3 ways to make difficult conversations less challenging

It’s no surprise that we all encounter difficult conversations at work. And yet, the biggest surprise of all may be that most people tend to shy away from them.

Numerous books and articles, for decades, have offered advice highlighting the importance of preparation, active listening, emotional regulation, or focusing on solutions to handle these discussions more effectively. 

However, large-scale surveys, both old and very recent, show that the majority of employees still avoid difficult conversations, except when they have no choice. This avoidance is not only morally costly but economically taxing, with each avoided conversation estimated to cost a minimum of $1,500, contributing to employee disengagement and turnover in the long term.

This raises some big questions such as, “How much do we really know about difficult conversations across the organization?” and “How can we improve our ability to handle difficult conversations?”

Based on our research and experience, we propose three strategies leaders can implement to make these crucial discussions easier for managers and employees.

Identify relationship-specific bottlenecks

Our first finding is that difficult conversations occur with managers and subordinates but also among peers and with HR departments. Importantly, the topics of difficult conversations varied significantly depending on a person’s role and relationship with the target person. For example, while managers find it difficult to provide feedback on their direct reports’ performance and behavioral issues during one-on-one meetings, their direct reports find these topics relatively easy to discuss with their managers.

Whereas most existing advice on difficult conversations focuses on improving personal engagement techniques—such as personal preparation, active listening, and emotional regulation—our findings indicate that without a clear understanding of the specific conversational hurdles inherent in different relationships, the impact of individual efforts to listen attentively and control emotions will be constrained in easing difficult discussions. How can we make something easier when we don’t fully grasp what it entails?

Organizational solution: Leaders need to systematically identify topics that are either avoided or unaddressed within various relationships, such as those between subordinates and managers or colleagues.

An effective, data-driven method is to conduct pulse surveys or focus groups to uncover the root issues causing communication bottlenecks and to devise tailored interventions. For instance, if these surveys indicate that the exchange of performance feedback is a widespread challenge across all key relationships, organizations should assess whether they provide regular appraisal opportunities and ensure that performance metrics are both objective and transparent.

Should the difficulty in conversations be asymmetric, as indicated by our study, organizations must investigate further rather than implementing a one-size-fits-all solution.

Develop ways the whole company can share feedback up to leadership

We humans naturally shy away from conversations that could dent our self-esteem, such as addressing our performance issues during one-on-one meetings with managers. Beyond the possibly painful hit to bonuses, the mere prospect of discussing this quarter’s dismal pen sales can be an emotional burden and cause for embarrassment. 

However, one striking finding was that the thorniest topics subordinates find in one-on-one meetings with their managers was addressing performance or behavioral issues of their superiors. At first glance, this finding may seem unusual, but upon reflection, many of us might find this situation all too familiar. Think back to when you’ve been more exasperated by your boss’s incompetence or misconduct than by their critique of your performance and the impact on your bonus.

The failure to address upward feedback, especially regarding superiors’ performance, carries significant organizational consequences. As observed across various social media platforms, junior employees often quit, formally or quietly, out of frustration due to their inability to confront incompetent bosses. Furthermore, the lack of due upward feedback inadvertently inhibits their boss’s performance since upward feedback is a crucial source of information for managers to enhance their own performance. 

Organizational solution: A practical organizational solution to facilitate upward feedback from employees to their managers is formalizing opportunities to comment on superiors’ work or performance. For instance, organizations might consider implementing 360-degree feedback, which allows everyone to share insights not only about their subordinates but also about peers and superiors. Research has consistently demonstrated that multisource feedback not only bolsters leadership and employee development but also group performance.

Without overhauling their performance review system, organizations can consider designing managers’ check-in meetings or team meetings to request input from juniors on the managers’ work. Soliciting input, particularly upward feedback, is a recognized method to ensure psychological safety—a shared belief within a team that voicing ideas, concerns, and mistakes won’t result in negative consequences. Psychological safety plays a pivotal role in fostering mutual learning between managers and employees, as well as facilitating difficult conversations and cultivating a culture of trust throughout the organization.

Conduct communication training for everyone

A final notable finding from our survey is that 56% of respondents believe their organization’s support for employees in managing difficult conversations is not sufficient. Our follow-up questions about the resources needed from organizations provide further insight into our final recommendations. 

In addition to arranging formal mechanisms, such as 360-degree feedback, for regularly sharing upward, downward, and lateral feedback constructively with stakeholders, it seems crucial for organizations to train employees in effective communication. Although individual effort is important, organizational-level training ensures difficult conversations occur in a shared language and within an organizational framework. If one person knows how to actively listen and focus on solutions but the other has not been trained, the conversation can remain awkward and cumbersome.

Organizational solution. There are ample resources, articles, and books offering skills and mindsets required for effective communication at work. Leaders should integrate these into their permanent training systems, for example, as a requirement for onboarding or performance appraisal. 

To design such programs effectively, organizations must consider the fundamental aim and definition of performance feedback—that is, sharing feedback on another’s task performance (yes, not on their nonwork related personality) with the goal of improvement.

We have observed in many instances that many difficult conversations about performance stay focused on blaming rather than helping the person do better next time. Similarly, many difficult conversations about conflicts remain fixated on deciding who is more wrong, rather than making them work together again. Thus, organizations’ communication training should begin by clarifying for employees the purpose of any difficult conversation at work: to be constructive and developmental.

Given the increasing challenges of being a modern manager, which include overseeing many difficult conversations, organizations can arrange additional training for middle managers. This will enable them to interpret a vast amount of data on subordinates and prioritize areas for improvement that align with organizational strategies.

In short, difficult conversations are challenging because they often involve discomfort. Psychologists encourage individuals to step out of their comfort zones by engaging in more difficult conversations. We believe the same principle applies to workplace discussions. The more we normalize and participate in these challenging dialogues, the better we handle them. A leader’s support is crucial in this process, especially when different stakeholders hesitate to speak up due to a lack of time, fear of retaliation, or simply the lack of the right communication skills.

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