top of page

10 Tips for Having Difficult Conversations

Silhouette of two people facing eachother with squiggle lines connecting their minds.

Difficult conversations are also essential conversations. This year, more than ever, many of you are having difficult conversations with leaders, team members, and donors, just to name a few. They are necessary, whether you are managing a team or simply working with another person to accomplish a goal, but that doesn't make them any easier. So, this week, we asked the DRG Group to share their top tips for having difficult conversations.


Determine a purpose I think one of my best tips is to determine the purpose of the difficult conversation first and what you hope to accomplish by having it. What do you hope to accomplish? What would be an ideal outcome? Watch for hidden purposes. You may think you have honorable goals, like educating an employee or increasing connection with your teen, only to notice that your language is excessively critical or condescending. You think you want to support, but you end up punishing. Some purposes are more useful than others. Work on yourself so that you enter the conversation with a supportive purpose. Allow the other person to ask questions

Questions serve a double purpose. Asking questions helps the other person process what’s happened, and it allows you to clarify and solidify details of the conversation. If you aren't sure that the other person fully comprehended the conversation, ask clarifying questions to check their understanding.


Make sure that a difficult conversation doesn't come as a surprise to the other participant.

As managers, it's our job to proactively address issues in real time so that your team member isn't caught completely off guard. This can lead to them feeling defensive and shut down in your conversation - making positive progress and accountability very difficult. Make sure you address issues, document as appropriate, and have a steady stream of back and forth feedback before it comes time for a heavy conversation. 

Make sure and frame your concerns or feedback from the lens of the greater team or organization - not your own frustrations or personal feelings.

If you are addressing a negative work behavior for example, describe the impact of that behavior on the whole team, the ability to meet team goals, or in contradiction to organizational priorities. This helps to remove personal emotion from the conversation and re-frames their role as a contributing member of the larger organization.   

When beginning the conversation, ask your team member to re-cap or explain the situation that is being addressed from their own perspective and in their own words. Doing this, instead of launching directly into your own interpretation of the situation, will shed some light on their intentions, mindset, and willingness to take accountability. This will tell you right away if you are on similar pages or not. It also gives them some influence on the narrative and gives you a chance to listen and formulate responses that are compromising in nature.

Don't shortchange yourself.

Having these conversations is hard and it's natural for us to avoid them or to talk ourselves out of the need to address what might be small issues in the grand scheme of things. We may tell ourselves we are overreacting, it will permanently affect the relationship with the other person, or perhaps that we wouldn't be supported by leadership or human resources. All of these things undermine our ability to manage a strong, healthy, happy team. When things, big or small, go unchecked, they fester and it erodes relationships and trust on a multitude of levels. Don't be afraid of difficult conversations - they will often surprise you and may be just what you and the other person needs in order to feel heard, validated, and at ease in the workplace. As my mother used to tell me - "Put on your big girl panties and do it!".     


Deal with the situation quickly and directly

So many managers I know like to put off the difficult conversations. This is avoidance and honestly the longer you wait the larger the issue or offense can become. When you need to have a conversation - just do it. Get the appropriate people in the room (or schedule a zoom call) and explain the situation from your perspective. If there is a problem - state the problem. Then state the issue and your hoped for outcome. Be sure to remain open and use "I feel" language vs. "you did" or finger pointing language. Make certain everyone feels heard and acknowledge their comments. If apologies need to be made - make certain that happens. Identify next steps.  Follow up after the call with an email synopsis of the conversation, clearly outline next steps and expectations for moving forward. 

Assume Noble Intent. So many issues with our staff and colleagues stem from misunderstandings, assumptions, wild imaginations, or confusion. We see what went wrong as something that was done on purpose to hurt or embarrass us or to make us feel less valued. Yet when we have a conversation with the offender typically what we learn is that it was not their intent. We made an assumption based on our own experiences - you know those ugly gremlins that remind us of our own insecurities. Recently two of my employees had an issue and both were extremely upset with the other. When we had an open dialogue about it we identified that both employees felt disrespected but for different reasons. When they faced each other and explained their own feelings and perceptions it became very clear that both parties made assumptions that the other was doing it on purpose. When they saw this they quickly apologized and came to an agreement to assume positive intent and if ever they felt misunderstood or disrespected to raise their hand and talk about it. We need to give people more grace - especially now. Everyone is tired and stressed and honestly our defenses are down. We need to start with trust and assume positive intent first. We need to quiet our ugly gremlins and remember we are all struggling in our own ways.  


Keep in mind what might happen if you DON’T have the conversation and use that as your motivation. 

It’s also helpful to start the conversation in a clear, concise manner.  There’s no need to wax poetic, so get to the point as succinctly as possible. Give the other person the opportunity to speak, as this should be a conversation and not a lecture from you.  Be prepared to listen but be ready to be met with silence.   And while emotions should be kept in check, that doesn’t mean you can’t be empathic. The anticipation of a difficult conversation is often worse than the conversation itself, so focus on making it happen and moving forward with the outcome.


Be prepared.

Write down your goals for the conversation and the key aspects you want to ensure are covered. You don't have to script out everything you will say -- and in fact this may inhibit your ability to listen to the other person -- but it does help to have a few bullet points as reference to keep the conversation from veering too far off course. 


It's important to tackle difficult conversations head-on and in a timely manner, and it's equally as important to not squeeze them into a packed schedule while running between meetings and Zoom calls.  Center yourself before entering the conversation and create enough space in your schedule to not be rushed. This helps ensure cooler heads will prevail if tensions begin to rise. 

What are your tips and tricks for starting and having difficult conversations? We'd love to hear them in the comments below.


bottom of page