The Ultimate Guide to Emotionally Preparing for Tough Conversations + 12 Essential Questions to Help

So, something's been bothering you. You're tired of pushing it away. You’ve decided it's time to speak up, and you’re starting to emotionally prepare for that tough conversation. But then? The floodgates open, and all those fears and worries come flooding in. 

Here's the thing about awkward, honest conversations: of course they bring up all kinds of emotional gunk. 

For you that gunk might mean feeling anxious about how it might go, or feeling overwhelmed by all of those possible outcomes and how to prepare for tough conversations, or feeling fearful about the things that lie outside your control that might take you by surprise, or maybe you feel stressed out about the pressure to manage all those variables and moving parts on the fly. No matter what comes up for you, it’s all reeeeally understandable and reasonable.

Feeling anxious about having an honest conversation is really normal; not necessarily because the ‘talking’ part is hard, but because of all the emotional and energetic stuff these conversations stir up. 

And that's exactly why, before you jump into the nuts and bolts of what you want to say, it’s wise to start by addressing these deeper fears, blocks, and anxieties first.

Clearing Out the Emotional Gunk First Makes Preparing for a Tough Conversation Easier

When we go into a hard conversation without clearing out our emotional and energetic underbrush first, we create the conditions for a wildfire.

Fun fact: states like California and Florida that are highly susceptible to wildfires have actually started adopting this practice of doing what they call controlled burns— intentional, contained fires that are meant to clear out all of the leaves and the vegetation that, left uncleared, could lead to a devastating wildfire.

In that sense, you can think of the work we’re about to walk through as doing your own version of a controlled burn.

By carving out the space to unearth your own energetic and emotional underbrush ahead of a charged conversation, you clear out the gunk that might otherwise turn a manageable conversation into an eruption of energy and emotion that becomes destructive.

When we go into a hard conversation without clearing out our emotional and energetic underbrush first, we create the conditions for a wildfire.

So what are the blocks that get in our way?

At the risk of being a bit reductive, there are generally four main types of energetic blocks that get in the way of us doing things we know on some level that we want or need to do:

• Limiting beliefs — the firmly held ideas, beliefs, or opinions that limit us in some way. We often learn these or were taught them from a young age, and have assumed them to be true for a while without giving them much thought.

• Interpretations —the stories we tell ourselves about a situation or experience, often unconsciously. They're based on our unique combination of life experiences, worldview, and filters.

• Assumptions — our beliefs about what's going to happen in the future, based on what's already happened for us in the past.

• Gremlin — the inner critic; the voice in our head that tells us we're not good enough in some way. This one is absolutely the most personal and tender of all four types of blocks.

We all bump up against these blocks in different ways, and at different times. It’s also important to acknowledge that this stuff is charged. And because it's so charged, it can be really challenging to untangle and identify these things on our own, and really see them clearly for what they are. 

This is where it can be really helpful to lean on an outside source of support to be that unbiased pair of eyes and ears, whether that's help from a coach or a trusted friend. They’ll be able to see things you can’t see and make connections that aren't obvious to you, simply because they're not as close-up. Plus, they can gently and compassionately help you find your edge, hold you accountable, and offer that extra layer of support and encouragement when the doubts or challenges inevitably pop.

Having said all that, there are definitely ways that you can embark on this work on your own—and that's what we're going to talk about!

Uncovering and moving through these blocks is exploratory in nature, so I highly recommend using journaling as a tool.

And if the word ‘journaling’ doesn’t do it for you, feel free to swap that word out for “free writing”, “talking out loud”, “mind mapping”—whatever will let you unload your thoughts without censors or judgment. Whatever you choose, try these questions to help uncover your own blocks.

Whatever tool you choose, here are some suggestions to help you create the conditions to get the most out of your journaling time:

• Put it on the calendar! Carve out the time, and treat it as sacred.

• Set up your environment so you'll feel comfortable and focused. That might mean putting on a particular type of music, having snacks or something to drink, or wearing something super cozy. Figure out the elements that are most impactful for getting comfortable and focused, and make them part of your ritual.

• Take a few minutes at the beginning to get grounded and into a good head space. You might try a short guided meditation, a few minutes of gentle stretching or yoga, or even a quick walk around the block just to get the blood flowing.

• Try starting with a little free-writing, to limber up your brain and get any of the clutter out that's distracting you or pulling your focus.
  

STEP 1:

Reflect on These 4 Questions to Uncover What’s Making This Conversation Feel Extra Charged

Once you're ready to start journaling, bring to mind the conversation or topic that's feeling challenging to you and go through each of these four questions, jotting down anything that comes up for you.

1. What beliefs am I holding onto that may be limiting me in some way?

2. What stories am I telling myself about this situation?

3. How am I allowing the past to inform my beliefs about the future, or potential outcomes?

4. What is my inner critic saying to me about this situation?

As you go through these and get all your thoughts out on paper, notice the ones that give you a little twinge of discomfort, or that maybe feel like you've hit on something bigger. Just put a star next to those as you come across them so you can find them later, and then keep going.

