Landing a career leap
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The Insightful Leader Logo The Insightful Leader Sent to subscribers on August 27, 2025
Landing a career leap

The end of the summer is here. With students starting school and the hint of fall in the air, it feels like a time of change.

This week’s newsletter focuses on big changes and how to prepare for them. We share career advice from Kellogg’s Rob Apatoff for business leaders on the verge of a major career shift—in this case, going from a job in one industry to another. And we hear from Kellogg’s Carter Cast on when a startup is ready to scale up.

Making the leap to a new industry

Over their careers, most business leaders will take a variety of jobs. While some will stay within a company or industry, others will make the leap from one industry to another.

According to Kellogg’s Rob Apatoff, the biggest challenge in this transition is often not the work itself, where experience and transferrable skills can go a long way toward ensuring a smooth transition, but the fear of stepping outside of one’s comfort zone in a new company culture.

“It is always a risk restarting your career and building credibility at another company,” says Apatoff, a clinical professor, executive director of the Kellogg Executive Leadership Institute, and former senior executive at several major brands.

Apatoff has made several high-profile sector jumps in his career. He says the first steps to making such a switch are determining when to jump and getting familiar with the dynamics of the industry you’re entering.

“You sure as heck better do your homework on that industry,” Apatoff says. “I don’t mean just about the company—I mean about its competitors, how transactions are done, what unmentioned potential problems the company you’re considering might be recruiting you to solve.”

Once you have made the leap, it’s critical to build credibility. Apatoff notes that learning the culture is as important as learning the business itself. Because even if the work feels familiar, the environmental dissonance of a new culture can undermine your confidence.

You also have to take time to listen and learn rather than barging in the door and trying to prove yourself before you have a grip on the culture. When Apatoff transitioned from the corporate world to teaching at Kellogg, he realized why that shift was so difficult for many executives.

“I quickly learned it’s because we came from a command-and-control, speed-to-market environment,” he says. “The shift to a more-collaborative academic culture was not automatic.”

Read more in Kellogg Insight.

Know when to scale

When entrepreneurs start companies, they are often eager to get their ventures past the early stages and achieve hyper growth. Whether the urgency stems from their own ambitions or their investors’ timelines, keeping it in check and ensuring that the scaling process is planned and executed deliberately can make or break a young company, according to Carter Cast, a clinical professor of strategy at Kellogg.

“Founders take money from investors, and the investors say, ‘go, go, go,’” says Cast. The result? “Founders start looking for ways to achieve hypergrowth without really asking themselves: Are we really ready to grow? Do we actually have product–market fit? Do we have the right team to double the business? Do our business metrics—around customer growth and retention, operational execution, profit margin—indicate that we are ready to grow, or are we trying to artificially push it?”

Key to being prepared is aligning the team, the investors, and the board behind a specific, defined growth plan.

“You identify the hill you want to take and the game plan to get there. Then you get your board and investors behind the plan so you all believe that aggressive scaling is the right path to pursue,” Cast says.

Scaling is both uncertain and expensive. To avoid burning through cash chasing unrealistic goals, Cast insists that leaders create a rigorous assessment of their product–market fit.

“This is the motherlode, the big kahuna,” Cast says. “If you don’t have product–market fit, the effort you spend to scale the business amounts to pouring money down the drain.”

Startup leaders also need to begin building the company for the capabilities they will need to have as they scale. That may mean looking beyond the walls of the company for new talent and expertise—including in the role of CEO.

“Sometimes a founder may be better off playing a specific role that they’re good at, and then bringing in a leader who has experience in scaling companies,” he says. “There are situations where the founder becomes the chief customer officer, but a chief operating officer is brought in to run the day-to-day operations.”

Cast has developed a handy preflight checklist to help entrepreneurs assess whether their companies are ready to scale.

Read more in Kellogg Insight.

“Frontline managers have an outsized influence on whether people stay motivated and see how their work matters. Leaders need to help them see that communication is a key part of their job, and give them the skills and tools to do it well.”

Shana Carroll, in Harvard Business Review, on how leaders can build buy-in for strategic change in their organizations.

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