Ways to Deal with a Chronic Complainer Empathize when appropriate. Redirect the conversation by changing the subject. Be intentional in your dialogue, and stay on topic. Lead by example; don’t complain. Ask before offering an opinion, and be mindful of whether the person can handle the truth. Don’t be dismissive (e.g., “It isn’t so bad” or “You’ll get over it”). After you’ve done all you can, draw a clear boundary around the time allotted for the conversation and how often you will talk.
