9 Things I Learned from My First Difficult Conversation

bigstock-123128063Did you know 35 percent of managers would rather skydive for the first time than address a problem with their team at work? That’s according to the Centre for Effective Dispute Resolution.

Effective leaders must know how to conduct difficult conversations with employees. Because of the common perception that conflict at work is bad, it’s no surprise that so many leaders shy away from having these discussions.

I don’t know that I’d ever want to jump out of an airplane, but I recently had my first difficult conversation with a direct report. I knew if I didn’t address the problem, things could escalate and become worse than they already were—but knowing that didn’t make the task any easier. This was new ground and I felt uncomfortable. But because I knew how important it was, I took a deep breath, closed the office door, and we had the discussion.

Now, having made it to the other side of that conversation with the working relationship still intact, I want to share 9 things I wish someone had told me to help me prepare for the experience.

  1. Don’t let fear hold you back

Before resolving to have that necessary yet uncomfortable conversation, I found myself silently seething about issues I could have easily done something about. Looking back, I know this wasn’t healthy for me or for my working relationship with the team. My regret is that I held off taking action because I didn’t want to be seen as overstepping the mark—especially because I was new to the team.

  1. Manage your emotions and preconceptions

Many people have worked in environments where emotions had to be left at the door. In fact, I got in trouble at a previous job when I came to work in tears after being in a car accident! As human beings, sometimes it isn’t possible for us to hide our emotions—particularly if they are strong or have been stewing for some time. A challenging conversation is more likely than others to become emotional. What starts as annoyance may escalate into sadness, frustration, or even anger. If you notice this starting to happen during a difficult discussion, as the leader you must manage your own emotions, be professional and mindful of the direct report’s feelings, and keep things under control. Remember, the other person deserves respect—even if you disagree with what they say.

  1. Preparation is key

When a challenging conversation is necessary, take time to plan how you’re going to open the discussion and approach the subject, as well as what you want the outcome to be. I found that making a few notes and having them for reference helped me remember my key points and kept the conversation from veering off topic—so don’t be afraid to use notes.

It’s important to open the conversation with the exact topic and behaviours you need to address. This allows the conversation to move forward and clarifies the reason for the meeting.

Imagine the ideal outcome for the conversation. Focus your notes on everything that needs to be covered and the meeting is more likely to come to a successful conclusion.

  1. Keep things friendly, relaxed, and conversational

I asked some of my close friends with leadership experience what they would do to make a difficult conversation more successful. The resounding answer was “Have tea or coffee, and biscuits.”

If this is the first time you have had a particular conversation, it should be informal, relaxed, and conversational. Talk to your direct report as a friend, not as their manager. This first discussion is about raising the other person’s awareness and nipping the situation in the bud. It’s about redirecting, not reprimanding.

  1. Ask the right questions

Ask open-ended questions—ones that require more than just a yes or no answer. You might find that the issue is not as straightforward as it seems. Also, this gives the person a better chance to express their viewpoint and maintains a relaxed atmosphere.

  1. Listen carefully

It’s all very well and good to ask the right questions, but it’s useless unless you are giving your full attention to the responses coming from the direct report. Listen with the aim of understanding. If you don’t understand, ask clarifying questions.

  1. Cooperate, support one another, and agree on how to move forward

The final part of your conversation should be positive. Work together to learn how you can best offer support to your direct report and what specific behaviours of theirs need improvement going forward.  If necessary, set up another meeting to review progress.

  1. It might not be as bad as you think

Generally, people want to do well. Team members want to achieve and to do the right thing. Don’t underestimate the human need to succeed and to be liked. You may find that your direct report didn’t even realise their behaviour was off track. Often, poor performance or misbehaviour is a result of misunderstanding and not intentional.

  1. Get higher level support

You don’t have to do this on your own. Ask someone at a higher management level if you can go to them when you have questions or need support in this area. Knowing someone has your back can work wonders, especially when it comes to gaining the confidence you need to have challenging conversations. The person doesn’t need to participate in the discussion, only to be available to give guidance when you need it.

Telling a direct report they are not meeting expectations is not an easy task but is an important part of leadership. Use these tips to help you tackle those all-important conversations with team members—no skydiving involved—as soon as problems arise. You will gain the respect of your team members by showing them you won’t shy away from conflict when a challenging conversation is necessary.

Do you have any other tips or advice for leaders about conducting difficult conversations and redirecting people’s behaviour? Make sure you share them in the comments!

10 thoughts on “9 Things I Learned from My First Difficult Conversation

  1. Excellent tips. I belive that a direct report could benefit from these as well. Meaning when you need to have difficult or uncomfortable conversations with your manager.

    • I think you’re absolutely right! The fear goes both ways, and no doubt a direct report will have the added pressure as seeing their leader as more senior, or more experienced, and wonder if they’re able to have difficult conversations in the first place.

    • Definitely! You can’t expect a direct report to meet your expectations if you aren’t willing to clearly identify them first; and then re-direct them as needed!

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  3. Right on, Jemma.

    And so much of what you make of conflict is how you look at it. It is so important to see it as an opportunity with positive possibilities. It’s not a failure! It’s not that someone did something wrong necessarily! It could be two passionate, smart people looking at something from very different perspectives. And the potential for good to come out of that in terms of stronger relationships, better work products, stronger team dynamic is amazing. But you are right, you have to tackle it.

    Thanks for the encouragement to step out and take advantage of these disguised opportunities.

    • You’re welcome! Sometimes it’s so much easier to sit down and talk things through face to face and make sure you’re aligned. Things can be explained much more clearly then they could ‘behind a keyboard’ – and often, you’ll find that what you thought were two totally different opinions or behaviours have the same underlying thoughts and values, just manifested differently.

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