On Having Hard Conversations With The People You Love

Communication is constant, and it fuels our lives. We bond with people we love by sharing thoughts and stories and encouragement. We connect with strangers by talking about common interests or shared experiences. Communication happens all the time, and often it’s so organic that we don’t even realize consciously that it’s happening.

But then there are those other times that call for a big, or difficult, or uncomfortable conversations. Whether it’s an incident, a situation, a concern, or conflicting expectations that need to be discussed, chances are it’s getting simultaneously harder to address and harder to ignore.

Those are the situations where “communication” almost-universally freaks people the hell out.

Having-Hard-Conversations-With-People-You-Love

I’m gonna go ahead and speak for most of humanity here and say that those are the conversations we love to put off. We run away from them, and let the unresolved feelings continue to simmer. We sweep them under the rug, hoping they’ll just go away already. We resort to small doses of everyday passive aggression to make our point. And none of it has ever magically fixed anything.

Hard Conversations Aren’t Relegated to “Bad Relationships”

There’s absolutely no shame in recognizing a snag in any of your relationships for what it is. Even the closest relationships can get bumpy, and it tends to be those same relationships where both partners choose to dig deep to work through those issues collaboratively and openly that stay the strongest.

Of course, the flip side of that coin is that getting vulnerable and having a difficult conversation with a close friend, parent, sibling, partner, or even a colleague you really like can be that much more gut wrenching. There’s a lot at stake, the words can get clunky, and our capacity for honesty and vulnerability can get real shaky, real fast.

Those are the times it can be especially tough to know how to start the conversation, let alone get through it gracefully.

Setting the Stage for Great Communication

This might be the planner and over-thinker in me, but I’m 100% comfortable saying that effective communication about a tough subject calls for some preparation. I’m not talking about scripting it out, showing up with notecards, or having A Master Plan. But personally? I’ve found that the times I’ve walked away feeling the most flustered and defeated from a conversation were the ones where I jumped in before I was ready, spoke before taking time to process, and fought to “keep up” instead of speaking with a sense of purpose.

Getting in the right headspace for sitting down to have a difficult conversation is huge, and it doesn’t have to be hard. In fact, doing a little personal prep work has this way of diffusing my nerves and letting me plug into my inner strength. It helps me feel more equipped for the already-difficult task at hand. And so, I want to share a few of my favorite Tough Conversation Hacks with you, to help you feel less squirmy and more empowered the next time you have to sit down and talk about something tough

Some ideas for approaching a tough conversation with Someone You Care About (so Little Things don't Become Big Things)

  • Get clear with yourself beforehand about how you feel and what you need. This step is gonna look different for a lot a people, but knowing what helps you calm your nerves and get clear on your goals is key. It might mean thinking out loud, getting your thoughts out on paper, or even just sitting quietly with your thoughts. I’ve found I feel much more powerful and less panicky in conversations when I’m super clear on what I’m trying to say, and what my goals are.

>> Pro Tip: If you’re feeling caught in the fog of overwhelm or confusion when it comes to what you’re trying to say and what you need, grab a pen and a piece of paper. Let yourself be uncensored, and just write how you feel. Once it’s out of your system, go back and sift through it for those critical nuggets that you can bring to the table.

  • Use the “sandwich method” and stay away from “you” statements. If you’re initiating the conversation, this one is a biggie. When you’re delivering something that might be hard to hear, it can be super effective to sandwich it between two gentler, more positive things. (Note: those two positive things must be true.) This can go a really long way as far as helping the other person feel cared for where they might otherwise get defensive if you kick things off with something accusatory. In the same vein, using “I” statements instead of “you” statements goes a long way in making sure no one feels attacked.

>> Here’s an example: Kate, you’re one of my favorite people to talk to, and I can’t tell you how much I love when we spend time together. The last few times you’ve had to cancel, I was actually pretty upset - I felt sort of unimportant to you in those moments. I hope we can find a time that works for you soon to grab a drink and catch up - I’d love to hear more about what you’ve been up to. Is there a good day next week?

  • Listen. No, like, really listen. Simple to say, tough to do. This means not interrupting, and maybe even more importantly, not tuning them out while you form your next point. Being attentive means not only listening to the words they say, but also making space mentally and emotionally to process the message they carry.

Pro Tip >> Stay extra engaged in the conversation and make the other person feel heard by practicing active listening, or repeating what they just said back to them, but in your own words.

  • Talk when you’re equipped to talk, and take a breather when you’re not. Rushing into a conversation when you’re freshly upset or still sorting through what’s going on in your head makes it way harder to boil down your thoughts and feelings into productive nuggets. Talking when you’re emotionally equipped to be productive can only help both parties feel like the conversation is healthy and productive. This can even mean taking a breather to step away for a few minutes mid-conversation - just be sure to do so tactfully, so you don’t give off an ‘angrily storming off’ vibe.

Pro Tip >> Embrace the pause throughout the conversation. In other words, if you hear something that catches you off guard or upsets you, don’t feel like you have to fill the silence and respond right away. Don’t be afraid to take a second, gather your thoughts, and choose your words intentionally.

  • Try your best to get to the root of the thing. This one can be tricky, but if you can manage to do it, it can make all the difference. Just this week, my boyfriend and I were hashing out a football season hurdle - what started as a struggle to find our critical balance of “How Many Hours of NFL Football In Our Apartment is Too Many Hours” eventually got stripped down to a really enlightening chat about my (maybe irrational) fears of a football shaped wedge in our relationship, and his sentimental family-based ties to the sport. Diving into that next layer of ‘what’s really going on here’ helped us address some of the more substantial concerns together, and understand each other more completely.

Pro Tip >> A little reflection goes a long way. The more often your flex your reflection muscles and check in with your intuitions, the easier it will be to tune into the core of what you’re feeling and where it might be coming from.

  • Reach out and bridge the divide. Those tense silences during tough conversations can be deafening. Even in the tensest of moments, don’t underestimate the power of being the first one to make the reach, to offer empathy, or to bridge the divide. A simple gesture can go a long way in shifting the tone and moving towards a resolution that feels emotionally satisfying.

Pro Tip >> Show up ready to give the kindness and empathy you hope to receive. (Sidenote: as someone who fell into a trap in the past using this approach, I should add: keep an eye out for a pattern of unreciprocated reaches. In other words, if you start to feel like you’re the only one to regularly offer empathy during tense conversations and you recognize it consistently, don’t allow that to become the standard of how you’re treated.)


At the end of the day, difficult conversations with the people we care about can be an opportunity to strengthen those relationships, and having some communication skills up your sleeve can help you do just that. As hard as it is not to lose your focus when things get tense, remember that difficult communication isn’t a competition. It’s not about winning or losing - it’s about advocating for your own wants and needs in a way that facilitates honest sharing and strengthened connections.

How do you handle difficult conversations with the people you’re close to? Have you tried any of these tactics? Let me know, either below or on Twitter. Want to continue the conversation? Let me know - I’m thinking a Periscope on the subject might be in order…!