The Art Of Uncomfortable Conversations: 8 Ways To Say What Needs To Be Said When No One Else Is Willing To Say It

Hard conversations don’t have to be harmful. These eight practices show how to say what needs to be said with clarity, care, and courage.

We’ve all been in situations where something has needed to be addressed, but no one wants to bring up the topic. This is particularly true when we know that the conversation is going to be awkward or stressful.

The problem with this is that unless the issue gets addressed, the underlying issue can worsen instead of healing. It can cause distance, resentment, and potentially even damage the person (and the relationship) permanently.

Here’s how to say what needs to be said when you’re the only person who seems willing to broach the subject.

1. Make sure you have all the facts before starting.

One of the most frustrating and unfair things to negotiate is a conversation that’s based on someone else’s assumptions, rather than facts.

A topic that may already be uncomfortable to navigate can become downright excruciating if you need to justify and explain yourself to counteract another person’s assumed perspective of the situation.

For example, years ago I was working on a construction site and was called into the foreman’s office. He promptly read me the riot act about a section of roofing that had been poorly constructed.

Essentially, he implied that if anyone in the house had been injured (or worse) because that section had collapsed, it would have been my fault because of my negligence and shoddy workmanship.

After he was done, I quietly asked him to check the roster for the dates that section had been worked on. It was only then that he realized I’d been offsite that week due to dental surgery recovery.

This is why it’s so important to make sure you have all the facts in order before proceeding. Many uncomfortable conversations could be avoided, or at least be far less painful, if they were based on reality rather than assumption.

2. Be direct but gentle.

There’s a huge trend these days in which people will “just tell it like it is” or blurt out what they think with “I said what I said”.

This is a very one-sided view, however, because it allows them to say whatever they want without taking into account how their words will affect the other person.

But that other individual has feelings too, and hurting them under the guise of honest self-expression may damage the relationship permanently.

No matter what the subject is, there are ways to broach it gently and tactfully.

For instance, if your partner has been a little less diligent with hygiene lately, rather than telling them they stink, you can mention that their deodorant hasn’t been working quite as effectively.

Alternatively, you can say that you’ve noticed they aren’t showering as often as usual, and ask if they’re struggling with anything that has been preventing them from doing so, and whether there’s anything you can do to help.

3. Use humor.

Humor is great for taking the sting out of uncomfortable exchanges. Instead of making them fraught with tense feelings and awkwardness, the discussions end up being more lighthearted.

This is ideal for negotiating difficult topics, and it’s as effective at the workplace as it is in personal relationships.

For example, privately giving an employee a gold star as a “biggest screw-up of the month” award and then taking them for coffee will have them laughing as the two of you negotiate how to fix their mess.

Similarly, cracking jokes with your partner about a potentially disruptive issue between you can help you resolve things both effectively and warmly.

4. Approach it calmly.

If someone has really upset you and that needs to be addressed, wait to do so until after you’ve calmed down. Get an idea of what you want to say without the heat of your temper potentially adding more problems than solutions.

Basically, release your anger or other challenging emotions beforehand and ensure that you’re in full control of yourself before raising the subject. Exercising, journaling, or anything that releases pent-up energy and emotions are great ways of doing this.

Otherwise, you run the risk of saying something in anger or frustration that you won’t be able to take back later.

5. Schedule a time to talk, and let them know what you’d like to discuss.

Few things can cause quite as much tension as getting someone in a captive situation and bringing up a difficult topic that they weren’t prepared to discuss.

This has probably happened to you at some point: you were having a chill, relaxing time, maybe reading a book or watching your show, and all of a sudden your partner came over, said “we need to talk”, and dropped a bomb in your lap.

Or perhaps your boss interrupted your workflow with a message asking you to go to their office. Immediately.

Instead, if you give the other person a heads-up that you’d like to discuss this topic, they have time to prepare for it — both emotionally and mentally.

They might even write down some notes to refer to that they’d like to address during the conversation, which would otherwise be forgotten in case they got flustered or upset.

6. Ensure that both people have a chance to speak and explain where they’re coming from.

A lot of issues stem from miscommunication. Basically, what feels like common knowledge or a well-known definition for one person might mean something completely different to someone else.

This is why it’s so important for both of you to explain what it is you’re thinking and feeling so neither of you is left guessing or assuming. This allows you both to try and understand where you’re coming from, and how you interpret the issue at hand.

There’s no guarantee that difficult conversations will ever be resolved cleanly, without any lasting hurt or frustration. But by taking this approach, you’re giving it every opportunity to do so.

Whatever the topic may be, you’re eliminating the perspective that one person is the victim and the other is the antagonist. Instead, you’re two individuals who have your own world outlooks and ways of doing things, and are trying to find a middle road to walk together.

7. Use the communication methods that work best for you both.

Quite often, uncomfortable conversations can have much healthier and faster resolutions if the means by which they happen are more comfortable for everyone involved.

For example, a person who gets flustered when discussing things verbally, or who needs extra time to process their thoughts before speaking, will often find it easier and less stressful to communicate via text.

Or in contrast, some people struggle to read tone by text or email and prefer face-to-face.

As such, when you’re broaching an uncomfortable topic with a person, determine the most effective and least harmful communication method possible.

You can even tell them that there’s something potentially difficult that you need to discuss with them, and to let you know whether they’d prefer to talk face-to-face, over the phone, or via text.

When a person feels more grounded and confident during the discussion, they’re more able to work with you for a healthy resolution.

8. Bend with the force, but don’t bow down.

This may sound esoteric, but it’s quite a simple concept.

Essentially, it means acknowledging other people’s point of view and doing your best to compassionately incorporate it, without compromising your own stance on the situation.

This is important because unfortunately many people behave as though getting total agreement and compliance from others is the only acceptable way to deal with a difficult situation.

But that’s not how equal, sustainable relationships work.

As such, if you’re confident in your stance and have no desire to acquiesce for the illusion of harmony, then a meek approach isn’t the one to take.

You can agree to find a middle ground that takes the other person’s preferences into account, but still stand firm in your decision. You can have no desire for dominance, but nor will you back down.

This may result in a scary confrontation if the other person gets very angry at you. All you have to do in this situation is to determine what to do with the force that’s coming at you.

The martial arts concept of Aikido works wonders here. Unfortunately, it has gotten a bad reputation in recent years in favor of more overtly intimidating martial disciplines. Yet the principle of the dynamic circle — essentially taking incoming hostile energy and redirecting it — is not just a means of survival: it’s a path of civilization itself.

Essentially you refuse to match the emotional intensity being directed at you, and instead redirect it back to the issue at hand. With a clear mind and clear vision, you can move the energy of this disagreement towards a path of peaceful and harmonious resolution instead.

Final thoughts…

Whenever you’re dealing with awkward or potentially uncomfortable subject matter, the key is to approach the discussion with loving care and compassion.

If this person is close enough to you that you want to resolve things and strengthen your relationship, then it’s likely that neither of you want to say or do anything that will cause more hurt than is necessary.

Kindness, humor, gentleness, and patience are the keys to overcoming any difficult topic. Storms may rage now and then, but the foundation between you will always remain rock solid.

About The Author

Finn Robinson has spent the past few decades travelling the globe and honing his skills in bodywork, holistic health, and environmental stewardship. In his role as a personal trainer and fitness coach, he’s acted as an informal counselor to clients and friends alike, drawing upon his own life experience as well as his studies in both Eastern and Western philosophies. For him, every day is an opportunity to be of service to others in the hope of sowing seeds for a better world.