Guide: How to handle the difficult conversation

The difficult conversation is important. But how do you go about doing it? This blog post gives you our suggestion for doing it.

By Poul Langagergaard

The difficult conversation is important. We talked about that in this blog post. But how do you go about doing it? This blog post gives you our suggestion for doing it.

We split the process into three phases: Before, during and after the conversation. But first let us take a quick look at some important basic principles on conflict communication.


3 important principles

Be open to different perspectives

Our ways to view the surrounding world are unique which is why a manager will not have the objective truth. It is important to be open towards employees and colleagues’ perception of different situations.

According to Anne-Suzette Humle (1993) you should go to a difficult conversation with this sentence in the back of your head: “In principle I am not more right than you are, but through a dialogue with you, I can possibly provide you with new perspectives to affecting/changing your previous view.”


Be clear in your communication

”In trying to protect the employee a lot of managers tend to “soften” the critical message about the challenges. However, this often has the opposite effect. If you are not honest and clear in your communication, you cannot expect them to act accordingly – or engage in a fruitful dialogue.”.

It is a good idea to be specific when you talk about some of the situations where the problems occur. Describe your observations instead of assuming that the employee is stressed.


Not a discussion but a dialogue

A conversation can be had in many ways. We recommend that the difficult conversation is to be considered like a dialogue rather than a discussion.

The purpose of a dialogues is to understand the other person and to be inspired, whereas a discussion is often about being right or convincing the other.

In the dialogue you must therefore listen and explain yourself, and it is important to stand by who you are as a person. It is not purposeful to look for faults in the other person, to defend yourself or try to claim that you know the truth. The dialogue is not a power struggle but a mutual learning process where neither party comes out on the other side as “loser” or “winner”, but as two enriched, yet different individuals.

With these principles for communication, you can now take on the difficult conversation.


Before the conversation – the preparation

According to Anne-Suzette Humle there are nine steps to take when preparing for the difficult conversation.

1) Get to the heart of the matter

  • How does Frank show his inability to cooperate?
  • In which situations does Helen show lack of cooperation skills? And what consequences has it had?
  • How often does it happen?

2) Can you understand the problem?

  • Take time to get into to problem
  • This is important in relation to the solution process. If you cannot understand the problem, it can be difficult to accept that it will take time to solve.

3) What are the goals for the problem’s solution?

  • If you do not have a goal for the solution, you do not know when the problem is solved.

4) How would you solve the problem?

  • This provides opportunities for taking action and sharpen attention to the solutions you come up with as well as the solutions the employee comes up with. ¨

5) The employee’s own resources/strengths

  • The likeliness that the employee is positive about the teamwork is bigger if the conversation starts out with positive expressions/praise for the employee.

6) Choose a time and place

  • Await 3-5 days between the agreement on the conversation and the conversation itself.

7) How long must a solution be on its way?

  • How long time must pass before the problem is solved?

8) If the problem is not solved – then what?

  • How serious is the problem? Is it acceptable that it is not solved?

9) Sell the conversation

  • Make sure that the two of you are alone when engaging the employee’s interest in the conversation.
  • Present what you would like to talk about without going into details.
  • Do not address the problem right away. As soon as you have mentioned the conversation, the employee will try to figure out a solution. This is good for the solution process itself and the reason why you do not address the problem right away.

When you have dealt with all nine steps and written your thoughts down, you are ready to take on the difficult conversation.


During the conversation

Begin the conversation

Before you begin the conversation, you should be aware of the physical settings. Make sure there is not too much psychical distance between the two of you (big desks or other big objects) and that you are both sitting within eye level. Keep eye contact and speak clearly.

It is a good idea to start of the conversation on a positive note because that will provide good conditions for the employee to be willing to open up and talk about the problems. Here you use your thoughts from the preparation for the conversation about the employee’s resources and strengths. The positive affirmations must be truthful and you have to be able to vouch for them.

Now you present the problem clearly and precisely:

1) What is the problem?

2) In which situations does it occur?

3) How often does it occur

4) What impact does the problem have for the work?

It is important to respect the employee and give him/her the opportunity to not answer the question. The conversation does not take place only on the conditions of the manager, but also the employee’s premises. Therefore the employee has the right to remain silent on questions, if they are experienced as offensive or crosses the person’s lines.


Mutual understanding of the problem

When the problem is presented, you must find out how the employee experiences the problem and if you can find a common ground for the rest of the conversation. As previously stated, none of you have the right to define what is the truth. You must therefore find out whether the employee agrees or disagrees with you in the perception of the matter. By acknowledging the employee’s experience, you show that you respect him/her and gains their trust.


The definition of the problem has three possible outcomes:
1) The employee rejects the problem

2) The employee agrees that there is a problem, but there is disagreement on the complexity of the problem and therefore to its solution.

3) The employee agrees that there is a problem that requires his or her action for a solution.

In outcome 1 where it is not possible to reach a common ground for a further conversation, there is no reason to try to convince the employee that there is a problem, why you have to end the conversation (see next point about finishing the conversation).

In outcome 2 the employee agrees that there is a problem, but that he or she is not the source of it. Hereby, the employee takes on the role of victim.

In outcome 3 the employee agrees, and the person is eager to get started on finding a solution for the problem.

In the last two situations, there is a basis for continuing the conversation and find out what circumstances the problem occurs in. This is done by asking questions such as: “What happens when…?”, followed by “What happens then…?”. Break the problem down and find out which behavior reinforces other patterns of behavior. This will give you a good sense of the problem and why it occurs.


