Board + Leadership

Help!! with Real Life Scenarios

How do we get "good" at decision-making?

Flip for Helia's take
Hear you! Most tools like RAPID and RACI just assign who decides and stop there.
What actually builds the muscle is a shared set of questions everyone in the org asks before any decision is made, so that EVERYONE is getting better at making decisions.
Read "Make Better Decisions."

Should we keep going?

Flip for Helia's take
One of the bravest questions you can ask.
Closing isn't failure. Sometimes it's the most values-led decision you can make. What if ending well is the ultimate expression of putting mission over everything else?
Read "Good Endings: When Shutting Down Is the Bravest Choice."

My board is overstepping. Do they not realize I run the org?

Flip for Helia's take
This can be silly (napkin colors!) or serious (interfering with personnel).
First, is it a hill to die on? Unless it's the Met Gala, let them pick napkins! If a member is going around you? Set clear boundaries NOW.
Read "Your Board Is Only as Good as Your Relationship With Them."

I need to make some hard decisions. Where do I start?

Flip for Helia's take
Leadership is hard - full stop.
There's no right or wrong, and no way to know what will come. What you CAN do: gather the people and numbers that give you an honest picture and lay out ALL the possibilities — even the scary ones.
Read "The Organization Doesn't Matter. The Work Does" for the questions to ask yourself.

My Board Chair feels more like an obstacle than an ally.

Flip for Helia's take
Delicate AND critical!
Start by creating shared expectations — what do they want to hear, how often, and how? What metrics matter? Then nurture it: a biweekly 30-minute coffee goes a long way. As you execute on what you've agreed to, trust builds.
Read "Your Board Is Only as Good as Your Relationship With Them."

I'm overwhelmed.

Flip for Helia's take
Been there! We all have.
The best path is asking for help — a board member, a coach, a peer, even AI! Get everything out of your head and onto paper. Be honest about what's there. And then bring someone in to help. Nobody can or should do this alone.
Read one leader's story in "I Want to Love My Job Again."

My board is disengaged. I can’t even get folks to respond to emails!

Flip for Helia's take
Common AND frustrating!
The best place to start is one relationship at a time. Coffee, a walk, really listening for what they care about and where they can help. Everyone has their own specific genius. Make it easy for them to use theirs.
Read "Your Board Is Only as Good as Your Relationship With Them."

I'm a new leader just starting in my new role...

Flip for Helia's take
BIG moment! (A friend once described it as the first few seconds of an Easter egg hunt — possibilities everywhere!).
Start with relationships. Be intentional, honest, curious. Gather from people at every level; find the influencers AND the doers. The wisdom is already in the room.
Read "Your People Already Know."

I'm transitioning out of my leadership role.

Flip for Helia's take
Transition is such a beautiful moment of opportunity!
One phase is ending AND new possibilities are opening — for you and for the org. Doing this intentionally, with grace and an abundant mindset, sets everyone up for what comes next.
Read one leader's story: "Other Lives To Live: When It's Time to Step Down."

Things feel tense... and no one is really saying anything.

Flip for Helia's take
So real — and hard to name!
Sometimes it's someone saying something sideways, sometimes it's the vibe in a meeting, sometimes it's just a feeling in your body that something's off. The move is to get curious before you get defensive — and to create enough safety that people can actually say the thing.
Read "Tell Me More Words."
Two emails a month — a real human’s story and a tool to use the next day.
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Ready for help?

a man smiles outside Adam Rubin Developing New Double/Triple Bottom Line Ventures Founder. Builder. Operator. Adam Rubin scales mission-driven ventures from idea to tens of millions of dollars.
A woman poses for a photo Claudia Caballero Leadership Transitions Claudia stepped down while she was ahead and she helps other leaders do so, too.
a woman smiles in black and white Nicole Pollock Strategic Planning Nicole has led the transformation and strategic growth of four organizations, managing operating budgets from under $1 million to $700 million, and led teams ranging from 3 to over 3,000.

Want to talk to someone who’s been there?
These folks have done this work inside orgs like yours.

All Board + Leadership Articles

Story Other Lives to Live: When It’s Time to Step Aside A Helia Member Story on Stepping Aside Gently
Claudia Caballero with Claudia Caballero
Resource Toolkit Claudia’s Stepping Aside Toolkit A guide to leaving well — with intention, clarity, and a plan that honors what you've built.
Claudia Caballero with Claudia Caballero
Resource Toolkit Mike’s Decision-Making Toolkit Everything you need to think through decisions — and build the muscle across your whole org.
Michael Chae with Michael Chae
Article Make Better Decisions How to help everyone in your org ask the questions that lead to better decisions
Michael Chae with Michael Chae
Resource Toolkit Nancy’s When To Get A Coach Toolkit How to find the right coach for you
Nancy Fournier with Nancy Fournier
Article When To Get a Coach On what becomes possible when you're not carrying it all alone
Nancy Fournier with Nancy Fournier
Article Your Board Is Only as Good as Your Relationship With Them Why a healthy, productive board starts (and ends) with one thing
Nancy Fournier with Nancy Fournier
Article Your People Already Know The Discovery360: a strengths-based approach to finding out what's really happening in your organization
Helia with Helia
Story Build Something Worth Belonging To A Helia Member Story on how to build an organization people fight to keep alive
Timothy Koide with Timothy Koide
Story Good Endings A Helia Member Story about when shutting down the org is the bravest choice
Katya Fels Smyth with Katya Fels Smyth
Story I Just Want to Love My Job Again A Helia Member Story on why you don't have to carry everything alone
with Anonymous
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.