3-Day Checkr Leadership Summit at SFO

After three immersive days at our San Francisco HQ with managers/senior managers from across the company, I’m returning to the team energized, grateful, and loaded with actionable insights. The opportunity to compare notes with so many talented peers on the art of leadership was invaluable, and the in-person format truly made a difference in building connection and trust.

This wasn’t a sit-and-listen conference; it was a highly participatory summit defined by practical exercises and role-playing that brought concepts to life. The core themes we dug into are the very ones we need to lean into right now to elevate our impact.

The Core Themes: Our Leadership Playbook

The sessions consistently reinforced a few powerful, interconnected themes:

• Clear Ownership (DRIs): Moving beyond the acronym to truly clarify who owns a decision or outcome.
• Direct-but-Kind Feedback: Normalizing Radical Candor—timely, clear, and empathetic feedback that helps us all grow.
• Cross-functional Empathy: Deeply understanding our peers’ perspectives and constraints when making trade-offs.
• Systems Thinking & Executive Communication: Seeing the bigger picture and articulating our work within it.

Sessions That Hit Home

A few sessions stood out for their immediate relevance to our daily work:

• Ownership in Action: We took the concept of a DRI (Directly Responsible Individual) to a deeper, more practical level, focusing on how to properly structure decision-making so ownership is unambiguous.
• Perspective-Switching with “MegaCorp”: A huge shout-out to Krista Moroder and Gio Granato for their brilliant exercises. Stepping into the roles of a VP of Engineering, a DRI, and a VP of Customer Success for the fictitious customer MegaCorp brought abstract cross-functional trade-offs into stark, relatable reality.
• Onboarding for Success: The session on Partnering for New Hire Success (led by Michelle Mosher, Jordan Brooker, Michaela Powell, and Zoe Mckenzie) was incredibly thoughtful. It provided a clear, actionable framework we can immediately apply with our next hires to ensure they ramp up effectively and feel supported.
• Navigating Leadership Layers: Michael Timineri’s session, “Navigating Strategic Leadership: Looking Up, Down and Across,” gave a crystal-clear structure for how we can effectively set context for our teams, unblock our peers, and coach our direct reports.

My Biggest Takeaway: An Actionable Communication Toolkit

One of the most memorable sessions was with Executive Coach Brooks E. Scott, who equipped us with powerful tools for public speaking and communication. This is a toolkit I’m excited to share and practice with the team.

The MCP Framework:

• M = Mindset: Check your headspace before communicating.
• C = Communication: The act of delivering the message.
• P = Precision: The clarity and sharpness of your message.

The Four Gears to Shift Into:

1. Gear 1: Explainer Mode — Shift from teaching to telling.
2. Gear 2: Learning Mode — Lead with curiosity before certainty.
3. Gear 3: Broader System Thinking — Swim outside your lane to see the bigger picture.
4. Gear 4: Create Space — Step back and invite other voices in.

Communicating with Executives:

1. Start with the bottom line.
2. Name the business impact.
3. Make the ask or recommendation.

Executive Context and a Must-Read

The Day 3 forecast chat with Daniel Yanisse, Jen Yeh, Luca Bonmassar, and Ethan Winchell was candid and confidence-inspiring, clearly outlining leadership’s focus for the next stretch.

During the Q&A, our CEO name-checked a personal favorite of mine: Patrick Lencioni’s The Five Dysfunctions of a Team. As a Lencioni devotee (I’ve read all his books, some twice!), I can’t recommend this enough. It remains my go-to recommendation for anyone who leads or influences, including technical leaders without formal people management responsibilities.

I also loved a powerful quote from Luca that perfectly captures our challenge: “Goal is top-down, Execution is bottom-up.”

A Quick Look Back & A Look Ahead

We capped off a full Day 2 with a fun outing to Holey Moley Golf Club. I teamed up with Callie Kelly, Michael Lee, and Yev Belov to compete on the 9 courts—and yours truly came in last! It was a fantastic chance to relax and connect with peers beyond the conference room.

The only downside? I had to step out to handle an incident and missed the “Build Trust, Build Confidence” session. I’m looking forward to catching up on the key takeaways from those who attended.

I’m incredibly grateful for the opportunity and excited to put these insights into practice. Let’s connect if you’d like to dive deeper into any of these topics!