Difficult Conversations: Why They Matter & How to Recognize When You Need One
MONTHLY NEWSLETTER | March 2025
Be honest, have you ever put off a conversation you knew you needed to have? Perhaps with a team member whose performance was slipping, a colleague whose behavior crossed a boundary, or even with yourself about a career path that no longer feels authentic?
If so, you're not alone. In my coaching practice, I've found that even the most accomplished executives struggle with difficult conversations. So many of us avoid them! In fact, most of my clients cite this as one of their biggest challenges.
In my former HR leadership roles, I had countless discussions with leaders who came to me frustrated with a team member’s performance, only to find out that they had not discussed this with the employee. How would you feel if you were that employee?
Committing to handling difficult conversation in a timely manner is probably the biggest time-saving hack you can develop as a leader!
So this month, I'm launching a three-part newsletter series on difficult conversations. In this first installment, we'll explore why these conversations matter and how to recognize when one is needed.
WHY DIFFICULT CONVERSATIONS MATTER
Difficult conversations are essential because they:
Bridge gaps in understanding: They bring to light different perspectives that may be causing friction or misalignment.
Set clear expectations: Whether this is what you expect from your employee or what your boss expects from you—do not operate from assumptions.
Build authentic relationships: True connection requires honesty, even when it's uncomfortable.
Create necessary change: Many improvements—in performance, processes, or culture—begin with a conversation no one wants to have, but everyone is grateful for at the end.
Reduce stress long term: While uncomfortable in the moment, addressing issues directly eliminates the ongoing stress of avoidance and its pernicious accumulation of frustration.
Demonstrate leadership: Your willingness to engage in difficult conversations sets the tone for your entire team demonstrating the proverbial “leading by example.”
Still not convinced? Research shows that the stress of anticipating a difficult conversation is typically far worse than the conversation itself. As one client reflected, "I spent 3 months dreading a 5-minute conversation that actually went very well and strengthened our working relationship."
WHY WE AVOID DIFFICULT CONVERSATIONS
Even as successful leaders, we often find reasons to put off important conversations:
Fear of negative consequences: Will this damage my relationships or reputation?
Concern about vulnerability: Will showing my true thoughts make me appear less confident or capable?
Perfectionism: What if I don't handle the conversation perfectly?
False harmony: Sometimes we convince ourselves that keeping quiet preserves relationships, when in reality it erodes them from within.
THE COST OF AVOIDANCE
When we avoid necessary conversations, we pay a significant price:
Living inauthentically: Each avoided conversation represents a moment where we choose external expectations over internal truth.
Increased stress: Unresolved issues consume mental and emotional energy, even when we're not consciously thinking about them.
Declining relationships: Without honest communication, trust erodes and misunderstandings multiply.
Lost opportunities: Some of the most growth-producing moments come from conversations we'd rather avoid.
As one executive I work with discovered: "The conversation I avoided for a year took ten minutes and would have saved me countless hours of stress and a project that went completely off track."
HOW TO RECOGNIZE WHEN A DIFFICULT CONVERSATION IS NEEDED
Sometimes, our avoidance is pretty much second nature, and can prevent us from realizing that it’s time for a chat. You might need to have a difficult conversation when:
You notice recurring thoughts about a situation or person—When your mind repeatedly returns to an interaction or issue, it's often a signal that something needs to be addressed.
You're experiencing physical or emotional symptoms—Tension, anxiety, irritability, or fatigue can be indicators that you're carrying the weight of an unresolved issue.
You're avoiding someone or something—If you find yourself steering clear of certain meetings, topics, or people, ask yourself what conversation you might be avoiding.
You notice changes in your behavior or performance—Are you less engaged, less creative, or less patient? This could be the result of unaddressed issues.
Your values feel compromised—When you're not speaking up about something that matters to you, you may feel a sense of misalignment with your core values.
You sense relationship deterioration—If trust, respect, or connection is declining in an important relationship, a difficult conversation might be necessary to restore it.
COMMON DIFFICULT CONVERSATIONS FACING LEADERS
Not sure if you’re avoiding any conversation? Here are common scenarios we can encounter at work, do any of these resonate with you?
Setting boundaries with colleagues who expect 24/7 availability
Declining opportunities that don't align with your values or vision
Addressing performance issues with team members, especially those you like personally
Negotiating for what you truly want rather than what's expected
Having authentic conversations about work-life integration
Expressing disagreement with senior leadership
The most successful leaders I've worked with have mastered the art of having these conversations promptly and authentically.
THIS MONTH'S REFLECTION QUESTIONS
What conversation have you been avoiding that, if addressed, could significantly improve your work or life?
What's the real fear behind your hesitation?
What's the cost of continuing to avoid this conversation?
Which physical or emotional signals might be telling you it's time for a difficult conversation?
Remember, your willingness to have difficult conversations is directly related to your effectiveness as a leader and your fulfillment as a person. Each conversation you've been avoiding represents an opportunity to live more authentically and lead more effectively.
As always, I'm here to support your journey toward purposeful leadership.
With appreciation,
COMING NEXT MONTH
In our April newsletter, we'll explore "How to Prepare for a Difficult Conversation," including specific techniques to clarify your intention, manage your emotions, and structure your approach for the best possible outcome.
"The single biggest problem in communication is the illusion that it has taken place."
-George Bernard Shaw
