Why Do Leaders Need to Lean Into Hard Conversations?

In psychology, one of the key characteristics that almost every human experiences is that when in crisis, they fear the unknown. It’s only human nature that in times of uncertainty, we look to people who have answers (or at least tell us they have answers). But it’s not that they’re looking for a specific person; what they are looking for is:

• Consistency and predictability
• To be seen, heard, and understood
• Recognition
• Autonomy
• Information

By leaning into difficult conversations well, leaders can provide these skills and build the trust and safety in the workplace that employees are looking for.

What Are the 7 Key Organizational Moments When Leaders Need to Lean Into Difficult Conversations?

1. The Environment Has Changed – Whether it’s a budget shortfall, loss of funding, negative PR, some things are always going to be out of your control. Your employees know and can appreciate that. What they can’t excuse is when you stay silent and/or remain opaque on what’s going on. Transparency is increasingly valued by younger generations, so pretending nothing is wrong or trying to remain overly optimistic will have the opposite effect.
2. Poorly Handled Leaves of Absence – With increased leaves of absence due to mental health issues, family care issues, medical concerns, etc. (already stressful situations), making the process before, during, and after complicated can sour an employee’s experience.
3. Cultural Value Discrepancies – Have you ever had a leader who was outwardly discriminatory, used racial slurs, or bullied other employees? Have you ever seen that leader be promoted because they’re a high performer? This is already distressing, but what adds insult to injury is if you have organizational values of “respect” or “belonging.” Organizational values can often be a buzzword at times, but if you have them and behave in ways opposite to them, it’s deeply demoralizing and damages trust in leadership.
4. Performance Evaluations – This doesn’t just mean during your annual performance eval process. This means on a day-to-day basis, are you appropriately managing performance and holding people accountable? Or are you allowing certain behaviors to slide? As the saying goes, “What you permit, you promote.”
5. Structural Changes – Perhaps you need to go through a reorganization, a RIF, or a turnover in leadership. These periods inherently come with intense unease and anxiety about the future, and a lack of empathy or belittling/dismissing that anxiety can quickly erode trust in leadership.
6. Workplace Harassment – In a 2023 HR Acuity Study, they found that 52% of employees have experienced or witnessed inappropriate, unethical, or illegal behaviors at work (including bullying, sexual harassment, and/or racism). This means that vast amounts of workplace harassment go unreported, and retaliation, or the perception of it, only reduces the number of people willing to report it. Leaders must ensure open communication with employees to create a culture where reporting feels safe.
7. Turnover – Turnover is inevitable, but how you handle that transition period can make a difference. While you can’t keep everyone, ensuring people have a smooth exit can have them leaving on positive terms and have them still be a champion of your organization. On the other hand, handling it poorly or being actively hostile can create a voice in the public that’s signaling a poor work environment to future potential employees.

The Call for Leaders

Leaders have an incredible responsibility to communicate effectively. To make it easier for you, try to remember this: no one is expecting you to be perfect. Your employees may think they want perfection, but they deep down know you’re human, too. What they’re looking for is to know someone cares about them and is willing to be there for them. It’s up to you how you want to answer that call.