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The Insightful Leader

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It’s OK to talk about your charitable donations
Sent to subscribers on December 20, 2023
It’s the season of giving, so you’ve probably gotten lots of appeals from charitable organizations hoping for that year-end donation—or perhaps you’re the one trying to raise funds for a cause you care about. If so, you know that getting people to open their hearts (and wallets) is no small feat.... more
Your customer’s mindset
Sent to subscribers on December 13, 2023
If you’re a marketer worth your salt, you’ve probably thought deeply about your customers’ needs and desires. But when’s the last time you considered their mindset? A mindset is a mental state that affects how we interpret and respond to things in our environment. In a recent The Insightful Leader... more
Inside the mind of a VC
Sent to subscribers on December 6, 2023
Over the last decade, clinical professor of strategy and venture capitalist Carter Cast has met with hundreds of entrepreneurs, listening to their pitches and reading their business plans. His aim: decide whether to invest. So what, in Cast’s eyes, makes a company stand out? This week, we’ll hear... more
Managing a worrier
Sent to subscribers on November 29, 2023
It’s natural for employees to wonder whether they’re doing a good job and seek occasional feedback. But what should you do if you’re supervising someone who needs constant reassurance? That’s one of the tricky management questions Harry Kraemer, a clinical professor of management and organizations,... more
AI comes with a big trade-off
Sent to subscribers on November 15, 2023
Have you started to incorporate ChatGPT or other generative AI tools into your daily life? If so, you know the trade-off well: either accept the AI-generated output as “good enough” or put time—sometimes a lot of time—into personalizing it so that it faithfully reflects your unique style or... more
On purpose
Sent to subscribers on November 8, 2023
What’s your purpose? It’s a question companies should ask employees more often, according to a Harvard Business Review piece by Maryam Kouchaki, a professor of management and organizations at Kellogg, and Isaac H. Smith of Brigham Young University. Sure, companies have their own missions, Kouchaki... more
You’re the boss! Now what?
Sent to subscribers on November 1, 2023
Getting promoted is great. But having to manage your former peers? Not always so fun. Over at The Insightful Leader podcast, Harry Kraemer had some advice for how to navigate that sticky situation. If you don’t already know Kraemer, you’re in for a treat: He was chairman and CEO of a... more
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
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