We Need to Talk: The Art & Science of the Difficult Conversation

Most people struggle with how to effectively approach conflict and difficult conversations. But mastering this skill is one of the best ways to guard against groupthink, consider multiple perspectives and resolve damaging workplace conflicts.

Tracy Cocivera
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Consider this situation: you’re a leader at a company whose founder is behaving badly and imperiling the business. But no one has the courage to say anything.  Then, with a start, you wake from your nightmare and realize you’re not working for an Uber or a WeWork but for an organization of well-intentioned people in which difficult issues requiring attention sometimes arise. It may not be anything as extreme as a CEO heading towards an implosion of galactic proportions but may just involve a superior who doesn't like communicating disappointing results. If no one is willing to speak up, how do you make the changes necessary for ensuring better results in future?

You need to be able to handle difficult conversations to resolve a range of common workplace conflicts, from competition for scarce resources and confusion about roles to misaligned goals and unpredictable policies. In a well-run organization, tackling tough conversations is (or should be) a practiced skill—whether with immediate reports, peers or even superiors. These skills are among the best ways an organization can guard against groupthink, consider multiple perspectives and engender trust.

Not every issue requires a difficult conversation. But what if team or organizational productivity and performance is at risk? What if differences in opinion are causing a stalemate? What if emotions are running high and someone is feeling threatened? Your people need to know how to bring these issues to the forefront and have productive conversations to find resolution.

One of the problems is that speaking up can be very uncomfortable. It’s a minefield in which a false step can damage important relationships. Do you really want that senior leader to feel that you are attacking her leadership style? Or, in the opposite direction, will you really be helping if you inadvertently demoralize your immediate report? 

Fortunately, the art and science of mastering a difficult conversation is a skill that can be honed with learning and coaching. There are ways of preparing for, initiating and conducting difficult conversations that are more likely to yield productive and positive outcomes than unintended negative consequences. 

What might your approach be? What steps might you consider? Here are four steps that can set you up for success:

Examine assumptions and check for understanding

It all starts with the right attitude, so begin with your own mindset. Analytical skills are necessary for determining which issues deserve a conversation and how to approach such conversations. Identify your goals in initiating a difficult conversation and examine your underlying management style, feelings and preferences. Do you have clarity of purpose, and are your impulses entering the conversation aligned with your goals exiting it? Productive conversations are unlikely to proceed from questions of who is to blame or who is right or who is going to fix it. Be honest about your feelings before having the conversation and manage them as you engage in the conversation. You’ll want to focus on the facts, not on preconceived assumptions and judgmental narratives. The objective of the conversation is to be an advocate and work together to find an answer. 

Create an environment of inquiry

Alongside your mindset, work on your skillset. A fruitful approach emphasizes mutual learning and understanding. What’s the perspective of the person you’re engaging in conversation? What’s their story? How do they see the matter differently, and what do they think is important? Strong communication skills are necessary for presenting the issue clearly and with empathy. The key is to be sensitive but forthright. Deep listening skills are necessary for gaining a broader perspective of the issue and for discovering a way forward. Encouraging people to engage in the conversation and share their perspectives helps build a sense of safety and keeps the intensity of the conversation low. Just as importantly, it forms the basis of sharing ownership of the issue and focusing on the problem, not the person. A productive mindset focuses on listening and giving feedback that addresses the issues and leads to solutions.

Have a plan and role play first

Formulate a framework and process to follow during the conversation itself. You need a flexible plan to ensure that your conversation reaches the outcome you imagine—that the communication is direct, you’re engaged in active listening, the intensity is kept low, the ownership is shared and the focus is problem-based. And since not all issues and interactions are the same (engaging an immediate report is not the same as engaging a superior), your plan needs sufficient flexibility to cover multiple situations, with contingencies in place in case your first plan isn’t unfolding the way you intended. 

Putting it into action: transforming a difficult conversation into productive conflict

It may be helpful to think of your conversation as passing through a series of phases. A situation phase establishes where and when the issue arose: “At our quarterly meeting last week…” Providing such context helps identify the matter you are about to discuss. A behavior or event phase directly describes what the issue is: “…you touched only briefly on our latest business results.” An impact phase addresses the effect of the issue and why it matters: “Although we have some ideas, my team and I feel uncertain about if and how we should change our approach.” A discovery phase opens the conversation up to other perspectives: “What’s your view of the results and how the team should respond?” The conversation is now positioned to focus on the problem at hand and consider a resolution jointly.

Conducting difficult conversations effectively is essential to business performance. Leaving conflict unchecked may not lead to an immediate apocalypse but may, nevertheless, lead to a steady and irreversible erosion of trust, engagement and performance. 

The inability to handle difficult conversations has wide-ranging negative business consequences. A company in which leaders across the board are capable of engaging productively when conflict arises—through active listening, understanding, advocacy and mutual problem-solving—are able to take control of a potentially volatile, disruptive situation and ensure that they reveal and address problems, hear and consider perspectives, and achieve successful outcomes. 

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