How to have hard conversations like a pro

Guest post by Dara Strickland

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…

Serious conversation is serious. (Photo by: astonishmeCC BY 2.0)
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.

Comments on How to have hard conversations like a pro

  1. I completely agree with the “diminishing returns” on research.
    When my husband and I have to talk about the hard things, it’s easy to get caught up in the pattern of “I don’t know anything about this, so we won’t talk about it until I know more.”
    It’s really hard for me to talk about things I haven’t had time to research, I get really overwhelmed thinking I’ll make the wrong decision. But what I’ve had to learn through couples counseling is that my partner will still be there to talk, whether I know all the specifics or not, so I shouldn’t avoid talking about a topic simply because I don’t have as many facts as I would like.

    • This is where I find setting the agenda ahead of time comes in handy. If my husband and I have something big to plan/discuss, we both will do research on the topic and then show up to our “coffee klatch” with our notes and research. That way, we can both be somewhat comfortable and have a place to start the discussion.

  2. Thanks! This is great timing. My fiance and I talked about needing to have a couple tough conversations (some money ones that hopefully won’t be too bad as I think we’re mostly on the same page; laying some groundwork in case of divorce, although we both believe in our marriage, and have confidence, as he pointed out, it’s better to set the groundwork, then ignore it knowing we won’t need it, than not have it; and what happens when one of us dies convos and taking care of aging parents someday convo.) This is super helpful.
    As a kid of a nasty divorce, I know we need to talk about it, but Idon’twanna. It is much easier to talk about “What if one of us runs away to join the circus?”. I can have that convo.

    • Caroline, I’m so glad you’re talking about that before getting married. When couples come in to talk to me about prenuptial agreements, I tell them that just going through their property and debt together and talking about who owns what will save them the first three fights in their marriage. Feelings about property ownership and debt are a big issue for people during their marriage, not just if they divorce.

      Nobody goes into marriage with the intention of separating – even Anna Nicole Smith’s goal was to be a widow!

  3. This is really useful advice – we’d noticed we’re much better at the big conversations when we’re out for a meal or a drink, and point one explains why!

    • My husband and I have a weekly “coffee klatch” where we sit down and talk. Klatch can be about big things (buying a house) or little things (meal planning for the week), depending on our needs. But, we call it coffee klatch because it is usually over coffee or breakfast on Saturday morning, when we’re well-rested, well-caffinated, well-fed, and our brains are clear. For big stuff especially, we go out to breakfast at a place with wi-fi and bring a computer, so that we’re not distracted by TV, the dishes, etc.

  4. Wish I’d had this months ago. My mother in law is trying to plan how to provide for my schizophrenic brother in law after her death. Difficult conversations all over the place. Will remember these, for sure.

  5. I love these posts; they tend to stick with me until I need them. Like, when my husband and I couldn’t get through a discussion about our divorce without fighting, it was eventually Offbeat Home advice that reminded me that we might do better via email, without emotion. Boom. Worked. We’re finally at a place where we can work on repairing our friendship.

    As we navigate the next few months of moving apart, managing our son, and the paperwork of splitting up, I’m definitely keeping thus post on hand.

  6. Point 4 is great – I can testify!

    Recently my significant other and I had to loan a significant amount of money to buy a new car. The money to pay it back comes from my job, but it was cheaper to have car, insurance and everything in the boyfriend’s name. According to our plan it will take five years to pay everything off, and I had to convince him to draw up an “emergency paper”.

    “Honey, but we won’t split up, won’t we.”
    – “Definitely not, but imagine I get transformed into a unicorn!”
    Yeah, that convinced him. ^^

    • I am now imagining employment you could get as a unicorn. Offering rides, posing for photos, appearances at birthday parties, sci-fi fantasy convention Guest of Honor, movie roles! Hopefully not lab experiment…

    • As I cannot use the “run away with the circus” scenario – because I actually have – I am totally borrowing magical animal transformation scenario.

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