What an Old Gumball Machine Can Teach You About How to Hire “A-Players.


Guest Blogger Chelsie Lee is the Co-founder and CEO of SHIPSI,

They always say that your first few hires can make or break your business. 


In my opinion, any hire you make in a key area can make or break your business.


That’s why it’s SO CRITICAL to have a process for vetting people before and after the hire, to make sure you have the right people on the bus. 


But obviously, it’s really, really hard to do that consistently. 


I was thinking about this the other day, as I walked past an old gumball machine.


Because here’s the thing: SHIPSI has made some exceptional hires over the years.


But our hiring has been far from perfect.


Every time we hire someone, it feels like a really, really expensive version of putting a quarter into an old gumball machine.


I have NO IDEA what flavor I’m going to get.

Maybe I’ll get an amazing gumball that ends up being everything I wanted and more. Maybe I’ll get a colorless one that doesn’t really taste like anything and just takes up space. Or maybe I’ll get a gross, crusty one that leaves a bad taste in my mouth for a long time.


It’s incredibly hard to tell which flavor someone’s going to be, before they join your team. 


But after hiring a few A-Players, here’s the big thing I’ve realized about finding them:


To find someone with skill, grit, and relentless drive—you HAVE to take a chance on people you’re unsure about. Just like when you put a quarter in that gumball machine. 


You have to put your money in, turn the crank, and see what comes out. 


So obviously the million-dollar question is this:


HOW do you vet enough people to find these A-Players, when you needed someone yesterday and each failed hire is so expensive?


The trick is this:


You have to QUICKLY and EFFECTIVELY see what kind of person you’re dealing with. 


You have to be able to tell what gumball just popped out of the machine, without investing too much into a bad one. 


Here’s how we at SHIPSI have found our top talent:


1. Hire slow, fire fast. 


You may have heard this old adage before. But if you’re having trouble finding the right people, I doubt you’ve actually been following it.


I can’t tell you how many people I’ve heard say, “We’re planning to hire slow, fire fast.” 


Know what I saw them doing 2 months later?

You guessed it. Hiring fast, firing slow. 


I get it. I’m guilty of it too. Because most of the time, it would be so much easier if they just worked out, right?


So we say, “Let’s give them a couple more chances to be who we were hoping they’d be.”


Or, “We need someone and they’re good enough for now I guess.”


Sure. That’s fine. But stop acting like you’re hiring slow and firing fast, because you’re not. 


These days, here’s how we do it at SHIPSI: 


Once someone shows us they’re not who we need them to be, we cut ties. End of story. 


If a couple of my key team members are consistently not getting what they need out of a hire, even after the expectations have been clearly laid out, they’re gone. 


If they’re not delivering the key results we need them to deliver, and they’re not showing signs of improving, they’re gone. 


If someone is clearly not a cultural fit, they’re gone.


There are too many great people out there who can transform your business right now

So stop chomping on that old crusty gumball and pony up another quarter already. 


(An important caveat here: Don’t bring a bad breakup into your relationship with the next employee. Your bad experience with a past employee shouldn’t lead you to create assumptions about the next person. It’s not fair if your self-fulfilling prophecy causes them to lose before they even start.) 


2. Don’t assume anyone is out of your league.


I recently made a hire that was WAY out of my league. 


I had initially offered this person a project, because I didn’t think I could afford him. 

He turned that project down. 


But it wasn’t because he didn’t believe in us. In fact, he turned down the project because he wanted to come on full time.


He believed so much in the vision of the company that he was willing to help build something special. 


And while it’s early, I firmly believe this hire will have the largest impact on our business of any hire I’ve ever made.


Your goal should be to hire people at each key position who are way smarter than you.


When it comes to that top “out of your league” talent,  make sure you’re asking. 


Because it never hurts to ask.


3. Use your network.


Putting out a job application will get you a ton of leads. But the best hires often come through backdoor connections. 


Ask your colleagues if they know anyone who would be a great fit for your job description. Reach out to those first. Referrals have been great for us. 


Ask investors, old contacts, industry connections, partners, fellow business owners, etc.


Also, be sure to ask if they’ve actually worked with this person, or if it’s just a friend. They need to have a visible track record of being a great employee.


If you don’t have referrals, look for someone who has done it before at a similar company stage and size, but also has experience working with larger companies (what you’re striving for). 


Finally, if you end up using cold leads from a job application, get them interviews with the team members they’d report to. Let your team members be a part of the decision-making process. They might see things you don’t. 


And again, be willing to cut ties quickly if you know it’s not going to work long-term. 


These 3 strategies have led us to our A-Players.


The biggest thing we’ve done to keep these people is to treat them incredibly well.

Remember, the job doesn’t end once you have them. You still have to retain them with a great work environment, autonomy, and respect. 


If your A-Players are inspired and happy, your company will be thriving in no time.



About the Author:

Chelsie Lee is the Co-founder and CEO of SHIPSI, the delivery technology platform that enables retailers to offer same-day and scheduled delivery without managing any of the logistics. She’s a retail, technology, and supply chain expert who has consulted 500+ top retailers and brands on business strategy, growth, and execution. Among her previous clients are Saks Fifth Avenue, New Look, UGG, O’Neill, Nike and more. In addition to being nominated for EY Entrepreneur of the Year, Chelsie is also a contributor to the Nasdaq Entrepreneurial Center, a mentor to emerging brands, a surf enthusiast, and a yoga instructor. She currently resides in Venice, CA.

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