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A Manager’s 6 Laws to Master Difficult Conversations

[4 min read]

How to successfully manage and handle challenging situations.


We can choose to evade difficult conversations. They seem too hard, and we don’t know what to say or how to say it, and unfortunately the problems remain unresolved. Sometimes we initiate difficult conversations and wish we knew how to handle them better. Luckily, there are well tested strategies we can employ to flip difficult conversations into constructive conversations.

Challenging conversations are part of a manager’s day-to-day life: whether it is a negative performance review with a team member, a phone conversation with an unhappy client, or negotiating a deal with a service provider. Difficult situations and conflict are generally caused by differences in Values, Wants, Needs and Expectations. But how to best handle these sticky situations, confidently navigate through these exchanges and making sure everything goes as smoothly as possible?


“The problems is not to HAVE that conversation. The problem is NOT to have that conversation.”
~ Martin Probst


In this fast-paced environment, we are required to hold more of these difficult conversations than ever before. Here are the 6 laws to successfully initiate, navigate and master them:


Law 1 – Things are not as they seem

When you are required to manage a difficult conversation, first and foremost acknowledge that things are not always as they seem to you. Each person’s reality differs from the next person, and are based on experiences, learned values, behaviours and fears. Remember the famous quote by Albert Einstein:

“We cannot solve problems by using the same kind of thinking we used when we created them.”


Law 2 - Don’t get caught up in the drama

Initiating and facilitating difficult conversations is inevitable for long-term success. After appreciating the fact that we are all different, the second step in finding resolutions is to ensure you don’t get caught up in the drama. You need to become the observer instead.

 Drama Cycle - Leadership Skills - Difficult Conversations


Law 3 - Think WIN/WIN

To think “Win/Win” is not just a conflict resolution technique, but much rather a philosophy of human relations. If you can find acceptable solutions for all involved parties and ensure that those involved feel that they have won in some way, you will empower creativity and ongoing healthy relationship.


Law 4 – Be prepared

If you do get the chance, it can help to plan by writing down some notes and key points before the conversations. Make sure, however, that this does not compel you to stick to a ‘script, and keep an open mind throughout the exchange.

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Law 5 - Structure the conversation

There are a range of tools and strategies to successfully structure a difficult conversation, and thus provide you with the confidence of a positive outcome. Let’s have a closer look at a couple of them:


Hierarchy of ideas

Hierarchy of ideas describes how to master difficult conversations by controlling the flow of conversation or ideas from abstract to specific, and vice versa. Hierarchy of ideas (Chunking) is a fantastic concept to understand, because many communication breakdowns are caused by mismatched ‘chunk sizes’. (For example: Luke may use smaller chunks than Jack. Therefore, Luke sees Jack as vague and confusing when he talks. Whereas Jack may see Luke as terribly boring and ‘caught up in detail’.)

Let’s have a closer look at this so-called ‘Chunking’ model:

 Hierarchy of Ideas - Chunking - Leadership Skills - Difficult Conversations



Your success as a communicator comes down to your ability to think up, down and across the communication ladder easily and effortlessly. The faster you can do this, the better you become at facilitating difficult conversations and turning dysfunctional situations into productive outcomes.

Managing a difficult conversation becomes easier when you understand the power of this communication strategy.

It makes it rather easy to find an agreement when being able to ‘chunk-up’ two people with different ideas. By leading them to the ‘WHY’ (Abstract), they will most likely quickly realise that they ultimately want the same thing (acknowledgement, recognition, etc.). Once an agreement (common goal) is reached, start to look at how the situation can be resolved by ‘chunking down’ (Specifics), and getting clear on the details. As soon as you notice negative emotions (frustration, anger, despair etc.) creeping in from one or the other side, remind them of the common goal and ‘chunk across’ (Lateral) to explore other opportunities by asking what else could be done to resolve the situation. In other words, consider different options that are available to maintain the agreement. Once you reached common ground again, it’s time to chunk down even more until a solution is found and both parties are clear on how to achieve the desired outcome.


GROW Model

To bring some valuable structure to the ‘chunk size filter’ during a challenging conversation, you can apply the GROW Model. This strategy is a four-step process that can be compared to planning a journey; establishing a goal (where you want to go) and determining your reality (where you currently are). Then it is about exploring the options (various routes), and the last step is about the way forward, in other words establishing the commitment to making the journey.

GROW Model - Leadership Skills - Difficult Conversations


Below is the overview as well as a few practical questions you can utilise at each step:

Examples for G: How would you like this situation/issue to be? How will you know that you have achieved the goal?

Examples for R: What have you attempted to do so far to transform this situation? What results did you get?

Examples for O:  What could you do if you had total certainty about the outcome? What could you do if you knew you could not fail?

Examples for W: Looking at your options, which action(s) stand out as being the action(s) that would bring you just one step closer to your outcome? When will you have completed these first action steps?


Law 6 – Reflect and improve

As with everything else you do, reflection is a vital part of improving your leadership skills. After the conversation, consider what went well, how you or the other person has reacted, and what you could have done differently to achieve an even better outcome.  



The techniques covered in these 6 laws are very simple but also very effective. Utilise them for any difficult conversation and be surprised by the positive outcome! With a little practice, what you have regarded as ‘difficult conversations’ are now not so difficult after all.


“Dare to make a difference!”

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