Hi Reader,

I just got back from an incredible ladies weekend in Park City.

I hate to brag, but I think we might have perfected the art of group travel with friends. My crew of five has journeyed through Spain, France, and California, with the only fight being over a croissant in Paris. Even though we have different budgets, preferences, work restraints, and intro/extroverted tendencies, it still ends up being a magical trip every single time.

One crucial step is how we plan together. We all bring our strengths to the table, and I run a pre-planning process inspired by how I facilitate Q4 offsites for my clients.

Since it's 2025 planning and offsite season, I wanted to share my favorite questions to go through with your team to set your next year up for success. You can also rinse and repeat these questions when you're starting with a new team/DR/boss, planning a project, or designing your relationship with your co-founder. You can even try a few with your family before your Thanksgiving travel.

Let me know how it goes!

CRUCIAL PLANNING QUESTIONS

1. What is the ideal way we want this (your trip, project, quarter, year etc) to go? How will we know? What will it look and feel like? How would we be acting/what would we be doing that would make this best case scenario happen?
2. What's our worst case scenario? What would it look and feel like? How would we be acting/what would we be doing that would make this worst case scenario happen?
3. What do we need from each other to make this best case scenario happen?
4. What potential challenges do we see ahead? How will we address them?
5. What implicit assumptions do we need to make explicit so we can be on the same page?
6. What do we want to do if things get hard/we have conflict?
7. What strengths/superpowers can we each contribute to making our vision real?
8. What weaknesses do we need to account for?
9. Given all this, what commitments do we want to make?

BUSINESS HIGHLIGHTS & TOOLS

• Lead a Career Planning workshop for Lyft on how you define success in your career and make it happen. See my top career planning tips here.
• Coaching with Instacart and Veterinary Emergency Group
• Facilitated an Executive Team offsite in Jackson Hole (ProTip: do your next offsite there!). We refined the Team Charter with a clear team purpose and operating agreements. We then used the Working Genius​ assessment to help the team be more strategic in how they utilize their strengths.
• Launched the 2nd year of a custom manager training program for VP-level leaders at an investment firm. We kicked off by discussing how we lead ourselves so that other people actually want to follow us. Check out this quick video on the 5 Levels of Leadership for a great primer.

Stay tuned for more updates, learnings, and leadership resources. Feel free to reach out if you need help with your next offsite!

Warmly,

Tracy Podell

Senior Partner, Evolution