10 Ways to Have an (Easy) Difficult Conversation



Being a great leader requires skills that aren’t always natural. One of those requirements is the ability to have a difficult conversation with individuals at all levels around you (including your boss too). Just to paint the picture, here’s a short list of some difficult conversations that you may face in your life as a leader:

  • Laying an individual or team member off

  • Terminating a position due to performance issues

  • Providing critique on a project or initiative to a team

  • Addressing poor performance with an individual

  • Turning down a request for a promotion or pay raise

  • Reporting a grievance

  • Receiving and investigating complaints

  • Admitting to mistakes

  • Turning down an employee's idea

  • Mediating a conflict between two or more employees

  • Telling investors about lack of results and/or performance in the business

  • Negotiating and/or asking vendors for new invoice payment terms

  • And more…

Your Leadership Opportunity

As a leader, you will have many partners, workers, and team members that you will communicate with on a regular basis. In each and every interaction, you are gifted with the choice in determining how you want to show up. You are responsible for your energy, word choice, body language and leadership presence in each and every one of those interactions.


As an inspiring and motivating leader, it is not only important to be at choice in how you show up, but you must also be aware of how the individuals around you are also showing up too. This ties directly into your emotional intelligence – and is a significant part of being able to have great communication skills, especially for those tricky conversations.


The More Aware, the Greater the Leader

The more aware you are, the greater leader you will become. The more aware you are, the more choice you have. The more then that you are able to adjust how you are communicating, when you are communicating, what you are communicating and more importantly, how to manage the overall outcome for everyone involved.



This awareness is especially true when it comes to difficult conversations or opportunities for constructive feedback. In these circumstances, being aware and in charge of your energy is the most important part – but not the only part.


To truly be effective with difficult conversations, consider the following best practices:

  1. Be prepared with what you want to say – in advance

  2. Request time with the individual(s) setting clear expectations on the topic and desired outcome (no one wants to feel ambushed)

  3. Pay attention to not only your energy as you start the conversation, but that of the individual or team that you are communicating with too (this includes where they are at emotionally, physically, psychologically, etc.)

  4. Know your “why” with sharing the feedback – both the intent and the desired outcome

  5. Consider collaboration and remember that these conversations are a two-way street; active listening will allow you to reach a great solution together (more on that here)

  6. Focus on the facts and deliver the information in a way that the individual will actually receive it

  7. Those facts include the change that needs to happen (without resorting to accusations or derogatory tone and comments), specific examples to help them understand, as well as the overall impact to the business

  8. All criticism should also include the “win-win” for the individual (why should they consider making this change)

  9. Reframe the situation as an opportunity for growth (not a fault or failure)

  10. Be thoughtful about the time and the place for the feedback (not while emotions are high, in a safe and confidential location, etc)

Leadership is the Act of Moving Forward

For an employee or a team to truly be able to move forward, they need to understand (regularly) what is working and what isn’t. That requires a strong ability to deliver feedback and opportunities for growth. That also requires a strong ability to have difficult conversations that others may not always want to hear – but will always benefit from. Feedback, after all, is a gift.

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