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Having Difficult Conversations That Make Your Collaboration Stronger

Strong collaboration sometimes requires difficult conversations — conversations that have the potential to destroy your collaboration or make it stronger. Any rupture can be repaired, if both people are willing to talk things through.

Here’s a four-step process to guide you through these discussions with grace, increasing the chances that your difficult conversations will strengthen the bedrock of your partnership.

(It’s a good idea to have difficult conversations one-on-one whenever possible. Trying to resolve conflict with an audience can turn the conversation into a performance where everyone — including you — is tempted to say the thing that makes them look good rather than being honest about what’s really going on.)

Step 1: Achieving Clarity with Compassion

A shared vision lies at the heart of any collaboration, but when conflict casts its shadow across our path, returning to that mutual understanding requires clarity. 

Start by describing the problem as you see it without casting blame. The goal at this stage of the conversation is not to establish who’s right and who’s wrong, but to lay out what’s happening or not happening that is undesirable, and to identify any constraints on the solution.what you’ve observed, how it affects the project, and how it makes you feel. What happened, what didn’t happen, and what would both of you like to happen differently next time? Stay focused on expressing the impact of the situation on the collaboration and on you personally.

Then clearly define the outcome you wish to achieve, and be as specific as possible by describing the results you want in tangible terms. What will change in each person’s workflow and communication style, and will you need to shift the project’s direction?

Make your desires known, not as demands but as aspirations for what the collaboration could become.

Be vulnerable and extend trust — let the other person know how you’re feeling, and explicitly ask them to help you find a solution. By expressing your feelings and opening up about your concerns, you’re not showing weakness but inviting trust. Step 2: Embracing the Art of Listening

Ask your collaborator how they see the problem, how they feel about it, and what they want or don’t want to happen.

And when they answers, do your best to avoid the trap of defensive listening, preparing rebuttals to each thing your partner says. Instead, listen with curiosity, seeking to understand the nuances of their perspective. 

Don’t ask “why” questions at this stage in the process, because they can make the other person feel like they have to defend themselves or make excuses. Instead, ask open-ended questions that invite elaboration rather than yes or no answers. 

  • “What’s your take on this situation?” 
  • “How do you feel about what’s been happening?” 
  • “What are your hopes for how we can move forward?”

Reflect back what you hear as they share, not only to confirm your understanding but to show them that you do value their perspective. This mirroring can reveal misunderstandings and assumptions, offering a clearer picture of the conflict and bringing to light the shared desires that may have been obscured by the fog of disagreement.

Step 3: Crafting the Path Together

The next step is to brainstorm solutions together. This is where the magic of collaboration truly shines, as you explore possibilities with an open mind. Your goal is not to find a compromise, but a true win-win solution that both of you are happy to move forward with.

Start by asking for your partner’s ideas for how the problem could be solved. As you listen, watch for unspoken expectations and assumptions that either of you might be making, poorly-defined steps in your workflow that might be creating problems, and environmental and psychological factors that might be adding friction to your collaboration. 

If you have a solution in mind, don’t ask the other person what they think about it, which is an invitation to be critical and poke holes in your idea. Instead, ask: “Here’s something I’ve been thinking about, but I’m not sure if it addresses everything. Can we work through it together?” You’re inviting them to be on the same team, while also leaving the door open for both of you to come up with a different solution together.

Collaborative brainstorming can uncover creative solutions that neither of you might have considered alone. This process of discovery requires openness and the willingness to pivot as new information and ideas emerge.

Step 4: Solidifying the Agreement with Gratitude

Once you’ve arrived at a solution, take a moment to solidify your agreement. Summarize what you’ve decided, outlining the actions each of you will take and the changes that will be implemented. This summary acts as a verbal handshake, a commitment to the new path you’ve charted together.

But don’t stop there. Recognize the emotional labor required by these difficult conversations. Acknowledge the effort, flexibility, and openness your partner has shown. Express your appreciation for their willingness to engage in the conversation and for the creative solutions they’ve helped forge. 

This recognition not only cements the agreement but also strengthens the bonds of your partnership.

When the Path Forward Is Unclear

What if your partner doesn’t think there’s a problem, insists on casting blame, refuses to acknowledge your perspective, or won’t agree to any workable solution?

If emotions are running high and either of you have hurt feelings to work through, it may be wise to pause the conversation, allowing time for both of you to reflect and regroup. The goal is to approach the dialogue with calm minds and open hearts, ready to listen and understand anew.

Difficult conversations, while challenging, are the crucibles in which stronger collaborations are forged. They require courage while rewarding us with deeper connections, enhanced mutual understanding, and a reinforced commitment to our shared creative ventures.

In the end, these conversations are not just about finding solutions to immediate problems; they’re about building a foundation of trust, respect, and mutual support that will sustain your collaboration through any storm. 

See you next Wednesday!