The Insightful Leader
A Weekly Newsletter
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How Useful Is Failure, Really?
Sent to subscribers on September 14, 2022
No one likes to fail. Yet most of us have been told over and over that there are great lessons to be learned from failure. We just need to “fail smart” or “fail fast.”
But is that true? Do we really learn a lot from our failures?Not as much as we may think, at least when it comes to our own... more
The Cost of Disagreeing with Your Boss about Politics
Sent to subscribers on September 7, 2022
A few weeks ago, I covered a study that shows how opting to not give an opinion on hot-button topics can backfire. People of all political stripes are suspect of those who try to avoid thorny topics, the research found. In fact, people are less trusting of those who try to stay out of the fray than... more
Tips for Naming Your Brand
Sent to subscribers on August 31, 2022
I don’t get the opportunity to start this email with a Shakespeare quote often, which is a shame. So I’m going for it today: “A rose by any other name would smell as sweet.”
But just how universal is that truism? Does it hold when you’re coming up with a name for a new brand?
Paul Earle, an adjunct... more
How Can Leaders Dissuade Cheating?
Sent to subscribers on August 24, 2022
Let’s talk cheating today. No leader wants to discover that someone on their team has been deceitful, be it fudging time cards or sales stats. So how can leaders set conditions that dissuade cheating at work?
In looking at this question, Maryam Kouchaki, an associate professor of management and... more
Does Your Brand Need to Exist?
Sent to subscribers on August 17, 2022
Brands are everywhere these days. At the grocery store, sure. But also in your Instagram feed, on banners sponsoring your favorite sports team, even on LinkedIn where people are cultivating their personal brands.
So what’s a new brand to do if it’s trying to break through all that noise?
“The world... more
Hiding Your Political Views Can Backfire
Sent to subscribers on August 10, 2022
When a thorny political topic comes up at work, do you jump into the fray to express yourself or do you prefer to stay out of it? For many of us, the second option seems safer.
While there’s an intuitive appeal to staying out of controversial issues in the hopes of dodging conflict, Ike Silver, an... more
Negotiators, Don’t Overplay Your Hand
Sent to subscribers on August 3, 2022
The job market remains strong—and wages are still increasing at a fast clip. Of course, so is inflation.
Perhaps that’s why employees are feeling particularly keen to negotiate on salary. That’s great! Kellogg professor Leigh Thompson is a big fan of negotiating on salary. But she cautions that... more
Should We Be Forced to Socialize at Work?
Sent to subscribers on July 27, 2022
How do you feel about participating in social events at work—those team lunches and happy hours, whether in person or on Zoom? Does it feel like legit bonding among coworkers or is it an attempt at forced fun?
The reality is, these social events have the potential to be both. Adam Waytz, a... more
Entrepreneurs: No Product? No Problem.
Sent to subscribers on July 21, 2022
How do you sell a product or service when it doesn’t yet exist? This is a challenge that most entrepreneurs face early on, after they’ve founded a startup but have nothing concrete to sell yet. It’s also a challenge facing anyone who is trying to sell people on an idea that is still just an idea.... more
Tips for Managing Up
Sent to subscribers on July 6, 2022
We talk a lot in this newsletter about managing teams. Today we’re going to tackle something slightly different: how to manage up and across.
The advice comes from two clinical professors of innovation and entrepreneurship. Carter Cast is a venture capitalist for Pritzker Group and former CEO of... more
Summer Heat Can Hurt Performance
Sent to subscribers on June 29, 2022
How’s your summer going? Here in Chicago, at least, we’ve had some really hot days already. And while I know some people love the summer heat, I unequivocally do not. And it turns out I’m not alone. Today, we’ll look at research that shows how heat can lead to negative behavior by employees. And,... more
A New Leadership Challenge: Political Disputes at Work
Sent to subscribers on June 22, 2022
Today we’re going to tackle a problem that was likely not on many managerial radars until fairly recently: how to handle political disputes among employees.
It’s pretty clear that simply banning political discussions in the office isn’t the answer. For example, at Basecamp last year, one-third of... more
Craft the Career You Truly Want
Sent to subscribers on June 15, 2022
Are you doing the work you want to do? Is it challenging and interesting, at least some of the time? Does it line up with the priorities you’ve set for your life? In a word, is your job fulfilling?
For those who feel like they’re not on a fulfilling path right now, we’ve got advice today from... more
Dread Networking? Here’s a Tip.
Sent to subscribers on June 1, 2022
We’ve all heard that professional networking is important. Building and sustaining connections can help you find your next job–or your next hire–and it keeps you informed about what’s happening in your organization or industry.
Even if we can all agree on its value, there’s a wide range of opinions... more
Encourage Smart Risk-Taking
Sent to subscribers on May 25, 2022
Failure is a topic I’ve touched on several times in this newsletter—from how to build resilience so you’re better able to handle failure to why even cringeworthy failure makes us stronger.
But it’s one thing to get yourself to a place where you’re comfortable with failure and quite another to... more
How to Project Confidence Even When You’re Feeling Unsure
Sent to subscribers on May 18, 2022
When you’re thrown into a new, challenging situation at work, how confident do you feel in your ability to navigate it? Do you march in, head held high, thinking, “I got this!”? Or do you worry that you’re out of your depth? If you’re consistently in this second camp, despite positive feedback from... more
DEI Work Is a Marathon. Keep Going.
Sent to subscribers on May 11, 2022
It’s been nearly two years since the murder of George Floyd spurred a major moment of reckoning for organizations that realized they needed to do more to improve diversity, equity, and inclusion in their ranks. Today, many of those organizations have come to realize that this is really, really hard... more
Set Goals You’ll Actually Achieve
Sent to subscribers on May 4, 2022
Knowing how to set goals is important, both for your own professional development and for managing others. Nothing too controversial about that. But Craig Wortmann wants you to know that less than 10 percent of us actually achieve those goals. And that’s a problem.
Reaching a goal is “weirdly hard... more
Leadership Skills of the Future
Sent to subscribers on April 27, 2022
The world—and the workplace—are changing at a sometimes-dizzying rate. Today we’re going to focus on what it’s going to take to be a good leader as organizations continue to evolve.
The topic came from a question from reader Suva Chattopadhyay. He is a leadership coach and facilitator with... more
The Case for a 4-Day Workweek
Sent to subscribers on April 20, 2022
Many employers face a conundrum these days: The combo of low unemployment, the Great Resignation, and two-plus years of remote-work options is making it difficult to attract and retain top talent, not to mention lure the talent they have back into the physical office. So workplaces are trying to... more