Succession planning is one of the most critical, and often misunderstood, aspects of running a successful business. In this candid conversation with Kevin Leahy, President & CEO of Connecticut Wealth Management (CTWM), we explore what business owners wish they knew earlier about timing, leadership, and preparing for the future.
Kevin shares why succession isn’t just about handing over the reins, but about envisioning where the business will be years from now, building the right team, and navigating the personal and financial complexities that come with transition. His insights offer a roadmap for business owners who want to set themselves and their companies up for long-term success.
Q: When it comes to succession or exit planning, what do you wish more business owners understood, especially around timing?
Most business owners only know a fraction of what’s involved, maybe 10 to 20%, because it’s not something most people have done before, or think about regularly. We’re focused on today or this week, not years from now. Even those who grew up in a family business or watched a transition happen might not realize how specific it is to those exiting and those taking over. Every business, leadership team, and family is different.
One of the biggest challenges is thinking too narrowly. We tend to evaluate the next generation or leader based on where the business is today, not where it will be when that person steps in. By then, the business could be dramatically larger or more complex, and the person you’re picturing today may not be the right fit for tomorrow.
And that’s just the business side. There’s also the personal and financial side: what it means for the founder or family, how the transition impacts wealth, values, and lifestyle. The technical stuff is usually manageable. It’s the emotional side, the personalities, and the unspoken expectations that make it tricky.
Q: How do you personally think about planning for your own future—your eventual transition?
Part of me still feels like I’ll be doing this forever. I love what I do, this business, and the people I work with.
But transitions happen, whether we want them to or not, so we’re “eating our own cooking” by building a leadership team that can carry things forward and gradually shifting responsibilities to those best suited for them.
Over time, I’ve learned where I truly add value and where I don’t. Instead of forcing myself into roles I’m not wired for, I place those responsibilities with people who excel in them. That’s better for the firm, for our clients, and for me.
While I hope to stay involved for a long time, especially in a strategic leadership role, planning ahead is part of the job. It’s a long runway, and we’re building it thoughtfully.
Q: If you could give one piece of advice to a business owner planning to exit in the next 5 to 10 years, what would it be?
Start by writing down what you want life to look like, personally and professionally, five years from now—and then again for ten years out. Where do you want to live? How will you spend your time? What role, if any, will you have in the business? What does the business itself look like? Who’s leading it? What are the financials? Who’s on the team?
Once you paint that picture, work backward to see what needs to happen between now and then. If you’re working 80 hours a week now but want to be at zero in five years, that’s a huge shift. Someone, or multiple people, will need to take over what you do today. You can’t just disappear without a plan.
The same goes for your personal life. If you want to spend more time at home, talk to your spouse about it. They may have their own full life and not be ready to rearrange it around your new schedule. We’ve seen plenty of situations where a partner says, “That sounds great for you, but I’m not giving up my routine for your retirement plan.”
And in your business, if you can’t openly share your vision with your leadership team, something’s off. Either you don’t have the right people, or you haven’t built enough trust—both of which need to change for a smooth transition.
Most people haven’t retired before, so it’s unfamiliar territory. You don’t know what you don’t know, which is why it helps to have a guide who can ask the right questions and hold up the mirror. Planning doesn’t guarantee perfection, but it makes a smooth landing far more likely.
Q: What would you tell your past self before becoming a business owner?
Learn how to lead and manage people.
I had no idea how important the people side of the business would be—or how little I understood it. Leading, motivating, managing…I came in with an empty toolbox of people skills. I’ve learned a lot since then, but I’m still learning every day.
No matter what kind of business you run, people are the common denominator. Success depends on whether your team is aligned, engaged, and working toward a shared vision. That’s true whether you’re running a financial firm, a manufacturing company, or anything in between.
We’re not just building systems or delivering services; we’re people serving people. Technical skills matter, but leadership is everything. If I had understood that earlier, I would have invested much more time upfront in becoming a better leader.
Q: When you think about how far CTWM has come, what stands out most about the journey?
Looking back at where we started, from a startup in 2010 to servicing well over 1,000 clients in 2025, our brand has grown as an outward reflection of the culture we built. People don’t just know us for strategy or technical acumen, but because of the culture and values we live by.
It’s exciting and a little scary to be part of something still growing and evolving. We don’t know exactly what it will look like years from now, but that’s part of the journey. We’re building it day by day, and for me that is incredibly fulfilling.
Wrapping Up
CTWM’s journey shows that a company’s true strength lies in its culture and the people who live its values every day. While the future may hold uncertainties, intentional planning, honest communication, and thoughtful leadership development create the foundation for lasting success. Preparing for transition isn’t just about business; it’s about preserving what matters most and building something even greater for the years ahead.
Interested in learning more about how we help business owners navigate growth, succession, and beyond? Contact us today!