The 3 Conversations Every Business Owner Should Have Before Year-End
I always heard that time speeds up the older you get, and I’m finding that to be true. At least it feels true. I’m 57 years old as I write this, and time seems to move much faster for me now than it used to.
When I was a kid, the span between Thanksgiving and Christmas felt like an eternity. The anticipation of all the cool toys I hoped would show up under the tree probably had something to do with it. Maybe you experienced something similar.
As an adult, the anticipation is different. I still enjoy the season, but I don’t experience time the same way I used to. Now, the stretch from early November to New Year’s? Blink, and it’s gone.
As leaders, we all have our own “Christmas list”—a set of things we hoped to accomplish by year-end. And because time speeds up on us, those things have a way of lingering undone. So whatever’s on your list, now is the time to start checking boxes. December 31 will be here before we know it!
With that in mind, here are three conversations every business owner should have before year-end.
1. The Delegation & Capacity Conversation
Many business owners are chronically overwhelmed. Dave Ramsey puts it well:
“If you’re doing everything yourself, you don’t own a business—you own a treadmill.”
You’re answering every email, handling every customer, making every decision. You’re exhausted, barely keeping up, and wondering why the business isn’t growing.
The only way off the treadmill is to shift from operator to leader.
That shift starts with an honest look at capacity—your capacity. If this is resonating with you, it’s almost certainly because you’re trying to do too much. Why?
It’s usually either a trust issue or a control issue.
Maybe you don’t feel you can trust your team with certain responsibilities. But why not? Chances are you already have the right people—you just may need to equip them better so they can step up.
Or maybe you have a capable, committed team, but you’re not comfortable taking your hands off the wheel and letting them drive.
And here’s the good news: you’re the problem.
Not what you were expecting, I know. But if you’re the problem, you’re also the solution. You can fix this—by training and developing your team, or by working on the control issues that keep you doing everything yourself.
Have an honest conversation, first with yourself and then with your team, about what’s preventing you from sharing responsibility. Chances are your team is already feeling some frustration from bottlenecks you didn’t mean to cause.
Invite their feedback. More importantly, act on it. Demonstrate good faith by implementing some of their suggestions on how to extend trust, increase shared responsibility, and streamline operations. You’ll help everyone start the new year less frantic and more effective.
2. The Team Performance & Leadership Fitness Conversation
Not all businesses and teams are structured the same. Some have a single owner and a handful of team members. Others have multiple locations or departments, each with its own team leader. At that point, you’ve added middle managers to your organization—and that means you have another leadership conversation to have before year-end.
Adding layers of leadership is a sign of growth, but it also adds complexity. You’re now responsible not only for your direct reports, but for ensuring those leaders are guiding their teams well.
Simon Sinek says, “Most things break in the middle.” He’s right. When there’s a breakdown between your vision and front-line execution, the results can be disastrous.
Think of yourself as the architect. You drew the blueprint of what you want your company to build. But if the front-line builders don’t follow the plan, the structure won’t turn out right—and your middle managers are the ones directing those builders every day.
So as the year ends, schedule a conversation with your middle managers to ensure they understand the vision and are leading in ways that support it. How will you know they get it? By asking great questions. As John Maxwell says, “Good leaders ask great questions.”
Here are a few to get you started:
Are our teams healthy or strained?
Is our leadership team aligned and equipped with the tools we need?
Where are the breakdowns—communication, accountability, clarity, trust?
How do we need to strengthen our leaders before adding new responsibilities or growth goals?
Evaluating the health of your leadership team is essential to preparing your company for its next chapter. Get this meeting on the calendar now so you begin the new year aligned and focused.
3. The Leadership Reset Conversation
We’ve all been there. Leading people is a high and noble calling, but it can be exhausting. It takes energy to be “on” for your team all the time. It wears on you—physically, mentally, and emotionally. Sometimes you just need a reset.
The third conversation you need to have before year-end isn’t with anyone on your team. It’s with a coach.
Wouldn’t it be nice to stop the merry-go-round long enough to take a breath and get clarity? A coach gives you something you can’t give yourself: an outside perspective.
You know your business better than anyone. That’s exactly why you sometimes need someone who doesn’t. When you’re deep in the day-to-day, it’s hard to see the bigger patterns—the habits that drain your energy, the communication gaps you didn’t realize you’d created, the places where control has begun to replace trust.
A reset conversation helps you:
Rebalance your workload
Identify what’s energizing you—or draining you
Strengthen your communication
Set better boundaries
Renew your confidence
Reconnect with the leader you want to be
If you need to realign your priorities, rebuild healthy habits, or regain the mental margin to lead well, press the reset button with a coaching conversation—even better, a series of them—so you can step into the new year with clarity and confidence.
The end of the year will be here before you know it. Trust me, I’m an old guy, and I know how these things work! Have these three conversations now so you can close out the year strong and step into the next one with focus, energy, and momentum.
