Two employees sitting in a cafe having a conversation.


Hard Conversations

Download PDF


Why are some conversations so challenging? A hard conversation is a discussion that makes us uncomfortable to even contemplate because we know what we’re going to talk about won’t be easy for the other person to hear. We worry and stew about how to have it: what to say, when to say it, how to start, and how to finish. We’re afraid we’ll hurt a relationship that matters. 

Two employees at a cafe having a conversation

Essentially, we’re worried we’ll lose someone’s trust. As social creatures, trust is one of the most valuable qualities we can share with another person. Creating an environment of trust between colleagues and stakeholders is essential for building a high-trust company (HTC).

Having hard conversations can sometimes be necessary, particularly when evaluating whether a team member is the best fit for your organization (Right Person) or their role (Right Seat). This can involve assessing their Competency, Commitment, and Capacity for their position (CCC).    


Since hard conversions can feel like we’re putting our high-trust relationships at risk, we’ve made it a point to learn all we can about trust, collaboration, and communication. One of our favorite experts is neuroscientist Dr. Paul Zak.

In his book Trust Factor, Zak provides eight critical factors for building and maintaining trust. He uses the acronym OXYTOCIN:

  • Ovation

    Recognize accomplishments with public praise.

  • eXpectation

    Time-limited, agreement-based challenges for colleagues.

  • Yield

    Get an agreement on what needs to be done and let colleagues run.

  • Transfer

    Teach and treat colleagues like adults.

  • Openness

    Be as transparent as possible and then some.

  • Care

    People don't care what you know until they know you care.

  • Invest

    Colleagues you want to keep want to grow personally and professionally.

  • Natural

    Be authentic, ask for help, and model excellence, respect, and humility.

We consider these factors when preparing for, conducting, and concluding hard conversations. Here are steps to prepare for a challenging conversation in your life.

Before the Conversation

The first step is identifying the need for a hard conversation. The reason could become known after one specific occurrence or from observing a series of events.

For example, during Weekly Team Meetings, you notice one of your team members, Cameron, is consistently late completing their To-Dos. They haven’t brought up any Issues to discuss, and they become defensive and agitated when asked if the team can do anything to assist them.

We recommend building a list of specific occurrences — at least three examples of when someone has gone against the organization's rules, policies, or Core Values. Maintaining specificity will help keep the future conversation on track.

With your list of examples completed, schedule some time with another leader in the organization. They may have advice to help you prepare. You may also wish to consult a business or executive coach.

The last step to prepare for a hard conversation is to try to understand the person you need to speak to as best you can. If you use personality assessments like Kolbe or TypeCoach, learn from their tools about how to best problem-solve with each other based on each of your profiles. Personalizing your approach helps avoid potential miscommunication that will surely derail the discussion.

The Conversation

Select an environment where both parties feel safe to share candidly without worrying about being overheard. Finding a neutral location — not your office — is a good idea.

Once you’re settled in the space, ask their permission to begin a tough conversation.  Even if they’ve agreed to a time and place to talk with you, they don’t necessarily know what’s about to happen. Receiving their blessing to begin lets us know they’re listening and are mentally prepared.

Approach the conversation with genuine care for who they are. One of the quickest ways to erode trust is by being disingenuous. Lying, belittling, or misleading someone may cause irreparable damage to the conversation and your relationship in the long term. It may sound cliche, but honesty truly is the best policy, here.

Clarify the outcome you’d like to reach from the conversation. For example, you could tell Cameron that your goal is to make sure they feel supported by the team and the company — that you’d like to cover any impediments they feel are stopping them from their Roles and Responsibilities.

Be mindful of the impact of your words and pay close attention to the other person's emotional state. Engage your ears and listen. Take note of physical cues and what they’re saying and asking. Acknowledge their feelings and avoid becoming defensive as they process the information you’ve shared.

As you work toward a win-win outcome, remember that positive results from hard conversations are not always immediate. We have these conversations because they’re the right thing to do for all parties.

Finishing the Conversation

  • At the end of the conversation, reiterate any decisions you’ve made. Turn expectations into agreements, and ask if the other person has questions, concerns, or additional thoughts.

  • For example, perhaps team member brought up they had fallen behind on their To-Dos because they were unfamiliar with the processes associated with a new project. They didn’t feel comfortable reaching out for help, so they spent much of their time trying to map out a structure other team members had already sorted out.

  • Now, you agree to share any standard operating procedures with them, recommend additional resources, and schedule a 1-on-1 to see if they have further questions. If the team member still has the Capacity for their Seat and the Commitment to the organization’s goals, do your part to bolster their Competency and confidence.

Core Disciplines of Hard Conversations

  • 1. Sincerely seek to be truthful, specific, and positive (TSP). We don’t believe in the adage “Respect is earned, not given.” Instead, respect should be granted to those we interact with from the outset. Respect means that you view your team members as people first. They were hired to fulfill their Roles and Responsibilities, but they’re not a cog in a machine. Knowing how quickly trust can be lost, our best advice for mastering hard conversations is to be truthful, specific, and positive.

  • 2. Model the openness, authenticity, and trust you seek to see in your team members. To have a high-trust company, we need to be exemplars of our Core Values. We’ve identified authenticity as a critical component of trust and believe leaders must lead with integrity. In this age of work, people have more opportunities available to them than ever before. Who we work for and with is critical. 

Hopefully Helpful Hints

  • Hard conversations are not about you. These conversations are for the person we’re speaking with. If they’re in the wrong role or not aligning with the organization’s Vision, then it’s best to address those concerns head-on and assist them in finding a better fit. 

  • When tensions rise, pause, breathe, and get curious. Maintaining a calm demeanor is critical for having successful hard conversations. Set a tone of civility and calmness to help the same postures reflect back to you. If you feel defensive, try to avoid making assumptions, consider what details you may be missing, and remind yourself of the bigger picture.
  • Read the experts. In addition to Trust Factor, we recommend Radical Candor by Kim Scott and Crucial Conversations by Joseph Grenny, Kerry Patterson, Ron McMillan, Al Switzler, and Emily Gregory. Very few of us are innately great at having these kinds of conversations. These books provide the research, examples, and discussions to help us improve the skills needed for difficult conversations. Be kind to yourself if this doesn’t come easy.


Having a hard conversation with a colleague can be daunting and challenging, but with the right approach, we can ensure that these conversations are truthful, specific, and positive. Mastering the disciplines associated with having hard conversations is essential to ensure a healthy and functioning workplace. These conversations go beyond the two people having the discussion; they foster a trusting atmosphere that promotes the organization’s culture.

What’s next? Visit the 90u Library or try Ninety today.

Let's get started

Use Ninety for 30 days. No credit card required.

Try For Free Get a Demo →