Real Leaders

How to Handle Founding Staff Once Your Startup Has Grown

Startups usually don’t have a lot—of money, resources, time—really much of anything. Most of the time, the founder has a great idea and a couple of friends or associates to help figure out how to move that idea toward reality.

The “team” consists of whomever the founder has nearby: a ragtag bunch that can be trusted to at least try and figure things out. Since there’s usually not much money, whatever problems arise, whatever needs to get done, you and your team have to figure it out on a shoestring. You have no choice.

When your startup gains traction and looks like it might make it, it’s usually the direct result of the heroic efforts of these early team members. With few exceptions, there’s usually a tireless jack-(or jill)-of-all-trades who knows a little about everything. But more importantly, they’ve got a figure-it-out mentality and they’re willing to learn and scrap and claw to get it done.

Meet Bounce-Around Betty. She’s been there since day one, she’s an amazing person, and she’s willing to do whatever it takes to get things done. You need someone to tackle creating your startup’s logo and your first set of business cards? She’s on it. There’s a problem with the supply chain? Betty will be on the first flight out tomorrow morning. Need to figure out the witchcraft that is Google Analytics or advertising on Facebook? She’ll dive in and learn the digital marketing basics to get you started. Whenever you need something challenging done, Betty jumps right in, headfirst, without knowing whether she’ll sink or swim.

In most cases, Betty can still be a great employee for your growing company, assuming she doesn’t lose that drive, that eagerness to learn, and that willingness to do whatever it takes that made her your go-to employee early on. But problems occur when we either promote Betty beyond her capacity or her role is so ambiguous as the company grows, that it causes confusion and problems with the rest of the team. 

Having a Betty on your team is a critical part of your early success . . . until it isn’t. There’s no hard-and-fast rule that says, “Two years in, you need to replace your generalists with specialists!” or “Once you’ve hit $1 million in revenue, bring in a COO!” It all depends on your company, your growth, and your vision—as well as your Betty’s skill set, emotional intelligence, and career goals. There’s a lot of moving parts here, and there’s no one-size-fits-all solution. Definitely more art than science!

Adding experience gives you the opportunity to start professionalizing your team, putting pieces in place for future growth. You’re confident that Bounce-Around Betty will always figure things out—but what if your team didn’t have to “figure it out” and already knew what to do? Betty was great on the phone with early customers, but she’s not the right person to design and build the customer service engine, including processes, tools, and the team you need for future growth.

In most cases, Betty’s a good employee who doesn’t need to leave just because you need more specialists. She’s a valuable member of the team and can continue adding value if she’s in the right role. Much of what happens with Betty will depend on how you approach the situation. As usual, it also depends on the personalities, expectations, and egos involved. If you demote Betty to assistant to the new VP of Sales without giving her a heads-up—yeah, that’ll piss her off. But do it right, and you can put Betty AND your company in a great position to succeed.

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Identify the role that plays best to Betty’s strengths and allows her to grow professionally, but also fuels the company’s growth goals. That’s easier said than done and may require some soul-searching and tough conversations.

If your relationship with Betty has a foundation of trust and open communication, you should be able to approach her and discuss the situation. Be honest with her. Her knack for figuring things out has been a great asset, but a different skill set is needed now. You need leaders who have skins on the wall. Sure, you want to help develop her skills so she can grow professionally — AND you need her to help position the company to achieve its goals.

If you find yourself struggling with situations like this, consider bringing in another set of eyes. Have your mentor or coach assess your Betty situation and give you their perspective. This helps to remove your personal feelings from the equation.

Remember, your goal isn’t to promote Betty until she fails miserably. You want to do what’s best for the company and ideally find the right spot for her to grow. This balance can be tricky, but with the right approach and the right Betty, it can be done! 

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