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7 easy conversation techniques to keep a difficult conversation on track

Henk Veenhuysen
by Henk Veenhuysen

Do you ever have a difficult conversation with your colleague at work? Probably. Before you know it, you are on an unbridgeable difference of opinion. Frustration and irritation strike. It becomes a never ending discussion with everyone full throttle in resistance mode. How do you tackle a difficult conversation? In this blog, I explain 7 easy conversation techniques to avoid derailing such a conversation. With a bonus: phrases best avoided in difficult conversations. Try them out!

updated: 4-nov-2023

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1. Make your opponent a partner

In a difficult conversation, it is no problem to see your interlocutor as an opponent. The enemy so to speak. You can spin this by introducing your interlocutor (literally) as someone standing next to you. You can do this in your mind but also physically.

Example: change positions yourself at the table. Instead of sitting across from each other, you sit next to each other. For example, each on a corner of the table.

2. Less persuasion more learning.

Conversations get derailed quite often because you try to convince the other person of your truth, vision or approach. Recognizable? Such a strategy often results in the other person giving you much resistance. No matter how beautifully, logically and eloquently you package it.

The conversation then enters the mode of arguing and justifying also known as the “true-not true” dialogue. If people are in this mode then learning (showing inquisitive behavior) is blocked and all the people at the table are in the trenches, only repeating their own ‘truth’.

A problem or disagreement can only be resolved if you are willing to examine how the other person sees it. Put (at least temporarily) your own point of view in the background. You can do this by simply and very deliberately asking questions.

For example, questions such as:

  • How do you view this situation?
  • What opportunities do you see?
  • Why do you think this can work?

This puts you and your interlocutor in a learning mode, which moves the conversation forward. You might just come up with a better idea if you better appreciate the other person’s expertise.

3. Transparently articulate your intention

Your transparency helps to have a good conversation. How to do that? Share your purpose of the conversation and what you want to accomplish with your interlocutor.

Examples to increase transparency:

  • (To Yourself) ‘I suggest that we put all objections to this proposal on the table so that we don’t miss anything when we come to a decision.’
  • (To the other person) ‘What do you want to get out of this conversation?’
  • (About the process) ‘I want this conversation to be open and unbiased. Let me know if I give this too little attention.’

> 25 practical tips to practically make your conversations more effective

4. Having not to many assumptions helps

In difficult conversations, I have often found that people make assumptions. For example, I ask them why they thought it was a difficult conversation. Often I get answers like, ‘His only goal is to move up a step. He doesn’t care if the team can do this.’ Or, ‘She wants me out of that position so this has to fail.’

They are all assumptions about the other person’s intention. Assumptions that are rarely checked. They often say more about those making the assumption.

Making (too many) assumptions hinders having a good conversation. It prevents you from properly understanding the situation, and it stops your creativity from seeing or thinking of other solutions. You run the risk of shutting down yourself, and that puts your conversation into a kind of stalemate.

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Having a difficult conversation
Be curious in a difficult conversation

5. Be curious in a difficult conversation

If you want to understand your interlocutor better, it can be helpful to abandon your own defensive posture. In doing so, you create an opportunity to take the conversation a step further. You can let go of your defensive attitude by asking good open-ended questions. Curious questions that clarify the other person’s perspective.

For example:

  • How does this affect you and your team?
  • In what ways are you dealing with this?
  • What is your interest?
  • What’s at stake for you?
  • Do I need to understand something better and what is it?
  • Is there anything that would help to do this more collectively

Don’t forget to thank the other person for his/her contribution!

Should you still be caught by your emotions in an awkward conversation and in danger of being blown over? These tips make it easy to stay on your feet in that awkward conversation.

6. Acknowledge your own part

Easy, of course, to show what went wrong and blame someone for it. Much more difficult is to recognize your own part in it all. What did you do or fail to do that caused the problem?

By acknowledging your own mistakes, you take responsibility. If you are leading by example, you encourage others to take responsibility as well. That’s a good fundament to step into the difficult conversation.

Difficult conversations in a team
Sometimes team members withdraw from important discussions for fear of causing an emotional outburst. If that happens in your team, it’s time to address it through a new way of thinking about emotions.(Davey, 2019)

7. Put your focus on the future

People are more than brilliant at maintaining and guarding their positive self-image. This is a major reason why receiving feedback is so difficult. Some examples? You then say “it’s not true” or “you see it differently.

It is smarter to focus on the future in a difficult conversation. You do this by asking questions such as:

  • What are you trying to achieve?
  • What do you hope to learn?
  • What ideas do you have to get it better?

Do you also struggle with awkward conversations? Then our 1-on-1 assertiveness training course “In 40 days more assertive” might be for you.

More about conversation techniques

All 7 conversation techniques deal with the content of the difficult conversation. Beneath that difficult conversation often lies a problem. It is then helpful to look at the conversation in a more process-oriented way. How does someone position themselves? How do you avoid resistance in a conversation? In the remainder of this blog, I will give you phrases you can better avoid in a difficult conversation.

Extra: phrases best avoided in a difficult conversation

Difficult conversations are difficult for a reason. Often emotions play up because in a difficult conversation you are likely to be more stressed and tense than usual. You then say something wrong very easily, despite the good preparation you have obviously done. And before you know it, your difficult conversation gets derailed because you offend or anger the other person.