Find the goal

When the problem is defined, the two of you need to find the goal for the solution. According to Anne-Suzette Humle, there are six conditions that must be met for you to reach the goals. They must:

1) be important to the employee

2) be realistic

3) be measurable

4) involve new positive actions

5) motivate to action

6) signal a beginning more than an end

If the employee previously has tried to solve the problem unsuccessful, the two of you need to evaluate these measures in relation to the definition of the goals.


Possible solutions

From here on, the conversation moves on to finding solutions to the problem. For that, you can use different kinds of questioning techniques.


1) Exception questions:

  • Are there any times when the problem is not/has not been a problem? Here the exception becomes a possible solution, where the employee organizes the actions needed to keep the problem at bay.

2) Miracle questions:

  • Have the employee imagine that the problem is solved (in “when-form” and not “if-form”). This question is used to get the employee in touch with what is needed to solve the problem.

3) Promotes and inhibits:

  • What conditions nourish the problem and what inhibits it?

4) Advantages and disadvantages

  • What are the advantages and disadvantages of the problem?

5) Reframing:

  • Ask for positive phrasings and understandings of the problem to shed a new light on it as well as new suggestions to solutions.

6) Reflective questions

  • Has the employee considered this or that solution? Brings alternative solutions to the table.

7) Success questions:

  • Ask about what is going well. This gives the employee the opportunity to see the problem in proportions as well as find out if some of the strengths can be used as a solution to the problem.

8) Other people’s problems:

  • Make the employee imagine that it is someone else’s problem. This shifts the focus away from the person and gives the employee the possibility to view the problem from the outside.

9) Coping questions:

  • Why is the problem not bigger/worse? Something is already being done and maybe more can be done about it.

10) Pessimistic questions:

  • Make the employee imagine the worst possible situation in order to free resources to try something new.

11) Scale questions:

  • Make the employee assess the problem, expectations, efforts and solutions on a scale e.g. 0-10. If the employee assesses the size of the problem as 8, you can ask “what would it take to make it a 7?” “A 6?” etc.


Finish the conversation

As solutions are being brought to the table, the conversation has reached its end. It is important to always finish it on a positive note no matter how far you are from a specific solution.

As mentioned previously, you may find yourself in a situation where the employee does not want to acknowledge that there is a problem. This can be frustrating, but still try to express respect for the employee’s point of view in experiencing the situation. It is very important to remember to take your time leading the conversation and not finish it right away.

Pressuring the employee is never the answer. Instead, arrange for another conversation a couple of days later and set 2-3 attention points for the both of you to look into until the follow up. Do not forget that every small step towards something constructive will be better than the starting point. You may experience that several small conversations with attention points will be necessary, but the most important thing is keeping a positive dialogue.

You may also find yourself in the situation that you and your employee agree that there is a problem, but you both see the solutions differently. Therefore, the employee will probably not be able to make binding agreements where he/she has to do something active to change the situation. In these cases, you can ask the employee to do an observation task. Here you encourage the employee to notice/observe/register certain conditions with the purpose to make them see solutions that he/she has not been aware of before. Set up a new meeting where you can follow up on the conversation.

If you and your employee through the dialogue have come to agree about the problem and its solution, the two of you can start to set the different solutions up with the goals. What will it take for you to reach the goals you have set? From here on, the two of you make specific agreements on tasks to do. This ends with a date for a new meeting to follow up on the problem.


After the conversation – follow up

Whether you make a specific agreement or not with the employee, it is important to follow up on the difficult conversation. Without following up all the work with having the conversation can be wasted and you will also be signaling to the employee that you do not appreciate the work the person has done to put an end to the problem.

If the difficult conversation ended without a specific solution, you have the following options:

1) Repeat the conversation, but involve a third party

  • It is quite possible that it might be the relationship between you and the employee that has "locked" the conversation in the first place, which is why a third party might be able to create a more constructive contact.

2) Make demands

  • Making demands is not equal to solving the problem. But it can sometimes be the only possibility if you disagree about something specific, e.g. scheduling working hours.

3) Accepting that the problem will not be solved

4) Transfer the employee

5) Letting the employee go


If you during the difficult conversation have found common ground regarding the problem and the goal, but not the solution it can take longer time to solve the problem - simply because the employee first can relate to their part when the problem occurs in the everyday life. Make up with yourself if there is “room” for the problem to last a while without being solved. During the difficult conversation you agreed to meet and discuss the situation again. In this conversation you should immediately ask what observations the employee has made since the last time. Has the employee become more willing to participate in the solution process? Take up the work to find a solution (see the question techniques further up) so you can make specific agreements.

If the two of you during the difficult conversation agreed upon the problem and solution, you use the follow up conversation to check the status.

Is the problem closer to a solution?

Is the problem unchanged?

Has the problem gotten worse?

Use the specific goals you defined during the difficult conversation to see how far you are from a solution. Make sure to praise the employee if there has been progress – this encourages them to continue trying to solve the problem.

Have there been no changes, or if the problem has gotten worse, you have to go back and figure out new solutions.



Anne-Suzette Humle: ’En samtale – to vindere’, 1993

Keld Kunze, Center for Konfliktløsning: https://konfliktloesning.dk/videnscenter/at-moede-og-kommunikere-om-konflikter/

O. J. Harvey og Marshall B. Rosenberg: ‘Nonviolent Communication’