Host: Erika McKellar, Host and Conflict Resolution Seeker 
Guest: Jason Loomis, the Chief Information Security Officer for Freshworks

In this episode of Bad Meetings Podcast, host Erika McKellar is joined by Jason Loomis, the Chief Information Security Officer for Freshworks, they delve into the intricacies of transforming these meetings into effective decision-making sessions.

Jason shares his extensive experience in the tech and cybersecurity sectors, tracing his career from financial controlling to leading cybersecurity efforts at prominent companies like JustFab and MindBody. Now at Freshworks, a global SaaS business solutions provider, Jason discusses the challenges of managing a large number of people in meetings and emphasizes the importance of leadership skills, teamwork, and conflict resolution in making sound decisions.

The episode covers innovative diagnostic tools that treat organizations like living organisms, underscoring the need for regular check-ins and continuous feedback to maintain organizational health. Jason also highlights the concept of time boxing to manage large meetings efficiently and shares practical strategies like pre-meeting preparation and rotating leadership roles to ensure more productive discussions. Erika and Jason offer actionable insights and tips for listeners to enhance their meeting culture, emphasizing the critical role of diverse perspectives and cognitive conflict in achieving better outcomes.

Key Time Stamps:

• Introduction: 00:04
• Jason's Background and Journey: 02:29
• Innovative Diagnostic Tools: 09:35
• The Importance of Regular Check-Ins: 11:52
• Experiences as a Serial Entrepreneur: 13:49
• Handling Long-Term Stress and Challenges: 27:08
• Identity in Business: 36:29
• Fun Facts and Personal Insights: 40:46

Notable Quotes

"I'm a big believer in the more people that are involved in the decision-making process, it's going to be a challenge, but the more involved, the more buy-in you're going to get, and the better the decision will be. You don't necessarily have to have just three experts in the room." - Jason Loomis.

Tools and Resources

Risk Register:A tool used to keep track of all the cybersecurity risks within an organization. Jason describes how the risk register helps prioritize and manage these risks effectively by documenting them and reviewing them quarterly.

Time Boxing: A strategy where specific time limits are set for discussing each topic. Jason uses a timer to enforce these limits, ensuring that the meeting stays on track and all topics are covered within the allocated time.

AI Integration in Meetings: Discussed as a future potential tool, AI could help provide real-time summaries and answer questions during meetings, aiding in decision-making processes by determining when there is sufficient information to proceed.

• Subscribe to Bad Meetings on Apple Podcasts or Spotify, where we’ll continue to explore the art of productive meetings.
• Do you have a meeting story or problem to share? Connect on LinkedIn
• Follow our YouTube channel for more tips and discussions on improving workplace gatherings.