How to have hard conversations like a pro

On Offbeat Bride we’ve been talking about tough conversations about marriage — why a ring isn’t enough. But how do you HAVE said conversations? Here’s lawyer and Homie Dara to show you the way…

As an attorney, a lot of my job is helping people have hard conversations. What do you want your spouse to tell your doctors to do if you’re in a coma? Who is the best person to manage the money you’re putting aside as a windfall for your intelligent but mentally unstable adult son? How are you going to split up holidays with your kids when you live in two different houses?

Over years of facilitating these tough conversations, I’ve come up with some steps that make them more productive and less painful. These aren’t just good for “legal” conversations — they can work for anything from talking about moving cross-country for a job to planning a birthday party…

1. Set a date and time

The first step is always to get the other person at the table to talk. Trying to have a deep conversation when the other person isn’t expecting it won’t be productive. Starting a conversation 10 minutes before Walking Dead comes on won’t be productive. You need to agree to a set date and time where you have minimal distractions and no competing obligations and you both know in advance that it will be your time to talk and plan. Have a partner who deflects attempts at hard conversations? Don’t accept “not now” — ask her for a better time, put it on both your calendars.

2. Make an agenda

Have a set list of what points you want to cover and check them off as you go along, so you both can see that you’re progressing. This also cuts down on distracting tangents because you can refocus on the current discussion by adding things that come up to the list or showing where they’re already listed for later discussion. If your agenda doesn’t fit as bullet points on a single page of paper, you need to plan a significant break in the conversation or split your list of topics into two different conversations on different days.

3. Bring scratch paper and a calendar

Nobody has a perfect memory, even for big stuff like “Who do you want to take care of the kids if we both die?” Use plenty of scratch paper to brainstorm, draw diagrams, and give your hands a way to burn off your nervous energy while talking and listening. Keep a clearly-designated “decisions” page to write down anything that’s settled. Use whatever your main calendar system is to look at the other events that might affect when steps of a plan must be done — mine is the Google calendar on my phone, though I used a big paper datebook for years before that.

4. Use analogies and hypotheticals

The key to this is to use humor to make talking about difficult things easier, not to avoid talking about them.

One of the things that can make a conversation hard is fear of a likely possibility — there’s a reason there are a lot more novels about serial killers than there are about car accidents. One of the tactics I use with clients who seem uncomfortable is talking about a situation that has the same outcome but that’s too absurd to be scary. Instead of talking about a couple dying in a plane crash, I talk about them dying on a mountain climbing expedition. Instead of talking about the possibility that a currently-married couple will get divorced, I talk about one of them running off to join the circus. The key to this is to always make the outcome the same and to use humor to make talking about difficult things easier, not to avoid talking about them.

5. Don’t focus on can/can’t but rather on want/don’t want

Unless one of you is a professional in the field of what you’re talking about, there’s going to be a lot you don’t know. I’m a proponent of research, but there’s a point of diminishing returns, especially when one of you is much more conversant in the details than the other. What you’re both experts in, however, is how you feel. Talk about what you want in a larger sense and focus on values rather than situations. If you need a professional (like an attorney or a financial planner) to help you with later steps, it’s much better to go to that person with a list of what you want generally, and ask for their expertise in how to achieve it specifically.

6. Start with where you think you agree

If you know you’re going to hit a spot in the discussion where you disagree, this is important to show the things you have been able to agree to already and start in a positive spirit of collaboration. If you don’t believe you’re going to disagree but have a hard time talking about something anyway, this is a good way to ease into it by discussing shared values. If you believe you’ll have an easy time talking and agreeing, still start with this – it will allow you to clear out any false assumptions that may lead to unintended problems later in the conversation.

7. Don’t get up from the table without the next step planned

A plan is useless without a discussion and a discussion is ineffective without a plan. Decide on many small concrete steps you need to achieve what you’ve talked about and don’t balk if you don’t know how to do something — make research online or consulting someone with experience one of your steps and assign it a date and time. This is where your calendar also comes in handy. Be realistic about when you’re planning the steps each of you are going to take and don’t over-schedule. Are you honestly going to call attorneys during the week your kids are off for spring break? No? Then it can wait a week. The easiest way to get so overwhelmed you quit is to plan everything to happen immediately; The easiest way to get so frustrated you quit is to plan things to happen too far in the future.