The Right Team For The Next Level

Firing a legacy employee you like is never pleasant, but for CEOs who want to level up, it's often a necessity. Four questions to ask yourself to determine whether someone is right for your company's future.


What do you do when you think you’ve outgrown long-term, legacy members of your team? Those employees who were once key members of your band of misfits, who helped you scrap and claw your way from startup to success. Do they fit in now that you’re professionalizing your team and adding key leaders who’ve done this before? How do you know if you’ve simply made a bad hire?

Most entrepreneurs hire reactively. It may work for some of you, but for the vast majority of us, that’s how we end up with people problems. I think there are at least three important things you can do at this stage of growth to build a great team. Before you even begin recruiting, you should: (1) know where your company’s headed; (2) know the key initiatives that will drive that growth; and (3) assess your existing team against those initiatives.

Where do you want your business to be in three to five years? Your vision for the company will impact your team’s hiring needs. Let’s say you’re planning to grow revenue from $10 to $25 million in the next two to three years; how do you plan to do that? Maybe you’re going to open a new office, launch a new product, or buy a competitor. Your answer to that question will help determine the talent you’ll need to achieve your goals. For example, if you’re going to triple revenue by simply selling more, you’ll likely need an experienced sales leader to build the infrastructure to scale that department.

No one has a crystal ball, and this isn’t a lesson in predicting the future, but you should have an idea that’s directionally accurate. If you don’t, you’ll be continually frustrated on the hiring front. Like Yogi Berra said, “If you don’t know where you’re going, you might wind up someplace else.”

This is honestly some of the hardest stuff I cover with clients. Even in my own story, I’ve had trouble identifying which team members were diamonds in the rough and which were just…rough. It’s not easy—especially when it comes to legacy employees you’ve come to know and love from your time together in the trenches.

I learned that there’s no way to just “know” who will make it long term. You can lose a ton of sleep over it, but you’re probably not going to wake up one morning and know that Mike is the weakest link, for example.

But in my nearly three decades working with high-growth, entrepreneurial companies, I’ve developed a few key questions you can ask yourself to identify the key players and the weak links on your team. It’s not an exact science (nothing ever is), but this will help you validate your gut feeling or provide some clarity. These questions originated with middle-market gurus like Gino Wickman, Verne Harnish, Jim Collins, and Brad Smart (among others), and they’ve been honed in hundreds of HireBetter client sessions over the years. They work.

As you read these questions, think about each member of your team: legacy employees, new hires—it doesn’t really matter. When you start assessing your team based on these simple questions—and answer them honestly—you’ll gain clarity.

1. Knowing today what you know about your organization and where you’re going, would you enthusiastically rehire this person for his current role?

I believe this is the single most important question you can ask yourself about every member of the team. Think about how this question can inform your decision-making moving forward. And remember that even if the answer isn’t, “Yes! I would enthusiastically re-hire her as my CFO!” it doesn’t mean you need to fire her. She just might not be the strategic CFO you need for this next stage of growth.

#2 Does  this person have the skills, experience, and tools to get us to the next level, however we choose to define that?

This one’s a little more nuanced than #1. Your employee may have the passion and skills, but does he have the experience required to get you there? If not, you may want to pair him with a coach or advisor who has that experience. Otherwise, the road to where you’re going is going to be filled with a lot of potholes.

#3 What if I had a team of this employee? How strong would we be?

This question can help you check your gut, since it’s a hypothetical exercise and will evoke an emotional reaction. If you get a sinking feeling thinking about that team, it’s a pretty good indicator for how you feel about the employee.

#4 What if this person came into my office and quit tomorrow morning. How would I feel?

Another good, gut feeling question. If reading that question made you panic and start thinking about ways to stop him from quitting, that may be your answer. However, don’t confuse a short-term pain in the ass with the right longer-term answer. If you’re anything like me, you hate the thought of dealing with any employee turnover.

But if someone does need to go then it’s time to put your big-boy or big-girl pants on. Terminating someone isn’t pleasant. No one likes to do it. But it’s not something you can outsource, and you definitely can’t hide from it. Tackle the problem head-on. Whatever you do, don’t sit idle. If you let the situation go on too long, your company could suffer. Don’t worry about hurt feelings or difficult conversations. You’re making your business stronger— and your team will probably ask, “What took you so long?”

Again, firing someone, especially a legacy employee you actually like, is not pleasant. Just remember: you’re making the best decision you can for your company.

Excerpted with permission from the forthcoming Who’s Your Mike? A No-Bullshit Guide to the People You’ll Meet on Your Entrepreneurial Journey (Per Capita Publishing, August 2022).


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