Introduction: 0:00

• Introducing Rachel Olchowka, Chief Administrative Officer & Corporate Secretary at Prizm Insurance and former Chief People Officer and General Counsel at Fetch. 
• Starting your legal career in litigation before going in-house at TransUnion. 
• Balancing your family life and school schedules with your work life.

Taking on the chief people officer role while serving as general counsel at Fetch: 2:25

• Clearly voicing your intentions to your CEO about taking on additional work when an executive steps away.
• Operating two executive roles simultaneously.
• Identifying your knowledge deficits and familiarizing yourself with those areas.
• Taking the time to understand processes and functions so you can excel as a leader.

The difference between CPOs and CHROs: 5:25

• Looking beyond HR in the CPO role to oversee office management, IT, and employee experience.
• Understanding your company culture through the way the HR team titles their executive role.
• Managing a mature and cohesive team that prioritizes cross-training and engagement surveys.

Encountering pushback from the executive team on HR policies: 9:01

• Easily finding consensus on new initiatives with an open and flexible executive team.
• Prioritizing negotiation, balance, and a critical push-and-pull before arriving at a solution.
• Making sure you are always making the right decision for every employee.

Crafting culture within an executive team: 12:35

• Entering the CPO role with legal skills, then acquiring operational skills on the job.
• Bridging the needs of each team and shepherding ideas to their completion.
• Forefronting objectivity during negotiations.

Establishing a comprehensive parental leave plan: 14:53

• Recognizing that every company will need to take a unique approach to parental leave.
• Considering the entire family unit, not just birth-giving parents.
• Incorporating leave for adoption, surrogacy, pregnancy loss, and more.
• Looking at extended leave as a positive opportunity for your team to grow and try new things.

Approaching the hiring process as a CPO: 19:38

• Needing to understand the work of the role that you are recruiting for.
• Understanding that seeking “culture fits” can create a homogenous team.
• Seeking out employees who are energized by fast-paced environments.
• Resisting the tendency to become a traditional HR function.

Comparing in-office policies against remote work: 24:40

• Prioritizing the flexibility to work from home when necessary.
• Finding a tendency in younger employees towards wanting to work and interact in the office.
• Relying on trust as a core value.
• Designing a welcoming office environment for those who want or need to come in.

Dealing with emotionally charged issues in the CPO/CHRO role: 30:57

• Contrasting the intellectual work of a general counsel with the interpersonal challenges of a CPO.
• Complementing each role with the skills that the other lacks.
• Dealing with employees and managers trapped in difficult situations.
• Maintaining boundaries within the CPO role while understanding that executive roles are 24/7. 

Recommendations to GCs who want to take on multiple executive roles: 36:34

• Recognizing that you can’t lead and be in the weeds all the time.
• Gaining an important ally by having a separate person fill one of the two roles.
• Digging into the complexities of metrics-driven goal setting.

Considering the right candidate for dual GC and CPO roles: 43:25

• Identifying lawyers who are energized by KPIs and addressing interpersonal challenges.
• Allowing passion to drive you into the role you want to take on.
• Life after leaving Fetch.

Book recommendations: 47:35

• Powerful: Building a Culture of Freedom and Responsibility by Patty McCord
• The Anxious Generation by Jonathan Haidt
• The Power of Full Engagement by Jim Loehr and Tony Schwartz

What you wish you’d known as a young lawyer: 50:19

• Being bold about what is and isn’t working for you.