Before You Have the Difficult Conversation

I've had plenty of conversations with business owners who are frustrated with an employee.

They don't like how the employee communicates, approaches a task, or handles certain responsibilities. They know something needs to change, and they're preparing to have a difficult conversation.

But when I ask what specifically they want the employee to do differently, the answer isn't always clear.

That's where I think the work needs to begin.

What needs to change, and what outcome would that change improve?

Sometimes there's a legitimate performance issue. Other times, the employee is getting the results the owner wants, just not in the way the owner prefers.

Owners have every right to establish expectations. But they also have a responsibility to understand the environment their employees are working in.

Owners and managers often know what needs to get done and believe the priorities are obvious.

But employees may be balancing priorities and requests the owner doesn't see: unexpected problems, interruptions, and competing demands from people throughout the organization.

What seems straightforward to the owner may be anything but straightforward to the employee.

And sometimes the owner is unknowingly contributing to the problem.

Think about how differently an owner and an employee might remember the same conversation.

An owner has conversations throughout the day, making decisions, shifting priorities, and moving on to the next issue. An employee may hold on to every word of a conversation with that owner, particularly when it involves their responsibilities.

The owner might forget the conversation ten minutes later. The employee may still be operating under those instructions weeks later.

I've also had to recognize that something I considered a passing comment could carry more weight with an employee than I intended.

Now consider what happens when the owner changes priorities without clearly communicating what's changed. The employee continues working toward what they understood to be important, only to discover that the owner's expectations have shifted.

The owner sees a performance problem. The employee believes they're doing exactly what was asked.

There's a famous line from Cool Hand Luke: “What we've got here is failure to communicate.”

The Captain isn't inviting a conversation. He expects obedience, and the failure, in his view, belongs entirely to the person who won't comply.

In business, we can fall into our own version of that thinking: I gave the instructions. If something went wrong, the employee must not have listened.

But before reaching that conclusion, why not ask a simple question?

“In your opinion, what are our top three priorities, in order?”

The answer might reveal a misunderstanding. It might also reveal that the owner has been sending conflicting messages.

That's why I believe a difficult conversation should begin with a clear concern and a genuine willingness to listen.

I don't believe in a one-size-fits-all approach to managing people. Different employees respond to different styles of communication. But everyone deserves to understand what's expected and have an opportunity to share their perspective.

That doesn't mean accepting excuses or avoiding accountability.

The manager's responsibility is to make expectations clear, provide the necessary support, and resolve conflicting priorities. The employee's responsibility is to meet those expectations and speak up when something gets in the way.

A successful difficult conversation doesn't necessarily end with everyone agreeing.

It ends with a clear understanding of what needs to happen next, who's responsible, and what success looks like.

If the same problems continue, accountability needs to follow. If new obstacles emerge, address them and keep improving.

Difficult conversations are sometimes necessary. But before having one, I'd encourage every owner and manager to ask themselves:

Have I done my part to help this employee succeed, and am I willing to hear how I might be contributing to the problem?