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Building the Billion Dollar Business podcast with Ray Sclafani

Episode #127

Do You Know Your People?

Building the Billion Dollar Business with RAY SCLAFANI

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Executive Summary

Followership Starts in Your One-on-Ones

As review season begins, Ray Sclafani, Founder and CEO of ClientWise, asks firm leaders to evaluate themselves before they evaluate anyone else. Ray defines followership as three beliefs your team holds: they believe in your vision, they believe you are committed to their development, and they believe you have their best interests in mind. He shares a six-question self-check that shows whether your one-on-ones are building real connection or just collecting status updates. Leaders who know their people develop stronger teams, keep top talent longer, and build the kind of firm that grows enterprise value well beyond the founder.

Key Takeaways

1

Your title gives you authority, but it does not give you followership. Followership is earned one conversation at a time.

2

Followership comes down to three beliefs. Your team believes in your vision, believes you are committed to their development, and believes you have their best interests in mind.

3

One-on-ones are where followership shows up. SHRM research finds employees who meet regularly with their manager are three times more likely to be engaged, yet Steven Rogelberg found roughly half of these meetings fall short of what they could be.

4

Career development is a retention issue. McKinsey found that a lack of career development and advancement was the number one reason people gave for leaving their last job, at 41%.

5

Run the six-question self-check for each person who reports to you. If you can't answer a question without guessing, that becomes the agenda for your next one-on-one.

6

When a team member asks to pursue school, coaching, or a program, help them go for it. They are telling you who they want to become.

Transcript

Well, we've just turned the corner into the final stretch of 2026, and if your calendar looks anything like mine, you know what that means. Performance review season is here. This is the time of year when teams start putting the final touches in place to hit the aspirational plan we all set back in January. Forecasts get tightened. Priorities get trimmed. Everybody's moving fast. But before you sit down to evaluate anyone else this quarter, I want you to do something first. Take a quick check-in with yourself, because the questions I'm going to walk you through today, and more importantly your honest answers to them, will reveal a lot about your followership.

Now, what's followership, you may ask? Back in 1988, Robert Kelley wrote a piece in Harvard Business Review titled "In Praise of Followers." His point was simple. We spend all of our time studying leaders and almost none studying the people who choose to follow them. And it is a choice. Korn Ferry put it plainly: leadership requires followership. To create it, they say, you must meet people where they are.

So here's how I define it for this conversation. Followership is whether the people you're responsible for leading believe three things. They believe in your vision. They believe you're committed to their development. And they believe you have their best interests in mind. Your title gives you authority. It does not give you followership. That you earn one conversation at a time.

Why does it matter? The best place to see whether you've earned it is in your one-on-ones. Here's what the research says. According to SHRM, the Society for Human Resource Management, employees who meet regularly with their manager one-on-one are three times more likely to be engaged at work. And 86% of highly engaged companies hold regular one-on-ones, compared with only half of disengaged companies.

But just holding the meeting is not enough. Steven Rogelberg, who studies one-on-ones and has written about them for Harvard Business Review, found that roughly half of these meetings aren't rated as good as they could be. In fact, in his research he couldn't find a single organization that trains its managers on how to run one.

Why should that worry you heading into review season? McKinsey found that the number one reason people gave for quitting their last job was a lack of career development and advancement, at 41%.

So let me ask you directly. How are your one-on-ones going? Are your team members showing up energized and prepared when they meet with you? Or are they showing up just to give you a status update and get right back to work?

Here's your self-check. Think about each person who reports to you, one at a time. Not the whole team. Each person. Ask yourself whether you can answer the following six questions without guessing.

One: When their week goes really well, what happens? And when a week wears them down, what's usually behind it?

Two: Do they know what kind of support they need from you right now, and have they actually asked for it?

Three: When they do something really great and hit it out of the park, how do they want you to notice? In front of the whole team, or in a quiet note? And when something misses the mark, how do they want to hear about it?

Four: Where do they want to be in the next two to three years? What skills, competencies, and experiences stand between where they are today and where they want to go?

Five: What matters to them outside of work right now? A move, a child starting school, a parent who needs care, or maybe a marathon they're training for.

Six: Have they completed their own professional development plan? Not the one HR might file away. A real one, in their own words. And have you read it and discussed it with them?

