For many ambitious professionals, climbing the corporate ladder is the ultimate goal. But according to Rob Kaplan, vice chairman of Goldman Sachs, reaching the upper echelons of management comes with a dangerous, often unseen pitfall: a sudden lack of supervision.
“When you’re junior, you’ve got senior people watching everything you do,” he explained during a recent master class conversation with Meena Flynn, Goldman’s chair of Global Private Wealth Management.
Kaplan added that the dynamic shifts drastically later on in an executive’s career: “As you get more senior and you get promoted, pretty soon the bosses are no longer watching you. The only people watching you are your subordinates.”
This lack of oversight creates a pileup of people who find themselves suddenly failing after a track record of astounding success. “I spent the last 20 years getting an avalanche of people coming at me who are highly successful for a period and then hit a wall,” he said.
Over his decades of experience—which includes two separate stints at Goldman Sachs, separated by stints teaching at Harvard Business School and serving as president of the Dallas Federal Reserve—Kaplan has identified a toxic combination that brings down senior management: isolation, blind spots, an inability to learn, and a lack of relationships.
When Goldman CEO David Solomon welcomed Kaplan back to the bank in 2024, he said that Kaplan brought “a wealth of knowledge, deep relationships, and significant global leadership expertise to his role as vice chairman.” In addition to engaging with clients and teams across global banking and markets and asset and wealth management, Kaplan’s role includes a specific focus on mentoring, leadership development, and the firm’s culture. He is the author of three books on leadership, What You Really Need to Lead, What You’re Really Meant to Do, and What to Ask the Person in the Mirror.
Everybody’s got a blind spot
Kaplan told Flynn that he stresses a holistic view as he mentors members of the bank’s executive ranks. “So every one of us, no matter how great we are, have things that everyone can see about us, everybody knows about us, except we’re not aware of it. That’s called a blind spot,” Kaplan noted. If these blind spots go unchecked, leaders become increasingly isolated, and their teams become afraid to tell them when they are off course.
To survive the senior management trap, Kaplan advocated for an unconventional approach: “You have to learn to cultivate your subordinates as your coaches.” While many executives fear this will make them look weak, he argued leaders should want to get advice from the people who observe them the most. “You want to encourage an atmosphere of debate, disagreement. You want to encourage people to tell you when you’ve done something that they don’t agree with.”
Either leaders don’t realize this or they only pay lip service to it, he said. They ask for feedback, then rebut it, and shut it down as soon as it arrives.
Kaplan recommended a highly practical step for executives managing large organizations: Conduct three or four one-on-one “skip level” meetings every week. These 30-minute sessions should be used to share information, check on employees, and ask for their advice on what the company is doing wrong. “You don’t have to always act on it, but the fact you listened makes people feel included and empowers them,” he explained, shifting the employee mindset from “I work for them” to “This is our firm.”
Another major stumbling block for newly minted senior leaders is an overreliance on past success. “The mistake many leaders make is, ‘I was very successful at this … and so whatever got me here is what I’m going to keep doing,’” Kaplan warned. Instead, leaders must assess their new situation and adapt their style accordingly.
This includes being hyperaware of the behavior they are modeling. Because subordinates can no longer interact with senior leaders one-on-one as often, they model themselves off the leader’s actions rather than their words. “If you say you want teamwork but you keep promoting producers who have sharp elbows and are not teamwork-oriented, [your team will respond] ‘Okay, I get it. You don’t really believe in teamwork; you believe in production,’” he predicted.
Alongside blind spots, Kaplan noted that senior leaders often struggle privately with a “failure narrative”—a story in their head whispering, “I’m not good enough” or “I can’t” when things go wrong. Overcoming this internal doubt requires processing insecurities with a trusted outside confidant. Furthermore, when setting the course for their teams, leaders must define their top three priorities, but should never do so in a vacuum. Getting buy-in and advice from the team helps leaders arrive at a stronger strategy and ensures that inevitable course corrections are minor rather than jarring.
Kaplan dispelled the myth that leadership is an innate trait driven by charm or charisma, saying: “My best advice is leadership is something you have to work at.” It requires continuous learning, curiosity, and the passion to push through tough days.
And when all else fails and the pressures of senior management become overwhelming? Kaplan offers a simple guiding light: “Go help someone else. Help a colleague, a client, someone in the community, a child. And I think that’ll get you back to center.”
