Solopreneur Networking: Navigating Difficult Conversations

This event will change the way you communicate about your business!  

When it comes time to address a difficult issue with a client, do you find yourself hesitating or avoiding the conversation altogether?

Whether it’s asking for payment, pushing back on scope creep, or addressing a misunderstanding before it damages the relationship, many solopreneurs find themselves navigating high-stakes conversations they were never trained to handle.

Katie Kolon*, founder of Mutual Ground Strategies and a professional mediator, will lead a practical session on how to approach these conversations clearly and constructively. Drawing on her experience facilitating difficult business conversations, Katie will walk participants through a framework for preparing for and navigating moments when expectations, boundaries, and working relationships are under strain.

Attendees will meet at 9:00 AM in the Guild Suite** for coffee, light bites, and open networking. We’ll start the program at 9:30 AM.

Participants are encouraged to bring a real situation they are currently navigating in their business. During the session, Katie will guide attendees through a structured process for preparing for difficult client conversations, with opportunities for small-group discussion and reflection.

We’ll close out the session at 10:30 AM and continue with open networking until 11:00 AM so attendees can continue the conversation and connect with others.

After the event, the ICA management is kindly offering tours of the building.  Do you think you may want to find space outside your home office?  The ICA has affordable space available!  Get a tour of this historic building see first hand their available office spaces.  

This event is open to all interested attendees.  Members of the Uptown Chamber of Commerce receive discounted pricing.  Attendees are asked to come prepared to work on actual communication from your business that you'd like a second set of eyes on.  This could be phrasing from a standard service contract, an email exchange you're unsure about, or any tough piece of client communication that feels out of sync with your intention. During the event attendees will work in small groups to edit and test phrasing on one another.  The Chamber will collect these samples ahead of the event.

*Katie Kolon works with business owners, leaders, and teams to build the communication and de-escalation skills needed to navigate conflict before it derails relationships, stalls decisions, or undermines trust. She is the founder of Mutual Ground Strategies, where she supports small business owners, founders, partners, and teams facing tension, avoided conversations, and relationship strain that makes leadership more difficult than it needs to be. Her work includes conflict coaching, workplace mediation, communication and de-escalation training, and facilitated conversations that help people address challenges directly and move forward with greater clarity. Katie is a certified mediator, mediation coach, and former employment law attorney. She has spent 15 years volunteering with the Center for Conflict Resolution as a mediator, trainer, and mentor, supporting high-stakes conversations where emotions, values, and business relationships intersect. Earlier in her career, Katie worked in cybersecurity and customer success and has held roles across nonprofit, government, education, and research settings. This breadth of experience informs her work with leaders navigating growth, uncertainty, and complex human dynamics.

**The Guild Suite is located in the historic Mutual Insurance Building at 4750 N. Sheridan Road. Built in 1922 as the headquarters for the Mutual Insurance Company of Chicago, the eight-story building later became home to a variety of nonprofit and community organizations. In the late 20th century, a group known as the Guild of Uptown used a suite in the building as a gathering and organizing space for neighborhood meetings and cultural programs. The space became informally known as the “Guild Suite,” a name that has endured as a nod to that period of community activity.