Spotlight: Winter Wheeler

Mon, Feb 16th, 2026 | by Miles Mediation and Arbitration | Get to Know our Neutrals | Social Share

Winter Wheeler is a former top civil litigator who has made her niche as an expert mediator and arbitrator. She is sought out for her unique, compassionate, and successful style of handling complex matters that involve a diverse range of cultures. We recently spoke with her to learn more about her work, and how she approaches working with clients.

What types of cases do you handle as a mediator at Miles?

My mediation practice focuses primarily on civil litigation, with an emphasis on personal injury, wrongful death, trucking and transportation cases, premises liability, employment disputes, and sexual assault. I regularly handle cases ranging from early-stage disputes to matters deep into litigation, including cases involving multiple parties, layered insurance coverage, and emotionally charged facts.

Because of my background working closely with both plaintiffs’ and defense counsel, I’m comfortable navigating cases where the path to resolution isn’t obvious at the outset.

Have you seen any interesting trends developing with those cases that attorneys should be aware of?

Yes, several. One notable trend is that mediations are happening earlier, often before full discovery is complete. That can be efficient, but it requires attorneys to be especially clear about what information is truly needed to move the needle versus what can wait. Having a strong rapport and a strong level of trust in opposing counsel is required.

Another trend is an increase in valuation gaps driven by uncertainty — whether that’s jury unpredictability, evolving damages models, or coverage concerns. I’m also seeing more cases where the biggest barrier isn’t the numbers, but misaligned expectations, emotional fatigue, or breakdowns in communication between the parties. Successful mediations increasingly hinge on addressing those human dynamics as much as the legal ones.

What’s your advice for newer attorneys, or those less experienced with mediation? What can they do to improve the likelihood of settling?

First, prepare your client for the process, not just the outcome. Clients who understand what mediation is (and isn’t) are far more flexible and productive participants.

Second, come in knowing your case, but also knowing your risks. Be ready to articulate both clearly and realistically. Settlement momentum builds when counsel can speak candidly about strengths and vulnerabilities.

Finally, stay open. Mediation works best when attorneys view it as a problem-solving exercise, not a miniature trial. Being willing to explore creative options, phased resolutions, or non-traditional structures can make the difference between impasse and agreement.

What unique skills do you bring to the table as a mediator? Why do clients rely on you again and again?

Clients often tell me they value my ability to build trust quickly, ask the right questions, and keep everyone engaged even when discussions get difficult. I’m direct but respectful, strategic without being rigid, and very attuned to the interpersonal dynamics that can derail negotiations if left unaddressed.

I’m known for being thoroughly prepared, responsive to counsel, and genuinely invested in helping parties reach durable resolutions. Because I’ve spent years working with attorneys on both sides of the “V,” I understand the pressures each side faces and I use that perspective to help bridge gaps and keep conversations moving forward.

Anything else new clients should know about you?

I take the role of mediator seriously. Parties are trusting me with significant decisions, real consequences, and often a great deal of emotional weight. I approach every case with care, neutrality, and respect for the process. I’m also collaborative by nature.

I view mediation as a partnership with counsel, not a performance. My goal is always to create an environment where parties feel heard, informed, and empowered to make thoughtful decisions whether that leads to resolution on the day of mediation or lays the groundwork for it shortly thereafter.

To schedule a mediation with Winter, click here.

ABOUT MILES MEDIATION & ARBITRATION

Miles Mediation & Arbitration is shaping the alternative dispute resolution (ADR) industry with our comprehensive professional services model that combines the expertise of our highly skilled, diverse panel of neutrals with an unparalleled level of client support to guide and empower parties to fair, timely, and cost-effective resolution regardless of case size, specialization, or complexity. For more information, please call 888-305-3553 or email support@milesadr.com.