Episode Summary
- The importance of establishing a consistent weekly cadence for one-on-one meetings to build trust and connection with team members.
- One-on-ones should focus on career growth, removing blockers, and relationship building rather than diving into urgent project work.
- New managers often lack training on how to handle personal conversations when team members share intimate details about their lives that affect work.
- Organizations need better resources and training programs to prepare managers for the human aspects of leadership beyond just project management.
- Setting clear expectations about what one-on-ones are and are not helps maintain their effectiveness and prevents them from becoming just another meeting.
Key Takeaways
- Schedule one-on-ones weekly if possible and treat them as non-negotiable meetings that shouldn't be skipped for other priorities.
- Clearly define what one-on-ones are for (career growth, relationship building, removing blockers) and what they're not (project updates, the only time you meet).
- Prepare for personal conversations by building a toolkit of HR resources, mental health support, and other assistance options before you need them.
- Focus on the human aspects of management - people will share intimate details about their lives that affect their work performance.
- New managers should seek out training and resources on emotional intelligence and difficult conversations, even if their organization doesn't formally provide them.
Productivity & Success Habits
Both Wes and Courtney emphasize the critical importance of establishing consistent cadences and patterns for effective management. Wes has developed what he calls "really solid patterns around one-on-one team meetings reviews" that he openly shares within his organization. His approach centers on creating predictable weekly rhythms where "there isn't a week that goes by that is the same but every week is the same there's a cadence of like the types of activities that are gonna happen throughout the week." This systematic approach helps managers scale their effectiveness beyond just handling immediate work tasks.
Courtney's productivity philosophy focuses on making management systems work for the individual manager first. As she explains, "my biggest tip on getting started was making the cadence work for you because for me that was tricky balancing my own workload um having direct reports knowing i needed to meet with them having no idea how often." She advocates for weekly one-on-ones as the optimal frequency, recognizing that consistency in these human connections prevents larger problems from developing. Both managers stress that these structured approaches aren't just about efficiency - they're about creating sustainable systems that support both manager effectiveness and team member growth.
Final Thoughts & Advice
The conversation concludes with a powerful call for more peer-to-peer learning among managers. Courtney emphasizes the unique value of "this like kind of lateral conversation of what do you do and how is it effective and what works and what doesn't work" rather than the typical top-down management training. She reflects on her own management journey, noting "back to being manager i didn't really have anyone to pull on say what do i do from the sides but i felt like i had to do it if it came from the top down rather than creating my own authenticity through seeing multiple examples."
Wes reinforces this collaborative approach, highlighting how "managers talking to managers" can create transparency about successes and challenges across teams. Their shared message is clear: effective management isn't about following rigid corporate protocols, but about developing authentic systems that prioritize human connection and consistent support. As Courtney's business tagline suggests, the goal is ultimately to "help others in business get better bosses" - not through mandated training programs, but through genuine peer learning and the courage to prioritize the human elements of leadership.
Notable Quotes
"We're humans right about getting the work done right within the human space. That human aspect that no one tells you about... you might have been working next to someone for three or four years and never knew those personal very intimate things that are happening in their lives that they will share with you because it is affecting their work."
— Wes Discussing how managers need to be prepared for the deeply human conversations that come with one-on-ones.
"You don't have to be someone's therapist as a manager but you need to understand it's coming and it's real and it's going to impact everything that your person does."
— Courtney Explaining the balance managers must strike when employees share personal challenges during one-on-ones.
"It's not just another meeting, it's not something that we skip... it's not the time to just hang out... and it's not diving into the work... it's not the only time we meet."
— Wes Setting clear boundaries about what one-on-ones are and are not to maintain their effectiveness.