Hard Conversations Don’t Need to be Hard

  • December 03, 2022
  • Kate Rogers

Hard Conversations Don’t Need to be Hard

Difficult conversations are an unavoidable fact of life. If you have ever been in a relationship (personal or professional), then you’ve had a difficult conversation. It wouldn’t be surprising if you’ve taken actions to avoid these conversations or found them stressful. Often, the experience of a conversation – for both you and the person you’re speaking with – comes down to how the conversation is approached.

The quality and success of your relationships and business depend on your ability to have difficult conversations, but what if they didn’t need to be difficult? Or at the very least, what if they could be a little easier? Frank Cesario and Bonnie Roberts Jones from Hicks Morley have identified key principles and conversation structures using their own experiences from having difficult conversations with clients and team members.

An essential part in having productive, difficult conversations is communicating the necessary information and having a clear idea about how you want to move forward. Follow the principles below to maximize the success of your conversations.

8 Principles for Difficult Conversations (and a Good Life Philosophy!)

  1. Change your mindset. Your mindset affects the experience of your conversation. If you think a conversation is going to be hard, it will be – and that will affect your ability to have a positive discussion. Instead, focus on the importance of having the conversation.
  2. Get to it. Difficult conversations will seem more difficult when they’re put off, so the sooner you have the conversation the better. But don’t rush in to it. Take time to prepare.
  3. Be prepared. Understand what you want to accomplish so you can come up with an action plan later in the conversation. Be sure to have a clear understanding of what you want to address and have examples and facts ready to illustrate your points. Have a plan for your conversation, but don’t be scripted, otherwise it will be challenging to remain present in the conversation and it will create a dynamic that isn’t conducive to a constructive conversation. 
  4. Content matters. Be direct and get right to the point, but be objective in what you say. It’s a good idea to provide examples of the topic or behaviour you’re addressing, as this will make it easier for your point to be understood.
  5. Be empathetic. Recognize that there is likely another perspective, so the better you can acknowledge what the other person is feeling and how they see things, the more likely they’ll feel heard, understood and receptive to continuing the conversation. 
  6. Slow down. Take time to deliver your message calmly. This will result in a more productive conversation. 
  7. Look forward. Strive towards a solution and create an action plan that leads to change. Incorporate solutions generated by you and the person you’re speaking with.
  8. Reflect and learn. You’ve just done the “hard” thing! Take time to consider what went well, what didn’t and how you can do better next time. It takes practice to get comfortable, but implementing your learnings will make it easier.

Common and Challenging Scenarios
Keep using the above principles, but be sure to give extra consideration to the strategies identified in these common scenarios.

Dealing with budgets

  • Prepare. Everyone in the meeting needs to be equipped with the appropriate information to have an informed and successful discussion. Let the other party know what you want to discuss so they can prepare to speak to those points.
  • Determine the right level of detail. Consider if you need to dive deep in to detail or if a high-level conversation is sufficient. 
  • Discuss before, during and after. Have frequent communication about the budget with the appropriate people. Get regular updates to manage expectations and stay on track. Talk about whether you met the budget or not and why so you can make constructive changes next time. 

Preparing someone for a negative outcome

  • The earlier, the better. Maintain transparency to help build your relationship; otherwise, the person you’re speaking with (often your client in this scenario) may feel blindsided. 
  • Explain your thought process. Get comfortable with your own thought process so you speak from a place of knowledge and confidence. And be prepared to respond to questions because you will get them!
  • Listen. Hear what the concerns are and understand what the impact is.
  • Be prepared to problem solve. Think in advance about what the impact will be so you can come equipped with ideas.

Your expectations haven’t been met

  • Establish a goal. Write your goal down so it’s clear to you, and refer back to it if the conversation goes off track and you need to redirect the discussion.
  • Explain your point of view. Share why it’s important to have this discussion and how the problem can be dealt with. Keep the conversation focused on the issue at hand and recognize the positive things that are also contributed. 
  • Consider the other perspective. Empathy is key here. Think about why someone isn’t meeting your expectations and respond to those factors. 
  • Prepare for an open discussion of solutions. Bring your ideas to the table and be prepared to listen to other ideas too.

Someone else’s expectations haven’t been met

  • Don’t delay. Delaying will impact your wellbeing and likely make the situation worse.
  • Prepare in advance. Sometimes you’ll need to have the difficult conversation right away, but, if possible, take some time to plan how you want to approach the conversation.
  • Explain the issue clearly. Get right to the point and take the guesswork out of the conversation.
  • Manage your emotions. Emotions are okay – and expected – but you don’t want them to interfere with your ability to have the necessary conversation. If you need to, put the conversation off for a brief period of time to compose yourself and explain why the conversation needed to be postponed.
  • Be armed with solutions. The person you’re speaking with will want to know two things: how is the problem going to be dealt with, and how will it be prevented from happening again? If you have time to prepare, think about the answers for these two questions.
  • Listen. The person you’re speaking with will have their own emotions, which may impact the conversation. Let them express themselves and respond with empathy.

Having difficult conversations is a skill, but if you put these guidelines in to practice, you’ll have a solid foundation to build on.