If you can answer all six for everyone you lead, you're genuinely tuned in. If you're blanking on a name or two, that's not a character flaw. That's your next one-on-one. And if you couldn't answer most of them, the relationship is running on assumptions, and people can feel the difference between being managed and being known.

Let me share a quick personal story with you. Early in my career, I made a commitment. Every year I would invest in myself: a course, a certification, a coach, something. Then I reached the executive level, and I had this gut feeling that I needed to go back to school and get my MBA. I wanted some credibility for my leadership role. I felt I hadn't been trained for what I was responsible for.

I brought it up with my boss at the time, and he told me flat out it wouldn't be useful. He didn't ask a single question. There was no curiosity, just a quick and short answer. "Don't waste your time, Ray." I was already leading more than a couple of hundred people and running a large business, he said. What would a classroom teach me that I wasn't already learning? So I didn't go, and I've always regretted not getting that education.

I suppose I learned on the job. And to be fair, McKinsey's research indicates that somewhere between 40 and 60% of a person's skills come from work experience. So on-the-job learning is real. But here's what that moment really taught me. When someone on your team comes to you and says, "I want to go back to school, I want a coach, I want to take this program," your job isn't to talk them out of it. It's to help them go for it. They're not just asking for permission. They're telling you who they want to become.

That's why I believe part of being a great leader is studying your team members the way you'd study a market, a competitor, or a P&L. How do they learn? Do they read? Do they watch? Do they have to roll up their sleeves and get into it? What are their real strengths? Not just what's on their resume, but what do they do better than anyone else on the team? What gives them energy, and what quietly drains them, even if they never say so out loud? When you know these things, your one-on-ones change. They stop being status updates and become the place where development actually happens.

As we wrap up, I want to leave you with the hardest question on the list. It's the one that's about you, not them. What is the one thing you, or maybe your organization, do that makes their job harder than it needs to be? Maybe it's a meeting that should be an email. Maybe it's an approval that sits on your desk for a week. Maybe it's canceling their one-on-one every time something comes up. Whatever it is, they already know. The question is whether you do too.

With each episode, we leave you with a few coaching questions, and today there are two. First, what part of today's episode made you pause and think about the people you lead? Second, what do you need to know about your team that would help you support them more effectively in achieving their career goals? Write your answers down before your next one-on-one. Then go find out.

Thanks for listening to Building the Billion Dollar Business. If this episode made you think of someone, whether a peer, a new manager, or maybe even your own boss, please like and share it with someone who needs to hear it.

Questions Financial Advisory Firm Leaders and Team Members Often Ask

What is followership in leadership?

Followership is whether the people you lead believe three things: they believe in your vision, they believe you are committed to their development, and they believe you have their best interests in mind. Ray Sclafani notes that a title gives you authority but not followership. Followership is earned one conversation at a time.

Why do one-on-one meetings matter for team engagement?

According to SHRM, employees who meet regularly one-on-one with their manager are three times more likely to be engaged at work. SHRM also found that 86% of highly engaged companies hold regular one-on-ones, compared with only half of disengaged companies. Holding the meeting is not enough, though; the quality of the conversation matters.

What questions should a leader be able to answer about each team member?

Ray offers six. What makes their week go well or wears them down; what support they need and whether they have asked for it; how they want to be recognized and how they want to hear feedback; where they want to be in two to three years and what stands in the way; what matters to them outside of work; and whether they have a professional development plan you have read and discussed.

How should a leader respond when a team member asks to pursue more education or coaching?

Ray's view is that the leader's job is to help them go for it, not talk them out of it. A request like this is more than asking permission. The team member is telling you who they want to become.

How can leaders prepare for performance reviews?
Ray recommends starting with a self-check before evaluating anyone else. Work through the six questions for each person who reports to you, one at a time. Then ask the hardest question: what is one thing you or your organization does that makes their job harder than it needs to be?

Build a Team That Chooses to Follow

The strongest firms are led by people who know their team and invest in their growth. ClientWise coaches partner with firm leaders to strengthen one-on-ones, develop next generation leaders, and build a culture where top talent wants to stay. Together, we'll design the leadership habits your next stage of growth requires.

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