Authenticity Never Retires
For more than 30 years, Kitti Lile helped executives navigate change, find their authentic voice and lead with confidence. Today, as one of The Osborn’s newest residents, she’s embracing a transition of her own — one grounded in lifelong learning, family and the belief that every new chapter begins by staying true to yourself.
You’ve helped leaders — from coal mines to corporate boardrooms — find their authentic voice. What drew you to executive coaching and speechwriting, and what’s kept you passionate?
I’ve often had an intuition about an individual wanting to know how to be more skillful at how they are presenting themselves or demonstrating competence. Executive coaching is focused on helping people build skills beyond their current capability. When asked if I might be a helpful resource, the question often became the beginning of an ongoing conversation in a coaching relationship.
From there, my career naturally evolved from training to executive development to coaching and speechwriting because they’re all rooted in relationships. People came to trust that my only agenda was helping them succeed and once my reputation spread the work kept finding me.
How is leadership evolving in a changing work environment?
One thing I’ve found fascinating is how our definition of leadership has changed. Earlier in many careers, leaders were rewarded for command-and-control styles. Today, authenticity, transparency and humility matter. When I coach leaders, I never criticize how they lead. I assure them the skills they are demonstrating today had served them well at a previous time. My role is helping them develop the next set of skills for today’s environments.
What advice do you find yourself giving most often, not just to executives, but to anyone trying to navigate transitions or build relationships?
Real change starts with knowing yourself. Sometimes people simply haven’t received feedback that could help them grow personally or professionally. I believe every transition deserves an ending before a beginning. Our culture tells us to move on immediately, but I believe people need time to reflect on what they’re leaving behind before they have the emotional energy to embrace what’s next.
Are you still consulting?
When I was living in Seattle, I did pro bono work. I’m not running a business anymore, but if anybody calls me, I’m happy to help. I love to see people succeed in ways they never believed they could. When a person who was terrified of speaking in front of a group can comfortably stand in front of 600 people and talk with poise and confidence, it’s absolutely thrilling for me.
What are some tips for building that confidence?
Well, this is my mantra. There’s no such thing as talking to a group. You can only talk to individuals in the group. If there’s an audience of 60 people, there’s 60 relationships with you in that room. Talk to those relationships one at a time. When you take a breath, move your eyes from one face to another. And before you stand up and speak, pick three words you want people to use to describe you after you speak — and don’t say ‘smart.’ Think big words, like ‘insightful.’ This will help you stay grounded.
I don’t teach ‘public speaking.’ I teach people how to have a conversation with a crowd.
After such a rewarding career, you chose to make The Osborn your home. What led you to that decision?
As I was thinking about the next chapter of my life, I visited numerous communities in Seattle but none felt right. They were vertical, institutional and disconnected from the outdoors and I’m a walker.
Then a friend mentioned a community on 36 acres in Mystic, which suggested senior living could look very different on the East Coast. I started researching communities near my daughter and her family and discovered The Osborn. My daughter and I walked in, and I knew it was my place. It felt warm, relaxed and welcoming. It’s hard to define, but you know it when you feel it.
Some people assume moving to a senior living community means slowing down. How has Independent Living allowed you to continue pursuing your interests and staying engaged?
There are so many opportunities to engage and learn here. One of my favorites is our News & Views on Monday mornings. It’s resident-run with resident speakers on topics such as the economy, scientific news and current legal issues. I’m so impressed by the caliber of talent and expertise in this community.
Another wonderful opportunity here at The Osborn is the ability to remain connected to the outside world. Many residents moved here from the area and maintain their friendships in the greater community. There’s a sense of activity and mobility in our environment that I find very appealing.
What excites you most about this stage of your life, and what would you say to someone who might be considering a move, but isn’t sure they’re ready?
I’d ask them how ready they are for freedom from home maintenance and cooking meals. We have resources available to us at all times for any circumstances — storms, snow, power outages and three restaurants.
I’d ask them how ready they are to move one last time with no need to move again. As we age our needs change, and having a continuum of care is wonderful.
I’d ask them how easy it is to find intellectual stimulation in their current circumstances and assure them that should they move to The Osborn they will have constant access to intellectual learning and activity with classes, outside speakers and a library club.
I’d ask them how often they anticipate kindness in their interactions with people. The Osborn has a culture of kindness. Residents are kind with each other. We have nice relationships with the staff, we laugh, talk and everyone is contributing to the well-being of our community. We have a group, the Women’s Guild, that meets once a month. I spoke to the group recently about my career. I began by thanking them: ‘I’ve always felt so welcomed… I could never have made this transition so easily without all of you.’
You recently returned from a trip to Bhutan, what’s next?
Africa in 2027.
