Stop Dreading Your Next Difficult Conversation

Coaching, Teams


It’s wishful thinking to imagine difficult conversations will never arise in the workplace. As inevitable as it is uncomfortable, you’ll likely have to initiate a challenging conversation with a colleague sooner or later. Whether dealing with differing opinions, navigating sensitive topics, or addressing conflict, finding the right way to approach this tough task will help you improve the likelihood of a successful outcome.

When Are Challenging Conversations Necessary?

As much as you may try to avoid getting stuck in a difficult conversation, many issues within the workplace will not dissipate if they’re not addressed. Still, simply ignoring the problem at hand is the way that 53% of employees choose to handle a “toxic” situation. Only 24% of employees would choose to address the situation directly. Avoiding a challenging conversation can prolong the problem, lower team morale, and hurt business productivity.

For context, let’s imagine a scenario warranting a difficult workplace conversation. You and a colleague may share responsibilities–whether that’s managing client communication, handling administrative tasks, or producing certain deliverables–but you find them delegating tasks to you. Maybe they’ve started to hand off client onboarding, report generation, or other tasks they also should be managing. As your workload increases, finding the right way to discuss this imbalance with your colleague can help you remedy the situation and come to a mutually agreeable resolution. Without the right communication skills, you could be among the 49.7% of individuals who don’t report a positive outcome, such as increased stress levels, resentment towards your colleague, or lowered performance as you struggle to get all the tasks done.

Preparing For a Successful Conversation

Challenging conversations are difficult for a reason, but taking the time to prepare can help you effectively communicate your point of view without sounding accusatory or aggressive. Here are a few steps you can take to make the conversation productive and successful:

  1. Determine Your Talking Points: Start by jotting down the key points you’re looking to communicate with your colleague. This can help guide the conversation, but remember, you don’t need to prepare a script. While you can try to predict what your colleague might say, the real-life conversation may not go as planned. Instead, approach the conversation with a flexible mindset and have a variety of potential responses ready to go. This will help you maintain a forward momentum throughout the discussion.
  2. Focus On The Facts: Many workplace issues can stir negative feelings and strong emotions. While you want to convey to your colleague how the issue is affecting you, you’ll also want to focus on the facts of the situation. By focusing on the facts, you can help to separate what might be assumptions from the truth. Armed with facts, this can help you support your argument and avoid making the matter too personal.
  3. Seek Understanding Over Agreement: When dealing with some challenging situations, it can be difficult to see eye-to-eye. Many workplace conflicts stem from misunderstandings, so establishing a mutual understanding between two individuals can ensure you’re not missing out on vital information. During the conversation, ensure your colleague feels heard and has the chance to express their perspective as well.
  4. Work Together to Find a Solution: These conversations are not about who’s right and who’s wrong. If your conversation has been successful and productive, it should result in actionable steps you and your colleague can take together to resolve the issue. You can also seek to agree on a timeframe for a follow-up meeting to revisit the situation and ensure everyone is on the same page.


Difficult Conversations Pay Off

Even with the best preparation, tough conversations will never be fun. Still, they can have a significant, positive impact on colleagues and the larger organization. These benefits can include:

● Strengthening workplace relationships and fostering an environment of trust
● Clearing up misunderstandings or misconceptions
● Reducing workplace stress by de-escalating issues
● Improving productivity and collaboration by removing roadblocks
● Enhancing communication skills

Thus, individuals within an organization need to identify when there is an opportunity for them to address issues with a challenging conversation. Not only will they be able to seek a better outcome for themselves, but these colleagues can also drive valuable change within the organization.

For leaders who are unsure where to start tackling their team’s issues, Connect the Dots can help teams develop new tools to engage and be productive with their teammates.

Contact us to learn more about our team development and performance solutions.

Our team-connect Survey Process


We start with thoughtfully diagnosing the team’s current culture by using available data, assessments and interviews.

This provides the team leader with a clear view of what is getting in the way of the team’s success.

We design a series of structured team sessions that:

  • Share the team culture analysis
  • Give team members the opportunity to talk through both processes and behaviors that need to be addressed
  • Productively provide feedback to one another
  • Develop both team and individual commitments that will lead to the team’s desired state


Measure progress by leveraging CTD’s team-connect Survey to:

  • Drive accountability and measure progress by collecting team feedback specific to one another’s engagement and behavioral change
  • Provide the team’s leader with a clear understanding of what he/she and the team need from each other to enable and support the team’s success
  • Share team and individual survey result reports