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Navigating Difficult Conversations in Interviews: A Leadership Approach

Writer: Michelle KempMichelle Kemp

Updated: Feb 20


Imagine this: You’re preparing to interview a promising candidate. As part of your routine prep, you conduct a quick Google search and discover something concerning in their past work history. Do you bring it up? Or do you proceed without addressing it?

 

This moment presents a critical decision point—not just for the interview but also for how your organization approaches leadership, transparency, and building trust. How you navigate the conversation can either disengage a strong candidate or foster an open dialogue that enhances mutual understanding. Both are critical to how the organization and culture are perceived.

 

At MK Consulting Group, we support organizations in navigating these sensitive yet important conversations. Over time, we’ve seen that the most effective approach is one rooted in curiosity, not assumption, and guided by intention, not bias.

 

Douglas Stone, co-author of “Difficult Conversations: How to Discuss What Matters Most”, states: “Difficult conversations are almost never about getting the facts right. They are about conflicting perceptions, interpretations, and values.” Using Stone’s statement as an ethos, we recommend two key strategies to help leadership and organizations approach these interview discussions to gain clarity and respect.

 

1️. Lean Into Curiosity to Gain Perspective

This subtitle may sound cliché, but trust us - it works. As human beings, our personal and professional experiences shape how we make decisions, approach challenges, and grow over time. Some of our greatest lessons come from both positive and difficult situations. When discussing a concerning detail, avoid making assumptions. Consider the interview an opportunity to understand the candidate’s journey (how they’ve navigated challenges, what they’ve learned, and how they’ve evolved). Adopting a mindset of inquiry allows you to gather insight into their perspective, assess alignment with your organization’s values, and clarify cultural expectations upfront. Here’s how to approach this conversation effectively:

  • Start with a shared belief. Acknowledge that career paths are complex and that growth is a natural part of learning.

  • Present the finding objectively. Frame the conversation as an opportunity for dialogue that is nonjudgemental nor confrontational. For example: “As part of our due diligence in preparation for this interview, we came across [specific finding]. We are an organization that values transparency and understand there’s always more to the story.”

  • Invite the candidate’s perspective. Ask if they are able and comfortable sharing insight into their experience.

  • Follow up thoughtfully. Explore how the experience shaped their decision-making and approach to accountability. Express appreciation for their openness, recognizing that sharing personal experiences is not required.

 

This approach encourages transparency and offers the candidate a direct experience of your leadership style. It also shows that your organization values open conversations, continuous learning, and mutual respect.

 

2️. Actively Listen Without Bias

It’s natural to filter information through our own experiences, but self-awareness is key when interpreting someone else’s story. How we respond in these moments impacts hiring decisions and reveals whether we’re allowing personal experiences to cloud what a candidate is truly communicating.


So, how do we get out of our own way? Here are critical questions to help check bias and stay objective:

  • Am I making assumptions based on my own past experiences (or potential triggers) rather than this candidate’s reality?

  • Am I approaching this conversation as a fact-finding mission or an opportunity to understand?

  • Is my reaction and line of questioning aligned with the culture we want to build within our organization?

  • Am I unintentionally dismissing or minimizing the candidate’s perspective to affirm my own assumptions?

 

Every situation is unique, and bringing unresolved workplace biases into the conversation can cloud judgment and lead to missed opportunities. Instead, stay present, receptive, and committed to understanding to ensure your hiring decisions are informed, fair, and reflective of your organization’s values.

 

In closing, tough conversations in interviews don’t have to be barriers. They can be bridges to shaping a culture where open dialogue, accountability, and growth thrive from day one. When organizations embrace these conversations as a standard practice, they build cohesive teams committed to challenging and supporting each other’s development. Leadership, in turn, fosters a workplace where trust and transparency serve as the foundation for long-term success.

 
 
 

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