How To Manage Difficult Conversations


Being able to manage and communicate a difficult conversation with an employee is a skill all high-performing managers must master. When speaking with leaders and managers, often the reason they tend to avoid these conversations is because in the past they have had a confronting and negative reaction from an individual they have challenged.

Regardless, not engaging in these much needed conversations often causes leaders and managers to:

- Feel like they are being taken advantage of
- Have continued poor results from individuals
- Encourage unwanted negative undertones in the working environment

An important aspect to managing difficult conversations well is to promote relationship over division through facilitating behaviour and not blaming and shaming any individuals’ actions.

Below is a model that differentiates between having an effective conversation (Engaging) and an ineffective conversation (Disengaging). To eliminate defensive behaviour and make room for people to really take what you have said on board, focus your conversation to the right.

How To Manage Difficult Conversations

Model Breakdown:

Leadership Presence

Your ability to recognize how you are feeling, your beliefs, your mental frames and avoiding or suppressing emotions will have a strong influence in the way you communicate to individuals and employees. It’s important for leaders to develop self-awareness before undertaking these difficult conversations. This will help create an authentic leadership presence which will command much greater influence.


Make a decision to have a conversation with the person/people that maybe don’t evaluate or appraise their own actions. Communicate in a way that states what is important to you instead of a judgment or a demand. When we make this commitment, we are facilitating their behaviour by focusing on solutions not problems. Focus on their actual behaviours, not the shaming of the individual. This will also open a door to be able to water new habits in the future.


Often the feedback individuals receive is useless. The intent of it and what it is that the individual needs to improve on are vague and they are, more often than not, left without knowing what actions to focus their attention on or how to create new habits.

It is critical to use succinct, positive language to promote a favourable response from the individual.

For example: if a leader/manager makes a vague and negative request such as, “ I want you to stop handing these reports to me so late”, the individual involved doesn’t walk away from this request with a new habit to go and put into practise, but rather, pressure and fear to not be late again. Useful feedback regarding this example would require:

- Understanding as to why the individual is handing in reports late

- A conversation that states what’s important to the manager and facilitates his/her performance for the future

- Support and follow up to nurture their new actions until it becomes a habit

Benjamin Young

Speaker | Coach | Trainer | at Job Performance Coaching & Training

I help executives, managers & team leaders to influence human behaviour and in essence get more out of individuals and teams in terms of execution and results, sustainably. I help both leaders and employees improve excellence, energy & productivity in the workplace. I do this by teaching three specific skill sets: 1. Dealing with having too much to do 2. Staying cool under pressure 3. Influencing Behaviour -(Presenteeism, Absenteeism, Underperforming staff, Constructive Feedback)

Comments (3)
Ling Lee

Ling Lee at Digital Marketing and Personal Branding

Great article as always Benjamin! I always like to use the sandwich method - good comment, bad comment, and good comment (in that order) so that my colleagues don't get discouraged!

Benjamin Young

Benjamin Young, Speaker | Coach | Trainer | at Job Performance Coaching & Training

Thanks Ling. I've noticed that the typical feedback sandwich still has it's downfall as it often packs a heavy punch with staff only focusing on what they have done wrong. Perceived 'threats' (bad comments) hold more weight than 'rewards' (good comments) for many of us...

View all (3) comments