ConnectWise’s Bryson Medlock on Leading without a Universal Playbook

The Story This Time

Bryson Medlock‘s path to Threat Intelligence Evangelism Director, CW Research Unit at ConnectWise positioned him to address what actually creates high-performing security teams: treating people as individuals, maintaining psychological safety during crises, and building systems that eliminate months of manual work. Bryson shares how his leadership philosophy draws from a bit of nerdiness, including nearly two decades of running D&D campaigns where managing group dynamics requires constant attention to who’s speaking and who needs encouragement to contribute. These frameworks translate directly into security team management, where recognizing that a fresh graduate needs hands-on guidance while a 15-year veteran needs autonomy and trust determines whether teams thrive or fracture.

The conversation explores how Bryson transformed ConnectWise’s threat intelligence operations from months of manual spreadsheet work into automated systems that generate insights instantly. He also touches on conducting difficult conversations by focusing on observable facts rather than assumed intentions, building trust through recognizing individual needs rather than applying uniform management styles, and why panic accomplishes nothing in security operations where most situations aren’t actually life-or-death.

Stories We’re Telling Today

• Why the most important step after any failure is simply the next one, and how this shapes hiring decisions for people who return after rejection
• Transforming threat intelligence operations from months of manual spreadsheet work into automated systems
• Building trust by recognizing individual experience levels and adjusting management style accordingly
• Conducting difficult conversations by focusing on observable facts and giving people the benefit of the doubt regarding their intentions
• Why curiosity about why systems work matters more than memorizing commands or collecting certifications
• How running D&D campaigns teaches essential leadership skills, including managing group dynamics
• Creating psychological safety during security emergencies by recognizing that panic doesn’t help unless it’s life or death
• Why kindness isn’t soft but rather creates competitive advantage through better team performance and reduced turnover

Too busy; didn’t listen:

• The most important step after any failure is the next one; some of Bryson’s best hires were people initially rejected who demonstrated growth and returned changed.
• Effective leadership requires treating team members according to their individual experience levels, not applying uniform management styles.
• Curiosity about why systems work separates career-long security professionals from those who plateau.
• Building trust involves conducting difficult conversations by focusing on observable facts rather than assumed intentions, then giving people the benefit of the doubt.
• Kindness in leadership creates competitive advantage through better team performance, reduced turnover, and environments where people actually want to contribute their best work

Skip to the Highlight of the Episode

13:44-13:58 “You have got to be able to know when to trust, and when to delegate. I think a lot of it comes down to just recognizing that what it means to be a human, everybody is an individual. Everybody’s got individual needs and wants and desires”