Mastering Tough Talks and Awkward Conversation

Life is amazing – except when it isn’t.

You work a double-shift at the lumber mill only to come home to notice that the six-pack you fantasized about drinking has vanished … into your roommate’s stomach; he still hasn’t paid you for the last eight times this kind of thing happened. Or, someone at work sabotaged your presentation to try to take you out of running for that promotion. Or, your landlord won’t fix the dishwasher, and for the third time this month, it flooded your kitchen.

We’ve all been here before. Despite your best efforts to live a conflict-free life, you’ve been served a hot, piping wooden bowl of TOUGH TALK – when you have to roll up the sleeves, take off the gloves, and have an awkward confrontation. The success of this conversation could be the difference between living the next six months in peace or living them in near-constant misery.

So, you want to make sure you don’t end up doing the latter? Then, pull up a chair (or whatever the equivalent would be if you’re on your phone) and take a gander at this playbook to crush the TOUGH TALK:

1. Make sure this is deserving of a TOUGH TALK
   OK, first thing’s first: Should you really be calling in the big guns for this one? If it’s your best friend and the offense isn’t that bad, can you just casually bring it up and talk it out like friends? If so, do that. Is this the first time your roommate drank all your beer? If so, don’t freak out about it. Keep it in perspective. You wouldn’t have an intervention with a friend just because they tried a cigarette once. Same thing applies here. The offense needs to be egregious or repetitive – or both.
2. Have a specific goal
   Before you rush in and get yourself slain, go into this talk with a specific goal in mind. Now, I don’t mean, “resolve the problem.” That goal is vague and could mean different things to different people. For your roommate who drank your beer for the umpteenth time, “resolving the problem” could mean that you let the whole thing go. That wouldn’t work for you. Instead, think of what you specific would like out of this situation. In the roommate example, maybe that would mean that he has to replace the six-pack by tomorrow or give you the money to do it yourself. Having an exact idea of what you want to get out of a confrontation is important when your opponent starts laying a guilt trip on you or simply doesn’t see the situation the same way you do.
3. Rehearse the conversation in your head
   Look, this one might feel silly or embarrassing, but if you do it, you’ll be thanking me later. Run through the conversation in your mind before it happens. Try to imagine the different ways the other person could respond. Will they try to deny it? Will they try to change the conversation to make it about something you did wrong? Think of the different ways the other person might try to derail this talk and take you away from resolving the issue in a way that makes you satisfied. Once you identify these potential detours, think of ways you can successfully get it back on track. It’s easy to get caught up in the moment and freeze up because you don’t have a comeback – so that’s why you think of the sassy comeback in advance. For example, the guy who sabotaged your presentation: Knowing him, he’s going to deny it – but if you go onto the company’s server and screenshot proof that the last update to your presentation came from his computer, you have something locked and loaded for when he claims in his whiny voice, “I haven’t touched that file in three weeks.”Three weeks? How about you edited it yesterday? Check … and mate.
4. Remain open-minded
   Not everyone is going to see things the way you do. They might think they were getting back at your for something they thought you did. They might explain their intentions in a way that actually makes sense. As much as you plan for all outcomes, they just might throw something at you that you weren’t prepared for. Make sure you listen and at least consider their point-of-view on the disagreement. You ultimately might not change your mind, but no one is going to willingly agree with you if you bulldoze them with your agenda without letting them get a word in.
5. Close the deal
   Close the conversation in a way that will make sure you move forward in the right direction. Everybody involved in the talk should have a mutual understanding of one another, specifically their expectations. Get all parties to verbally agree to specific actions, like trading off dirty dishes every day (unless you’re #blessed enough to have a dishwasher). If necessary, have consequences for not living up to this verbal contract-of-sorts. If people aren’t sure of exactly what they are supposed to do to resolve something, then it’s easy to slip back into the same patterns of behavior.
6. Have a backup plan
   Always have a backup plan that doesn’t depend on this person. In any negotiation, you have to be prepared to walk away. Too often, people go into this conversation assuming that the other party will agree with them or compromise, but that doesn’t always happen. When someone isn’t listening to you and is unwilling to meet you even halfway, then you can’t simply go, “Aw shucks, I gave it my best. Guess we’ll do whatever you want.” You’ll be miserable. Don’t do it. Instead, plan alternatives in advance. If your landlord simply will not fix the dishwasher, produce a quote for a repairman and see if you can deduct that amount from your rent if you pay for the repairs. If they won’t agree to that, tell them that you’d like to get out of your lease since they aren’t living up to their end of the agreement. If that doesn’t work, sublet your apartment for the remainder of the lease or see if there’s a legal way you can terminate the lease agreement. You don’t want to do any of these things, but you have to be prepared in case you get stonewalled.