Everyone’s definition of a difficult conversation is different. Maybe you’ve perfected the gentle goodbye when it comes to dating , but you’re struggling to tell your boss that you plan to resign if a long-promised promotion doesn’t come through soon. Or perhaps you can confront a colleague taking credit for your ideas with ease, but feel weak at the thought of telling a friend that you just aren’t willing to sink thousands of dollars into her destination bachelorette.

Whatever our personal relational Everest, we all have to navigate hard conversations — big and small, life-changing or ultimately rather trivial. If you avoid them entirely, you could end up resentful, drained and doomed to a coffee drink you hate because you can’t bear to tell your barista that it is not, in fact, your regular order. But you can arm yourself with a few tricks for making them more bearable, and productive.

Here, we asked two experts in the art of having hard conversations for their best advice. Most of the dread you feel about having a hard conversation probably stems from a fear of disappointing that person, especially if you have people-pleasing tendencies. “It comes down to a belief that it makes you a bad or selfish or ‘too sensitive’ person when you bring up issues,” says Najwa Zebian, author of ” The Only Constant: A Guide To Embracing Change and Leading An Authentic Life .

” “The difficulty really has nothing to do with the other person, and more to do with bel.