A wake-up call for leaders

I’m tired of hearing leaders avoid the conversations they know they need to have. I’ve made the same mistake myself—a mistake that cost someone five years of their career.

It's time for leaders to wake up.

Look, I enjoy writing these weekly articles because, more than anything, my favorite part of being a leader and CEO is the people side of business. I love challenging people to think bigger, achieve more, and become the best version of themselves, both personally and professionally.

This is my opportunity each Sunday to challenge and inspire nearly 3,000 leaders across professional services and beyond. Pretty cool...

While most of my articles are meant to educate, provide alternative perspectives, and drive new ways of thinking... today is going to be different.

Frankly, I'm growing tired of hearing about leaders who are avoiding the direct, difficult conversations they know need to be had within their organizations.

• “He’s only got a few more years left; let’s be nice.”

• “If I push, it could hurt the culture.”

• “Maybe I can help her get there if I invest more of my own time.”

The reality is that while you try to protect someone’s feelings at the expense of what the firm needs, you are absolutely defining your culture—just not in the way you likely intend. Do you really want to define a culture that tolerates underperformance, avoids straight talk, and allows strategic priorities to take a backseat to personal comfort?

Your ultimate allegiance is to the organization and the collective team, pushing the organization toward where it needs to go. If someone is inhibiting that effort and progress, that's a problem. And it needs to be addressed for the sake of the organization and the person.

A personal story...

I get so passionate about this topic of having difficult conversations because I have a personal story of regret. I wasted years of someone’s professional life because I was afraid to have a difficult conversation.

I’ve talked about the role of the CEO being to help people become the best version of themselves they can be. Sometimes that means teaching people, challenging them, encouraging them, inspiring them, etc.

And sometimes that means having difficult conversations to deliver feedback to help them grow and evolve. Early on in my career in leadership, I struggled with this, and that meant I often delayed having these difficult conversations.

In one particular case, I wasted 5 years of someone’s professional life.

I knew this leader wasn't right for the organization. They saw things differently and weren't bought into the vision of where the firm was headed. Talented person, but misaligned. That reality was affecting their individual performance and their willingness to collaborate, which therefore affected the greater success of the organization.

Instead of having the difficult conversation that would have provided the person the opportunity to grow professionally and personally—which was definitely to counsel them out of the organization so they could find a better fit—I delayed it.

"Maybe a new role will spark something in them."
"Maybe more development will help."
"Maybe if I give them another 6 months, they will figure it out."

So I didn't do anything. I waited...and waited... and waited... until 5 years had gone by. 5 years of knowing something needed to happen, but being afraid of having the difficult conversation. 5 years of time where that individual could have found an organization to develop and thrive in.

Ultimately, we ended up coming to a resolution with that individual, but 5 years too late. And I regret it to this day. It still haunts me because it wasn't fair to the organization, and, more importantly, it wasn't fair to them.

The value of the hard conversations

I’m seeing leaders I work with continue to struggle with having these same types of difficult conversations. I get it. They are hard. I mean, they’re called difficult conversations for a reason…

Think about it, though… if you’re really here to empower people to be the best version of themselves, don’t you think having a hard conversation can help someone get there?

I do. Because I’ve seen it happen countless times.

It’s often the hard conversations that illuminate people’s blind spots and shortcomings. And although it may hurt in the short term, it allows people to grow.

The more of these I’ve had, the easier they get because I have more evidence that these conversations are ultimately in the person’s best interest. As a leader, don’t make the same mistake I did by waiting. Don’t waste someone's limited number of professional years.

We owe it to our people to have the difficult conversations because avoiding them can be incredibly costly to someone's development and the organization's potential success. Just like great performance and alignment compound over time, so does underperformance and misalignment.

Allegiance isn’t an either/or

Some leaders say, “I don’t want to be a jerk. I care about the people here.”

Good. You should! But allegiance to the firm doesn’t mean abandoning humanity—those two things don't have to be mutually exclusive.

You can be gracious to the individual AND intentional about what the organization needs. You can have empathy AND hold people accountable at the same time.

What you can’t do is let avoidance masquerade as kindness. Avoiding the conversation robs people of the chance to improve and keeps the firm from moving forward.

So here’s my challenge:

Think about a difficult conversation you know you need to have. How do you know when you need to have one? Because you can feel it, I guarantee it. And you've likely felt it for a while.

Are you allowing your desire to be nice, protect culture, or protect the person to delay the conversation you know needs to be had?

Remember: Culture isn’t built by avoiding discomfort; it’s built by how you handle it. If you want a firm that performs at its highest level, choose the conversation you’ve been avoiding. Do it with grace. Do it with intention. But do it — because the strategy, the culture, and the future of your firm (and the person's professional career) depend on it.

Pick one conversation you’ve been avoiding and schedule it this week.

With intention,
Alan D Whitman