Dear Leaders

A weekly letter with actionable leadership ideas.

Leading Through Tough Conversations

By Hamza Shayk

Dear Leaders,

As a senior executive, there’s no skirting around it: you will need to have tough conversations.

From delivering feedback on subpar performance to discussing company changes that might not be popular, these discussions are unavoidable. More often than not, executives sidestep them, fearing potential repercussions. But doing so often leads to deeper complications than merely facing the conversation head-on.

The High Cost of Silence

There’s a simple equation in business that’s often ignored: avoidance equates to compound interest. By avoiding a challenging conversation today, you’re allowing issues to grow, often at exponential rates. Small problems become departmental breakdowns. Minor misunderstandings escalate into major misalignments. Essentially, avoiding a ten-minute talk now could lead to a month-long crisis later.

Why Dive In?

Facing tough conversations offers clarity and alignment. It ensures everyone is on the same page and working towards the same goal. More than that, it showcases leadership. It reflects a leader’s commitment to proactive problem-solving, growth, and the betterment of both individuals and the organization.

Before the Talk

Before diving into the conversation, there’s groundwork to be done.

1. Emotional autonomy. There’s a distinction between being empathetic and being emotional. Emotion can cloud judgment. Empathy helps understanding. Before the conversation, take a moment to detach from your emotions regarding the issue. Don’t approach the conversation with personal biases or preconceived solutions.

2. Anticipate reactions. People rarely react the way you expect them to. Play out the conversation in your mind, considering potential responses. This mental exercise will equip you to remain balanced, even if the conversation takes an unexpected turn.

During the Conversation

Traditional advice would tell you to “be direct” and “state facts.” Here’s what they don’t tell you:

1. Listen to the silences. When confronted with a challenging topic, people often communicate more through their silence than their words. What they choose not to say sometimes gives deeper insight than their actual words.

2. No exit strategy. In today’s era of open-floor offices, it’s easy to have these conversations in passing or on the go. Resist that urge. Choose a space where neither of you can easily exit, ensuring that the conversation reaches its necessary conclusion.

3. The subtlety of blame. Pointing fingers is an age-old no-no. However, executives often unconsciously assign blame using subtle language, leading to defensive reactions. Instead of saying, “You missed the target,” phrase it as “The target was missed.” It’s not about being passive; it’s about being accurate without being accusatory.

After the Dust Settles

 Once the conversation is over, the real work begins. Here’s how to proceed:

1. Monitor non-verbal cues. Over the next days or weeks, pay close attention to the individual’s behavior, especially non-verbal cues. This will help you gauge the true impact of the conversation and whether any underlying issues remain.

2. No broadcasts. Maintain the confidentiality of the conversation. Water-cooler talk can damage trust irreparably. Ensure the individual knows that their concerns and challenges will remain private.

3. Revisit, but don’t nag. Schedule a time to revisit the topic, ensuring there’s follow-through on both ends. But don’t continuously bring it up. Trust them to make the necessary changes.

In Conclusion

Tough conversations aren’t just a requirement; they’re an art. They demand a balance of assertiveness and empathy, of clarity and openness. While the road might seem treacherous, the other side often holds the keys to growth, innovation, and deeper alignment.

Here’s a rule of thumb: If a conversation is hard, it’s probably the one worth having.

As a senior executive, it’s not just your job to have these conversations, it’s your responsibility to master them. So, the next time you find yourself avoiding that talk, remember that leadership isn’t just about guiding teams to success but navigating them through challenges as well.

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