STEP 2:

Do Some Deeper Digging to Help Those Blocks Lose Their Charge, Using These 4 Questions 

Once you've gotten it all out onto the page, go back to those ones that you put a star next to and start to (gently!) interrogate them a little bit further with some deeper questioning:

1. How true is that, really? (Put another way: What evidence do I have to support that belief?)

2. What counter evidence do I have to debunk that belief?

3. What's another story that might be true here?

4. How would it feel to believe a different story?

Remember to show yourself loads of compassion during this process! This work can trigger a lot of stuff, and it's SO important to remind yourself that your feelings and your experience are valid.

Then hopefully, once all that underbrush has been cleared out, what you're left with is a fresh understanding of what’s really bothering you, and how you want to move forward with that information.

Keep in mind: the fact that this thing has lost some of its charge doesn't necessarily mean you won't feel any fear or discomfort around having this conversation—feeling some of that stuff is still really normal! But hopefully you won’t be left carrying quite as much of that flammable energetic stuff that's ready to catch fire and pull you off your emotional center in the moment. 

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Now that you've identified and worked through some of the stories, interpretations, and beliefs that were getting you worked up around this conversation, hopefully you can see much more clearly what this conversation is really about, and what you’re hoping to get out of it.

4 (More!) Questions to Help You Name a Single, Clear Purpose Going Into this Conversation

01 | What do you *really* want to get out of this interaction for yourself?

Some examples of what that goal or purpose might sound like:

• To make a request or to ask for something you need

• To ask for clarity about something 

• To be heard or seen in an authentic way

• To share a boundary that you've been holding back from sharing honestly

• To understand the other person's perspective or reasoning

• To come to a solution or compromise together with the person(s) you're talking to.
  

02 | What do I want out of it for the other person, and/or the relationship?

It might also be helpful to widen your lens a bit as you're identifying a purpose, and to consider that same question from a few other angles beyond yourself. As in, what might you really want for the other person(s) involved? Or for your relationship with them?

• Maybe you want this other person to have the space to share their perspective about a situation.

• Maybe you want to use this honest conversation to clear the air and mitigate confusion for everyone involved.

• Maybe you want to set an example as a leader by staying true to your values, even if it means going through some short-term discomfort of a conversation

• Maybe you really want to find a true win-win solution for everybody involved, which means getting all the cards on the table and looking at them honestly together.

• Maybe you want the other person to have the opportunity to know the truth about what's going on with you, even if it feels awkward to share it in the moment.

Quick disclaimer: my strong recommendation here is to NOT let this become an excuse to fall into old patterns, like avoiding conflict or putting everyone else's needs or comfort ahead of your own. This is about finding a way to consider the bigger picture or long-term benefits that this conversation might serve, or to understand its purpose in a more holistic way.

03 | Is that goal you just uncovered in integrity?

Be honest with yourself here about what your real purpose is, and keep an eye out for any potential red flags. 🚩

For example: if you land on a goal of wanting to make sure the other person knows how wrong they are, or to convince them to change their mind on a topic where you know that's very, very unlikely… you may want to reconsider whether this conversation is truly worth having, or how you can shift your goal to something more fair, productive, or likely to be successful. This is partly about recognizing the limits of what's ours to control, and staying within what Mara Glatzel calls our “sphere of influence” when it comes to our expectations and definitions of success. 

04 | Can I get this need met another way?

You might also realize the thing you thought you wanted to say is actually something you can work through on your own, without needing a conversation—and if that's the case, that's great! 

Just keep in mind that that's different from talking yourself out of having a worthwhile conversation because it feels scary in the short-term. 

The key to knowing the difference goes back to the bigger question of whether a conversation is worth having in the first place. Try to make sure you're responding to a genuine realization that you can truly get your needs met without having to have a conversation, vs. reacting to the fear of having a tough-but-beneficial discussion.

At the end of the day, it's about making conscious choices.

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Name Your Deeper Purpose, and Let It Be Your Anchor

By this point you’re (hopefully) feeling much clearer about the true purpose of this conversation, and what you’re really hoping to get out of it. 

Here’s what’s cool about that: uncovering a simple, clear purpose for having this conversation can significantly shift both how you feel about having it, and how you want to approach it. Ideally, you should be able to distill that purpose down to a single, simple sentence. 

Some examples of what that sentence might sound like:

• “My goal is to tell my partner I want to start a budget, and to ask for their support in finding a solution or tool that works for us both.”

• “My goal is to help my boss understand that I need more detailed information up front for future projects and tasks, to be able to do my best work in less time.”

• “My goal is to make sure that my friend who's in town visiting understands my boundaries around how many nights I'm comfortable having her stay with me, so that we can both really enjoy our time together.”

Once you find that one sentence that feels resonant to you about what you're really hoping to get out of this conversation, let it become your anchor. 

Write it down somewhere. Take time to really sit with that sentence, and revisit it often leading up to this conversation.

Because under stress, we can lose sight of the long-term goal and it's easy to get caught up in the short term reactions to what's unfolding. We might fall into old habits, like wanting to avoid conflict and just smooth things over as fast as possible, or being reactive and letting things escalate. 

But having that anchor—your key purpose for this conversation—gives you something to come back to. It gives you a direct path back to your truth and your integrity and your values that you can come back to, even when things start to get heated or stressful.

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