02 September 2019

Leadership 101: How to Have Courageous Conversations at Work

Soft Skills / Talent Development
courageous conversations



One of the most important skills that any leader must have is the one you will never get any praise for and it will never be part of a competency assessment. You won’t even get positive feedback when you use it. However, it is a skill that is essential to the motivation, performance and the success of your team. That skill is the ability to have courageous conversations.

In a recent Dilbert comic strip, Scot Adams introduced a new character – the toxic employee.

Every relationship is touched by the toxic employee – trust vanishes overnight; every idea or glimpse of creativity drowns in waves of negativity. Star performers become less productive or worse, start looking for other jobs just to get away from the poisoned atmosphere.

You, as a leader, need to intervene as soon as possible to prevent the rot spreading – toxicity is infectious.

Face up to courageous conversations

It is easy to opt for a “wait and see” approach to dealing with the situation – we want to avoid conflict and disagreement. Having a difficult conversation is painful for the employee and just as awkward for the leader as they have to deal with the fall-out.

soft skills
Soft Skills Development
Building the critical skills needed to succeed in the modern workplace
soft skills
Soft Skills Development
Building the critical skills needed to succeed in the modern workplace

Even in cultures where saving face is not a big deal, it is a huge face issue to challenge someone’s core behavior and personality. This is a situation that requires a courageous conversation.

In many ways, the worst part of any leader’s job is not dealing with an individual’s poor performance but telling a good employee that their job is at risk of redundancy through no fault of their own.

Helen had been the office manager for a medium-sized business for over 30 years and had grown the role quite considerably. She was now looking after the entire admin team of about 15 people. When the business was bought by a competitor, it was clear that her role had become unnecessary.

It was possible to re-deploy the more junior admin team, but her role was covered by a combination of HR, finance and operations and there were overlaps with similar functions in the competitor – there was no room for a generalist.

Further reading

She had worked with Kate, the CEO, for the past eight years. Helen’s son had done work experience in Kate’s office. They had built up a friendly working relationship. But now, Kate has to call her in and tell her she is losing her job. That takes a special kind of courage.

Evolutionary psychology

Our brains work overtime to help us preserve relationships and avoid anything that threatens the stability of our interactions with other people. Having a difficult conversation is working against an entire evolutionary process.

A 1998 Harvard Business Review article on the business implications of evolutionary psychology discusses how Stone Age humanity developed an aversion to loss and become hardwired to seek comfort. Our pre-historic ancestors worked hard to maintain harmony.

Given that we are fighting thousands of years of precedence, how can we put aside evolution and have courageous conversations that achieve the most impact with the least damage?

We need to consider three factors:

  • Time
  • Place
  • Manner

The first two are simple, although crucial. The third is much more complicated.


Don’t delay.

Have the conversation at the first opportunity, even if you must move around meetings and tasks to fit it in. The earlier you have the conversation, the easier it is to prevent greater damage.

Whatever the issue is, not starting the conversation is dangerous. The office gossip network may work quicker than you think; the damage of poor performance may spread quicker than a computer virus.

Resentment, anger, frustration and disengagement are simple emotions that don’t require much fuel. Dealing with the issue immediately removes the oxygen from the fire and brings it under your control.

soft skills
Soft Skills Development
Building the critical skills needed to succeed in the modern workplace
soft skills
Soft Skills Development
Building the critical skills needed to succeed in the modern workplace

Similarly, dealing with an issue is the ethical thing to do. Whether a redundancy or poor performance, your employee needs to know the situation as soon as possible. They have lives and plans and will make work and personal decisions based on what they think their future holds. If you withhold that information from them, you increase the damage to their lives as well.

The UK-based mediation service ACAS suggests that delaying the conversation may:

  • Mislead the employee into thinking nothing is wrong
  • Remove the opportunity to improve
  • Lower morale of other employees


It goes without saying that you should have the conversation in private. But is your office or meeting room in a public place? Does it have glass windows? Will you be returning a distraught or angry employee straight back into an open-plan office?

