Getting to the Heart of Difficult Conversations

Written By: Jim Grout

Like many leaders, I always found it challenging to have the “difficult conversation” with staff members when it was needed. But over time I got better at it when I discovered the key to getting to the root of the issue. I showed up with heart. That may sound polyannish but here’s how it worked.

Since our beginning, my hope was that we would be a mission driven organization and a workplace culture where people could have a sense of purpose, do good work that they enjoyed, grow their careers and make a salary to support themselves and/or their families. When these things happen, people are generally happy with their work. Engaged and happy staff make for engaged and happy customers. It’s not just a good formula internally but a good business plan for success.

So my first question when having a difficult conversation with a consistently challenging staff member was… “Are you happy here?” This rather disarming question seemed to cut to the heart of the matter and shifted the conversation from me to them and inevitably to a deeper discussion about what wasn’t working for them. Life is short, people have options and they should be encouraged to pursue what truly makes them happy. Whether that includes High 5 or not is up to them to decide. 

Are there aspects of your work culture that bring you joy, purpose or connection? What are they?

Putting off a difficult conversation?

Sometimes, the most powerful way to navigate a difficult conversation is to start with a simple question and a genuine willingness to listen. When we approach challenging dialogue with curiosity and compassion, we create space for deeper understanding and meaningful connection.

Want to put this approach into practice? Join us for our Navigating Challenging Dialogue Essentials workshop or chat with us about a private session to help build the skills to approach tough conversations with confidence and care.

Ready to Lead by Example?
Bring these leadership philosophies to life.

Pick up a copy of Jim Grout’s When In Doubt…Give Them Your Heart. It’s packed with real-world stories and reflection questions designed to help you connect, empower, and lead by example in your own community.

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