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When It Feels Easier to Just Do It Yourself
The most dangerous instinct in leadership is this: “It’s easier if I just do it myself.” That instinct feels productive in the moment. It solves the immediate problem and keeps the team moving. But repeated often enough, it quietly trains your team to depend on you for answers, decisions, and direction. And eventually, you become the person holding everything together. Most leaders have said these words to themselves more times than they can count and underneath that thought

Jessica Crooker
Mar 83 min read


From Carrying the Work to Building the Team: A System for Turning Work Into Growth
If you read my article When it Feels Easier to Just Do it Yourself , you might have recognized yourself in it. Solving problems all day long–in emails, in meetings, in direct messages, in the hallways…Doing mental gymnastics as you jump from meeting to meeting..Carrying more of the work than you used to. Always dreaming about pausing time to just get caught up, so the work can be manageable again. And even though your team is working hard, you still feel like everything depe

Jessica Crooker
4 days ago3 min read


I Thought I Was Developing This Employee. They disagreed. Here’s Where I Went Wrong.
The areas of opportunity for this employee were clear to me. At a weekly 1:1, I delivered feedback, explained the behaviors I wanted to see, and followed up with an email recap to ensure clarity. It was a hard conversation in many ways— there were lots of dynamics at play, some within my control, some not. While I was focused on the current situation, the employee voiced frustrations about past leaders and situations they felt were unfair. I wasn’t expecting the conversatio

Jessica Crooker
Apr 15, 20252 min read


Three Traits of The Most Valuable Team Members
When Something Isn’t Clicking—Start Here Every leader has been there. You’re coaching an employee, giving feedback, offering support—but...

Jessica Crooker
Mar 25, 20253 min read


7 Years Later: How My Strengths-and my Leadership-Have Evolved
In 2017, I took the VIA Character Strengths Assessment for the first time. My top strengths back then? Judgment, Kindness,...

Jessica Crooker
Mar 18, 20252 min read


The Leaders Who Truly Invested in Me Had This in Common
Leaders don’t build teams. They build the people who make teams great. I’ve worked for a lot of leaders over the course of my career— nine different leaders in the last ten years. There’s good and bad in that. Every time I was given a new leader, it felt like a step back. I had to prove myself again, rebuild trust, and help them see my strengths. In many ways, it was frustrating—like starting over, again and again. But in hindsight, I see something else. Working for differe

Jessica Crooker
Mar 12, 20252 min read


One Way You’re Missing Out on Huge Growth Opportunities? Staying Inside Your Bubble.
It’s easy to stay focused on your own company, team, and work—especially if you’re at a larger, well-resourced organization. But if...

Jessica Crooker
Mar 5, 20253 min read


The Career Path Myth
Unpopular Opinion: I hate the phrase ‘career path.’ Why? Because it sets leaders and employees up for unrealistic expectations and...

Jessica Crooker
Feb 25, 20252 min read


Confessions of a Fun Killer
I have a confession to make. I’m not fun. There. I said it. I'm the ‘fun killer.’ Some years ago, I was responsible for a two-day...

Jessica Crooker
Jun 2, 20242 min read


4 Unexpected Reasons Why Leaders Should Delegate
A Tale of Two Cooks in One Kitchen My soon-to-be-husband and I cook most of our meals at home. We have a pretty good system, too–one...

Jessica Crooker
May 20, 20243 min read


From Invisible to Valuable: Refining Your Vision
A leader told me he is concerned about how much (or little) his organization values his team’s work. As a result, he feels a sense of...

Jessica Crooker
May 19, 20242 min read


A crucial mistake leaders make: ignoring cultural shifts
I started working at a founder-led company in its 10th year. The entrepreneurial spirit upon which it was founded was palpable. Cultural...

Jessica Crooker
May 11, 20242 min read


This is your sign to connect
One of my team members recently told me: “I feel like we’ve been ships passing in the night a lot lately.” Uh-oh. This is not good...

Jessica Crooker
May 6, 20243 min read


Hidden Threats to Your Team Culture: The Unspoken Rules That Undermine Success
Photo by Kristina Flour on Unsplash I bet you can think of one or two unspoken “rules” of your team or corporate culture. They aren’t...

Jessica Crooker
Apr 16, 20242 min read


Debunking the Myth: Employees don't leave jobs, they leave leaders.
POV: One of your employees resigns. How do you feel? A. like a failure of a boss B. anxious that productivity will slow C....

Jessica Crooker
Apr 13, 20242 min read
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