How to Handle Difficult Conversations at Work

Roanne Innes, Business Coach and Leadership Consultant, shares her top tips on how to maximise your ability to handle tricky conversations.

As a manager, difficult conversations are part and parcel of our working lives. Most people shy away from these situations and few relish the prospect of sharing difficult messages. Fears about what to say, how to deal with the other person’s response, and concern for the individuals impacted, can knock even the most experienced leader’s confidence.

Business is not always plain sailing and having difficult conversations is an inevitable part of the role of the leader.

The most difficult conversations are the ones that go beyond fact-based discussions and touch on topics that are more sensitive or personal in nature (lack of advancement, letting people go, or behaviour issues) and the ones that have been avoided and left to fester over a long period of time. The simple act of not addressing something in the moment can turn a straightforward conversation into a difficult one.

How a manager handles difficult conversations can have a huge impact on their relationship with their team. A poorly handled conversation can erode trust and negatively impact morale and productivity and that will mean your team will struggle to reach their goals and perform at their best.

So what causes us to avoid these tough conversations?

  1. Difficult conversations never get “easy” because they inherently involve confrontation no matter what the topic.
  2. People’s reactions make difficult conversations unpredictable.
  3. Often high-stakes conversations get “sprung” on the manager.
  4. Most difficult conversations are emotional.
  5. Most people have never been coached to have these conversations with the right balance of empathy and assertiveness.

Here are tips on how to prepare for your next difficult conversation:


While it is important to take action when something is not right, it is also important to have a clear evaluation of the situation before having the conversation. Take some time to review behaviours and attitude. Consider how the person interacts with others and what impact that is having. Be very clear on the issue and have evidence on hand to support it.


Take some time to review what is going on. Try not to jump in until you have all the facts, particularly if there are other people involved. Is this a one-off occurrence or repeated behaviour? Remember that people do have an off day. Make your own judgement of the situation.


Based on your assessment, decide the best course of action. This will enable you to be well prepared prior to confronting the individual concerned. Things to consider include:

  • Is this behaviour out of character? Is something else going on?
  • Does this person require some specific coaching around skills, behaviours, values?
  • Are there bigger issues at play? Perhaps suggesting some counselling support may be of benefit.
  • Is it a disciplinary matter? Discuss with your HR advisor.


Don’t put off the conversation. Delaying confrontation of the issue will not make it any easier nor will it make it go away. Find a private space to ensure confidentiality. Over the page you’ll find a roadmap that can be used for any coaching situation and is especially useful when engaging in these difficult conversations.

The 8 STEP coaching Model

by Christopher Stowell

Step 1: Be supportive

What will you say to open the discussion? The more supportive you are, the more effective you will be. Support can be shown by recognising value, demonstrating empathy and active listening.

Step 2: Define the topic and needs

How will you phrase the topic? Discuss the concern or development opportunity with the employee. Don’t start with an accusation. State your concern or issue in a specific, descriptive, non-hostile way. Offer your observations and data. Listen to their side of the story. Be willing to admit if your own actions as a leader have contributed to the issue in any way. Be very clear on what improvements you need to see from the employee. State and re-state your expectations.

Only one issue at a time should be discussed. Make sure to communicate adequate support during this step via active listening, asking questions and clarifying your intentions.

Step 3: Establish impact

What questions will you ask to create impact? Why should the employee consider revising his/ her actions or approach? Often the employee has a blind spot or is unable to see the full range of effects of their actions. The best way for the leader to create impact and employee self-awareness is to establish a very vivid example, one that puts the employee into direct contact with the problem or issue. Remember, change is sometimes preceded by an abrupt awakening or discovery.

Step 4: Initiate a plan

What is the plan moving forward? Who should contribute to the plan? Collaboration is the highest form of support so involving the employee in creating the plan is critical. Leaders should consider themselves as catalysts or facilitators of the plan, not the creators of the plan. The plan should be specific, simple, clear and feasible and the goals clearly understood.

Step 5: Get a commitment

What will you say to ensure commitment? Just because a plan is built, you can’t assume that the commitment is there to deliver on that plan. You need to ask for it! ‘Will you try it? Do you think this will work? What could be done right now to get started on this plan?’ This step will signal any hesitation and whether the employee is saying ‘I can’t’ (due to lack of knowledge, skill or ability) or ‘I won’t’ (because of a belief that the plan won’t work or because of a lack of motivation to change).

Step 6: Confront excuses and resistance

What excuses might you face? The role of the manager in this step is to get the employee to focus less on excuses and reasons things won’t work and more on what can be done. Talk about what is within the influence and control of the employee, what bits and pieces are controllable. The employee needs to see that the manager intends to confront resistance and excuses and is not willing to accept inactivity.

Step 7: Clarify consequences, don’t punish

What is the consequence if they do or do not change? Positive consequences have more impact than negative ones. Consequences that are relative to the employee’s personal goals or objectives carry more motivational weight. Do not use negative consequences if they are not needed.

Step 8: Don’t give up

What can you say to show them you have not given up? This step occurs at two different time points: during the meeting and after the meeting. During the meeting: establish a precise date, time and location to meet again and follow up on progress. Take the initiative to verify, rehearse or review one final time the next steps that the two of you will be taking.

After the meeting: your followup actions become an important indicator of your willingness not to give up. If you invested the time and energy in getting the employee to understand the problem and plan a course of action, you need to invest some definitive time for follow-up. It is important that you know your limitations and don’t be afraid to seek help or advice. AMP

Want to know more? For more information call Roanne on 0418 100 748, visit or email

Roanne Innes

Roanne Innes

Roanne Innes is a Business Coach and Leadership Consultant who helps grow Medical and Aesthetic Health businesses and the people that lead them. She specialises in the development and implementation of business growth and acquisition strategies, leadership coaching and building high performing teams.