailPoint Technologies and a director on the board of ActivTrak, spoke with Adam Bryant, a senior managing director at The ExCo Group, and David Reimer, CEO of The ExCo Group. McClain also served on the NACD 2025 Blue Ribbon Commission. In the interview below, they discuss how artificial intelligence is reshaping boardroom priorities, why succession planning should focus on future leadership capabilities, and the value of adaptability and vulnerability in today’s CEOs.

This interview first appeared in Adam Bryant’s LinkedIn series, “The Director’s Chair.” 

Reimer: How have conversations in the boardroom evolved? And are there issues that should be getting more airtime in the boardroom?

McClain: The topic du jour, of course, is AI. I've never in my 40 years in the tech industry seen something quite this dramatic. It’s moved from barely on our radar a couple of years ago to the predominant theme today. The board’s role is to ask the right questions about risks and opportunities that AI presents.

In terms of what’s missing, I’ll mention DEI [diversity, equity, and inclusion]—a topic that was front and center for a time and then went rushing out of the news. We've swung pretty hard in the other direction. Yes, there was some virtue-signaling before, but now it’s as if people think it doesn’t matter at all.

But it’s well-documented that a more diverse team performs better, and diverse is measured on all kinds of vectors, including race, gender, background, and mindset. Companies have to make sure they have an incredibly diverse leadership team that is well prepared for the range of things happening in the world.

Bryant: As a director, what is your best question to probe for whether a company is encouraging employees to use AI in meaningful ways?

McClain: Good questions to ask are: While I assume you're trying to expose this capability to your employees so they can individually improve their work, what are you doing to rethink some of your most critical business processes? And how AI might truly transform how you provide that service or business process to be able to do what you’re doing but possibly 20 to 30 percent better?

Another approach is to ask: If you were starting a competitor company today to try to kill us, what would you do? With all the new technology, and without the history and legacy processes we have, what would you do if you wanted to come after us? If we wanted 10 times [the] improvement, not just 10 or 15 percent, what would we do differently?

As a board member, you have to push yourself, your fellow directors, and the leadership team to get outside your current framework of how you think about disruption. If you see some possible new approach, you should figure it out. You should not try to hide from it. You should embrace it, because somebody else will embrace it and they will take you out.

Reimer: What are the two or three X factors that you're looking for in candidates for the CEO role?

McClain: I look for diversity of experience. I think about the situation at my company, which is midsized and growing. I love people who have both Fortune 500 experience and some start-up experience. I like people who know what it takes to operate in a big machine, and they know what it takes to operate with a scrappy team.

People sometimes try to fake that start-up experience, saying that they were part of a Skunk Works inside a big corporation. But that’s not the same as a true start-up. I'm also testing for culture and values thinking. We still see lots of evidence that there are many valueless leaders in the world today. They can do well for a while and build great businesses, but they usually hit a wall.

I care about values and culture a lot. So, when I’m interviewing a CEO candidate, I will ask about that: What do you think your role is as the leader in setting the tone on values and culture?

I also like to hear people's discussions of their failures. Tell me what kind of failures you had and how did you navigate them? You learn a lot from how they answer that. Are they still looking back at that episode with bitterness and blaming people? Or are they focused on what they learned and took away from that experience to make them better now? Anybody who is over 50 better have a couple of failure stories to share. Otherwise, they are likely in denial.

Bryant: How are conversations among directors around succession planning evolving?

McClain: Whatever helped a leader to be successful in the last two to three decades may not have a lot to do with what’s needed to be successful in coming years. So, anything that takes a rear-view approach to assessing talent is likely to be a problem.

What's worked in the past may not matter now. The best jockey isn't the best race car driver. In this environment, you need different kinds of leadership skills and capabilities, and that starts with being flexible and adaptable and also having the strong values and character that we discussed earlier.

As you think about succession, you have to define the future as best you can to understand what you are going to need three to seven years from now. As a board, you have to be incredibly clear about what you’re hiring for.

Reimer: How do you complete the sentence, “The hardest part of leadership is…”

McClain: Being vulnerable enough to admit that you don't know things and asking for help. Leaders can get into trouble because they think they have to know everything and be the smartest person in the room. They have to be comfortable admitting what they don’t know and acknowledging that they need some help.