One expert suggests going to a neutral venue if possible. Emotional reactions will not cause embarrassment in front of colleagues and both sides will have the opportunity to compose themselves in private.


The single most important factor in having effective courageous conversations is how you communicate. A recent Forbes article suggests some specific tips:

  • Have a plan
  • Be direct
  • Be specific
  • Mind your language
  • Listen

Have a plan

It is important that you plan out your conversation. Jot down on a piece of paper your key message and keywords for your evidence. Try and work out what questions the person may ask and have answers or documents ready.

Planning out the conversation will not only help you stay on track, it reassures both you and the employee that you are in control – it will reduce nerves and will not obscure your key message. Try also to think about possible responses you might get to the points you will raise and plan how you will respond.

Further reading

Be direct

The more we spend time on padding out a conversation, the more confusing we are to the listener. Be direct without being harsh. Don’t hide away your key message in encouragement and positives. Come to the point quickly and directly. This directness shows your sincerity and the importance of what you have said.

Hiding away criticism in a “feedback sandwich” makes it appear less significant and gives the listener the opportunity to ignore the “meat” of the sandwich.

Being direct will give your employee the opportunity to respond to the criticism directly as well. You will be able to listen more effectively and have more chance of addressing the situation.

Be specific

When you are discussing poor performance or other disciplinary issues, you should be as specific as possible.

Describe the situation or issue with concrete examples, explain the negative impact and outcomes and detail the next steps or required improvement with consequences. The next steps should always include what specific improvements you want the person to make.

I have recently received three complaints from your bigger clients about how you talk to them. They have said that you are rude and often make mistakes in your pricing. Last week, Xavier Avelino asked for a quote for 1,000 liters of paint and your proposal talks about 10,000 liters. When he questioned the figure, you replied that it was his fault for not being clear.

soft skills
Soft Skills Development
Building the critical skills needed to succeed in the modern workplace
soft skills
Soft Skills Development
Building the critical skills needed to succeed in the modern workplace

This customer has now gone to another store and we have lost a very important and influential customer. You should consider this as a formal warning. I will be monitoring your client relationships during the next 6 weeks. If there is no evidence that you have reduced mistakes and have changed the way you talk to customers, we will need to look at the next steps, including your future in the company.

Mind your language

Language can be a poor tool for communication – it can be ambiguous. Don’t say, “your work has been OK” or “that wasn’t very good, was it?” This kind of sentence is ambiguous and can easily be misinterpreted. Similarly, use specific pronouns and active verbs to add impact.

Don’t say,

It has been noticed that not all of your work has been completed to the standard we expect.”

This is impersonal, obscure and shifts responsibility to a vacuum. It is much clearer to say,

I have noticed that you have not completed your work satisfactorily.”


The word conversation comes from Latin. Its meaning is more to do with interacting with other people you are familiar with than talking (e.g.: conversant with the leadership team, or with new technology). This implies that conversation is two way – not just you talking but listening as well. Once you have explained the issue, you must then give your employee the opportunity to respond.

Further reading

Make sure you listen to hear, rather than just waiting for your chance to talk. Let them explain their side or offer mitigation. No matter how well you understand your colleagues, you can never know absolutely everything about them and their situations.

You will learn more by listening to your colleagues during a difficult conversation than you will in 10 team meetings.

In a redundancy situation, you will learn about their real hopes and fears; they may make suggestions that can improve team performance.

One of the greatest leaders of all time, Nelson Mandela wrote in his autobiography, ‘I learned that courage was not the absence of fear, but the triumph over it. The brave man is not he who does not feel afraid, but he who conquers that fear’. To have a courageous conversation requires a leader to make the decision to overcome their fear of conflict and relationship damage.

Mandela needed the courage to have difficult conversations with PW Botha and FW de Klerk – two conservative apartheid supporters. Without Mandela’s courage to speak directly and to listen, the transfer of power in South Africa would have been much bloodier. True leaders overcome their fear and face up to having courageous conversations with their staff.

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