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When people hear “executive coaching,” they usually picture a struggling leader who got assigned a coach to fix a problem. That’s a myth. The best leaders I work with don’t wait until there’s an emergency. They bring in a coach before there’s a fire to put out. I recently published a new article with the International Coaching Federation (ICF) covering 5 unexpected times it’s a good idea to hire an executive coach. Here’s one: when you lack confidence. Imposter syndrome doesn’t disappear when...

If you read the news these days, the world can feel bleak, to put it mildly. Between mass layoffs, political chaos, and international conflict, many of my clients are telling me they feel overwhelmed and exhausted. I try to be intentional about how much negativity I let into my life, so this week, instead of adding to it, I want to share three moments that recently gave me hope. 1️⃣ A handwritten congratulations card. Each week, I carve out time to mail congratulations cards to clients who’ve...

Oops... Thanks to those of you who caught the time discrepancy for this Thursday’s LGBTQ+ inclusion panel. I clearly hadn’t had enough coffee when I wrote this email. We’ll be starting at 8 AM PT (11 AM ET). 👉🏼 Register now for this important conversation. See you on-screen! ~ Kyle | CaffeinatedKyle.com

Managers are the #1 driver of psychological safety, yet in small and medium-sized businesses, they’re often undertrained for today’s political climate. With anti-LGBTQ+ rhetoric at an all-time high, the stakes are real. How do you support LGBTQ+ folx on your team when many players are actively campaigning for their erasure? How do you repair trust when something goes wrong? What do you do when a manager’s own discomfort or uncertainty gets in the way? This Thursday, June 18—in just two...

LGBTQ+ rights are under attack in the United States and globally. As of this writing, the ACLU is tracking more than 500 anti-LGBTQ+ bills in the U.S. alone. While self-disclosure has always carried risk for LGBTQ+ professionals, it can feel particularly tricky, confusing, and downright unsafe in the current political climate. I’m a career and executive coach for tech leaders, and even the most confident individuals bring me questions and uncertainty about disclosure. That’s why I dedicated...

“Is this company truly accepting of everyone? Will I feel welcome here? Should I disclose that I’m LGBTQ+ during my interview—or ever?” Job searching looks fundamentally different when you’re a member of the LGBTQ+ community. Beyond putting your professional accomplishments out there, which already feels vulnerable, you’re also navigating questions about identity, disclosure, and personal safety. As a career coach who partners closely with LGBTQ+ leaders, and as a fellow member of the queer...

After a 5-day vacation in Vegas with my parents, I’m heading back to Santa Barbara rested, recharged, and ready for several busy weeks of coaching and speaking engagements. 🧖🏼♂️ As a recovering workaholic, I am always working on truly disconnecting while on vacation. Finding balance when you have a busy career is tricky, especially when you love your work. It’s a topic that clients often bring up to me during their coaching sessions—and there’s no perfect solution to the question of...

“Executive presence” is a phrase that gets tossed around constantly in leadership conversations. If you’re searching for a new role, preparing for a promotion, or stepping into senior leadership, chances are you’ve heard that you need to “develop” it. For years, it’s been positioned as the gold standard. The message was simple: if you wanted to lead, you needed to sound the part, look the part, and carry yourself a certain way. But here’s my issue: much of what we call “executive presence” is...

Last week, a tech job seeker reached out to me frustrated that they had secured employee referrals to a half-dozen tech companies yet didn’t receive a single interview. Employee referrals used to be a silver bullet. Not anymore. In today’s competitive job market, employee referrals no longer carry the same weight they once did. I wrote a comprehensive article breaking down how tech firms’ employee referral programs have changed, why they no longer guarantee interviews, what you actually need...

I’m back from The Ritz-Carlton in Marana, Arizona! 🌵 I attended and spoke at the 2026 TroopHR Member Retreat, which brought together ~150 global HR and talent acquisition leaders. It was my first time in the state, and it didn’t disappoint. The views were unreal, the conversations were memorable, and the insights were spot-on. What I love about this special event is that I get to learn what’s happening right now in executive search, not just theory or “best practices.” In addition to...