Evolv3 Consulting
About Services Leadership Insights Resources Coaching Corner
Login
← Back to all posts

Find Success in Difficult Conversations

Dec 09, 2024
Share to…
Share

When you hear the word "leader," what comes to mind? That title can have countless meanings, but our team defines it uniquely.

A leader is someone who influences others.

Think about influence – the responsibility and the scope. It might be an executive driving a company or department toward ambitious goals and building strong cross-functional relationships. It could also be the team member navigating shifting scopes and deadlines with colleagues they don’t manage – but do have influence with. It could also be the caregiver negotiating with a rambunctious toddler or an independent-spirited, sharp-tongued pre-teen.

Influence happens everywhere. And that means, in some capacity, we’re all leaders.

At some point every leader must deliver unpopular news. No leader escapes this task, but few of us are trained in the art and science of it. As frequent recipients of unpopular news, we know it’s rarely done well, but unless we purposely train to do better, we’ll continue the trend. 

You’ll notice that I didn’t say “bad news.” I’m deliberately using “unpopular” because the word “bad” has an emotional weight that’s entirely unnecessary. Often, we rattle ourselves by recalling dramatic reactions to bad news we’ve witnessed or experienced. 

Let’s be clear. Navigating these conversations expertly has nothing to do with your ability to sugarcoat, appease, or dance around the hard part. It has everything to do with understanding how best to prepare, deliver, and reflect those unpopular bits of news. Let’s dig deeper into those three stages.

  • Preparation: How to set yourself up for success.
  • Discomfort: Understanding your emotional responses and how they impact others.
  • Reflection: Why review and reflection are critical for growth.

Preparation is key. 

You’ve likely heard me say, “I don’t have a detailed bone in my body.” While structure and detail might not come naturally to me, preparation is my secret weapon I use to maintain an easy-going demeanor. My leadership style – quick thinking, big-picture focus, and unflinching directness – requires thoughtful preparation and prevents my strengths from becoming my pitfalls.

Leadership requires preparing not only for your message but for the uppercut—the challenging questions or unexpected reactions.

Let me share a story. There was a leader I worked with who epitomized detail orientated, was analytical to the core, and read every pre-read of any size and came armed with sharp questions. I often watched as confident people walked into a meeting, deck in hand, ready to kick a proverbial can down the road on a missed deadline or budget overrun with a padded presentation and the hope to avoid scrutiny. No chance. Within moments, this leader would zero in on the very thing the deck’s author hoped to avoid. I watched it happen – over and over again. It was a masterclass in the pitfalls of unpreparedness. I would watch the deck’s once proud owner stammer through responses, unable to address any follow-up. The room would grow tense. The clarity wouldn’t come. It was uncomfortable to watch, but it was always a front-row seat to the benefits of being prepared and the efficiency that could be added to the process by influence. 

 

Do you run to or toward confrontation?

We all know one thing about ourselves – how we feel about debate and confrontation. Some of us thrive on it and others avoid it like the plague. Neither approach is inherently wrong – it’s just how we’re wired. Understanding how your wires are wired, that’s crucial.

We can’t control how others react to our words, but we can control the intention and delivery behind our message.

Personally, I’m an “anything to tick things off the list” type. I thrive on action and resolution, so I’m tempted to dive into tough conversations immediately. I’ve learned that my drive for closure, though, can sometimes overshadow others’ needs to process and reflect. It’s emotional intelligence that informs that lesson. I know that, if I’m not mindful, my urgency can come across as dismissive, even when my intention is progress. My sense of accomplishment in “solving the thing” can inadvertently dismiss others’ emotions, making me seem insensitive.

This awareness is where true leadership shines.

 

Make review a powerful new habit.

I firmly believe in the power of review and reflection. After a challenging conversation or the conclusion of a business transformation initiative, reflecting on the experience is a powerful way to grow. I consider myself a forever student – especially as a coach – learning new ways to lead and grow every day.

Reflecting on challenging conversations – what went well, what didn’t, and why – is a non-negotiable step in growth.

