Navigating Difficult Conversations

Trying to Keep it Positive


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Often what makes a conversation feel difficult is when the message conveys information we feel will be offensive or potentially upset the receiver. There is a desire to be sensitive to the feelings of the other person but the need to correct an issue is still dominant. Many people can be easily upset by negative feedback and respond with anger, guilt, or sadness. This can be particularly poignant if the criticism triggers their defensiveness (Lazarus, 2011). Constructive criticism is meant to be an approach to offer this potentially ill received feedback with the goal of improving the situation (WiseGeek, 2003).

Two penguins fighting

When approaching one of these conversations, it is important to know what you want to say ahead of time. You need to be able to provide clear information on what the problem for you is. The problem should be able to be reduced to a reasonable, unemotional statement of action and should not focus on the person but a specific behavior. It is also important to consider the relationship with the intended receiver. The type of effective conversation you have with your life partner would be very different with how things would be phrased for someone who you have less of an emotional relationship with, such as a community member or potential third party partner (Walters, 2001).

So you've considered what you want to say, so how do you say it? First thing to keep in mind is the location. Depending on the issue and your relationship you need to choose where and what time is going to be the best to have this conversation. A location that is comforting to the receiver may be beneficial but if you do not have a strong relationship with that person, they could see this as encroaching on their space. Once the space has been decided, ensure there is some comfortable seating, as tense energy tends to remain lower when sitting during a potentially emotional conversation than when standing (Sun, 2008).

Start with a neutral opening

So to approach to start the conversation off in the right direction it's best to start by opening the conversation neutrally. Some neutral openings could include

Have the person describe what happened
  • This approach turns a fault-finding conversation into a fact-finding focus
  • Try not to focus on the undesired behavior but instead focus on gathering information on what made things go wrong
  • Keep your questions open-ended and avoid "yes" or "no" style questions
  • Try to avoid phrases such as "what's wrong" that will trigger defensiveness (Gallagher, 2009)


"When situations like this happen, how do you usually handle it?"

"If it were up to you, how do you think we should address this problem/situation?"

Ask the other person how they are doing
  • This approach reminds the person of your concern for their well being while still attempting to gather information on what could be wrong
  • Often in relationships, we can get into a rut and take for granted that our partners will be upfront with any concerns they have. It is important to remember that sometimes we need to show our care for our partner
  • If this conversation is not with a partner or someone you are very close with but still connected to, asking how they are doing will establish a more positive rapport (Gallagher, 2009)

Make a neutral observation
  • These statements should always be about facts and never about feelings
  • They should be related to the topic at hand and not small talk (Gallagher, 2009)

Instead of: "You've been distant lately", a neutral statement would be, "I notice you've been really engaged in some areas of your life right now"

Instead of: "You didn't respect the boundaries of my partner/You didn't respect my boundaries", a neutral statement would be, "Sometimes a play session can get really intense and it's easy to get carried away"

Use the "I" technique where you relate things to your own behavior
  • People can learn a lot by the simple observation of behavior so we can use ourselves as a model to address certain errors
  • This can be effective because it corrects without criticizing
  • If faced with a situation you can't relate to personally, you can still use this opening by relating it to observations of what others have done (Gallagher, 2009)

Instead of " I don't feel safe engaging in kink with your lack of knowledge/experience", a neutral opening would be "I know when I play with someone, I always want to know the most about that kink to ensure my partner is safe"

"I've seen lots of people do that"

"This is a common mistake for people"

Ask questions

Ask Questions button

Now that you've opened the conversation on safe ground, keep this momentum going by asking good questions. This is another key part of a positive dialogue because it gives the person a chance to speak and describe the situation and their behavior in their own words. While we may feel we are angry and don't want to hear what they have to say it, this step is important. Through questions we may find out additional information about the person's motivations and thoughts that may dramatically impact the outcome. The other advantage is that by empowering the person to speak, you show that you care about them and you increase their willingness to listen to you (Gallagher, 2009).

During this phase of the conversation, remember that what you do not hear can be just as important as what you do hear. What is not said can point to potential sensitive areas of the conversation (Gallagher, 2009). Good questions should be on topic, open-ended, paraphrasing and empathetic. Paraphrasing what has been said so far can help clarify any information to avoid misunderstanding or miscommunication. It also shows that you are listening and understanding the position of the person.

Asking questions that are empathetic takes nothing away from the strong points of your position but they do help erase any doubts that the person may have in our understanding (Gallagher, 2009). Some good empathetic questions could include:

How do you feel about that?
How did that affect you?

As with many of the other stages of this dialogue, try to keep you emotions in check and avoid questions/phrases that will place the person on the defensive and most like elicit an explosive or negative response such as, "What were you thinking?" or "Why?". Some phrasing placed in questions can also trigger the defensive response from someone such as "Help me understand". This phrase was originally used with the best intentions but due to overuse and sarcasm, it will trigger a negative response for many people now (Gallagher, 2009).


