Most likely, your roommate isn’t going to want to talk about her housekeeping habits. Your brother doesn’t want to hear that his fiancé propositioned you at the company picnic, and there will never be a good time to tell a significant other that something is amiss in your relationship.

When you’re steeling yourself for a sit-down, know that no matter how difficult the conversation, it’s better to get it on the table. Remember, discomfort doesn’t have to spell disaster. It may not be smooth sailing either, but you can use the tips below to help steer clear of a crash landing:

Plan your approach
It’s okay if your words don’t come out as planned. In fact, it’s better to stumble than to launch into a rehearsed performance. It’s best to take some time to think about your approach before you dive in. Define what your intentions are to yourself and know what result you want from the other person. Consider how your intentions will sound to that person and take into account their insecurities and communication styles.

Not every approach is right for every situation or person. If you’d rather your lover avoid a certain technique in bed, make a sensitive but off-handed comment about it. Or better yet, stress how much you love that other things he does. If a friend has been making your personal life public, you may want to have a heart-to-heart over lunch. If you need to tell your brother you haven’t dismissed the loan you gave him last year, it’s probably best to schedule an appointment to talk about it. When you adapt for the particulars of each situation, you give yourself a fair chance at smooth execution.

Timing is (almost!) everything
When the subject matter is already tough, timing can make or break your conversation.

Here are a few timing tips to consider:

• Avoid having your conversation in the wake of a bad day or a crisis.
• Choose a time when you will have sufficient time to have an involved conversation.
• Make sure you will both have an opportunity for some alone-time afterwards, should you need it. You might even have an escape plan in place, like errand you have to run or another appointment. That will give you both some time for thought before you settle on a resolution.
• Don’t wait for the perfect moment. It will never appear, and you’ll put off your confrontation indefinitely. Instead, try to create a moment that is as conducive to your conversation as possible.

Be confident…
Though there may be a wrong way of expressing them, your feelings are never wrong. If you need to, reaffirm this fact before you enter any confrontation. Mentally review what needs to be changed and why, or talk it over with a sympathetic friend. Remember: talking about a problem doesn’t create it. It was already there. You’re doing everyone involved a favor by bringing it to light.

…but remember the give and take
Backing out on a roommate agreement? Agree to help find your replacement. In an amicable breakup, always concentrate on the positives, like the value of your time together or the qualities you’ll always admire. Even if the conversation is about something as trivial as doing the dishes or spending more time at home, you can offer to amend inconsiderate habits of your own. Of course, offering an exchange on your end shouldn’t mean your approach is diffident or apologetic. Be firm or you run the risk of having to do it all over again.