(4d of 5 in The Rules of Naked Management)

Who?

In the mid-Nineties, the Chicago Bulls’ star player, Michael Jordan, decided to retire even though he had plenty of playable years left in him. Even more surprising, he decided he’d go play professional baseball.

Not surprisingly, Mr. Jordan didn’t achieve the same level of success between the bases as he did between the baselines. Within two years, he admitted that baseball was not for him.

But when he attempted to return to basketball, no one would have him. Team after team passed on him. They wouldn’t even consider him for a coaching position. Eventually Michael ended up having to take a low paying job in retail to support his family.

At best, Michael Jordan is but a sad footnote in the history of basketball, and a sad but common parable of the human race: a man following a dream, only to have his life destroyed in the end.

…

Bare with me… I’ll get back to that (obviously false) story in a bit.

Why Assume It’s True?

A few weeks ago (I’m behind…) I wrote about the importance of encouraging your employees to dream. Without a dream to move towards, they won’t push themselves. Once they have a dream, it’s usually fairly easy for them to envision a few small steps they can take that will move them closer (for example: go ask a potential mentor to lunch).

And yet, often there is a hesitation to take even the small step; a worry that if they fail in achieving their dream, their professional lives will be over. Often this hesitation is strongest in your stars as they think they have the most to lose. And as a result, too often, your employee never takes the first step.

That’s where the concept of “Looking at the Negative” comes in.

The Power of Negative Thinking

Let’s revisit the process again for getting something done:

1. Daydream: Form a vision of what you want do.
2. Be Lazy: Come up with one small step that moves you closer.
3. Look at the Negative: Look at the opportunity cost of that step, and if it’s too large, go back to step 2.

Then, TAKE THE STEP!

We’ve covered the dreaming and being lazy in the last article, but “Looking at the Negative” is the key to dealing with hesitation. As a manager, your job is to force your hesitating employee to look at the negative. Yes, I mean force: Make them uncomfortable; Make them list all the things that could go wrong and the consequences; Make them squirm as they try to justify why such trivial things are stopping them.

Do this, and all sorts of obstacles will vanish under the scrutiny of examination. For example, your employee may worry if they ask a mentor to lunch that they’ll be rejected, but when they think about it out loud they’ll see the only real worry is schedule availability, not personal rejection. They may worry that they’ll be laughed at if they do an architecture talk in front of the entire Engineering division, but will quickly realize that the worst result is someone offering free help in presentation skills afterwards (really…).

In addition, if an employee verbalizes the negative before he takes his step, and decides to take the step anyway (for example, realizing that some assholes will laugh at you if you give a sucky presentation, but trying anyway), it makes it much easier to get through the bad when it happens.

In general you’ll be amazed how successful a technique it is to get your employees to verbalize their fears out loud.

But occasionally one “negative” or “opportunity” cost may not be easily dismissible: Your employee, particularly your stars, may worry that they’ll lose their job and destroy their careers if they fail in their next career endeavor.

That’s where Michael Jordan comes in.

The Consequences of Failure

Here’s the truth about career development: if you are a star today, but fail in something different tomorrow, you will always be welcomed back in your old role (although not always at the same company).

If you were an excellent engineer, and then fail in marketing, someone will always take you back as an engineer.

If you were an amazing designer, and then fail as an account manager, someone will always take you back as a designer.

And, as if you believed the bullshit I wrote at the top of this article, if you were a great basketball player, and then fail in Major League Baseball, basketball will welcome you back as you decimate all opponents again and win another three championships.

I’m not suggesting that people plan for failure – quite the opposite, you should expect and envision success.

But realize that if you don’t succeed, it’s not that big a deal. That’s what Michael Jordan teaches us. Even if (in the unlikely event) your employee fails in a new position, they can always fall back.

Oh, there will be some short term embarrassment (Jordan definitely got shit in the media), they may need to find a new company because their old job is filled, but once they go back to being a star again in their old role, naysayers shut up really really quickly.

As a manager, when you see someone hesitate because of fear of failure, coach them to think through what the real consequences are, and most will see the light: in career development, risks are rarely as dangerous as they appear.

Cracking the Whip

Now, if you’ve done the steps I’ve been writing about, and with a bit of luck, you’ve now gotten your employee to actually take one small step towards a brighter career future.

How do you (again remembering how little you matter in this process) get them to take the second step?

Simple… be a manager and crack the whip… which I’ll talk about next.

– Art