Movie recipes

It’s well known that Hollywood movies follow a few, proven recipes: someone’s leading a happy life, until a bad thing happens and forces our hero to go on a mission; there’ll be a giant set back (usually bad news for the hero’s best buddy), and 15 minutes before end the hero breaks through, resulting in everything ending well (except for the best buddy). I watch most movies in airplanes (it’s hard to work or sleep while they serve “food”), so I can bear the repetition as my investment in real and opportunity cost is limited.

Nevertheless, there’s always something to be learned, even from Hollywood movie recipes. One of the more common movie themes starts with a person leading a seemingly normal life. For one or another reason this person engages someone from the underworld to do some dirty work for them. To at least initially save the character’s moral grounds, they justify their actions based on a pressing need or a vague principle of greater good. The person from the underworld often comes in form of a hitman, who is tasked with scaring away, kidnapping, or disposing of a person who stands in the way of a grand plan. One of the more elaborate examples of this genre is the movie Fargo. However, it’s also bit complex to be used as a metaphor for digital transformation. Instead, if you haven’t seen it, forget about IT for a bit and just watch the movie.

So let’s take a simpler and more recent example, The Accountant with Ben Affleck. Here, the CEO of some robotics company hired a hitman to dispose of his co-founder who may be onto his financial manipulations. The company also hired an accountant to investigate some irregularities with their bookkeeping. As it turns out, the accounting brings a lot more skills to the table than anticipated. After a lot of action and countless empty shells, things… (spoiler alert!) don’t end well for the instigator.

The digital hitman

Coming back to the world of IT and digital transformation, we can quickly see the analogy: a business leader is under pressure from the board to change the organization to become faster and “more digital”; there may be some amount of dirtywork involved, such as re-orgs or, worse, layoffs. But it’s in the name of greater good, i.e., saving the company. Wouldn’t it be easiest to recruit some sort of digital hitman, who can clean the place up and gently disposes of any naysayers before he or she disappears as quickly as they came?

The natural candidate wouldn’t be as good looking as Ben Affleck and wouldn’t bring a trailer full of firearms. Instead, they would come with credentials such as having held a major role at a successful, brand-name digital company, having led a corporate innovation center, or having run a start-up incubator. He or she would would be full of energy and promise, and would have one or the other trick up their sleeve. Sadly, though, things are more likely to end up as in the movie than in a successful transformation.

Crossing over into the unknown

The key challenge in hiring someone from a different world (under or not) is that you won’t know the world you’re crossing over into. For example, you wouldn’t know how to pick a good candidate because the whole premise is that you need someone who has a very different background and brings completely different skills. You also won’t understand the unwritten rules of engagement in the other world. While as an IT leader you may not have to worry about someone else outbidding you to turn your own hitman against you, you may still a few snags. For example, the transformation expert you are hiring may feel that it’s entirely reasonable to quit after a half a year as that’s how things work where he or she comes from. Or the person may expect to just ignore all the corporate rules - after all they are here to challenge and change things, right? Or, they may feel it’s OK to speak about all the shortcomings of your organization in public.

As a result, some of the stories involving a digital hitman don’t fare much better than in the movies. While luckily the body count generally stays low, many things can go wrong: a lot of money is spent, a lot of expectations are set and missed, and the anticipated results aren’t achieved. The new innovation center may not actually feed anything back into the core business (you might have just bought FaceBook stock). The new work model may be shunned by employees. The staff may lack the skills to support the shiny new “digital” platform. Lifting and shifting all servers to the cloud may not bring any visible benefits. The list goes on.

How about the enterprise hitman?

Naturally, the issue is symmetric and not limited to enterprise companies wanting to become more digital. So-called digital companies that are looking to engage enterprise customers are also prone to look for the enterprise hitman, usually hired from a household-name enterprise vendor. The results are generally the same, or more likely worse, for the simple reason that digital companies consider the transition to be “enterprise ready” to be easier.

Who to look for?

Transforming a complex organization without any outside help is going to be difficult - you won’t even know much about what you are aiming for (and may not have realized that there isn’t a stable target picture). So how do you go about finding a good person to help you? As usual, there isn’t an easy recipe, but my experience has shown that there are a few things that you can do to improve the odds:

  • First of all, don’t expect a digital hitman who carries silver bullets to kill your legacy zombies. Look for someone who has shown the stamina to see a transformation through.
  • Having worked for a “digital” company doesn’t automatically qualify a person as a transformation agent. Yes, they’ll have some experience working in the kind of organization that you’re inspired by (or compete against). However, that doesn’t mean they know how to take you from where you are to where you want to be. You can’t just copy-paste one company’s culture onto another - you need to plot a careful path. Lastly, they may be extremely frustrated with your existing platforms and processes and leave quickly (I was often frustrated but I didn’t throw in the towel!). Look for someone who has had some exposure to enterprise systems and environments.
  • Knowing how a digital company acts doesn’t mean the person knows the kind of technology platform that’s needed underneath. Yes, “move to the cloud” can’t be all wrong, but it doesn’t tell you how to get there in which order and with which expectations. Therefore, find someone who can ride the architect elevator at least a few floors down.
  • Smart advice is relatively easy to come by compared to actual implementation. Look for someone who has spent time inside a transforming organization as opposed to looking on from the outside.

If you feel that these suggestions will narrow down the set of available candidates, you are likely right. You are also likely engaging in the first important exercise for any transformation: putting wishful thinking aside and bracing for reality.