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Holding Difficult Conversations: Tips For Leaders

Source | | Eric Pliner

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.

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