Everyone wants to be understood and it is rare that someone, even if they acted wrongly, will see themselves as in the wrong without rationalization for their behavior. Openly acknowledging that these things happen to others, even yourself, can bring down the defensiveness of another person. This can create a stronger positive bond and keeps the person actively engaged in the dialogue. Until you get used to this process, this will feel very unnatural and is one of the more difficult steps in the dialogue. It is important to remember that acknowledging that it happens does not mean that you approve or condone the action/behavior (Gallagher, 2009). This is a way to let the person know that you understand that they are human and, as humans, we make mistakes. As angry as you may be, acknowledging shows the person you are not outside of reason.

Fortunately, despite the difficulty we may have with this step it can be broken down into three easy levels
You recognize the person's feelings
The key here is to paraphrase and not just repeat what they said (Gallagher, 2009)
You accept their feelings as being valid
Feels are never wrong. It is okay to acknowledge that accept that those feelings are there, even if you don't agree with the reason for those feelings. (Gallagher, 2009)
You recognize that others have experienced the same feelings
The key here is that going in opposition to our natural instincts and identifying with someone increases your credibility with that person (Gallagher, 2009)


Two people talking

Here is the time where you get to really talk about what is on your mind. It is important to be completely frank about the real issues and discuss only the facts, leaving emotion at the door. You are not attacking their integrity or their character but stating the behavioral facts that are bothering you. At this time, since you've given them to chance to speak about their decisions and acknowledged that these things happen, this part of the conversation should be less emotionally charged. You should take advantage of that and keep the person involved in the solution process by asking them how they think it should be resolved. Be sure to allow for back and forth dialogue. By asking them their opinions, you are enlisting them to help you find solutions and this encourages them to be accountable for their actions as well as the solutions (Gallagher, 2009).

Two heads with gears moving

Now many of you may be wondering when you get to show your emotions. There is no easy answer to this, this approach focusing on a non-threatening approach to difficult conversations. Your ability to show emotions depends on the strength of the relationship between you and that person. If the conversation is with a serious partner, you may have more freedom to express your feelings but if the conversation is with someone who you do not have such a strong bond with you will have to keep your feelings more in check. The important things to consider when deciding how much emotion to put into this conversation is that if you show negative emotions, you can trigger a strong defensive reaction that will undermine all the positive building you've done so far and showing strong anger has a strong possibility of permanently changing the relationship in some way (Gallagher, 2009).

All those considerations in mind, your emotions are just as important as those at the other end of the conversation and if this is to address a serious crossing of boundaries or violation those feelings should be discussed (Gallagher, 2009). If possible, you should try to communicate your emotions in a calm way. Remember that those who are close to us will react strongly to our distress, even if it is directed at them. If defensiveness ensues due to your emotional release, the conversation could rapidly escalate out of control and end up being very damaging (Gallagher, 2009). To try to control this, you can control your own physiological responses.


Now that you have discussed the problem and brainstormed some solutions, give them an incentive to make those changes. If the discussion is with your partner, you probably have a good idea about what motivates them so use this to your advantage. This increases the likelihood of a follow through on the resolution.


Ending the conversation in the right way is vital because we often remember the last thing someone says, we often look for validation that everything is OK, and it is the time to reinforce a positive relationship. This is typically done by changing the subject by sharing interests or discussing future plans. Follow your gut instinct; this will generally serve you best (Gallagher, 2009). The only thing you should avoid as a closure is setting expectations. A good closure should leave both people feeling good and strengthen the relationship for the future, this can be damaged by making demands. If expectations need to be outlined, do it at the proper time and do not make it the end of the conversation.

Recommended Reading

These books have been read and reviewed by Keeping it Kinky and we recommend them as resources in the area of communication

Getting to Yes partial book cover
Getting to Yes
Kashiko | September 14, 2012
All about communication and negotiation without giving up what is really important to you
Read Getting to Yes Review
How to Tell Anyone Anything partial book cover
How to Tell Anyone Anything
Kashiko | September 14, 2012
How to navigate difficult conversations
Read How to Tell Anyone Review
Written September 21, 2012 | Updated April 25, 2015
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Article References

Gallagher, R. S. (2009). How to Tell Anyone Anything: Breakthrough Techniques for Handling Difficult Conversations at Work. New York: AMACON.

Lazarus, C. N. (2011, 10 29). Constructive Criticism. Retrieved 10 18, 2012, from Psychology Today:

Sun, C. (2008, 01 25). 10 Ways to Make a Difficult Conversation a Little Easier. Retrieved 11 21, 2012, from TechRepublic:

Walters, J. (2001, 08 03). The 4-1-1 on Constructive Criticism. Retrieved 10 18, 2012, from INC.:

WiseGeek. (2003). What is Constructive Criticism. Retrieved 10 18, 2012, from Wise Geek:

Image References

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