There is no doubt that difficult conversations take courage, however, they also require experience, strategy and a genuine desire to help someone improve. It is much easier to avoid the conversation, but no one wins from putting off difficult feedback. If there is something genuinely important to tell an employee, there is a strong chance they really need to hear it. 

It is common for leaders to not want to risk relationships or experience confrontation, but whilst avoiding the conversation is the safe path, it will never lead the employee to the right destination.  Courageous conversations are powerful and have many benefits.  When done well, they can enhance relationships, build trust and create positive behaviours and actions.

12 tips to conquer courageous conversations 

The following are 12 tips to help conquer courageous conversations:

1. Be Brave

It is normal to fear a difficult conversation, but it is not healthy to sweep the issues under the carpet and convince yourself that “it will sort itself out”. This is an excuse driven by fear.  Ask yourself:

  • What will the consequences be if I do nothing?”
  • “Can I accept those consequences?”

Asking these questions helps to hold yourself accountable for the decision not to be courageous.

2. Know your WHY

Before embarking on a courageous conversation, it is a good idea to consider your ‘WHY?’ This is around reflecting on the purpose of the conversation and what you are hoping will be achieved. Courageous conversations have risks, so it is critical to have carefully considered your intent and desired outcome.  Ask yourself:

  • “What am I trying to achieve?”
  • “What do I hope will change as a result of this conversation?”
  • “What is the risk to having the conversation?”
  • "What is the risk of not having the conversation?"
  • “Is it my place to initiate this conversation?”

 3. Accept the discomfort

Instead of fighting discomfort, accept that it is part of the conversation as those who have the courage to address difficult issues will reap the rewards. It is true that some things are difficult to say and even more difficult to hear, but if both parties can push past the discomfort there can be a positive outcome.

4. Frame up the conversation

Jumping into the deep end of a difficult conversation creates a ‘sink’ or ‘swim’ outcome.  It is a good idea to frame up the conversation by seeking agreement from the employee to share some feedback.  Some suggestions include:

  • “Laura, I have some observations from your work on project X that I would like to share with you. Are you open to us having a discussion this afternoon?”
  • “Ning, over the past week I have been reviewing customer orders as part of our quality assurance checks. I am keen to share some feedback with you to ensure that we have the same understanding.  Are you free now so that we can have a chat?”

 Once you have the employee’s agreement, you can start sharing the feedback using the following structure:

  • WHY you want to share feedback
  • WHAT you would like to discuss (include positives and the area of improvement)
  • HOW this gap impacts (the team, the business, productivity, team morale etc.)

5. Set the tone

A difficult conversation will usually have strong emotions on one or both sides of the conversation.  The more sensitive or serious the situation is, the more likely that raw emotions will be involved. Never attempt a courageous conversation when emotions are high.  Be prepared by practising what you want to say and enter the conversation with an even tone, good eye contact and open body language. If emotions become heightened, restate the intent of the conversation and suggest a break in the discussion.  For example:

Matt, I can see that this conversation is upsetting for you.  I value you as an important part of my team and for that reason, I need to share this feedback with you. My intention is purely to bring awareness so that we can work together to close the gap.  Would you perhaps like to take a break and we can meet back in an hour to continue our discussion?”

The employee is likely to mirror whatever emotion that they see from you, so be sure to set the appropriate tone for the conversation.

6. Tell your truth

In the moment of truth, it is tempting to ‘sugar coat’ the message to soften the blow.  Leaders will often over-inflate the positives and play down the negatives in an attempt to keep the relationship intact and avoid confrontation. Disingenuous compliments or overly positive dialogue about performance is not sincere and will only make the problem worse.  The authenticity of feedback combined with a genuine approach will be the best road map to success.

7. Perception is reality

The saying ‘perception is reality’ can be true for both the employee and the leader.  Whilst we all like to believe that our reality is the correct one, there are usually other perspectives that are worth considering. It is possible that there is information that the employee has that may change your perception, so try holding judgement until the issue has been explored. Consider using language that invites the other perspective to be shared:

I understand that I am not out on the road with customers like you are, so I appreciate that I might be missing some key information.  Are you able to help me to understand why three of our customers missed their deliveries yesterday?”

 8. Discuss the ‘undiscussable’

Yes, this is where the ‘courage’ part kicks in.  When issues are not raised, there are serious consequences such as increased poor behaviour, lower productivity, mistakes, loss of customers and lower engagement. Dancing around the issue or avoiding it altogether is a recipe for disaster. Be brave enough to discuss the undiscussable and remind yourself that you are helping the employee and the business by doing so.  An added benefit is you will be a far more effective leader knowing that you can ‘face the storm’ and come out the other side stronger. The benefits far outweigh the discomfort.

9. Rise above poor behaviour

 If you roll around the dirt with a pig, you will both get muddy – but the pig is the only one who will enjoy it”

How you plan for, approach and deliver the difficult conversation is well within your control, however how others act and respond is not. This is true in all areas of life so it is important not to let the poor behaviour of others impact our own.  It is tempting to ‘roll around in the dirt’ but it serves no purpose to descend to the poor behaviour of others.  Stay in control, keep an even tone and pace and re-state your intent and desired outcome.  If the behaviour continues, close the conversation.

10. Be kind

There is a saying that ‘the best form of defence is attack’ and when we are courageous enough to share difficult feedback, we should not be surprised when employees become defensive or provide us with feedback of their own.  If this occurs, be kind and remember that their actions may be because they are hurt or embarrassed. Distinguish the problem from the person and invite the employee to work with you on a solution.

11. Clearly state the desired outcome

It would be a shame to have the courage to enter a difficult conversation, only to exit without a clearly agreed outcome. Don’t assume that the employee understands what specifically you want to see in their behaviour or performance. Make a clear statement and seek agreement to the change. An example could be:

I would like to see you arrive 15 minutes prior to the commencement of your shift time so that you have time to organise yourself before the first customer arrives.  Do I have your commitment that you can make this change?”

If you are unable to find common ground and agreement, it is important to schedule an alternative time to keep the conversation going and hopefully progress with a new perspective.

12. Focus on the windscreen, not the rearvision mirror

 It is easy to lay blame, make excuses and come out swinging, but the real skill is around helping the employee to accept the feedback, draw a line in the sand and look forward through the front windscreen. After all, it is much bigger than the revision mirror.

Look for solutions; not to blame

The intent of a courageous conversation is to look forward to solutions not backward to blame. Possessing the courage to have a difficult conversation should be celebrated, but leaders need to be realistic about outcomes and immediate change as the conversation may have had an emotional impact. The employee needs to be in the right mindset as it is human nature to accept unresolved issues rather than tackling the challenge of change.

Nevertheless, conducting a courageous conversation is a tool that helps leaders to resolve relational conflict. The conversations help you to speak your truth, be authentic and vulnerable and reach new levels of success. They may not always turn out the way that we want, but we can't let fear overtake our courage as where there is no risk, there is no reward.

Further information

For assistance with your workplace matters, Members of Ai Group can contact us or call our Workplace Advice Line on 1300 55 66 77 for further information.

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Georgina Pacor

Georgina is Senior HR Content Editor – Publications at Ai Group. She is an accomplished Human Resource professional with over 25 years of generalist and leadership experience in a broad range of industries including financial services, tourism, travel, government and agriculture. She has successfully advised and partnered with senior leaders to implement people and performance initiatives that align to business strategy. Georgina is committed to utilising her experience to create resources that educate and engage and is passionate about supporting members to optimise an inclusive workforce culture that drives performance.