Try it and see what results. After your next challenging conversation, take a moment to reflect and consider how the situation unfolded. Be intentional and consider every aspect: the issue at hand, its root cause, the stakeholders involved (both intentional and unintentional), the outcome, and your sentiment a few days later. It’s this last element that is often overlooked. There is immense power in taking a step back to observe how the parties are interacting once the initial intensity has subsided.

What would change if you made a habit of it? I think you’ll find it a quick way to change persistent unhelpful habits.

Consider how this practice improves a thorny issue in youth sports – parents and their gametime commentaries. During a recent parent meeting for my daughter’s team, the director shared their “24-hour rule.” The rule requires those in a child’s life to wait a full day before discussing a particular game with coaches. It’s brilliant. In that time, emotions settle, fresh perspectives emerge, and everyone is in a better position to think critically.

 

I’ve made a concerted effort to apply this rule day to day. Although I’m naturally inclined to address things head-on (that is, “Red Needs” as informed by my Birkman results), I’m finding the pause significantly improves my ability to navigate complex situations. It’s not easy, but tools like a notes app and voice memos help me channel and organize my inevitable initial thoughts. I’m not setting out to change my personality. I’m setting out to learn mechanisms that take strengths into account and yield an even more effective leader. 

 

Yet, what’s inevitable will still happen.

Leadership isn’t about avoiding conflict; it’s about managing it effectively. In fact, leadership isn’t about perfection. It’s about preparation, self-awareness, and a commitment to continuous improvement.

While challenging conversations are inevitable, they don’t have to be overwhelming. I’m inspired by the genesis of a framework called “Restore Harmony through Conflict Management.” It’s a concept rooted in minimizing stress and fostering understanding. When we make a habit of managing conflict well, we reduce stress for ourselves and create healthier, more effective environments for everyone around us.

 

What’s your approach?

Challenging conversations are part of every leader’s journey. I’d love to hear what strategies have helped you navigate these moments effectively or, if you’re still honing this skill, what one area you’d like to strengthen.

Drop a comment below and let’s start a conversation about how we can all grow as leaders. Vulnerability is welcome here. Growth starts, after all, with being honest about where we are and where we want to go.

You’ve got this. Remember that when you face your next challenging conversation.

Was this post helpful? Share your feedback. 

Responses

Join the conversation
t("newsletters.loading")
Loading...
Mapping the Invisible Org Chart
The Politics of Progress   Author: Onika WilliamsRead Time 5-min | Read post online You leave the meeting thinking alignment happened. The strategy was solid, concerns were addressed, heads nodded around the room, and nobody openly pushed back. But then within 48 hours, the energy changes. Responses slow down, a stakeholder suddenly “needs more time,” and a decision – one that sounded settled ...
Conflict Without Casualties: Why This Still Feels Hard
  Author: Onika WilliamsRead Time 4-min | Read post online I wrote about conflict last year – how it builds trust, how it surfaces what’s real, and how avoiding it slows everything down. You read it. You got it. You probably even agreed with it. And still… here we are. Because the issue isn’t whether you understand conflict.It’s how you’re showing up when it actually happens. You Can Feel It. ...
Why Great Leaders Struggle At Home
The leadership you measure at work often goes unexamined at home. Author: Onika WilliamsRead Time 4-min | Read post online Some of the most respected leaders I know struggle the most at home. Not because they don’t care.Not because they’re bad partners, parents, or friends.But because the leadership they practice all day at work often disappears the moment they walk through their front door. T...

Evolv3 Consulting

Every week, you'll find insights to inspire and empower you as a leader. Put these actionable strategies, personal growth tips, and the latest in leadership thinking to use. We want to see you lead more effectively and with greater impact.
© 2026 Evolv3 Consulting, LLC. All rights reserved.
About Us Speaker Request Contact Us Terms and Conditions Disclosure Agreement Privacy Policy

Join Our List

Get actionable insights to help you grow as a leader!

By submitting this form, you're agreeing to receive marketing messages from me to the phone number provided above. Data rates may apply. Reply STOP to opt out.