The CEO Inner Circle: Who You Need in Your Corner

Business leaders face tough questions. So, let’s start with a few of our own: Remember when pandemic shutdowns inspired hairdressers to take up hiking and waiters to plunge into white water rafting? What do you imagine life was like at the helm of an outdoor products company at that time? (Hint: it was not awesome.)

Resorts shuttered. Campgrounds closed. Supply chains disappeared.

Heather Stone found herself President of a company on the precipice of failure. What served as a life preserver for her and her CEO as they navigated these treacherous waters were the capable and trustworthy leaders at their side.

“Our inner circle,” Stone says. “We were trying to keep this company from falling apart, and the only way we could keep our own heads above water was from the support of these people. How in the world can you go through something like that without the support of an inner circle?”

Here’s another hint: you can’t.

Everyone knows that “It’s lonely at the top,” but only leaders really understand the weight of that isolation. A company’s financial health, sustainability, and vision rest in the hands of the CEO. When the stakes are this high, leaders need support — in business and in life.

More than half of this nation’s senior executives report feeling lonely, a problem that the American Medical Association cautions puts leaders at a 29% increased risk of heart attack and a 32% increased risk of stroke.

Vistage Master Chair Irina Baranov says CEOs don’t necessarily seek out a business sounding board “to get healthier and have a better marriage. But in reality, that happens. Personal development often goes hand in hand with leadership development.” Because when you are given the space to focus on the big picture, that big picture ends up including you, too, as she says, “The graph only goes up. It’s amazing.”

The relationship between overall well-being and strong social connections is so strong, that some medical experts have half-jokingly suggested doctors “prescribe friendships.”

While that may be a bit tongue-in-cheek, there is no denying that strong CEO inner circles lead to the kind of creative thinking and clear-headed decision making that successful leadership requires. And with ever-shifting headwinds in geopolitics and finance, SMB leaders today are asking themselves one of the most important questions of all: “Whom should I have in my corner?”

Inner circles span the spectrum from spouse and childhood best friend to mentor to a fellow CEO peer. Ideally, your trusted circle comprises a mix of experiences and backgrounds — and not all of them should have “skin in the game” when it comes to your decision-making.

However, those that do have a financial stake in your company’s success should be insightful enough to see the “Big Picture,” says Leo Bottary, a Vistage speaker and founder of Peernovation.

Choose a C-Suite Team You Can Trust

Assembling diverse experts willing to set aside personal agendas to help CEOs realize their goals is “the difference between having a cross-functional team and a dysfunctional one,” Bottary says.

“One of the difficulties that CEOs have in the C-suite is making sure that those people understand that they’re not in the room because they’re great at marketing or finance or legal, but they can close the door and put their enterprise hat on,” he said. “You need people who are going to do what’s right for the business, which might mean saying, ‘Hey, marketing is going to take a hit this year, but that’s what’s needed to move the business forward.’”

Of course, building a team is just another way of saying “hiring,” which can be a challenge for CEOs, both economically and emotionally, Baranov says.

“There are certain critical positions that are particularly challenging for CEOs to fill, especially if they haven’t filled them before,” she adds. “CFO, Head of HR, COO, and now Head AI. Whether those positions are vacant because someone left or they have never been filled, a company can really struggle. A CEO can really struggle.”

Baranov says that she has seen the investment in building the right team of advisors and trusted professionals pay off.

“If you’re the visionary, and all you’re doing all day long is running the operations, your company may never grow beyond a few million in revenue,” she says. “So, if you have your sights set on scaling your company, you can’t afford not to make the investment in hiring and developing the right people,” she said.

Look Beyond the Business

No matter how committed to the “Big Picture” the executives in your company are, they are still executives in your company. When problems get messy, complicated, or — as in Stone’s case — existential, having a close inner circle outside the C-suite or boardroom can help anchor your perspective and keep you moving forward.

“You need people you can bring your mess to,” says Stone, who is now a Vistage speaker and CEO of Practical PhD, a firm that teaches leaders how to have successful Right Hand relationships “People who will listen and help rather than criticize People who will not expect you to posture. You can’t always get that from the inner circle team that you pay in your company.”

One of those people might be in your bed. Studies have found a strong correlation between happy marriages and career satisfaction. Other members of your inner circle could come from the early days of your youth, peers from outside your industry or trusted mentors.

This strong, diverse inner circle allows you to process issues and learn from disparate experiences and expertise. In 2020, Stone’s inner circle tipped her off to government funding solutions and other ideas that helped her keep the company afloat.

Seek Truth-Tellers who Challenge Your Blind Spots

As you assemble your inner circle bouquet, don’t underestimate the importance of a few thorns, Baranov says. She references bestselling author Adam Grant, who advocates for a “challenge network,” a group of helpful critics who help you see your own blind spots.

“If all you have are cheerleaders, you’re not hearing enough truth to course correct or to really improve yourself,” she says.

Bottary agrees. Being challenged is a key factor in growth.

