I regularly hear from the women I coach that there are few things that make them more uncomfortable at work than anticipating having a difficult conversation.

Often, the source of the discomfort is due to the anticipation that a relationship is at stake.  While empathy and compassion are definitely wonderful and important leadership qualities, it can become problematic if your concern for others is driving you to put off conversations that you know need to be had.

Here are some tips for how to make the experience less painful and more successful:
 

BEFORE THE MEETING

Get clear: Before you engage in the conversation, clarify what your ideal outcome is.  How do you want to feel?  How do you want your counterpart to feel?  What do you want to walk away from the discussion with?  While you can't control the outcome, understanding what you want to achieve will help you guide the process in that direction.

Reframe: Much of the discomfort of difficult conversations comes from how we frame the situation in our own minds.  Instead of a conversation about poor performance, could this be a discussion about how you can support the other person's development?  Instead of an argument about whose idea is better, could this be an opportunity to co-create the best way forward?

Prepare: For especially difficult conversations, instead of jumping straight in, you can improve the odds of it going well by taking time to prepare in advance.  Consider what day, time, and location will be most conducive to your counterpart being open to and comfortable with the discussion.  How can you set the scene to help him/her feel clear about what to expect when you meet?  What can you do to keep yourself calm and focused during the conversation?

Help the other person prepare: Flicking a meeting invitation through at the last minute with, for example, the subject 'Performance Discussion' and no other context will likely strike fear into the heart of the person receiving it.  In a fear stricken state, your counterpart will most likely not be open to hearing what you have to say.  Share your positive intention with the other person in advance so that they are less likely to feel ambushed or defensive.
 

IN THE MEETING

Set the scene positively and powerfully: Do not start by apologizing or playing the victim (eg "I feel so bad having to tell you this...").  State your positive intention up front to frame the discussion as an opportunity to find a solution, establish mutual understanding, to support the other person in their development, etc.  

Here's a powerful example of scene-setting in a situation where a manager needs to deal with an incident of poor performance (taken from the book 'Quiet Leadership' by David Rock).  After thanking the team member for engaging and checking that now is a good time to have the conversation without distractions, the manager kicks off the meeting in this way:

"I want you to know that there's nothing to be overly concerned about, your job's not in jeopardy, and more important, I am not here to get on your case about what happened.  In fact, I am not going to talk about what happened much at all.  What I'd like to do is see how I can best help you fulfill your potential in your role, if that's something you're interested in."

Ask questions, listen, and clarify as needed: Invite your counterpart to share his/her views and, as difficult as it may be, listen without arguing or interrupting.  When the other person feels heard rather than judged, he/she will be more likely to respond in kind.

Take ownership of your feelings and perspective: A "you are wrong" accusation is sure to get your counterpart's back up in no time.  Instead, using "I feel", "I think" or "I see it differently" language to take ownership of your perspective will help to diffuse any defensiveness. 

Commit: As relieved as you may feel to have reached an agreement or to have otherwise come to the end of this particular conversation, do not leave the meeting without agreeing on next steps.  What will be done, by whom and by when?  Establish clear expectations so that both parties can follow through.

Acknowledge: Letting the other person know you appreciated their openness and willingness to engage with you will encourage them to do so into the future.