The etiquette of leading a difficult situation/conversation

Picture this: Someone says something that did not sit well with others on the team. Somebody is consistently tardy. Someone eats stinky food in the breakroom. Someone took a client from you who was clearly identified as a target who was engaged in your customer management system/database.

These are all challenging, disappointing and tempting to be “bury-your-head-in-the-sand” experiences. They are difficult to process and often even more difficult to navigate, and communicate, through.

The etiquette of difficult conversations includes many aspects to work through the conditions positively and productively. As a result, the etiquette of a difficult conversation includes the following:

• Engage your empathy. Empathy is not sympathy. Don’t feel sorry for them, or you, rather, consider what they may be thinking, or feeling, and what is likely on their mind, and on their calendar, at present. Have consideration, and compassion, for them as a human being and for the fact that as humans, there is a lot going on, yet ignoring something difficult is not leadership. 

• Get agreement, even permission, for a time, location and the topic you want to discuss. Don’t blindside someone and be thoughtful about location and circumstances. Then, at that time and location, ask the person how they are doing as it relates to the topic (or in general), and then ask them how whatever topic you are about to talk about is going. When you do this, they have an opportunity to head things off at the pass by sharing if there is a challenge, they can save face and bring up any issues themselves, rather than you’re having to bring them up. If they think things are going smoothly and you do not you will quickly get a sense of how far apart you are on this. Jumping in with “We have a problem with X” will evoke defense, where checking in, and listening, will give you their perspective.

• If they believe things are OK, or even good or great, let them know how you believe things are going. It is often useful to use a five-point scale, with no partial points, to get an unemotional rating on where each of you stand. Let them say their score first, so they have an opportunity to share reason and information before you jump in with theirs. Writing down numbers, as simple as it sounds, is a good way to stick with your premeeting thoughts and not waver. Sharing true feedback is key to leadership, and relationship-building, when that feedback is meant to be constructive and set them up for success. 

• Engage, and use your emotional intelligence, and refrain from emotional statement, and extremes such as “You always do X” or “You never …” or words like “nobody” or “everybody.” By being specific with examples, and work result, as well as overall impact, it is factually based. We, as humans, are a series of habits, and emotions, and if we are aware of that, we can avoid lashing out by keeping in mind it’s not likely the other person wants to disappoint, anyone, including you.

• Be open to what the other person has to say, even if it is very defensive. Write down what the person’s comments are. This will assist you in staying calm and hear what is being shared. Additionally, it is perceived by many that writing things down indicates respect, and importance, so that allows those you are with to know you are serious and being thoughtful. When you agree, share “You are right,” and when you do not, either say nothing or consider “You may be right” or “You absolutely have the right to feel that way” since you cannot ever dictate how people experience things, you are acknowledging them fairly.

• Do have the conversation until it is clear who is doing what. Watch “we” statements in the solution aspect of the difficult conversation, as it is something like “I am counting on you to do A and B by date. You can expect that I will handle X in order to support you by date. Is that agreeable?”

• Set up a plan for when the two of you will reconnect. Do not leave it loose with a comment like “Let me know if I can help you” since that can sound, or feel condescending, and skip the “I am not mad at you” for that is not emotional intelligence, rather that brings personal feelings into a professional discussion. Rather, state something like “Please schedule a meeting with me every other Wednesday, for 15 minutes at a time, that is open on both of our calendars to recur for the next three months so that we can collaborate on your success moving forward” or “What do you think is a good recurrence of revisiting this to ensure you are able to have the success discussed?” 

When you get through the conversation, and reach agreement, you’ll be in full sync. Will it be easy? Not likely. Is there an ease to the flow? Yes. Having a formula for moving through is not a script, rather a guideline to practice for you and be kind toward the other person. 

Yes, it is so much more enjoyable celebrating wins than tackling difficulties, or losses, with others. Still, since minimizing recurrences is huge, addressing difficulty early, and clearly, will lead to fewer and fewer instances since you will be allowing for conversation, perspective and agreement.

Debbie Lundberg is the founder, and CEO, of the Florida-based firm, Presenting Powerfully. She is a 12-time published author, certified virtual presenter, certified life coach, certified leadership coach and certified image consultant. She co-hosts the Business of Life Master Class podcast. Her book, Remote Work Rockstar, has become a guide for working and leading virtually.

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