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How to Manage Entrepreneurial-Minded Employees

How to Manage Entrepreneurial-Minded Employees

By: Emily Bennington, Monster Contributing Writer

See if this sounds familiar. You’ve just brought on a new hire (say a Gen Y or new grad) who you really like… well, except for one small problem: They’re gunning to move up.

Like, now.  

And while you think they’re just dipping a toe in their current role, they’re pushing for more responsibility and higher pay. This is a very tricky – and very common – dilemma for managers today.

In fact, I just interviewed a young woman who was 12 weeks into the workforce and already frustrated with her career. She worked for a great company, had a great manager and liked her job – so what was the deal?  Get this: Her position had a two-year promotion track.

"Two years is like a decade to me," were her exact words.

Managing Racehorses
I know, I know: You’re thinking that’s ridiculous and she should feel lucky to be employed, right? Well, frankly, that’s the problem. Because for as much as we like to moan about how long we had to pay our dues (and walk 8 miles in the snow) while insisting the next generation do the same, the fact of the matter is that it’s a different world.

Yes, we can blame the parents for coddling their kids to the point that they expect you to cave in too.

But it still doesn’t change the fact that top talent – a.k.a. the ones we all want to hire – are like racehorses behind the starting line. They’re stomping, chomping at the bit, and just waiting for the doors of opportunity to fly open so they can chase the career carrot.

Perhaps you recall the feeling. After all, it’s the reason you started your business in the first place. You wanted that entrepreneurial paradox of control and freedom. And so do they.

Stoking Entrepreneurial Engagement
Alright… maybe you can’t give them control. (After all, that’s your job, right?) But there is something else you can give that means just at much – if not more – at this stage in their career. You can give them progress.

Because here’s the thing: It's easy for new grads to feel as if they're falling behind when we're all surrounded by tales of 27-year-old CEOs. (Geez, even I feel behind sometimes!) But if your hire feels that he or she is learning, growing, and advancing their skills and network they will reward you with employee loyalty

Just ask my first boss, Skip Lineberg, who turned what was supposed to be a temp job (for me) into a six year partnership – not to mention a book deal.

In retrospect, I’m a little embarrassed to admit this but when I started working with Skip I asked for a promotion after just nine months. Here is the super-savvy way he managed it.

First, he listened. He didn’t try and convince me that I was too inexperienced or that nine months in the workforce was a little too early to get yippy about moving up. Instead, he heard me out and, after I made my case, he said he’d give it some thought.

Then, he asked me to prove my worth. He presented me with a simple one-pager called, “Prove you’re worth it.” It was a list of 10 tasks — I had to pick seven to complete – in addition to the keeping up with the responsibilities of my current role. The list included things like:

  • Picking a system in the office I felt could be improved and telling him how I’d fix it. 
  • Hosting a Lunch ‘n Learn for the rest of the staff. 
  • Attending a professional development course. 
  • Reading a classic business book and writing a summary of what I learned and how I was going to apply it to my job.

You get the idea.

Next, a check-in. He asked me to check-in with him after I’d finished a task or if I had any questions along the way. After that, I was on my own. And while my manager never gave me a formal deadline (I suspect that was a not-so-subtle initiative test) it took me about 6 months to get all seven tasks complete. However, when everything was said and done I got the promotion – and he got to buy some time.

He also got to evaluate how I handled stress, how I solved problems, how committed I was, observe my employee attitude and if what I would bring to jumping through those hoops to earn that new position. 

Smart cookie, huh?

This was definitely a win-win for both of us and an exceptional example of great management skills.

So if your Gen Y workers or new grads – or any employee really — feels like they’re ready to move up, but you’re not quite sure, remember: Make ‘em prove they’re worth it.

If they are – trust me – they will.

Author Bio:
Emily Bennington
specializes in two distinct forms of career transition: college students entering the workforce and women leaders entering executive management. She is the author of Who Say’s It’s a Man’s World: The Girls’ Guide to Corporate Domination  and Effective Immediately: How to Fit In, Stand Out, and Move Up at Your First Real Job. Emily is a frequent speaker on the topic of career success and has been featured on Fox Business, CNN, and ABC. She can be reached online at emilybennington.com, on Facebook or on Twitter.