Mastermind Hot Seat: How Do I Actually Start My Own Mastermind Group??

In honor of the 100th episode – I want to celebrate the idea of community. More specifically, the coming together of like minded people to support, cheer one another on, and hold one another accountable. 

I put out a call a month ago for people to share their coaching questions. Every few shows, I’ll snag a question and will answer it on the podcast as a shorter, more focused episode. The idea is for it to be like a coaching hot seat in a true mastermind — a focused, intentional aiming of attention towards a single person’s issue or challenge. 

For those of you would like my eyes on a question or challenge you’re navigating, you can share at – and thank you to everyone who has taken the leap and left a question for me to answer.  

So to celebrate you all, my listening community, I’m launching my first coaching Hot Seat on the mastermind by answering one of the questions. And I’m starting with a question about community! How meta is that.

This one is from Natasha in Louisville. Thanks Natasha! You downloaded my Mastermind Toolkit and your question was:

This sounds really amazing, and like exactly what I need as a new-ish executive director at my organization. But as a newish person, how do I form one of these magical groups? Where do I go to find other people? How do we decide to be a group? What does this look like in practice? 

So I’m kicking off with this question also because it goes to the heart of where I even got the idea for this podcast. 

My own experience as a nonprofit founder and ED was transformed by my participation in an incredible mastermind of women EDs. That group of fellow EDs was one part of a trio of supports that I believe were responsible for not just the growth of my organization, but my tenure and mental health as a leader.

The trio was my peer mastermind, which I’ll talk about in a moment, a leadership coach, and my mentors. 

They served different roles – my coach was my guide and my expert consultant, which is what i do now as a coach. I had 3 mentors that I met in my early 20s and to whom I turned for thought partnership and guidance. And finally, my Sustainable Sisterhood.  

So, Natasha, here’s what I’d say. 

First, I’m so happy you’re exploring this. You didn’t ask this question – the should you, question- but YES. You should form a mastermind. Absolutely. 

One of the things that struck me about being an ED, which I didn’t expect, was how lonely it could feel some times. How out on a limb by myself I could feel, even as I grew my team and board, and was blessed to have both an incredible team and a board that I worked well with. 

Even with those, there were times when the buck stopped with me – when decisions about compensation or benefits fell on me… when I had to tell my team that we weren’t hiring that person they said they absolutely couldn’t live without… when I was sitting up at 2am going back over cash flow statements to figure out how to scenario plan around pending funding cliffs… 

In those moments, it was my mastermind group – the group of other EDs who just got it – that I reached out to. First, they were out on their own limbs, and there’s comfort in that. 

Second, we all have our zones of genius, and my group of women each had our own. So there was always someone in the group who had tried something I hadn’t tried… mastered something I hadn’t mastered… taken a chance I was wondering if I should take… had the spreadsheet for the very thing I was trying to figure out. 

Ok – so that’s the why. 

Here’s the how. 

First, the way my group came together. We didn’t all know one another. I met one woman at an event and we started having breakfast, I had just had coffee with another woman, and was like – I’m having breakfast next month with Kemi — you should come. We’re going to talk about our upcoming board meetings and spit ball ideas for getting people more engaged. Turns out, Chitra was a WHIZ at getting people engaged! We did that 2 or three times – we spent one breakfast walking through a compensation sheet that I’d started using to bring my leadership team more fully into the budgeting and financial health of our org – and they wanted to know how to start having those conversations. We talked about getting your board chair to back off and let you make decisions.. And after 2 or 3 meetings one of us said: this is magic. Let’s each invite one other ED friend and make this a more regular thing. And so the group was born.

So mechanics: Here are 5 steps and 3 lessons:  

  1. You can start with 1 or 2 people – it doesn’t have to be a full group to start. 
  2. Look for some sort of parity 
    1. This can be whatever feels comfortable for you 
    2. Missions and orgs and sizes were all different – $150K to $1.5M; youth and art… 
    3. Half founders and half took over from founders, so that wasn’t intentional, but was super interesting… 
    4. Artists and lawyers and from finance and from theater 
    5. but we were all within the first 5 years of being EDs and that’s a unique moment
  3. Start with people you know. They don’t have to be friends, but Look for people you talk and share with easily, and people you think you’d trust with your questions, vulnerabilities, wins and failures. 
  4. Name what you’re interested in – Have a breakfast or coffee and introduce the idea of a regular group.  I’d like to start meeting regularly as a mastermind. To share resources, be accountability partners, and serve as sources of support for one another. 
  5. Make the conversations functional from the start – these aren’t just work meetings. These women were with me through the birth of both of my children, and I brought the babies to our breakfasts. We celebrated birthdays, and supported one another through losses… We always broke bread and sometimes shared a drink… and we were friends. 
    1. But at the core, we were there to make one another stronger as EDs. So there was always a practical aspect. We had a loose hot seat – each meeting, 2 or 3 of us got the full attention of the rest of the people in the group. We also left time to ask one another questions – hey Suzy, the roll call at your last even raised $100K. Would you walk us through that? 
  6. Create a container —  Ours grew organically, but I’ve facilitated and suipported the development of a dozen of these in the past five years: set a 6-month time line a revisit after that; create an email chain or Slack workspace just for the group; meet regularly at the same time. 

3 lessons

  1. Be generous – if you have to share, share it
  2. Be abundant – you are not in competition with one another 
  3. Be vulnerable – it only works if you ask the questions you’re afraid to ask and get the help you’re afraid to ask for


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