When’s the Best Time to Have a Difficult Conversation? Now.

Last Updated: Apr 20, 2021 | Executive Coaching, Leadership, Office Communication

Most leaders have at least one difficult conversation on their radar. Whether it’s with an employee, a colleague, or a supervisor, there’s a good chance that you are either anticipating one, putting one off, just becoming aware that one is needed, or, ignoring one — hoping it will go away.

As seasoned executive coaches, we’ve learned the value of addressing a difficult conversation head-on, as soon as you realize one is needed. First, by taking the initiative early on, you avoid letting something fester. Left to simmer for three months, what could have been a relatively calm, focused 15-minute conversation may become a highly emotional defcon-1 event! And working virtually hasn’t made things any easier. The sooner you address an issue, the better. For more, read Arden Coaching’sThe Upside of Having Difficult Conversations.

Second, by taking the initiative to have a difficult conversation, you expand your comfort zone and grow as a leader. Difficult conversations are never easy, but you will become more adept, confident, and effective communicating in tough situations and reaching a desired outcome.

Let’s get ready for a difficult conversation right now. 

1. Prepare… don’t rehearse

Preparation for a difficult conversation is critical. What’s really the problem? How might the person I’m meeting view the situation and respond? What’s my desired outcome (and how do I get there)?

That said, don’t try to rehearse a “script.” You’ll be so busy reciting your lines that you’ll be unable to listen carefully. Also, you don’t know how the person you’re meeting will react or respond. In Shakespeare’s Hamlet, when the actor playing Hamlet speaks to the actress playing his mother, Gertrude, he knows what she’s going to say next. You do not enjoy that advantage.

2. Stay focused on your overriding goal

In the heat and stress of the moment, don’t lose sight of your desired outcome and how you want to be working with this person going forward. That’s all that matters. Scoring “points” may feel good (briefly), but letting your emotions take control and winning arguments for the sake of winning arguments will only muddy the waters, put the person you are speaking to in fight-or-flight mode, and get in the way of achieving what you originally hoped the difficult conversation would accomplish.

3. Certain things matter more in a virtual meeting

Are you meeting virtually? Keep your background clear of visual distractions. Make it clear that you are in a “private” space — don’t address an employee’s issue while your spouse is preparing dinner in the background. Make as much eye contact as possible. In addition, be as specific and focused as you can. Vague, abstract, or conceptual feedback is more difficult to connect with when the meeting is virtual, or over the phone.

4. Commit to clear, unemotional, concrete communication

Just because you want your difficult conversation to be thoughtful, productive, and free of personal rancor, that doesn’t mean the other person wants that — or will respond in that way! People may behave defensively, angrily, passively, or aggressively. They may react with sarcasm. They’ll threaten, they’ll shout, they’ll cry, they’ll become unresponsive. And what are your hot buttons? We all have them. How will you respond when someone pushes one? How will you react to this barrage of unproductive behaviors? 

Keep your message clear and consistent. Stick to concrete, fact-based stories and examples of the issue you are trying to navigate and resolve. Use neutral, moderate language — keep everything, including your emotions, in the “middle.”

Have your conversation NOW

Acknowledge that if this were a simple issue, you would’t need a “difficult conversation” in the first place. So respect the fact that this is not easy — for anyone. Prepare now. Consider your points, anticipate possible responses, and set your sights on an outcome. Then have your difficult conversation!

For more about having difficult conversations, read Arden Coaching’s blog, “6 Tips for Having Difficult Conversations.

To learn more about having difficult conversations, leadership skills, and executive coaching, contact Arden Coaching at [email protected] or 646.684.3777.

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