A new way to engage

Communicate with clarity, compassion, and honesty.

For many people, hard conversations never actually happen. It feels easier to avoid awkwardness or discomfort, but over time, that avoidance keeps us from feeling fully known and truly connected.

Have Hard Conversations was created to help you move toward action and clarity in situations big and small. Whether you are needing intensive coaching to change your overall relationship with hard conversations, focused coaching on a specific topic or facilitation of a particularly high stakes conversation we are here to help you develop the skills you need to stop avoiding and start engaging.

Check out our offerings below.

Let's work together

In 4–6 months of ongoing sessions, we’ll work together to:

  • Recognize your default patterns in conflict and where they come from

  • Shift how you interpret tension, disagreement, and discomfort

  • Strengthen your ability to stay present instead of avoiding or escalating

  • Develop language that feels honest, direct, and authentic

  • Practice real-life conversations as they arise

The Coaching Intensive

When it’s not just one conversation, it’s a pattern. If you tend to avoid, overthink, shut down, or leave conversations wishing you’d said something different, this track is designed to help you build a new way of relating to conflict altogether.

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Focused Coaching for a Specific Topic

Whether it’s sharing something personal with your parents, asking a friend to show up differently, or expressing something you’ve been holding back, this coaching track helps you prepare for the conversation you’ve been avoiding.

In 4–6 focused sessions, we’ll work together to:

  • Clarify what needs to be said and why it matters

  • Identify the dynamics at play in the relationship

  • Develop language, structure, and timing for the conversation

  • Practice through scripting and role-play

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Facilitated Conversations

When the stakes are high and multiple people are involved, a neutral third party can help move everyone toward clarity and understanding. 

Common topics include:

  • Divorce or separation

  • Parenting and family dynamics

  • End-of-life care

  • Estate decisions

  • Money and shared responsibilities

Through 3–4 mediated sessions, relevant parties meet with a facilitator to:

  • Share perspectives in a structured environment

  • Identify priorities and points of agreement

  • Work through areas of tension or misunderstanding

  • Develop a clear, mediated agreement for moving forward

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Let’s talk about it

Avoidance isn’t a solution. It’s time we start engaging.

Book a free consultation

  • Our relationship with our kids was always pretty good and easy but as life changed so did all of us and we realized we needed to be different parents to our kids in their adulthood. Aging, money, being grandparents and health were all topics we just weren’t talking openly about and it started to take a toll on our relationships. We needed skills and direction in order to have the kind of relationship we and our kids wanted and John was an invaluable resource. He helped us identify goals and develop language and with his guidance we can now handle these hard conversations on our own.

    — Parents of Adult Children

  • We had done couples therapy in the past and while it helped us understand some of our core challenges and history we were still just avoiding the harder conversations with each other. Everything felt high stakes and black and white so we just kicked things under the rug. John helped us normalize conflict and difficulty and then helped us learn how to have hard and healthy conversations. We will always have conflict but we now have a strategy and plan for how we engage it in. To say it saved us and made life easier would be an understatement.

    — Stressed Partner

  • I avoided conflict, discomfort and hard conversations nearly always. They made me feel nervous, wrong, scared and I honestly thought that “good” people just didn’t have challenging interactions. Working with John helped me identify the core beliefs I had that shaped this cycle which then allowed me to develop a different way of being. John was direct, clear, compassionate and brought expertise and humor that made it all worth while. I can now ask for what I want, say what I’m feeling and communicate more directly and even though it is still hard at times, I do it.

    — Chronic Avoider and People Pleaser

  • Our parents were getting older and we just couldn’t figure out what to do much less how to talk to each other about it. Emotions were high, we were all scared and sad and just wanted to ignore it all. John was able to guide our family in a few sessions to an understanding and agreement about end of life care and money that helped us stay focused on what really matters and stop wondering what if.

    — Family with Stage of Life Conflict

  • I was having a really hard time with dating and had gotten feedback that I seemed closed off or like I wasn’t always being honest. It was true. I didn’t know how to open up or say what I liked or didn’t like. John helped me realize this wasn’t something that people just knew how to do but that it required learning, training, direction and feedback. The coaching sessions with John, especially the role play, allowed me to feel less anxious and more comfortable being myself. Dating and really all of my relationships now feel easier and more real.

    — Anxious Dater

  • I’ll be honest I was skeptical this would help me or even make sense. I had been in therapy before and just didn’t get the results I wanted. A friend suggested coaching with John and I gave it a shot. In just a few sessions the concept of relationships and intimacy being hard by nature just resonated more with me than therapy ever did. John allowed for my annoyance and negativity and never made me feel like I had to become a fundamentally different person to have the relationships I wanted. We focused on how to share, talk and be honest instead of trying to make things good and nice. I have to say I now feel more understood by friends and family and I feel closer to them too. Who knew talking about hard stuff was good.

    — Converted Skeptic