8 Top Tips for Starting Fearless Conversations

McKenna Princing Fact Checked
Two people talking outside.
© Lucas Ottone / Stocksy United

Maybe it’s a relative who makes inappropriate comments at family dinners, a city friend who’s perfecting their Seattle Freeze or a colleague who loves to give (bad) advice. You want to say something, to speak up, but don’t know where to start.  

Whatever the situation, initiating a conversation where you know there will be tension isn’t an activity most of us seek out. In fact, you may be avoiding it as though your life depends upon it.  

But staying silent rarely improves relationships. So, are you ready to follow the lead of experienced-difficult-relationship-chronicler Taylor Swift and Speak Now? If so, here’s where to start (Right as Rain’s version).  

(Showing empathy is) Better Than Revenge 

It’s important to approach any difficult talk from a place of empathy, even if the other person is frustrating you or behaving in a hurtful way (though not justifying their behavior if it is harmful).  

To do this, try the old ‘put yourself in someone else’s shoes’ adage, recommends Elizabeth Umphress, a professor of management at the University of Washington Foster School of Business whose research focuses on ethics, diversity and inclusion. 

“Acknowledging that you cannot possibly know someone else’s lived experience but actively attempting to imagine another person’s perspective helps us be more empathetic, decreases prejudice, allows us to be open to different ideas and frames the conversation in a way that is more likely to be heard by the other party,” she explains.  

This Is Me Trying (to listen actively) 

There’s one caveat: Research has shown that most people aren’t great at the whole empathy thing, says Kira Schabram, an assistant professor at the Foster School who researches compassion. 

It isn’t that people don’t want to be empathetic — it’s that we don’t often take enough time to fully understand the situation and what is needed to repair it. 

Active listening means removing distractions (no checking your phone), making eye contact with the person who is speaking, not interrupting them and asking clarifying questions if you don’t understand something. When they are done, you can also paraphrase what they said back to them, such as, “If I understand you correctly, you’re saying that …” Umphress recommends. 

If you naturally nod your head or verbally affirm the person — “I see” or “That makes sense” — that’s good too, but don’t focus so hard on doing these things you forget to truly listen. Trying mindfulness can also help, and research has shown its benefits when honing empathy, Schabram says.

I Wish You Would (be honest) 

Truth time: Most people don’t want to compromise. A compromise is seen as meeting in the middle but ultimately can mean both people end up unsatisfied.  

Instead, Schabram prefers a strategy called integrative negotiating, where you both try to come up with an out-of-the-box solution that works equally well for both of you. 

“Integrative negotiation recognizes that two or more people are not fighting each other: they’re fighting a problem, so how can we resolve it?” she says. 

Instead of compromising, is there a way to think outside of the box so both people involved get what they want or something that is equally appealing? Say a couple regularly fights about who does the dishes each night. Instead of compromising — such as by alternating who does the chore — they could invest in a dishwashing machine or start making more one-pot meals, Schabram says. 

Question…? (your intent) 

Before having the conversation, Schabram recommends asking yourself: What do I want to get out of this? Am I just wanting to be heard or hoping for a specific outcome?  

Recognize that while you may not get everything you want, you can at least try, and setting some goals ahead of time can help you focus what you say and can limit the chances for misunderstanding. 

“To create your goals, you might think about talking with a trusted friend or mentor, or a therapist, before the conversation. Try to make your goals specific and realistic for the conversation,” Umphress says. 

You Need to Calm Down 

Schabram notes that many of these strategies for having difficult conversations come from a place of rational thinking, which isn’t necessarily what’s going on when we’re upset and emotions are high.

Postponing a conversation until both of you are less in your feelings could be the right decision. And, if you start feeling upset again when you resume, try mindfulness techniques like deep breathing to self-regulate. 

(Timing is) Delicate 

Consider arranging a time for the conversation like you would a meeting, and ensure the timing works for both of you. When you start talking, ask if it’s still a good time for the other person — and ask this of yourself, too. If you’re feeling more reactive and less ready to listen, reschedule. 

Don’t Blame Me  

No one likes to be blamed or shamed, and the automatic response to either of these things is to get defensive or turn the accusation back on the other person — which isn’t conducive to a productive conversation. 

“To avoid a negative spiral, try to make ‘I’ statements — talk about your own perspective and try not to make assumptions about the other party’s perspective because you’re likely incorrect because we’re not mind-readers,” Umphress says.  

Not blaming means not passive-aggressively blaming someone if you have to apologize, something along the lines of, ‘I’m sorry for what I did, but …’ 

“Try to avoid the word ‘but,’” Umphress says. “Using the word ‘but’ erases what you had previously said and negates your apology.” 

(Operate from a) State of Grace 

It’s easy to bring baggage into difficult conversations, baggage being memories of the ways the person has hurt you or other attempted conversations that haven’t gone well.  

While ignoring or completely forgetting about past baggage may not be possible, try to set it aside and focus on the specific reasons you’re having this particular conversation in the first place.  

“It’s a good idea for you (in your head) to acknowledge that yes, that history exists, and it might be important to acknowledge it – and also acknowledge that working through that history can be a long-term goal while the short-term goal is your original specific goal for the conversation, which might be to initiate the healing process,” Umphress says.