How to Tackle Difficult Conversations in the Workplace (A Step-By-Step Guide)

Knowing how and when to have a difficult conversation is a vital skill for anyone in a workplace and is one of the key pillars of conflict resolution. The need to have a difficult conversation can arise for various reasons. A difference in values or perspectives, unmet performance targets, or disrespectful behaviour will, at some point, need to be addressed.

Here are some familiar scenarios I regularly encounter in my work as a conflict resolution specialist.

Approaching Someone About Their Poor Performance
Matt has been dropping the ball at work for several months. While he still shows up every day on time, he’s often not really present and seems distracted most of the time. His colleagues have been picking up the slack, but they’ve started to complain to their manager, Sam. Sam has noticed the changes as well and decided to have a conversation with Sam about it.

  1. Preparation
    Sam gathers facts, data and concrete examples illustrating Matt’s poor performance. This includes specific projects or tasks where timelines were missed and emails illustrating when Matt said he would do something and then didn’t follow through.
  2. Choosing the right time and place
    Knowing a difficult conversation should never come from a place of anger, Sam chooses a time and date in the near future for a private meeting. They book a quiet meeting room that makes it easier to have an open and honest conversation.
  3. Starting with a positive
    Sam starts the conversation by acknowledging Matt’s strengths; how even though they can see it’s been a struggle, Matt has continued to show up day after day, which shows commitment.
  4. Using the right language
    Sam ensures they use “I” statements to express their concerns about the observed decline in performance.
  5. Being specific and objective
    When providing examples to Matt, Sam focuses on the behaviour, not Matt’s personal traits.
  6. Listen to their perspective
    Sam leaves plenty of time for Matt to give their perspective on the change in behaviour and performance. This gives Sam insights into the challenges Matt has had.
  7. Identifying root causes
    Together, they can identify the root cause of Matt’s performance issues. His partner has been diagnosed with an illness that requires intensive treatment, coupled with a change in process at work that has meant Matt needs to do additional tasks he doesn’t have time for.
  8. Set clear expectations
    Sam and Matt discuss specific steps they will take to address the performance issues. Matt agrees to take a day-a-week carer’s leave to support his partner, and Sam will investigate the change in process to see how that can be better managed.
  9. Follow-up and monitor progress
    Sam puts a fortnightly catch-up in the diary so they can check in and ensure the steps they’ve agreed upon are working.

Approaching Someone About Their Disrespectful Treatment of You
Brooke’s co-worker, Helen, continually talks over her in meetings. Whether it’s just the two of them, or a broader team meeting, if Brooke says something, Helen cannot help but interrupt her. It’s been happening for several months, and other colleagues have commented on it to Brooke. She decides to speak to Helen about it.

  1. Preparation
    Brooke gathers examples of when Helen acted disrespectfully. This includes specific meetings and what was said.
  2. Choosing the right time and place
    Brooke asks Helen if they can chat privately. She books a room away from their colleagues’ eyes and ears.
  3. Starting with a positive
    Brooke begins by talking about the positives of their working relationship.
  4. Using the right language
    She uses “I” statements to express her concerns.
  5. Being specific and objective
    When providing examples to Helen, Brooke focuses on the behaviour, not Helen’s personal traits. She communicates the impact the constant interrupting is having on her mental health and well-being.
  6. Listen to their perspective
    Brooke gives Helen the opportunity to respond. Helen says she was unaware she was doing it but can see from the examples that she is indeed interrupting her constantly. She says she feels terrible about it.
  7. Setting boundaries and expectations
    Brooke says she appreciates Helen’s response and hopes they can have a more positive working relationship going forward. Had Helen responded defensively, Brooke would have highlighted the consequences of the behaviour continuing and communicated that she may have to lodge a complaint if the behaviour doesn’t stop or she would ask for a neutral third party to mediate.

I cover this and more in my highly popular workshop, Manage Difficult Conversations and Communicate Better. Everyone can benefit from improving their communication skills—it leads to a happier, more harmonious workplace.

To book your workshop or discuss your organisation’s needs, reach out to me on 02 8036 5558 or email