How Women Leaders Are Redefining Success Together

written by
Barbara O Stephenson

Last week, I went on a retreat with my women’s business group, the Women’s Presidents’ Organization (WPO). The WPO champions the exchange of ideas among forward-thinking women at local, regional, and international levels. This has been a blessing for me, after years of exploring different CEO peer organizations like Vistage or CEO Roundtable.  You know the saying ‘it’s lonely at the top’ ? Well that resonates deeply with me, as often, business owners like myself can only confide in peers about the highs and lows of entrepreneurship. Employees may not always grasp the stress of a bad day, looming risks, or the desire to occasionally disconnect. Despite women closing the educational gap—representing over half the workforce and earning 60% of advanced degrees—men still lead in confidence, leadership roles, and the ability to fail upward. Which is why I really wanted to join a group of women leaders for when I need to show my vulnerable side.

I mean there are certainly men who lack confidence, who worry about looking the part, or who struggle to keep the status quo everywhere. It’s just more common to find the threads of running a business, trying to be everything culture expects of us, and keeping up with the mental load of a household with other women. So yes, we discuss nannies to help us, HRT, we talk about techniques to find balance, lend a sympathetic ear, or give a sharp verbal slap (with love) when we need it. And yeah, sometimes we talk purses or shoes like men talk business cards (I joke).  And it’s crazy empowering when a fellow woman CEO starts talking about how to fix a supply chain issue or starts to dig into EBITA and financial analysis. 

At our retreat, our coordinator highlighted a key difference between corporate and WPO retreats: the focus isn’t necessarily on strategizing but on connecting personally with peers, should that be your need. The goal isn’t to come out with a strategy unless you want one. I like this low pressure approach because if you simply need a break and want to connect on a more personal level with your peers, you can do that. However, I found myself asking business questions more often than not about corporate structure, pre-build manufacturing, and employee empowerment during our breaks, hikes, and meals. We did an all day training about Traction or the EOS system, I’ve been implementing some of those learnings but that’s another blog post. 

The women in my San Francisco chapter are amazing – each of us have a different businesses and yet we are all engaged in the same purpose to thrive and help those around us to be the best that they can be. We did end the retreat with a discussion of 2024 goals and what we’d like help on from the other members.  Which is why I joined the WPO and love it.  Because we all want to be held accountable and have someone yell if they see a pitfall ahead.

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