Navigating Difficult Conversations
Ever had one of those chats where you rehearse the whole thing in your head, then your voice betrays you and does that shaky thing as soon as you start? Or maybe, like me, you get the red face (it means you’re not breathing well enough) or the lump in your throat or shaky hands. If you work or deal with people, it’s likely you know exactly what I’m talking about.
Difficult conversations are the brussel sprouts of work. No one’s thrilled about them, but they’re good for you (and your team) in the long run.
I doubt you wake up thinking, “Yes! Today’s the day I have that awkward chat!” But, avoiding tough conversations doesn’t make them go away. In fact, it usually gives them time to fester and grow. Addressing issues early shows you value your people, care about the outcome and aren’t afraid to dig in to keep things on track.
The Emotional Hurdle
Big feelings (think: fear, frustration, defensiveness) can pop up fast. They’re not a sign the conversation has gone wrong; they’re a sign that you care and it matters. The trick? Notice the emotion, take a breath, and steer the chat instead of letting the chat steer you.
Your Gallup Strengths can also play a big role here. If you lead with strengths like Command or Communication, you might find stepping into these conversations comes more naturally, possibly even with some enjoyment? But if your dominant themes are Harmony or Adaptability, you might prefer keeping the peace, making tackling conflict feel like walking through mud. The key is to know your wiring (name it), work with it (claim it), and build strategies to fill any gaps (aim it). Your strengths don’t dictate whether you can have tough conversations, they just give you a map for how you’re likely to approach them and how you’ll feel about the process.
Caring with Clarity
Kim Scott sums it up beautifully in her book and TED Talk, Radical Candour: Care Personally. Challenge Directly.
Skip sugar-coating that avoids the real issue — it’s not kindness if it stops growth (I’ve also heard this referred to as the Sh!t sandwich).
Skip blunt-force “truth” with no care — it kills trust (I love the analogy of delivering the message with a mallet instead of a scalpel).
The sweet spot is honesty delivered with humanity. That’s where trust lives and change happens. The reason to be radically candid with someone is because you care about them deeply.
Making It Real
Susan Scott reminds us in Fierce Conversations: the conversation is the relationship. Avoiding what needs to be said erodes connection just as much as saying it poorly. Susan’s mantra: “come out from behind yourself into the conversation and make it real”. This is a gentle push to show up fully, even when it’s uncomfortable. Because the health of your culture depends on the quality of your conversations.
Rumbling with Courage
In Dare to Lead, Brené Brown calls it “the rumble” - the messy, open discussion where the goal is truth over comfort. In a rumble, clarity is kindness and avoidance is the opposite. Brené’s work reminds us that vulnerability isn’t weakness; it’s the foundation for trust. When you step into a difficult conversation with curiosity instead of judgement, you create space for win:win solutions that stick.
Practical Tips & Tricks to Get Started
- Acknowledge feelings — You can understand and empathise with someone without agreeing.
- Listen like you mean it — Words, tone, body language. All of it and be genuine.
- Manage your own reactions — Pause. Breathe. Then choose your response and keep breathing all the way.
- Stick to what’s real — Facts, behaviours, events. Not assumptions.
- Keep your eye on the goal — You’re here to solve and improve, not to win.
From Awkward to Opportunity
Handled well, difficult conversations can and should actually strengthen relationships. They can boost trust, clear the air and set the stage for better teamwork - this is true in both your work and personal life. So next time discomfort knocks, open the door and you might just find progress standing there, ready to rumble.