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The Insightful Leader
A Weekly Newsletter
Don’t sweat the big stuff?
Sent to subscribers on October 22, 2025
When Amazon Web Services went down on Monday morning, chaos ensued. A glitch in its database disrupted numerous apps—from Zoom to United Airlines to Venmo—affecting the work and lives of millions across the globe. It even cost me my hard-won 103-day streak on Duolingo.
Yet I wasn’t too concerned.... more
How the global economy hits home
Sent to subscribers on October 15, 2025
There is a lot going on in the world right now, to put it lightly. And while international politics used to be something we could just read about in the morning newspaper and put aside, breaking developments in trade policy, immigration, and other issues are increasingly affecting our businesses,... more
When rebrands meet backlash
Sent to subscribers on October 8, 2025
I still remember how my parents reacted when I told them I wanted to switch my college major junior year. It was an uproar. I found out the hard way that there’s always considerable risk when debuting a “new you.” In a way, it’s the same kind of risk companies face when rebranding.
This week, Tim... more
How AI can inspire creativity
Sent to subscribers on October 1, 2025
Whenever I use AI as I write, my attitude is generally, “You think you’re better than me? Let’s see how you’d phrase this.” More often than not, I leave these interactions feeling slightly better about my own creative abilities.
It’s my strange little way of “competing” with the robots.... more
Some feedback on feedback
Sent to subscribers on September 24, 2025
How are you doing? Or, more importantly, how am I doing?
It’s a question that, if answered honestly, specifically, and actionably, can help aspiring business leaders take their careers to the next level. But getting good feedback can be tough, especially for women in the workplace.
This week,... more
Don’t oversell yourself
Sent to subscribers on September 17, 2025
Whether due to economic uncertainty or the spectre of AI replacing jobs, competition in the workplace appears to have grown especially stiff in recent years. It feels like we almost have to project an inflated version of ourselves if we want any chance of getting a new job or finally securing that... more
AI is not one-size-fits-all
Sent to subscribers on September 10, 2025
Like many of you, I’m trying to figure out what artificial intelligence can do for me. The promises made by AI companies are so broad and bold that it’s hard to zero in on what I actually find useful.
When it comes to preparing business leaders for the future of AI, it’s not one-size-fits-all... more
Soft skills still matter
Sent to subscribers on September 3, 2025
Show of hands, anyone else spend time with family over Labor Day weekend? Between scheduling activities, meal plans, rentals, and saying “no” to frivolous expenses like novelty kettle corn, I joked to my significant other, “Do we need a family office?”
It’s a question Kellogg’s Matt Allen hears... more
Landing a career leap
Sent to subscribers on August 27, 2025
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... more
New game, old moves
Sent to subscribers on August 20, 2025
My oldest daughter starts kindergarten this week, and because I’m that parent, she will enter having already endured a battery of first-grade-level worksheets. It’s a playbook that’s rooted in my long-held belief that early academic success begets future achievement.
But relying on any kind of... more
No, you’re not an imposter
Sent to subscribers on August 13, 2025
“Settled in yet?”
It’s hard to pinpoint the moment when a new role feels natural—especially when it involves a jump to management or leadership. And while you wait for the dust to settle, imposter syndrome can creep in.
“Self-doubt often spikes when we stretch ourselves into something new and big,”... more
Manager or leader?
Sent to subscribers on August 6, 2025
When you think of leaders, what characteristics come to mind? What about managers?
While we may be inclined to categorize them with different personalities and skill sets, they may not be as different as we think.
This week, we share career insights from Kellogg professor Harry Kraemer on... more
Icebreaker or iceberg?
Sent to subscribers on July 30, 2025
“What do you do in your spare time?”
It’s an interview question that serves as both an icebreaker and a soft datapoint to help generate a more three-dimensional picture of the person you could soon call a colleague.
But could this seemingly innocent conversation also amplify preexisting biases... more
Are your teams aligned?
Sent to subscribers on July 23, 2025
There are few chores more rewarding than claiming points from a credit card, however humble the return might be. So you can imagine my delight over the weekend when I cashed out hundreds of dollars at the click of a button.
But not all rewards programs make it so simple to claim benefits. A lot of... more
Leaders, beware the “ostrich approach”
Sent to subscribers on July 16, 2025
It’s the economic story that won’t go away: tariffs. In the last week alone, the Trump administration has threatened new taxes on imports from Mexico, Canada, and Russia, while still negotiating the aggressive rates announced in April with countries around the globe.
The ultimate result of these... more
Learning from the competition
Sent to subscribers on July 9, 2025
This past Saturday marked the start of one of my favorite summer traditions: watching the Tour de France over my morning coffee.
While Le Tour is often thought of as an individual event, it’s the team tactics that make it extra fascinating. Instead of every man for himself, teams of eight work... more
When leaders say “I’m sorry”
Sent to subscribers on July 2, 2025
Fireworks, barbecue, and a festive day off from work spent with loved ones. What more can we hope for as we welcome the Fourth of July?
How about an apology?
Though problems and conflicts aren’t typically what we look forward to for the holidays, they tend to happen anyway when family and friends... more
Can AI boost careers?
Sent to subscribers on June 25, 2025
When generative AI started taking over the news cycle a few years ago, I—like plenty of others—found myself wading through the stages of grief, trying to make sense of what it meant for my role at work.
This week, research from Kellogg’s Bryan Seegmiller and Dimitris Papanikolaou points to a... more
The right time for feedback
Sent to subscribers on June 18, 2025
Can we talk to you for just a second? Don’t worry, it’s nothing bad, but ….
We get it, feedback can be dreadful. At their worst, notes can feel like ambushes, anxiety inducers, or long-winded speeches from leaders. But for managers, providing employees with thoughtful reviews is essential.
This... more
Aging into (and out of) leadership
Sent to subscribers on June 11, 2025
Good morning,... more
