Purpose Built Blog
February 10, 2023
Communication Debt Part 2- How to Have Hard Conversations
by Reini Chipman and Miles Lasater

“You can’t stop the waves, but you can learn how to surf.”

– Jon Kabat-Zim

Think about the last time you made it through a hard conversation. It could’ve been providing some hard feedback for a direct report, talking about a pay increase,  calling a colleague forth for their behavior towards a client, or discussing a sensitive personal issue that is affecting your life and work. 

Afterwards you were probably experiencing a lot of different feels, including a sense of relief. 

Phew! I’m soooo glad to be on the other side of that.

Ah… that beautiful moment in time where we relish in completing a challenge. For most of us, we’re a little buzzed with residual energy yet exhausted all at the same time. We might treat ourselves to something indulgent to reward our effort. And hopefully we can sleep soundly that night having moved through something that was “stuck”.

Then a few days go by. Maybe even a couple weeks, but that next scary conversation is usually looming right around the corner.

Oof. Not again!

The waves of communication are a natural and necessary element in any business. As we discussed in Part 1 of this series, fundamentally, business is made up of conversations and effective conversations drive the bottom line. One could argue that effectively “being in conversation” is our biggest work as leaders. And if you’re signing up to be a leader, you’re signing up for a journey filled with one conversation after another. 

In this article we share some perspective and tips we’ve picked up along the way as we’re continuously honing the craft of conversation. 

Beliefs + Mindset

We’ve all had those moments where we want to bury our head in the sand and hope the sticky situation goes away. And it’s always OK to take a brief timeout when we need one. But surfing the big waves is about getting off the warm cozy beach and diving into uncertainty. 

Stephen Covey’s work asserts that beliefs drive behaviors and behaviors drive results. We also know that we have the power to change our perspective. Before we jump into tactics for having hard conversations, it’s important to explore the stories, narratives, and beliefs we’re holding. Here are a few inquiry questions to get you started:

  • Part of what makes hard conversations hard is we don’t know what will happen once we start the conversation. What is your relationship with the unknown and uncertainty? What purpose does it serve in your life?
  • What stories did you hear growing up that impacted how you think about communication and conversations? Do they still hold true for you?
  • If you were to write a 1-3 sentence narrative stating your current perspective on hard conversations, what would it be?
  • If you could rewrite that narrative and choose a new perspective to try on, what would you choose?
  • From your unique vantage point, why do hard conversations matter?
  • What’s at stake when you don’t have the conversations you know in your heart need to happen?

Often what we fear about a conversation we need to have is discomfort - we think, “Oh my, it's going to be awkward and uncomfortable.” We naturally want to avoid it. And the truth is sometimes people get really upset, or angry. But there is a difference between reaction and response. The way someone reacts in the short term can be vastly different than their overall response, which happens over the long term of a relationship. 

If we want to be trusted as leaders who can surf the continuous waves of communication, we need to get our hearts and minds right first. When we’re intentional about the perspectives we hold, we are more likely to shine our brightest through every decision we make and action we take.

Who’s Driving The Conversation? 

We tend to think of hard conversations as a thing that we need to initiate. But that’s not always the case. Often someone else is working up the courage and a plan to have a conversation with us that they’re nervous about. If we roughly estimate that we drive 50% of the hard conversations and imagine that the other half come to us, then it stands to reason we need to practice 1) noticing the signals, and 2) being approachable, present, and ready to engage.

What are signals we might observe that someone needs to talk to us about something hard? Perhaps they are avoiding eye contact or constantly rescheduling. Or maybe they ask you how you like to receive feedback and if you’re in a place to receive feedback. Sometimes folks will ask you to meet in person or change the geography of your normal meeting space when they have something important to dig into. Think about opportunities where you can tune in to these sometimes subtle signals.

That being said, having a keen ability to pick up on signals only gets you part way there. Without building a reputation as someone people can come to, you’re at risk of missing critical communication flow that you need to lead effectively. The best leaders are excellent listeners, skilled at receiving and integrating feedback, and viewed broadly as someone who builds safe and trusting relationships. Sometimes we need to drive the conversation, and sometimes we need to let it flow to us.

Building Strength + Agility For Conversations


Regardless of who’s driving, there are infinite ways to do conversations well. We’ve outlined some of our favorite tips and tactics below. 

Ensure All Participants Are “Resourced”

The phrase Human “Resources” is often fraught with negative connotations, and for good reason (we’ll save that deep dive for another day). However, when it comes to conversations one of the best ways to ensure they are productive and successful is to ensure that all participants are well resourced. What we mean by this is, everyone has what they need to be able to access and participate in the conversation. 

Here are a few ways to check in before or at the beginning of conversations and ensure the right conditions exist for all participants to show up at their best:

  • Assess the power dynamics. If you’re driving a conversation with someone who is more senior than you, what do you need in order to feel that you can show up at your best? If you’re having a conversation with someone who may perceive you as having certain kinds of power, what can you do to ensure this isn’t blocking your ability to get the right outcomes? 
  • Check your bias. Reflect on your own stereotypes, prejudices, and discrimination. Educate yourself - if you’re a member of the dominant culture you can build trust by proactively seeking to understand the experience of folks in marginalized groups. And finally, practice mindfulness. Pay attention to the thoughts and associations you have about people with different characteristics and identities.
  • Timing can make you or break you. To the degree you can, ensure the conversation happens when both parties feel prepared and have the right energy to show up at their best. 
  • Consider the format. Some folks prefer written communication, while others prefer in person. There are many formats that can work. Explore the options and get creative. Sometimes a walk outside can completely shift a conversation in the direction it needs to go.
  • What matters most? Clarify what matters the most for each participant. When they take a step back and look at the big picture, what matters most to them in this particular conversation? It might be something minor or major, but it’s important to align on and honor what is most important for each participant. This builds common ground and enables all parties to more effectively access the conversation.