“Your inner circle isn’t always about getting your questions answered, it’s about getting your answers questioned,” Bottary says. “Successful people ask for help. They don’t see it as a sign of weakness; they see it as an act of resourcefulness.”

An inner circle delivers the insight, perspective, and depth of experience that no search engine or solo reflection can replicate.

As Baranov says, “CEOs tell me all the time that having the support of their inner circle has not just incrementally, but exponentially leveled up their businesses, and more importantly, their lives.”

How Solid Is Your CEO Inner Circle?

Ready for another tough question? Being isolated is no way to lead or live. Having an intentional, strong inner circle keeps leaders grounded, supported, challenged and inspired. So, how strong is your CEO inner circle?

Use this simple diagnostic to evaluate whether your inner circle is helping you grow — or quietly constraining your leadership:

Who Challenges You?

Finding people in your CEO inner circle who can offer useful disagreement is critical, Baranov says.

“When you’re processing an issue, undoubtedly, somebody in your inner circle will say, ‘I’m so proud of you. Go you.’ And somebody else will say, ‘You know what? You need to rethink what you just said,’” she says. “You need both kinds of people to inspire robust conversations within a safe space.” Stone observes that a trusted “Right Hand” is often the only one at the company who will challenge you rather than just agree.

Who Shows Up for You?

A high-functioning CEO inner circle is not built on agreement; it is built on participation. Bottary says it’s important to pay attention not only to how people show up for you, but whether they show up at all. He relates a story about a CEO who got annoyed that his Vistage peer group commented on his lackluster attendance record.

“He said, ‘Look, when I miss a meeting, I’m the one who loses,’” says Bottary, the Vistage Speaker. “So, I paused for a few seconds and asked the member sitting across from him, ‘Would you mind giving me one minute on what’s lost for the whole group when Richard can’t be at a meeting?’ And he starts talking about the very special gifts and contributions that Richard brings to the table. And then I ask another member, and so on. By the time I get to the third, I look at Richard. He’s welling up in tears. He had never seen himself that way, even as a CEO.”

Who Grounds You?

The CEO role carries a unique emotional and psychological weight — one few people truly understand.

“CEOs are supposed to be experts, and they often feel a need to appear strong and smart in front of their people. So they need a safe space with their own peers (other CEO’s) where they can be vulnerable,” Baranov says. When it comes to your CEO inner circle, “The name of the game is, ‘I don’t know.’ I don’t know how to hire a CFO. I don’t know how to lose those 20 pounds. I don’t know how to have a better marriage. I don’t know. Help! That is the goal, to create a safe and courageous space where CEOs can become their best selves and build their best companies.”

Who Helps You Think About the Future?

“A transition happens as a company experiences significant growth, and the CEO starts to think, ‘I need a real bench,” says Stone, author of “Winning Together: How CEOs and Their Right Hands Build a Relationship That Works.” “But a lot of these CEOs find it challenging to build that bench.”

One place to start, says Bottary, is any place you wouldn’t normally think to look.

“When you learn about a process that’s practiced in one industry or one sector that’s unheard of in your own, it could be a competitive differentiator,” he says. “You’ll never find out unless you seek people who offer those perspectives.”

Common CEO Inner Circle Gaps

A common error is to trust solely on integrity, Stone says.

“I worked with a CEO in the chemical industry whose very senior, right-hand person signed a multi-year, multimillion-dollar contract with a customer they’d been trying to land for a while,” she says. “You would think the CEO would be excited, but the contract included fundamental provisions that were unsafe. The CEO said, ‘I physically cannot honor the contract — it would blow up the building.’”

The “Right Hand” leader wasn’t missing trust. He was missing expertise. Stone says that when building an inner circle, a leader needs to decide what level of delegation they and the company need – and then bring the right person into the fold and train them so they don’t make critical mistakes, rather than just assume they will somehow magically know what you have learned through years in the role.

Strengthen Your CEO Inner Circle in the Next 90 Days

Use this practical checklist to build a stronger CEO inner circle:

• Create psychological safety. Build an environment where you can ask questions and admit mistakes without feeling you’ll be vilified.
• Embrace differences but align on values.
• Delegate with intention and trust your gut: If there is something you’re not willing to delegate, there’s a reason.

Build Your CEO Inner Circle with Vistage

For many leaders, some of the strongest members inside their CEO inner circle aren’t inside the company at all. They’re peers — fellow leaders who understand the pressures of the role and are willing to question assumptions, challenge blind spots, and share hard-won experience.

Peer advisory groups create a space where those conversations can happen. In a confidential room of fellow CEOs, leaders can test ideas, wrestle with difficult decisions, and hear perspectives they might never encounter inside their own organizations.

“There is a value in being in a room where there is a mix of people who have been there, done that, or people who are going through the same thing as you,” says Baranov.

If you’re looking to strengthen your CEO inner circle, explore Vistage membership. Peer advisory groups bring together CEOs from non-competing companies to share perspectives, challenge thinking and help one another make better decisions.

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