The Insightful Leader
Sent to subscribers on March 4, 2026
After my kid’s swim practice, we always have this dilemma: When do we leave? If he plays with teammates, we run the risk of overstaying and losing critical homework time. If we leave early, he misses out on fun and forming friendships that could last for years to come. Honestly, it can feel as serious as figuring out when to leave a job.
Departing too early carries risks, as does staying too long. So what’s the best way to keep an eye on your career (or my kid’s 50-yard backstroke) and keep everything on track?
This week, Kellogg’s Sanjay Khosla offers tips for getting your exit strategies just right.
Plus, we’ll discuss the power of delay in negotiations, according to eBay.
Clocking out
“Often individuals leave a company when it’s too late,” warns senior fellow and adjunct professor Sanjay Khosla.
That’s why Khosla contends that people should start eying the exit when their time with a company has reached the equivalent of “5 to 12,” as he likes to say—and not when it’s 5 minutes past. In other words, recognize when a positive experience has peaked and you’re approaching diminishing returns.
Khosla identified three signs that you may have reached “5 to 12” in your current role.
For one, is your professional growth within an organization stalling? Khosla advises looking outside. Consider leaning on a network of people you know and trust—what Khosla calls a “circle of influence,” which could include colleagues and managers from both inside and outside your company.
Next, many people leave companies because they have terrible supervisors. When managers make unreasonable demands and take credit for your work, it can put a career clock at “5 to 12” fast. As hard as it can be to leave a place you may love, getting away from a horrible leader is worth it for the sake of your career growth.
Lastly, don’t risk getting too comfortable. Work that starts off rewarding can sometimes become mundane or even mindless. To grow your career, it is important to recognize when it is time to step out of your comfort zone and get excited about work again.
“Don’t wait for a crisis to force your hand,” Khosla says. “Try and take your career and your own path in your own hands as much as you can, as early as you can.”
Read more at Kellogg Insight.
Negotiation tips from eBay
Whether it’s buying used furniture on Facebook Marketplace or negotiating wages and contracts, bargaining is a fundamental part of doing business. But which strategies work best?
Historically, research has suggested time—or more specifically, how buyers and sellers delay in responding to offers—is a powerful bargaining tool.
Kellogg’s Caio Waisman and coauthors wanted to find out what really happens when buyers and sellers take longer than usual to respond while negotiating the price of a product. To do so, they studied one of the largest and earliest online marketplaces: eBay.
Waisman found that the longer a person took to respond to an offer or counteroffer, the less likely the other side was to continue negotiating. And this decision had different downstream effects for buyers and sellers. The more the seller delayed, the less likely the buyer was to buy the product. In contrast, the more the buyer delayed, the more likely the seller was to agree to sell the product at the buyer’s offered price.
These findings mirror the longstanding theory that delay is a signal of bargaining power. “Showing that people in a large, informal setting delay somewhat consistently with how theory suggests they would—that has value,” Waisman says.
Read more at Kellogg Insight.
“Most of us don’t have a lot of self-awareness, even though we think we do.”
— Carter Cast, speaking to the Northwestern University Alumni Association on factors that can make—and unmake—brilliant careers. After watching the webinar, learn more from Cast at Kellogg Insight.
Have a great week!
Blake Goble, marketing manager
Kellogg Insight