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The Insightful Leader

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What your portfolio says about you
Sent to subscribers on October 25, 2023
What’s in your portfolio? Are you betting big on lots of high-risk, high-reward stocks, or are you mostly playing it safe with U.S. treasury bonds? How you answer this question likely reveals something important about your personality, according to some interesting new research by Kellogg associate... more
How to overhaul bad meetings
Sent to subscribers on October 18, 2023
Be honest. Do you know how to run a really good meeting? Most people don’t, says Sanjay Khosla, a senior fellow and adjunct professor of marketing at Kellogg. The majority of meetings spend too much time rehashing the past—which immediately puts teams in a defensive posture—and not enough time... more
Pay, promotions, and merit
Sent to subscribers on October 11, 2023
Ever looked at your workplace’s org chart and speculated about how much money the people above you are making?It’s natural to wonder, especially in organizations where bonuses are rare and promotions are the surest (or only) path to a bigger paycheck. Learning your boss was making more than you... more
A career guide for introverts
Sent to subscribers on October 4, 2023
Is there hope for introverts who want to get ahead in their careers?That’s the question Leigh Thompson, a professor of management and organizations, tackled in a recent edition of her Substack newsletter, “Dear Professor.” For the naturally reticent, a fear of getting overlooked is reasonable,... more
How a luxury brand is born
Sent to subscribers on September 27, 2023
If you visit Canal Street in Lower Manhattan, you’ll find yourself surrounded by knockoff designer handbags. Gucci, Versace, Hermès, Louis Vuitton, Chanel—they’re all there, all available for $100 or less, some virtually indistinguishable from the real thing. So why are people still willing to put... more
Pitch your idea—and yourself
Sent to subscribers on September 20, 2023
Are you ready to take the plunge and make the business idea you’ve been honing a reality? If so, you’re going to have a lot on your plate—conjuring a compelling new product concept, iterating on your idea until you feel you are ready to go to market, and building a trusted team to help you test and... more
The 2 creative types your team needs
Sent to subscribers on September 13, 2023
When you’re confronted with the blank page, what happens? Do you freeze, unable to generate ideas, or are you overcome with the urge to jot down notes and doodles? How you answer this question is a great way to diagnose your “creative type,” according to Gina Fong, a clinical assistant professor of... more
Socialized by social media
Sent to subscribers on September 6, 2023
In middle school, how did you learn what fashions and bands were considered cool? It’s possible someone told you, but there’s a good chance you picked it up simply by watching what your classmates were listening to and wearing. (Certainly, that’s how yours truly ended up with butterfly clips and... more
Why hire when you can “upskill”?
Sent to subscribers on August 30, 2023
Does your organization have the hiring blues? If so, you’re not alone. A lack of qualified applicants is hitting small businesses particularly hard; a recent survey from the National Federation of Independent Business found that 60 percent of owners were trying to hire new employees and 92 percent... more
Walk, don’t run, toward your goals
Sent to subscribers on August 23, 2023
Are you, like me, experiencing the “wait, how is summer over, and how did I get nothing done” blues? If so, you’re probably also in the throes of that panicky impulse to tackle all of the things, right this second. But there’s a case to be made for taking a deep breath and slowing down. In a recent... more
Why you need a CV of failure
Sent to subscribers on August 16, 2023
I’ll let you in on a little behind-the-scenes secret about The Insightful Leader newsletter: every week, I’m a little afraid I’ve messed it up somehow. What if there’s an embarrassing typo? What if I accidentally send it to the wrong recipient list on the wrong day? There’s a good reason we’re all... more
A thoughtful way to roll out ChatGPT with your team
Sent to subscribers on August 9, 2023
Of late, there’s been a frenzy to incorporate ChatGPT and other AI tools into all manner of operations and workflows. This is no surprise. But what’s the role of a manager during this strange period, when we know generative AI will change work but don’t yet really know how? For some clues, I sat... more
Get more from your performance review
Sent to subscribers on August 2, 2023
A few weeks ago, we discussed the best (and most motivating) ways to evaluate employees from a leader’s perspective. This week: how to be evaluated as an employee. Or rather, how to make your own performance-review experience as positive as possible. A more productive conversation Some of this... more
Twitter, X, and naming a brand
Sent to subscribers on July 26, 2023
What’s in a brand name? Twitter, one of the world’s most recognizable brands, is now X. Pundits say the rebrand is part of Elon Musk’s bigger goal to create an “everything app,” where users can come to do, well, everything. Whether X ends up delivering on this isn’t yet clear. What is clear is... more
Small team, big impact
Sent to subscribers on July 19, 2023
Do larger teams produce more innovative ideas? Many of us intuitively think so. After all, more people, more ideas, more innovation—right? Not exactly, Dashun Wang explained at The Atlantic Progress Summit, held last week. The real answer, he said, turns out to be a good old-fashioned “it depends.”... more
Can Threads become a habit?
Sent to subscribers on July 12, 2023
Last week, like a lot of other people, I took my first tentative step into the world of Threads, Meta’s Twitter competitor. I haven’t actually posted a thread yet (and by the way, what’s the verdict—are we saying “threaded” as a verb?), but I was curious to get a sense of how the platform felt.... more
Will "stack ranking" destroy your office culture?
Sent to subscribers on July 5, 2023
About a decade ago, Microsoft famously ditched its controversial (and allegedly culture-killing) “stack ranking” employee review system. Yet stack rankings, and other relative-ranking systems in which employees are rated against one another (often with the poorest performers seeing a pink slip),... more
Are you delegating enough?
Sent to subscribers on June 28, 2023
It’s common for leaders to worry about whether they’re making the right decisions for their organizations. But many don’t worry enough about whether they should be the ones making those decisions in the first place. Knowing when to own a choice and when to delegate it is one of the most important... more
Invite a newcomer to your next meeting
Sent to subscribers on June 21, 2023
As a child, I was notorious for insisting on what I called “the regular.” When it came to food, clothes, books, music, and just about everything else, I wanted the same things I’d had before. Keep your novelty and give me continuity, please and thank you.There are good reasons for leaders to seek... more
Grow as a leader without burning out
Sent to subscribers on June 14, 2023
Becoming a better leader takes time, and time isn’t always easy to find. Rather than burn yourself out trying to squeeze professional development onto your already-overflowing plate, you should think strategically about how to prepare yourself for new leadership opportunities, says Kellogg... more
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