So how do you address that? How do you make sure that your message comes across well AND how do you consider the other person’s feelings at the same time?

I’d like to share with you the phrases and words that can get you into trouble in a difficult conversation. It is the language that I have noticed when counseling people that causes tension to build in a conversation. They are indispensable to further refine your interview techniques.

1. Don’t assume that your point of view is clear

Sometimes you think you are 100% right. You then use words like “that it is clear to you without a doubt” what happened. This behavior is called naive realism. That is, you assume that your (apparent) objective reality is also clear to and shared by the other person.

If you think about that for a moment you know that “objective truth” is rare. A situation is almost never black and white. All situations and their assessment are colored by your own values.

Using phrases like this indicates (unintentionally) that the other person is stupid and that what they think about it is unimportant. That will add extra tension to a conversation. So you will have to make an effort to make your point.

Phrases and words that cause tension in the other person:

  • It is perfectly clear to me that …..
  • I am without a doubt when it comes to …
  • I am convinced that …
  • Evidently it is so
  • There is no denying that…

2. Don’t overdo it

When speaking to someone who often upsets you, it is easy to use words like “always” or “never.

You never let me never speak out…
It is always the same with you ….

Exaggeration or generalization makes you less credible. It leads to your interlocutor probably saying “it’s not true” and then asking you for proof of where and when it all happened.

The use of such words (always, never) leads the discussion to be about “the number of times it happens” rather than the content. It is best to keep the focus on ending or starting specific behaviors.

3. Don’t tell what the other person should do

If you tell someone what you think he or she should do then there is a judgment on that. When you say to someone, “you should actually do A,” you are indirectly indicating that “A” is the way it should be done.

And that all other directions are not ok. Usually, people will not be so willing to agree to “your direction.

Sometimes it is helpful to have direction; for example, if you are responsible for the culture within a group or organization. In that role, you can say what you would actually prefer to see.

Your interlocutor will feel judged; as if they can’t come to their own good judgment or decision to address a particular situation.

Try using these phrases

Use these phrases to increase your influence and avoid judgment.

  • Have you considered this?
  • Is this perhaps a possibility?
  • Have you thought about ….
  • I would like to share a thought with you. Is that ok?

4. Your feelings are not the other person’s fault.

You cannot always prevent the other person from “triggering” you. (The other person says something that hits a nerve inside of you). This produces in you a natural emotional reaction and sometimes stress. While perhaps tempting, blaming the other person for that does not help so much.


You have a work meeting and your colleague interrupts you as soon as you open your mouth. You get red spots on your face, your heart races like crazy, and you might as well say it makes you “terribly angry that he interrupted you. If you do it this way then in 9 out of 10 cases it ends in an endless discussion.


No one likes to be blamed for anything. Especially if it hurts the other person. The first reaction is to go into defensive mode instead of a heartfelt apology.

Choose a different style

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Instead of blaming your feelings on the other person, you can say 1 of the following:

  • If you interrupt me so quickly then I feel you don’t respect me. Would you stop doing that?
  • Would you not interrupt me until I finish speaking?
  • You can also just leave your feelings your feelings and stick to the substantive issue at hand.

This way you keep it nice and assertive.

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having difficult conversation with colleague
Leave the integrity of the other person intact in a difficult conversation

5. Leave the integrity of the other person intact

If you work with someone, and this person does something different than what you expect, you would quickly disqualify this course of action as unprofessional, wrong or unethical. When you use these kinds of words, you should not be surprised that the other person will “go knee-deep in resistance mode”.

People have a strong need to think of themselves as neat, wise and morally wise. If you describe their behavior in a way that diminishes their self-esteem then chances are they will become defensive. The focus is then no longer on the actual problem or behavior. And that’s a missed opportunity.

You could say this if something is not desirable:

  • Indicate that failure to meet deadlines jeopardizes the goal/project.
  • Tell them that posting fake reviews is not consistent with the organization’s core values.
  • Say that covering up mistakes denies us the chance to learn from mistakes.

6. Don’t say, ‘it’s not personal

Probably you have heard this one: ‘it’s not personally, but ……’. This statement often means that it is actually very personal to the person you are saying it to. If someone is angry, touched by your statements or because you did something you sprinkle quite a bit of extra salt in that wound by saying “it’s not personal.”

Better to acknowledge that you realize it affects the other person personally or has personal meaning. Should you find that difficult to say, you can choose to avoid the “it’s not personal” part in the conversation.

Summary interview techniques

This is how to have a difficult conversation

  1. Make your opponent a partner

  2. Don’t go convincing

  3. Be clear about your intention

  4. Don’t make assumptions

  5. Be curious and open

  6. Acknowledge your own part

  7. Put the focus on the future

Get busy

When you start practicing these conversation techniques, you will immediately notice that your difficult conversation will improve. Just try out one of the examples and make a start. Choose the conversation technique you like best. This way you will easily learn it in practice and become more assertive.

Free introductory call,

Run into a lack of assertiveness or self-confidence?

Want to get rid of that, once and for all? Then my 1-on-1 coach approach is really something for you. Lets get acquainted first, no strings attached. See if we have a 'click' and if I can help you.

> Schedule your free call now

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