Three Convictions: Why Leadership Requires Difficult Conversations

Published September 24, 2018


Conflict ManagementLeading Others

Years ago, a friend of mine quit his job as a consultant to take a senior leadership position at our church. After a few months in the role, I asked him how things were going. I was wondering how ministry life compared to his marketplace experience. His response was instantaneous. “I had no idea how much of my role would involve difficult conversations.”

That pretty much summarizes the difference between consulting on leadership and actually leading, doesn’t it? Leadership is ripe with difficult conversations.

GLS faculty member Sheila Heen has helped explain why. Difficult conversations are the product of deeply caring about things that matter greatly.

Leadership is ripe with difficult conversations.

Over time, we’ve increasingly tried to encourage our organization’s leaders with the biblical features of difficult conversations in hopes that they’d lean into them to a greater degree.


There are three critical convictions I hold regarding leadership and difficult conversations.


1. Difficult conversations aren’t just part of a senior leader’s job; they’re at the very core of it

I’m often reminded of the way God intended the people of Israel to be cared for when he outlined a support structure to Moses through his father-in-law in Exodus 18. His goal for Moses, expressed in verse 22, was for these newly appointed leaders to “Serve as judges for the people at all times, but have them bring every difficult case to you; the simple cases they can decide themselves.”

To optimize the support of all the people—and to facilitate the most sustainable leadership possible—God’s vision was for the most senior leader to be freed up, specifically for the most difficult conversations. We try to remind our leaders, especially our most senior leaders, that difficult conversations aren’t just part of the job; they’re the very essence of what it means to be a senior leader.


2. Difficult conversations are essential if you really love someone

Sometimes people avoid difficult conversations out of care for the person. We remind them, though, that Jesus’ care for people deliberately engaged in difficult conversations. Think about an instance like His conversation with the rich young ruler. This young man approached Jesus because he was curious about what it took to experience a life with God.

In Mark chapter 10 it says, “Jesus looked at him and loved him. ‘One thing you lack,’ He said….” Jesus provided the hard truth to people around Him because of His perfect love for them. To Him, skirting issues or avoiding difficult conversations prevented a full expression of love for people. We remind our leaders that the greatest gift you can give the people you serve is the honest truth.

We’ve found that the more our leaders can associate difficult conversations with expressing love, the easier and more effective those conversations can be.


3. Difficult conversations are necessary for people and organizations to grow

The ultimate benefit of difficult conversations is the benefit they bring to the individuals we are leading. There’s a positive by-product for everyone when difficult conversations become the norm for the culture of your organization.

Ephesians 4:15 teaches, “Speaking the truth in love, we will grow to become in every respect the mature body of him who is the head, that is, Christ.” Difficult conversations done well—where hard truth is spoken from a heart of love—serve not only to provide information, but also to stimulate transformation.

Difficult conversations are one of the greatest crucibles for growth. We’ve seen tremendous growth in individual character development, team health and unity, work performance, organizational effectiveness and ultimately community impact as we’ve grown in our commitment to having these difficult conversations.


As we’ve experienced the benefit of difficult conversations both personally and organizationally, we’ve made a deeper commitment to encourage our leaders to engage in them.

The more we appreciate the gift of difficult conversations, the more frequently and effectively we’re able to engage in them.

It was a shock for my friend to have difficult conversations in his new job. Now, when we orient new people to our workplace, one of the core values we highlight for them is, “We go there.” It’s a statement that declares our desire to consistently lean into difficult conversations and to set their expectations accordingly.


Difficult conversations are a tremendous gift.

  • These conversations are the core function of what it means to lead.
  • These conversations must come from the core motivation of love for people.
  • These conversations are for the core purpose of growing individuals and groups.


The more we appreciate the gift of difficult conversations, the more frequently and effectively we’re able to engage in them.

The next time you’re tempted to avoid a difficult conversation, consider what you’re missing, lean in and go for it!

About the Author
Jeff Lockyer

Jeff Lockyer

Lead Pastor

Southridge Community Church (St. Catharines, Ontario)

Jeff Lockyer is the Lead Pastor of Southridge Community Church, a multi-site movement where each location serves a community need in their part of the Niagara Region. He is passionate about leadership development, serving as the Chair of the Board of Global Leadership Network Canada and co-hosting The Global Leadership Summit's GLS Podcast. A former national team runner, Jeff lives in St. Catharines with his wife Becky and three children.

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