Surviving your company’s Steve Jobs wannabe

Just because your company is diseased doesn’t mean it’s poorly managed. For example, if Walter Isaacson’s biography of Steve Jobs is to believed, Apple under Jobs was a sick place to work. By any other reasonable measure, it was very well managed.

Apple isn’t the only example of a company that’s both dysfunctional and successful — a fact that’s simultaneously puzzling and depressing to those of us in management consulting. For IT leaders trying to achieve next-generation status, it’s worse than puzzling. It can, depending on the disease, range from apoplexy-inducing aggravation to near-insurmountable challenge. But for anyone in IT, the ability to recognize the symptoms of various business diseases, accurately diagnose them, and figure out how to handle the situation is a critical survival skill.

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Last week’s Advice Line described stir-the-pot leadership — a particularly bad business disease. Let’s take on one more; a correspondent who asked to remain anonymous calls it the Great Dictator syndrome.

How to spot a Great Dictator

We’re not talking about companies run by Charlie Chaplin. Instead, we’re looking at companies run by CEOs who have all of Steve Jobs’ worst characteristics (except, perhaps, his poor hygiene) without any of his saving graces: the supreme certainty that they’re right, without actually being right often enough to justify their high opinions of themselves.

Because business culture flows downhill, arrogant autocracy is the company’s standard leadership model, while cowering toadyism is the preferred way to “manage up” — though not because Great Dictators have bad tempers. For the most part, they don’t. They don’t need them. Their excessive confidence allows them the inner peace to remain calm as they issue ludicrous instruction after ludicrous instruction.

No, the cowering is a result of a Great Dictator’s favorite phrase: “If you can’t get this done, I’ll find someone who can.” Their preferred means of providing information is on a need-to-know basis; their preferred mode of communication is giving orders; and their preferred organizational listening channel is nonexistent — because who needs one? Finally, their preferred decision-making organ is their pancreas; they trust their guts far more than any form of evidence or logic.

How savvy IT leaders deal with a Great Dictator

As is the case with stir-the-pot leadership, the savviest IT leaders leave for a healthier environment. If, however, this isn’t an option, the best defense against a Great Dictator is to master the fine art of Yeah But.

Of course, you don’t ever say, “Yeah, but …” That’s too obvious. Instead, smart IT leaders learn to say in response to every order their Great Dictator gives them (because a Great Dictator never merely makes a request): “We can do that. Here’s what it will take.”

For more complicated orders, they’ll offer, “We can do that. Give me a week to put a plan together so I can tell you how long it will take and what it will cost.” In other words, “yeah, but,” but with a more businesslike phrasing.

However, this won’t always work. Anticipating your preference for planning and accurate estimates, a Great Dictator might tell you, “I’ve decided SAP is holding us back. We need to move our ERP into the cloud. That shouldn’t take more than three months, I’d think.”

Your reply: “We can do that. Here’s what it will take: a miracle” — that is, if you’ve decided to take advantage of option No. 1 after all and catch the next flight home to live with your parents for a while.

Your reply if you want to remain an IT leader: “We can install a cloud-based ERP alternative in three months — less time, really. But installing it and making the business run on it aren’t the same thing.”

Part of making this work is to find an interpretation of the Great Dictator’s order that’s reasonable, and restate the order in those terms. Your goal with a Great Dictator is to turn orders into conversations, and your relationship from serf to confidant. This isn’t easy. It isn’t always possible. When it isn’t possible, you and your organization will go from failure to failure because the nature of the orders you’re given will make success unachievable.

Dealing with the other dictators

It’s worth pointing out that in a business afflicted with Great Dictator disease, IT will find itself dealing with more than one Great Dictator. While it’s usually the CEO who sets this style, the CEO may not be the only person to adopt it. Far from it — the mind-set tends to trickle down. If everything thinks they’re “internal customers,” IT will be on the receiving end of orders from every petty dictator in the company.

It not limited to companies with Great Dictator CEOs, either. Companies with weak CEOs often end up with Great Dictators pervading the next level of the corporate hierarchy.

Whether the CEO is a Great Dictator whose style everyone else adopts or so weak that dictators grow up around them, you need more than a set of techniques for personally dealing with the CEO. You need to provide everyone in IT with strategies for dealing with a steady flow of demanding self-styled customers, all of whom insist that they’re the top priority. Drop everything and take care of them, or else.

The solution is to establish a formal request management process, with the work queue completely visible: the request, the requester, and estimated effort and time needed to fulfill. No matter who the dictator is, other than the CEO, everyone in IT knows to direct them to the request form. If a dictator refuses to make use of it, their IT contact offers to enter the request for them. And if they insist their request belongs at the head of the queue, authorize everyone in IT to tell the dictator in question that they lack the authority to bypass the queue — the dictator will have to talk to the CIO if they want an exception.

The CIO (you, in this hypothetical company) agrees to put their request at the head of the queue, so long as they clear it with all of the requesters currently in front of them. That’s the end of the matter because everyone in front of them is a dictator, too.

This all sounds great. None of it has a very good chance of success, though, because dictators reach their current positions of influence by being very good at getting their way. Being reasonable? That’s for other people.

So while these techniques are worth trying, don’t be surprised if they don’t work. If you can’t redefine your conversations and relationship with the Great Dictator, voting with your feet is a pretty good choice.

It’s as the late, great W.C. Fields advised: “If at first you don’t succeed, try, try again. Then give up. There’s no use in being a damn fool about it.”

This story, “Surviving your company’s Steve Jobs wannabe,” was originally published at InfoWorld.com. Read more of Bob Lewis’ Advice Line blog on InfoWorld.com. For the latest business technology news, follow InfoWorld.com on Twitter.