Demonstrate you care about the person.

Ideally, long before a hard conversation is needed, you've already invested in getting to know this person or these people: What matters most to them: What their top values are; And bonus points if you know their communication style and preferences.

In her book “Leading Below The Surface: How to Build Real (and Psychologically Safe) Relationships with People Who Are Different from You”, LaTonya Wilkins calls out that building real relationships requires intentional resourcing, much like exploring the depths of the sea:


“The deepest levels of the ocean are hard to get to. Some research even says that we are only familiar with 0.05% of the ocean floor. Since oceans are dark and murky, it takes vast resources and a long-term commitment to be able to reach the lowest levels. Like getting to the depths of the ocean, to get to the deepest and most authentic levels of leadership, we have to commit vase and consistent resources to form real (and psychologically safe) relationships with people who are different from us.”

Learn non-violent communication principles.

Learn non-violent communication and add it to your toolkit. Here’s a quick overview of the NVC model for conversations:

  • Observation: what would a camera record about the external world? Without judgment what is the most objective statement you can make about what happened?
  • Feeling: what emotion did you feel?
  • Need: what deeper need does this situation remind you of? Some fundamental ones are autonomy, physical wellbeing and connection
  • Request: what is the action you want the other person to take in the present?

While clarity on your request can be helpful, don’t use the lack of a request as an excuse to postpone conversations too long.

Don’t believe everything you think.

There’s a lot of pressure (in US business culture especially) to “be right”, and yet as humans, Kathryn Schulz would argue that we’re all wrong all the time.  

If you can express your perspective with room for other viewpoints the conversation may be more constructive. If you speak inarguably there is less room for debate. State facts about your inner state. Couch things without judgements to start: “After you arrived at 11:13 for an 11:00 am meeting with the client, I felt a flush of anger and  embarrassment. The story I have is that arriving at the agreed start time shows respect.” rather than “You are always late for client meetings. Today was the most recent example of your disrespect for me and our clients.”

As you move through a hard conversation, focus on how to “get it right” as a team versus obsessing over “being right”.

Avoid Gottman’s 4 Horsemen.

While John Gottman’s lab studies personal relationships, we can learn lessons that carry over to the business context. The “Four Horsemen” can signal great danger to a relationship: Criticism, Contempt, Defensiveness, and Stonewalling. 

Here are some recommended antidotes to avoid them:

  • Start with I statements
  • Remind yourself of the other person’s good qualities
  • Acknowledge your part or mistakes including apologizing when appropriate
  • Take a break if needed and appropriate or take conversations a topic at a time

Shift from current state to future state.

If you begin to feel stuck in a conversation, or find that you’re spinning around in circles…it can be helpful to switch gears and do some future visioning together. Is there a positive picture of a compelling future, and is that worth exploring together?     

Think Kind not Nice

Were you told growing up that “if you can’t say something nice, then don’t say anything at all”? It may be time to reframe your approach.

You can demonstrate care for someone without being “nice”.

As a leader, clear is kind. Seek to be this kind of kind without focusing on nice.

Not all things need to be said. 

There are some who will advocate for saying everything on your mind and it can work when both sides of the conversation opt-in. Yet full candor is not the dominant work culture. Engaging in conversation about everything you think may not be necessary.

For example, if you react to the way someone chews it’s probably not critical to address for a business relationship. But if you have recurring thoughts about their performance, finding a way to talk about that is important.

Phone a friend.

Great leaders know when to ask for help and guidance. You can practice with someone.

Share the slips, integrate the learning.

Consider Wilkins’ invitation to “share your slips”. What part of this situation do you own? Is there anything you’re embarrassed by or ashamed of? What might you be learning right now that you need support on?

“This isn’t the same as shaming or even admitting your failures. Sharing your slips is the process of admitting that none of us are perfect and, as humans, acknowledging that we exclude to belong. Sharing your slips is backing your wholesome goal with full honesty. Nothing is pristine, and the path to truly accessing below the surface leadership will be full of slips. Some people even describe slip sharing as spiritual. It’s a rebellious level of vulnerability that propels you into deeper levels with others. Sharing your slips is about embodiment, not accomplishment.”

In Conclusion

Having the big conversations and making the big decisions is what high performing leaders do. This is a lifelong journey…

There are many right ways to do conversions and nothing is pristine. It’s ok if things get a little messy. Humans are naturally creative and resourceful beings.

Keep practicing, keep integrating failures and feedback,  and celebrate wins big and small. and when you get knocked off the surfboard take a beat and then get right back on. 

In part 3 of this series we’ll explore how you can safeguard your company and stay out of communication debt.

Further Reading + Learning

If you want to learn more about this topic we suggest the following books. We have learned a lot from these books and have more to learn! If you have others to suggest, please let us know.

Center for Creative Leadership on Tough Conversations

Conscious Leadership Group on Clearing Conversations

Nonviolent Communication Model

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