Jessica & Andrea’s Co-Leadership Toolkit

Get aligned on how you’ll lead together, and who decides what, before you make it official.

Jess Skylar with Andrea Chen


This toolkit brings together two tools Jessica Allen and Andrea Chen used as they shaped their co-CEO partnership at Propeller. Use them to test your alignment with a potential partner, spell out who decides what, and head off the unclear lanes that cause many co-leadership models to fall apart.

From the Helia Library — based on the article Co-Leadership Can Absolutely Work, from our Coffee Chat with Jessica Allen and Andrea Chen.


What’s Inside

The two resources are meant to be used in order. Start with the questionnaire, because the matrix is much easier to fill in once you agree on the big picture.

01 — The Partnership Questionnaire: Co-Leadership Alignment Questions

Eleven questions you and your co-leader each answer and then discuss together. They cover your vision for the partnership, how you’ll support each other, and what you’ll do when you disagree. Start here, before you define roles, to find out whether you’re aligned on the things that matter most.

02 — The Co-Leadership Decision-Making Matrix

Propeller’s draft template for assigning who approves, who leads, and who must be consulted on decisions across HR, budget, programs, communications, development, impact, and facilities. Use it once you’re aligned and ready to formalize your model and bring your board along.


When Resources and Templates Aren’t Enough

These tools can help you get aligned and define your lanes. They can’t do the personal work that makes a partnership possible. That includes separating your identity from your role, which Andrea says took her years and a coach. They also can’t tell you whether co-leadership is the right model for your organization right now, or help you figure out how to bring your team and board along. If you’re a founder wrestling with whether to share the seat, that’s usually where talking with someone who has done it makes the difference.


If you want help with co-leadership

Andrea Chen founded and led Propeller for 15 years, lived through the whole co-leadership arc, and now coaches other leaders through it.

She’s a good fit if:

  • You’re a founder deciding whether and how to share the seat, and you want to talk with someone who has actually done it
  • You want to explore a shared-leadership or co-CEO model and don’t know how to introduce it to your team or board
  • You want to talk honestly about ego, identity, and holding the work without clutching it
  • You’re thinking about succession and want it to strengthen the organization rather than destabilize it

Connect with Andrea!

Book a chat Email

About Andrea Chen

Andrea Chen founded and led Propeller for 15 years, growing it into a New Orleans institution for entrepreneurs building businesses as catalysts for change. She’s also spent years doing the quieter work of learning to hold her identity as her own — which, it turns out, made her a better leader and a better partner. She no longer checks in on Propeller, and she means that as the highest compliment.

Work with Andrea
Take what’s helpful, leave what’s not, and make it your own.
Subscribe For More

More Articles & Resources You’ll Love

Helia’s Social Contract
We keep all Helia articles and resources free because, in the world we want to live in, people share generously and we all feel less alone! If anything in our library helps you, pay it forward — share an article, recommend a contributor for our Library, and when you need support, hire one of our brilliant Collective members.