Content Manager? Creative Director?

Have you had more good managers than bad in your career? What were the qualities that made the difference?

When I was at a big national web company, IXL, I loved the fact that towards the top of the org chart there was a Chief People Officer. What a commitment to what really counts, the people doing the work.

When I was a reporter, I was always struck by how reporters got promoted to editors, even when their reporting talents (great writers, dogged diggers) didn't always translate into editor talents (people skills).

I've only had limited experience at officially being a boss, a year running statewide Virginia operations for UPI being at the top of that list. I've had some experience in a "first among equals" role, and I worked hard to justify the distinction. I've had a ton of experience in managing up, what I call leading from the bottom.

You should get more credit for managing up than managing down. It's a lot harder..

***

To land a job as a boss, you need three things. The first is experience at being a boss, which is the same Catch 22 every college grad runs into. You have to have experience to get a job, but you have to get a job to get the experience.

The second is longevity, a way to work your way up the ladder. Trust, as they say, is consistency over time. My career in the post-industrial American economy is way short on longevity, thanks to companies going out of business, companies being bought up or split up, or companies caught in big macro trends (ala the dot bomb of the early 2000s or trying to sell cars online in the middle of the Great Recession).

As my friends and neighbors head towards the good life at the top of their careers, I repeatedly get to start again from scratch. That's not a whine, that's just bad luck and/or life in post-industrial America. The good part is I've accumlated an impressive amount of experience and training in a variety of marketing/media skills.

The challenge is turning that into a spot higher up the org chart.

* * *

The third key in getting a shot at being a boss is to find a good boss. It goes to a line I heard once from political consultant Rich Galen: "'A' people hire 'A' people, 'B' people hire 'C' people."

When the director of the Chrysler Museum of Art was taking a victory lap for a successful reopening, he told a lunch meeting of the Hampton Roads chapter of the Public Relations Society of America that I had "almost singlehandedly" kept the museum in the public eye during 16 months of renovations.

He had brought me in originally to make changes, big changes, and about six weeks into the job, there's a big meeting in his office with a lot of the top people. Here it is, I thought, the moment where the new guy gets reined in.

And I was told to keep it up, that I was bringing exactly what was needed.

That's exactly what I did for years. Then he retired. Then came a new director. And then I found myself looking for a job. Again.

* * *

Because I've done so many different things in two decades of web sites and online marketing, and because I had a long journalism career before that, I wind up being a real handy guy to have around. As I digest ads, read websites, go through my email inbox, I'm constantly struck at the little things that could be done to make them better. Well, sometimes big things, too.

At companies of a certain size, a one-man marketing department is perfect, and a writer who can also design and code is cost-effective. I've had a lot of "/" jobs. Hell, most of my jobs have been "/" jobs.

In larger corporations this can become problematic — if you're a jack of all trades, are you a master of all, too? The presumption is you can't be. Otherwise you wouldn't be in the position you are in, that is, looking for a job.

A.J. Leibling, a legendary writer back in the glory days of newspapers, used to answer that conundrum this way: "I can write better than anybody who can write faster, and I can write faster than anybody who can write better."

I've always loved that quote, and always wished I had the inherent arrogance to craft a version of my own, something on the lines of:

"If someone knows more code, I'm a better designer. If they're a better designer, I'm a better writer. If they're a better writer, I know more code."

I say "inherent arrogance" because I've never been a big horn-tooter, a self-promoter. I've always let my work do the talking.

But here's the thing. Aren't multiple talents exactly what you need in a boss? Isn't that a key component in being able to communicate effectively with the people on your team, that your experience can help them avoid a costly mistake?

And how exactly do you demonstrate people skills to someone you've never met, a prospective boss somewhere on the other side of your computer screen? Does your cover letter mention that your ex-wife was a shrink and that you learned a lot of psychology from her? Do you tell people you're a grow-on-you kind of guy in a first-impression world?

Or do you just keep applying for jobs on down the org chart?

* * *

Here's another peril. At some point, with a resume as long and deep as mine, prospective employers wonder if you'd be happy if you were NOT the boss. There's an "he's overqualified and he wouldn't be happy" pre-judgment that's all too common. This is, I suspect, almost always fatal when it comes to landing the job.

My craziest theory on the difficulty of working your way up to the top involves curly hair. Think about it. We've never had a president with curly hair. There are few titans of industry with crazy hair. Visualize congressmen, business people, men in the the military — maybe there's just something intrinsically non-serious about curly hair. Does it just suggest fun instead of business?

Well, if it does, at least it's a theory that thins with age.

* * *

So to be clear, there are reasons why there are no Chief Better Officers presiding over a constellation of websites. First, and most importantly, that's normally the description of the CEO.

Second, even if you had the technical brilliance to pull it off, even if you had the skills and intelligence to improve the language, design, code-base, strategy — all of it — you'd still need incredible levels of diplomatic skill to succeed.

People generally hate consultants coming in and they secretly fear someone from the outside pointing out their alleged failings. The Chief Better Officer couldn't be a dictator about things. It would take a considerable amount of buy-in to succeed and the benefits, not only to the enterprise but to the employees, would have to be clear. That's right. The people made happy by a CBO would range from end-users to corporate bean-counters, from employees to wanna-be employees impressed at the quality of work.

It's such a fantasy it has only one concrete benefit.

It becomes an excellent exercise in thinking about how you could be a better boss.

* * *

As I sit here thinking for a hobby, nervously twirling a curl of hair, it's time to move this discussion from the abstract to the concrete. So I would suggest that when it comes to molding the next generation of management talent:

You need a fast learner with good instincts.
Here's just one example. At the Chrysler it was "suggested" that the web guy also know video, and be able to have a Glass Studio video online within a week of the Grand Opening. So in addition to my regular duties, on a five-week schedule that began with not knowing the camera or the software or even glassblowing for that matter, I delivered this.

You need someone who can work on, or lead, a team.
There's a trained way to talk to creatives, to give feedback that's actionable and productive. There are ways to motivate and to encourage participation. Always remember that every great idea has some goofy ideas in its family tree. The idea acorns can be as important as the delivered oaks.

You have to balance what you want to say with what your customer is looking for.
Anticipation, and delivering on expectations, is a key to success. This applies not only to website organization but also to tone. I'm a big believer in understanding brand attributes, and I believe your customer/visitor is always your best source of information.

The most important computer language of all is English.
There's a reason so many TV showrunners are also the writers.

To conclude, in a world where there are too many government websites that are disorganized and hard to navigate, where there are too many corporate websites dominated by org-chart thinking instead of putting the user first, where business sites repeat errors perpetrated by the inexperienced and a Chief Better Officer is a fantasy position in search of a dream...

... I'm an email away.

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