Connecting with Allie Ottoboni

How have relationships influenced your professional development and leadership style?

The best advice I’ve ever received is from my mom (hey, Jan!): "Be gentle with yourself." I remember hearing this as a toddler during a tantrum, a teenager amid high school drama and on and off as an adult when we hit those painful boulders in life. This mantra has been so important because it’s set the foundation for the most important relationship we all have – with ourselves. If we can lead from a place of being gentle with ourselves, it’s so easy to extend that care to others. I’m motivated by leading a team and providing experiences where people feel a strong sense of belonging – that unspoken feeling of, “I’m safe here and my whole self is welcome here.”

On the professional development side, I think the fact that both my parents were public school teachers for a long time really shaped my desire to learn. I am always up for a new course, a new way to approach work, new perspectives, and new voices to listen to. I’m a development nerd because I just don’t think I’ll ever be done learning. I try to tune into what I’m curious about, rather than learning things with a goal of become an expert.    

Do you have any tips for maintaining and building strong relationships?

Really listen to people. I read a great book last year – You’re Not Listening by Kate Murphy (plenty of copies available on eBay!). One of my favorite quotes is:

“Everybody has something going on in their heads, whether it’s your child, your romantic partner, your coworker, a client, or whoever. To listen well is to figure out what’s on someone’s mind and demonstrate that you care enough to want to know. It’s what we all crave; to be understood as a person with thoughts, emotions, and intentions that are unique and valuable and deserving of attention. Listening is not about teaching, shaping, critiquing, appraising or showing how it should be done (Here let me show you, don’t be shy, that’s awesome, smile for Dad). Listening is about the experience of being experienced.”

The concept of being experienced and understood is so profound and so needed. And to listen deeply in our fast-paced world can feel really hard! I am constantly working through this and trying to be better. Listening is a huge way for us to show care and build trust – the foundation for all solid relationships. 

How have you intentionally built inclusiveness into your circles?

I was shy as a kid and was most comfortable staying quiet, not getting called on and was content to just fit in. Even early in my career, I can remember sitting in meetings often feeling like I had nothing to add – or that maybe I would be wrong (and wouldn’t that just be the worst?!). I let insecurity and perfectionism run the show. 

It took me a long time to find my voice and my confidence, but I’ve taken this learning and turned it into something that I love to do – reading rooms (virtual or in person) and tuning into whose voice is being heard, whose voice is occupying too much space, what perspectives might be missed and what’s happening in the room that might not be stated, but is felt. In a gentle way, I try to make space for people who may be feeling quiet, who may not feel that their perspective matters. We have so much to learn from those quieter and often lesser-heard voices. 

What community or communities are you proud to be a part of?

I’m thrilled and proud to be a part of Chief – a membership network focused on connecting and supporting women leaders. I’ve made great friendships, been inspired, felt heard, worked through challenges and felt myself growing through this network. 

I’m also so happy to be in the broad community of philanthropy. There is so much heart, so much good disruption happening right now, and I’m motivated by the people I get to work with, organizations that are doing the work and leaders in the sector who I draw inspiration from. Philanthropy is so flawed, and at the same time, we have such an opportunity right now to reshape it.    

Who’s a Connector that's made a difference in your life?

My sister, Sara, is the ultimate connector! She will find swimming lessons for your kids, connect you with that person you should talk to about your career and pull off a virtual fundraising drive in the same day. She is a powerhouse, a role model, a true friend, a gem.