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Conversations with the Inspiring Chaili Trentham

Today we’d like to introduce you to Chaili Trentham.

Thanks for sharing your story with us Chaili. So, let’s start at the beginning and we can move on from there.
My background is in higher education and I have my Masters in Leadership, with an emphasis on Leadership Development. After spending several years working in a leadership position designing training and developmental programs on a university campus, I left to pursue other projects in leadership while still teaching in the Leadership department. Coffee on Leadership was a natural way for me to continue to design conversations around leadership in that time. It isn’t so much a brand, but rather my personal philosophy on accessibility of leadership development–I believe everyone is a leader in some capacity because we have impact and influence in our networks. So, we all need to journey with a growth mindset looking for opportunities to learn and develop ourselves in our personal and professional lives. When we do this, we are more aligned, happier, and healthier.

I grew up working on weekends for my grandparents at a farmers market and learned a foundation of business principles from them, but on a much deeper level learned the importance of focusing on the people you serve through your business and leadership. When our commitment to our mission has purpose and value rooted in our community, every decision we make has exponential impact. When I began to dig into the lessons I learned from my grandfather, the farmer, I discovered that the leadership paradigm is no different than the ecosystem of an organic farm–when we want success for the whole, we start with each individual part and tend to the roots first. So organizationally, we must care for every individual in our span of influence and recognize that responsibility runs deep. In our faith communities or friendship circles, this symbiotic relationship in the development of others is no different. I get the opportunity to live some of this out by developing people at all levels of organizations, and I love that the impact spreads because they take that knowledge and wisdom and pass it along. Leadership is communal and should highlight how unique individuals come together and engage well on behalf of a greater goal.

We’re always bombarded by how great it is to pursue your passion, etc – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
Imposter syndrome, comparison, projects/events that just don’t work–there are always struggles for young entrepreneurs. My advice is to always keep moving forward, even if you don’t know for certain if it’s the right decision or direction. I try not to be paralyzed by fear of the unknown and move myself from a space of “what ifs” to “regardless of outcomes, what can I learn from this?”

In a huge place, like LA, there are a hundred other people with a similar vision or business plan. For me, those are people to learn from and study, support, empower, and join into conversation with. I have always loved building up community and being a cheerleader for others and so I built that into what I do. Shift your mindset from scarcity to abundance and know there are big things out there for you too, it might just not be your turn yet–then get back to the grind because hard work and kindness always pays off.

So let’s switch gears a bit and go into Coffee on Leadership story. Tell us more about the business.
My bread and butter is leadership development for businesses and organizations. I design conversations around work/life integration, creativity in your role in the workplace, and how whole leader development can springboard employee experience, but I am most proud of moments when an individual will reach out and talk about how leadership development changed their mindset about their capacity to lead others. For some, it’s just the way I have chosen to reframe the definition of “leader” to include everyone at every level of an organization or season of their business. When we commit to the responsibility that brings, we can dig into the work that needs to be done to better ourselves and the people around us. It’s not rocket science, it’s a commitment to individual growth while recognizing the communal aspect of the leadership paradigm–and I am so proud that my work allows me to create that space for others to engage in conversations with one another that are meaningful.

Do you have any advice for finding a mentor or networking in general? What has worked well for you?
You MUST build a mentoring network that is non-traditional. Get rid of the idea that you have one mentor who you meet with once a week for business advice for the rest of the year and somehow will get promoted along the way, and instead embrace the network of people who pour into your regularly as a constellation of mentors. My mom did not go to college but gave me the best advice when I was pursuing a graduate degree program. I had a boss who shaped what I believe about the integration of work/life balance and gave me some of the best parenting advice when I had two kids under the age of two. I go to friends who work in other industries for feedback on project ideas because my friends in tech know prototyping and failure and resiliency better than I do, and friends in the creative entertainment industry can help me shape stories. We have something to learn from everyone. I even put the women I admire, yet don’t know personally, on my mentor list–Michelle Obama and Sheryl Sandberg have been significant in my leadership journey because of the wisdom shared in their books. I study them and reread them, watch their interviews, and call on those lessons when I need them most. This concept of a mentoring network is one that grows and expands and allows you to be connected. Some people are up close and know every detail of my life and work, where others were mentoring voices for season, but it all adds up in the development of who we are and who we are listening to and learning from. Grow your network, value those individuals, tell them you are learning from them, and don’t be afraid to ask questions of whoever you are sitting across from.

Contact Info:

  • Email:
  • Instagram: @chaili

Image Credit:
Michelle Chaisson

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