4 characters who can slow down your digital transformation – and how to deal with them

You're likely to encounter some of these characters on your digital transformation journey. Here's who to be on the look out for, and how to work more productively with them
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digital transformation characters

As unpredictable as technology can be, people are worse. Anyone in the trenches on a digital transformation can attest to the many, many ways the human element can get in the way of best-laid plans and roadmaps. 

That said, one of the saving graces of that human unpredictability is it can be a bit … predictable. As diverse as our emotions and experiences are, sometimes it’s hard to shake the feeling that one is meeting the same characters over and over. 

Below, we’ve captured four characters that people report encountering repeatedly on the digital journey – recognize any of them?

Spoiler alert: You yourself may have elements of all four – and it’s worth taking a minute to look at the Suzy, Hank, Toby, and Bob within. 

[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]

Character: Suzy Skeptic

What you experience: Plainspoken and incisive, Suzy Skeptic can be an appealing character – until she starts lobbing grenades at anything that smacks of newness. Suzy’s seemingly no-nonsense critique of digital efforts attracts a shocking number of followers – who wouldn’t trust someone making such clear, common sense arguments?

What to do: Parse out what’s real skepticism – borne of Suzy’s not-inconsiderable intelligence – and what’s “skepticism-as-a strategy,” borne out of a deep-seated fear of change but persisting due to the organizational clout it seems to attract. Address the true skepticism head-on – engaging in real time with valid criticisms to improve digital efforts. To deal with the “skepticism as a strategy,” fight fire with fire – putting forth plain-English messages illustrating why the skeptics are wrong. 

[Read more from Melissa Swift: Why people love to hate "digital transformation."]

Character: Hundred Thousand Foot Hank

What you experience: Hundred Thousand Foot Hank is as flashy as Suzy is low-key. As a vocal champion of digital transformation, Hank plays the part to the hilt, matching a square jaw and artfully rumpled hair with an assortment of carefully chosen fleece vests. The issue is, though, that playing the part is the extent of his capabilities; despite his soaring rhetoric, Hank’s technical acumen is paper thin. Hank will happily lead the organization down meaningless or counterproductive pathways, charging ahead as an army of technologists protest in his wake.

Hank will happily lead the organization down meaningless or counterproductive pathways.

What to do: You don’t want to completely disenfranchise Hank – the momentum he creates can be very helpful. But you don’t want to slavishly follow his dictates, either, knowing he can’t distinguish between smart ideas and truly terrible ones. It can be helpful to pair a Hank with a technologist as his full-time helper/handler – assuming you have a technologist on hand with the requisite assertiveness and sense of humor. Alternately, you can appeal to his ego – telling him he can tackle strategy while you handle execution (and subtly shade the strategy back into workable territory). 

Character: True Believer Toby

What you experience: At first glance, True Believer Toby seems to fit Winston Churchill’s description of a fanatic as someone who can’t change his mind, and won’t change the subject. Toby’s passion for an ordinarily useful transformation process or technology – anything from Agile or DevOps to artificial intelligence or robotic process automation – has somehow escalated into the obsession zone. What started out as healthy enthusiasm and appropriate focus has become the only topic Toby is willing to engage on – and woe betide anyone who might seem to be criticizing his sacred cow. Co-workers have started to avoid Toby in the break room – fearing another proselytizing lecture. 

Put Toby to work winning hearts and minds via a smart “translator” who can extract his most relevant talking points.

What to do: Put Toby to work winning hearts and minds via a smart “translator” who can extract his most relevant talking points and put them in business context for others. