Holding Difficult Conversations: Tips For Leaders

Jun 7

Leaders are always called upon to engage in challenging and difficult conversations. That’s appropriate: if leadership is about creating the conditions for others to manifest change – or, in an organization, creating the conditions for others to deliver on a strategic change agenda – then being able to engage and support others in engaging with challenge directly is part of the remit.

In this moment, though, we find ourselves navigating overlapping crises within our organizations and in the world more generally – and many of us are experiencing intense emotion and responsibility regarding these crises ourselves. How, then, do we hold difficult conversations in a way that is supportive of others, productive, and meaningful, rather than just superficial or performative? How can we create space for legitimate engagement, particularly regarding content that may be brand new to us?

Taken together, these dozen tips for holding difficult conversations may be overwhelming. Consider each on its own merits, based on how it helps you to bring your strengths as a leader and communicator to life and how it may help you to manage some of your own gaps and learning opportunities, particularly amidst a challenging dialogue about unfamiliar, new, controversial, or especially important content.

1. Be clear about the purpose of the conversation. Why are you holding a difficult conversation? Are you looking to connect? To create space for others to share grievances? To inspire or influence change? To make room for an unspoken dynamic to come to the surface? What do you want to get out of the conversation? Starting with clarity of focus about your intent and your desired outcomes – even if they don’t manifest exactly as you hope – will help you to return the conversation to its purpose in its most difficult moments.

2. Where you’re uncertain or uncomfortable, start off by acknowledging that you may get this wrong. Many leaders get to positions of authority and responsibility by being really good at getting things right: we sell successfully or manage well or know the answers or the history, and we can sit at the helm of an organization that needs this skill set. We’re used to getting things right, and once we’re in senior roles, we are at even greater risk for confirmation bias (that is, the tendency to spot data that reaffirms our existing points of view). In a difficult conversation, we may not get it right – and that has to be okay. We have to be prepared to acknowledge and apologize for our mistakes when others call out that we’ve gotten it wrong.

3. Position yourself – to remind yourself and to help others to understand your vantage point. Are you a learner? Are you new to this topic or discussion? Are you speaking as an expert? As the CEO? As a community member? Where are you speaking from personal experience and where are you speaking from hypothesis? Start off by noting the vantage point from which you are speaking and, where possible, avoid generalizing or broad conjecture, especially about perspectives with which you are less personally familiar. Use examples that are recent and relevant. Speak from your personal experience: your experience is your own.

4. Embrace emotion. It’s tempting to suggest that the best approach is to be unemotional. But part of what creates the difficulty in difficult conversations is that they are often rooted in deeply emotional and personal experiences. Where you feel emotion, acknowledge it. Where you hear emotion from others, acknowledge that, too. Make room for emotion, as it is often a powerful driver of change.

5. Repeatedly connect back to your values. Explicitly tie your comments to what matters to your organization, to what you believe, what you stand for, and what you will do to affirm those values in action even more than in words.

6. Listen more than you talk. As you are challenged, the temptation to react will be intense. Don’t give in to that temptation. Instead of reacting – which is often accompanied by a heightened physical sensation or a rush of adrenaline – pause, listen, pause again. Ask questions for clarity and understanding. Pause one more time and really take in the message beneath the language and tone. Only then should you respond. A clever leader once noted that when we have a reaction to a medication, our bodies are rejecting it, but that when we respond to a medication, our bodies are healing or soothed by the treatment. The same is true of words.

7. Join with others in the conversation. Resist the impulse to judge others, particularly those who speak forcefully or with emotion. Watch out for the defensive tactic of calling people out. Pointing out others’ mistakes is a distancing behavior that says to the commenter, “I’m better than you” or “I know more” or “we’re not alike” or “we’re not in this together.” Think, instead, about what racial justice activists will sometimes refer to as “calling in” or what others might refer to as “coaching” behaviors: ask the commenter if others might have a different point of view, ask what desired outcome might be preferable, ask about their intent and how that might differ from their impact. Engage others in the dialogue as partners – instead of getting defensive or responding by distancing, ask the group, “What do others think?”

8. Engage with curiosity. If you are preparing to defend yourself, you are unlikely to hold space for a difficult conversation. Plan to learn and engage from a position of genuinely wanting to hear or learn something that you didn’t know before the conversation. Make space for individuals with differing points of view to share their perspectives, fears, and concerns. Ask, “What do you want me / us to hear or know?” or “What would you like to be different?” Invite participation from quieter members, and create an expectation of sharing the floor.

9. Assume positive intent. Holding the expectation that others mean well is perhaps a cliche, but such an expectation is valuable nonetheless. Consider: if I am to believe that this individual wants something good to come from this conversation, what else will I need to hear, understand, or believe? How will I respond in kind? Answer questions as though every interrogator, no matter how emotional or intense, is genuinely asking a question of you and not attacking you, and answer accordingly. Remember that there is likely a power imbalance between you and the questioner, and their boldness is a sign of bravery and courage. Respond with appreciation for that bravery and courage.

10. Ask the group for help. If you’re truly unsure how to answer, ask the group, “What do you want me to hear right now? What do you want to hear from me right now? What are you hoping I’ll say?” Listen carefully to their response and decide whether you can honestly say what they want to hear with integrity. While it may be difficult in the moment to decline a group’s strong invitation to give a particular answer, the intensity of the disappointment and rejection will be multiplied many times over if you are experienced as lying or operating without integrity.

11. Focus on three components of inclusive leadership: curiosity, courage, and connection. Individuals who experience their leaders as authentically inclusive report that these leaders demonstrate curiosity (creating the conditions for learning and creative thinking via receptiveness to others’ ideas and experiences and seeking clarity of understanding); courage (taking risks, empowering others, and accepting discomfort via a blend of vulnerability and generosity); and connection (understanding themselves and their own identities and gleaning legitimate value from the appreciation of others, achieved via a combination of strong self-awareness and real relationships).

12. Make commitments, confirm those commitments, and follow up. A powerful conversation can have value in its own right, from the perspective of creating space for emotion and expression, fostering psychological safety, and conveying important information. But the power of a difficult conversation goes to another level when it inspires action and change. Close out your conversation by making commitments to action and confirming the accountabilities and delivery dates for those commitments. Make a point to follow up personally, where possible, with those involved to thank them for their contributions and to reassert your commitment to change and action.