5 Steps for Handling Difficult Conversations at Work

Are you putting off a difficult conversation at work? No matter how strong your culture may be, how many friends you have at work, or how predictable your boss is, difficult conversations will make their way to your desk one way or another. It’s natural to want to avoid these conversations— it’s uncomfortable.

Some easy examples are having to fire someone, telling your boss you’re unhappy with their management style, or responding to negative feedback you received in a previous difficult conversation.

These discussions are never fun, but you can walk into the meeting feeling prepared and confident in your stance by following this five-step framework. But before we even dive in, let’s start by reframing our mindset from a “difficult” to a “growth” conversation!

1.  Prepare Ahead

This may seem obvious, but when you foresee or know a difficult conversation is ahead, the first critical step is to prepare, prepare, prepare. If you don’t, you’ll likely end up with a bigger conflict on your hand or a dissatisfactory resolution.

Start by writing down what you want to achieve during the meeting and what your end goal is. Working backyards, think about your issue and your goal and write down what points are most important for you to get across to them. If you end up with an overwhelmingly long list from avoiding a conversation for too long, spend time thinking which ones are most important to help prove your point and achieve your end goal. Avoid the “me” versus “you” and focus your grievances or points on how they are harming the company.

It should be kept in mind that most conversations don’t always go as planned, but preparation allows you to walk in with a clear mind, well thought-out points, and examples to help you make a better case.

2.  Focus on Facts, Not Feelings

Even the calm and collective can become defensive when personal attacks are thrown their way. A difficult conversation is harder for the recipient to blow off or. avoid when they are presented clear examples and/or data as evidence. Framing the conversation around harming and helping the company, rather than people, makes this step easier.

  1. Start by clearly stating what the problem is, how it is affecting the company, and what your end goal for the meeting is.
  2. Calmly go through your pre-planned points, again stating the direct affect each point has on the organization.
  3. Be honest, but not defensive.This is not intended to be a one-way conversation.
  4. Keep the tone respectful, open, and calm. You are solving a problem, not holding an interrogation.

3.  Recognize, but Don’t Sympathize

Once you have laid out the problem, allow the other person to express their point of view and opinion. If you are dealing with someone who consistently interrupts you, you should start the meeting by saying something like, “I’ve thought a lot about [topic] today, and have X points I would like to get across. I want to make sure I clearly express myself, as this is an important issue for the organization, so I ask that you wait to respond until I finish.” Once it is their turn to speak, however, you must show them the same respect and become an active listener, ultimately allowing for an open conversation and a positive resolution.

  • Keep an open mind to understand the other person’s perspective. Listen without prejudice and bias.
  • Restate what they say to make sure both parties are on the same page. This technique of paraphrasing is often used in counseling and is helpful to avoid misunderstandings.
  • Listen without showing agreement, this can make the conversation halt altogether because the problem still exists even if they have a plausible reason to explain it.

4.  Focus on the Organization, Constructively

As mentioned before but worthy of its own section, make sure the conversation resolves around the bigger picture— how this issue is affecting the organization, be it culturally, financially, strategically, etc. Of course, you will have to get personal, still. You also need to focus on the “I” instead of the “you.”

Emphasize the issue rather than the person who may have caused it. You can also help the conversation go smoothly by mentioning a time where you went through something similar.

  • Emphasize the issue, not the person causing the issue
  • Don’t minimize your stance, but don’t push your narrative either
  • Be assertive, not aggressive, about what’s best for the company
  • Provide honest feedback and constructive criticism
  • Make finding a workable solution your NO.1 priority. This could be a change in strategy, policy, or even a behavior— for the both of you!

5.  Create Your Action Plan

Most conversations end without any action plan because one or both parties aren’t receptive or prepared. If you have followed the framework so far, getting to a possible solution should be on the horizon.

The last and most crucial step of having a difficult conversation is to not walking out feeling better emotionally (thought you should!), but with an action plan.The goal of having a difficult conversation is to see some change, be it in behavior, attitude, or strategy. Make sure that this agenda and front and center of the discussion.

  • Ask all participants for input on next best steps. If something is unclear, go back to the discussion table and hash out details of what needs to be changed and how.
  • Don’t end the conversation until there is a possible action plan which works for everyone or upon agreeing to digest the conversation and reconvene (put the meeting on the calendar before you leave).
  • Remember it is “us” versus “the problem.”
  • Keep an open mind and focus on constructive feedback and problem-solving.
  • Put your action plan into a SMART goal framework, ensuring your conversation has a lasting impact.

A difficult conversation is going to be difficult no matter what, but some preparation and empath can make it a manageable and potentially rewarding experience. Think about how the difficult conversation is leading to a mental health platform and things will start looking better soon!

And lastly, when you are dreading a difficult conversation, remind yourself that with a positive outlook and a growth mindset, your difficulty can become an opportunity.

Tom Finn

Chief Executive Officer

Articles you also might like

The Power of Recognition: Celebrating Employees for Success

The power of recognition in the workplace can’t be understated. Learn why a culture of recognition is crucial for employees and how to build one.

Read more
push arrow to go to next page

Tom Finn

Chief Executive Officer

Communication vs Collaboration: How to Understand Key Differences

Comparing communication vs collaboration? We define each term, highlight how each is related and key differences to keep in mind.

Read more
push arrow to go to next page

Tom Finn

Chief Executive Officer

How Self Management Can Help Your Career

One of the best practices workers can incorporate to become more productive, and subsequently more successful in their careers, is to develop effective self-management skills.

Read more
push arrow to go to next page

Tom Finn

Chief Executive Officer