Five must-dos before a tough conversation

Been putting a conversation on a backburner? You are not alone in that.

It is a fact that no matter how good our relationships are, all of them eventually reach a fork in the road. A need is not met, expectations don’t match, and goals diverge. This is par for the course in any relationship, be it a platonic, romantic, or a business relationship. When we reach these pivotal points, a tough conversation needs to be had. We need to say what’s on our minds in order to get on the same page with the ones we care about most. But this can be scary for many reasons. We might fear hurting people, ending a longstanding relationship, or getting rejected. Though these conversations may seem daunting, they aren’t impossible. Here are five things that will help you to get into the right headspace for a tough conversation.


These days ‘self-care’ is a term that is bandied about often enough to where everyone has their own pet definition of what it means. For the purpose of preparing for a tough conversation, think of self-care as any activity that helps you get clarity in your mind and peace in your heart. It should be something that allows you to zoom out and get a bird’s eye view of the situation at hand. It is only when we zoom out and see the bigger picture that we can truly assess where we are and where we want to go. Having done this, we can see the fastest way to get there. Once you have done the yoga, eaten the eclairs, soaked in a bathtub, or done whatever self-care looks like for you, you will be in a better position to move on to the next stage in the planning process.

Intention Setting

Before you utter a word, before you draft that email, before you send that text, you must have a clear intention for doing so. To start thinking about your intentions, ask yourself a few key questions. If you could wake up tomorrow and have this situation look exactly how you want, what would it look like? What would be different? How would you be feeling? What would there be more of or less of? Would you even still be in this relationship? Setting intentions is all about taking accountability for your needs and desires. Simply acknowledging what you want to have happen is the first step to making it a reality. However, it is crucial to remember that we only have control over our intention, not the outcome. Take some time to make peace with the fact that you may not get what you want out of this talk.  The other person may be unwilling or unable to come to an agreement with you and that’s ok. Despite this, however, the practice of communicating your needs is still good practice for future relationships where others are better equipped to meet them.

it is crucial to remember that we only have control over our intention, not the outcome.

Recruit Your Team

Don’t be afraid to reach out to people around you to support you while you prepare for and perhaps even after you carry out this tough conversation. Take a self-inventory of your needs. What kind of support would help right now? Do you need practical support (i.e. a place to crash, a ride, or some money)? Do you need emotional support (i.e. advice, a shoulder to cry on, someone to just hold space for your emotions)? Do you need social support (someone to spend time with, someone to invite you out, and someone to share hobbies with)? Once you have taken stock of your needs, think about who might be willing and able to help you out. It is a good idea to think of people who are sufficiently invested in your well-being to be genuinely excited to contribute to your cause but who aren’t directly impacted by the outcome of this tough conversation. In other words, your team members should care about your tough talk but not because they have something to gain or lose from its outcome.

It is a good idea to think of people who are sufficiently invested in your well-being to be genuinely excited to contribute to your cause but who aren’t directly impacted by the outcome of this tough conversation.


Many people resist the idea of practicing what they are going to say in a tough conversation. This is likely because TV and movies have us convinced that we should be able to wing an epic monologue on the spot just by the sheer force of our passion.

The truth is that even the best communicators like professional negotiators, counselors, and teachers spend hundreds of hours training for the tough conversation they have every day. As a former HR manager, I can share that I spent countless hours watching videos, participating in role-plays and simulations before I felt confident firing, disciplining, and even hiring employees. Even though the tough conversation for which you are preparing is likely with people with whom you are generally able to speak candidly and spontaneously, when you are preparing to talk about something delicate, it is still worthwhile to apply the same discipline to preparing for that as you would in a professional context.

 To prepare for your tough conversation, write down the key points that you want to go over. This step makes it real. There is something about putting pen to paper that lets us fully take ownership of our words in a way that no other medium can really replicate. Refer to the intention that you set. Are the things you are saying in line with your intentions? If you’re not sure, ask someone on your team. See if you can practice the conversation with them. Allow this person to give you feedback on your tone, body language, and other nonverbal cues that may be supporting or hindering your message. Continue to practice and get feedback until you really feel a sense of ease and confidence when you speak about this topic.


Once you’re feeling ready to really dig into your tough conversation, you can start planning the logistics. When will you have this talk? Pick a time when you don’t have too much on your dance card in terms of social, financial, family, and other obligations that might make it difficult to be fully focused on getting this done in the way that you intended. Think about what is going on with the person with whom you are planning the talk. Though there is never an ideal time for this sort of conversation, some periods are better than others. Make allowances for extenuating circumstances, but do not get carried away by perfectionism. Remember that done is better than perfect.

When thinking about an ideal place for a tough conversation you may want to think about the way space contributes to the emotional, physical, and cognitive safety of everyone involved. Physical safety is a primary concern especially when you are dealing with someone who may react violently. If you feel that your physical safety is in question, by all means, choose a place that is in close enough proximity to people that can support you should the situation get out of hand even if this place isn’t as private as you might have liked.

Places that offer cognitive safety allow you to think clearly, make decisions collaboratively, and express yourself without hesitation. Minimizing noise and other distractions helps create a sense of cognitive safety.

Locations that can help foster emotional safety are those in which you can create a level of comfort that allows all of the people involved to feel a sense of connection and trust. While cognitively safe spaces like meeting rooms and therapists’ offices can help us open our minds, emotionally safe spaces help us open our hearts.

When choosing a space to hold your tough conversation, go back once more to your original intention(s). Let it/them inform the kind of space you want to create.

To sum up, preparing for tough conversations might feel daunting, but the more you integrate tough conversations into your relationships, the more natural it will feel. If you are planning a tough conversation and need a bit of help with any of the steps above, be sure to reach out- I am looking forward to joining your support team.

Leave A Comment

Your email address will not be published.