In my years of experience in people management and senior leadership teams ( it amazes me that I get to say that because in my mind I am still 25), one big challenge consistently blocks the way and that is navigating what is perceived as a difficult conversation. Most likely, that means it is an important conversation. These moments are critical for fostering clarity, addressing issues, and driving growth, yet they remain a stumbling block for many leaders time and time again.
Fear
Why? Because the fear of the conversation often looms larger than the conversation itself. We build it up in our minds, imagining the worst possible outcomes, and let anxiety paralyse us into inaction. The thing is, postponing these conversations only compounds the problem. I’ve seen countless situations where delayed conversations have spiralled into tangled HR messes that are far more challenging to untangle than addressing the issue early on would have been. The cost of avoidance is often much higher than the discomfort of action.
Skill
Think of it this way: Approaching difficult conversations is a skill. And like any skill, it requires practice. For example, during your first run or gym session, you might feel out of shape, make mistakes, or struggle to find your rhythm. But with time and consistent effort, you build strength, refine your approach, and see progress. Strengthening your conversational muscles is no different. You will make mistakes along the way, but each attempt is an opportunity to learn and get better!
Prepare
Preparation is key here. Don’t treat these conversations as an afterthought or tack them onto the end of a meeting. Instead, value them. Set aside dedicated time, create a focused environment, and approach the discussion with the respect it deserves.
Feel the discomfort
Allow yourself to be nervous or anxious. That’s OK. As Susan Jeffers famously said, “Feel the fear and do it anyway.” That discomfort is a sign that what you’re about to do matters. Lean into it, and remember that your courage can foster trust, clarity, and progress.
Ultimately, difficult (important) conversations are a gateway to stronger teams, better relationships, and more effective leadership. The more you face them, the more capable and confident you’ll become. So, next time you’re tempted to avoid an important conversation, remember: the fear is temporary, and the more you practice, the better you’ll get.