Whether with a direct report, colleague or even your manager, you might find that you have to have a difficult conversation with those you work closely with. These conversations might be awkward or uncomfortable depending on their nature. When this comes up, you might find yourself wondering, “How do you start an uncomfortable conversation?”
Read on for some dos and don’ts so you can handle an uncomfortable conversation with grace, compassion and confidence. Just because a conversation might be on an uncomfortable topic doesn’t mean the conversation itself has to be uncomfortable.
The best thing to do is to try to have a conversation when an issue is small, rather than wait until it escalates into something more serious. This will help prevent feelings from becoming too big or someone feeling blindsided by the conversation.
For example, if you're a manager and need to talk to a new employee about the appropriate dress for your office, try to do it before one violation turns into your employee dressing inappropriately for work every day. If the feedback is about communication or performance issues, come prepared to share examples and discuss how you’ll move forward together.
Don’t wait for an employee’s performance review to give negative feedback on performance — give team members a chance to correct issues, learn and grow. It will make for a much more productive working experience and better conversations come review time.
When having a difficult conversation, be clear about the issues you are seeing. Provide specific examples. For instance, if the issue is an employee who is chronically late, give an example and share the impact. You could say, "When you were late setting up for the board meeting last week, I felt anxious because I want the board to see our department as competent and professional. When you come in with handouts at the last minute, your hair is a mess and you're sweating, you look rushed and I don’t feel prepared to present.”
Using the same example as above, you should try to understand why something is happening. If the person you’re speaking to is habitually late, it's a little different from being late one time. If the person was late because the printer broke and she had to go offsite and beg a printer to move her job to the head of the line so the board meeting could start on time, you may want to praise her creative problem-solving instead of just reprimanding the lateness. If you were to reprimand this employee in this situation, think about how they might feel — they went above and beyond and still got a talking-to! If she was late due to poor organization or a lack of ability to manage her time, that's a different conversation, and you should make sure she understands the impact of her actions.
While you might get some emotional responses from the other side, try to stay calm and listen. The person may get defensive. If you’re feeling like you won’t be able to continue a productive conversation, end the conversation and agree to reconvene once the other person has had time to process their emotions and you can have a productive conversation. Make sure to hear from the other person as they may have some information that changes your perspective on the situation at hand and the best way to move forward.
Remember that on the other side of the conversation is a person with feelings. Use "I" language when you can, instead of "you." For example, instead of saying, "You royally messed up," say something like, “I noticed a number of errors in the report that went to our largest client yesterday. I need you to double-check your work and ask a colleague to proofread for you so that it doesn’t happen again. Can we work together on a plan to ensure client work goes out error-free?”
After the conversation has ended, document a summary and the action each party agrees to take. This will help keep everyone accountable for what they’ve committed to do, and should the issues continue or escalate, this will serve as appropriate documentation. Loop in human resources or other senior leaders as needed.
While it might be easy to assume that someone knows they're making mistakes, getting on your nerves or generally not doing what you expect, the first step in a difficult conversation might be sharing your expectations and explaining where the other person fell short. For example, “When I asked you to create the budget for next quarter, I expected to see funds allocated per trade show and not just a lump sum. I need to see an itemized budget sheet so I can get a better understanding of how you plan to spend the funds.” Not, “The budget sheet for next quarter is missing details. Please be more specific”.
Some leaders will say praise in public, criticize in private. While a difficult conversation doesn’t necessarily mean criticism, it might. Be sure to have your difficult conversations in private to give the other person room to have emotions, ask questions and discuss productive ways to move forward. This will also minimize any gossip that might result from the conversation. While other people in the organization may need to know the conversation happened, they don't need to see or hear it.
Try to have a conversation in the afternoon. If it's especially sensitive, the other person involved might want to leave the office to cool down. This way, they'll have had time to get the bulk of their work done and focus on the day. The exception to this suggestion is if you're letting someone go. Don't terminate an employee at the end of the day on a Friday. If you do this, you're sending them off into the weekend where they can’t get the support they may need.
While some people may like this technique, others believe it weakens feedback and/or puts a person on the defensive. Which feedback feels more genuine and powerful to you?: "That was a great presentation, but you said 'um' a lot and forgot to mention the 5-year goals for the project” or “Thanks for your hard work on the presentation. I heard you say 'um' a lot and didn’t hear the 5-year goals for your project. To me, it looked like you were either nervous or unprepared. How can I support you so you feel more confident and better prepared for next month’s status update?”
In the first example, the person receiving the feedback might feel that the person giving the feedback is lying: Was it really a great presentation if I said "um" so many times and I forgot an important section? Try to get right to the point when giving difficult feedback and save the praise for when it's really well-earned!
After a difficult conversation, check in. If the person you had a conversation with seems to have heard the information you shared and made positive changes, recognize that. If it doesn’t happen overnight, that's okay. Recognize the progress where you see it. If you’re not seeing progress or improvement where you need to, you might need to have another conversation or escalate the issue. Remember to keep good records of these conversations in case performance doesn’t turn around.
There are many situations at work in which you may need to have a difficult conversation. These include:
Depending on the nature of the conversation, you may need additional or niche support. Consider checking out Kim Scott’s resources on her website. Kim is a former Google and Apple employee turned coach and author. You can also check out Shari Harley's Candid Culture for more information on how to say anything to anyone.
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