Thriving organizations don’t fear difficult conversations

“Supervisors often intervene far too late in challenges caused by individual employees in the workplace.”

This was the comment made by the CEO of a highly successful company to their supervisory team during a coaching session where we were discussing the challenges of leadership.

And it’s true. Postponing a difficult conversation is human, and supervisors often have understandable reasons for doing so, such as:

1. The individual delivers strong results, and addressing the issue might negatively impact performance.

2. The matter has been raised before, and real change doesn’t seem likely, so the situation is tolerated, one way or another.

3. The other person is unlikely to take the feedback well and will probably react defensively or emotionally

4. The conversation is expected to be lengthy, and there are currently more urgent priorities to handle.

5. Addressing disruptive behavior or working methods feels unpleasant, and it seems possible to postpone it until the next performance review without major consequences.

6. There’s a doubt: are things really the way they seem? Or is there a deeper issue behind the problem that must first be understood?

The word feedback is emotionally charged in many ways. It often creates an imbalance between the person giving it and the person receiving it. The one in a higher position “knows the truth” and delivers it—good or bad, in private or in public. The one in a lower position is left to either kiss up or protest.

In an ideal workplace, conversations, also the difficult ones, can take place openly and without delay, regardless of the roles or hierarchy involved. A culture of open dialogue is built in a community where learning, asking questions, and listening are valued, rather than one where decisions, problems, achievements, new directions, and other important matters are simply just announced. In such organizations, leadership has its finger on the pulse. They know what’s really going on, and the entire organization works toward shared goals in a coordinated way. Most people genuinely want to participate and do meaningful work.

To truly stay in tune with the pulse of the organization, difficult conversations must not be pushed into the future. The threshold for honest dialogue lowers when I admit my own fallibility. Even when I’m fairly confident in my point of view, I remain open to asking, listening, and reevaluating. Instead of only giving feedback, I’m willing to have a conversation. Good decisions become easier to make when I’ve explored the issue from multiple perspectives.

Throughout my coaching career, I’ve witnessed the life transitions of hundreds of people who’ve been laid off. Losing one’s job against their will is often a moment of crisis, stirring deep emotion. In the midst of that crisis, few people see the potential upside, though it often emerges later, with time. After layoff discussions, people almost always ask: “Why me?”, but they rarely get an answer. Instead, they must come up with one on their own. My advice? Choose an answer that gives you strength and encourages you to look forward.

As an external coach, the positive sides of change, and the new possibilities ahead, are often visible to me right away. Sometimes a person struggles for years in a role that doesn’t suit them, even though a better fit, something more aligned with their values - something that makes them smile on Monday mornings - might be just around the corner.