Managing Difficult Conversations

Written by on November 26, 2022

In almost every capacity of our lives, we find ourselves having to have difficult conversations from time to time. Whether you are telling a board member that they did not deliver on a certain project or talking through a head coach’s performance review, difficult conversations are an inevitable part of management. Most of the time we would like to overlook or even try to minimize these types of conversations–we feel like if we look the other way or ignore the problem, then maybe it will go away. Anyone who has been a part of any organization knows though that they don’t usually go away–not without significant consequences. When we ignore something, it becomes like a small grain of sand that continues to irritate us, even if new grains are not added. Over time, the sand becomes so bothersome that we become increasingly irritated and annoyed. What if we had just said something in the first place? What if we had taken the time to talk through a situation instead of taking a back seat and hoping it works itself out? In healthy organizations, including youth sports clubs, it is important to face these difficult conversations head-on. Many times expectations may have not been clear in the first place, so spending some time clarifying those helps stop problems from moving forward. Having difficult conversations early leads to more unity and harmony in the end.

In most cases, if you don’t say anything, the offending behavior or problem continues to happen as you grow more and more irritated. It is wise and good planning to think through potential problems ahead of time and know, how you and even your board will respond. How should board members be talking to each other when a member of the board is not doing the tasks assigned or pulling his or her own weight? How should a leader respond if the Head Coach of a club team is not living up to the outlined expectations? Having these conversations has a lot of value in getting the board member, the coach, or even the club back on track, but it also has value because the Head Coach can use this same model with his or her staff. The Head Coach can learn that difficult conversations do not have to be feared and that they are an opportunity for growth for everyone involved in the club.

As a member of any organization, it is important to face the conversations head-on and without fear. A great way to build trust with your team and your board is to show them that you will manage inappropriate behavior or behavior that goes against the culture and productivity of the team. Of course, for this to happen it is important that you have clear guidelines and expectations. What are you expecting from your board members? What are you expecting from your Head Coach? This is something that should be revisited again and again–this is the arrow or the final destination that everyone should be working towards. When you need to have a difficult conversation with someone, you can use those clearly defined expectations to point them back to the end goal. Not only do these conversations help point people back to the main goal of the program, but it also allows people to grow and improve in how they work and serve the team or organization. If you continue to ignore difficult conversations, people spend their time spinning their wheels, not accomplishing anything in the end. Having these conversations early leads to improved performance and time management.

If you are preparing for a conversation that you feel may be difficult, you’re more likely to feel nervous and upset about it beforehand. Try these strategies to manage the task ahead of you:

  • Frame the conversation in a positive way that will likely add a lot of value to the work and the work atmosphere. For instance, you’re not giving negative performance feedback; instead, you’re having a constructive conversation about development. You are asking your Head Coach, “How can we do a better job of meeting the goals we outlined at the beginning of the year?”

  • Instead of making the conversation about the person, it should always be about the work they are doing. This not only helps you to focus on your end goal, but it also helps the person you are talking to not be as defensive. If you can avoid the other person becoming defensive, you will have a much more productive conversation.

  • A difficult conversation tends to go best if you try to think of it as a productive conversation instead. Re-frame your thought process to focus on the outcome, instead of focusing only on the conversation. The conversation, no matter how difficult, should lead to an opportunity for the person to grow and realign with the goals and expectations of the organization.

  • One way to move past the fear of a difficult conversation is to plan your approach. It is important to think about what you will say and also how you think the person will react.

  • What will you say to get the conversation back on track if it derails? Hard conversations can quickly take a turn in a direction you were not ready for, so it is important to be prepared with a way to move forward and stay on topic.

  • Once you have a difficult conversation, make sure to follow up with the person frequently. Are you seeing improvements in the areas that needed work? This is a great time to offer some positive feedback and reassure them that they are on the right track. This will hopefully spur the person toward the end goal. Instead of letting a lot of time go by, set aside time to come back to the issues that were talked about and follow up, noting how they have been improved upon. In the end, facing these types of conversations head-on leads to a more productive organization, with fewer cracks in the foundation and overall structure. Since a healthy organization should be everyone’s standard, hopefully, difficult conversations are met with an ability to grow and change, while everyone works towards one common goal.



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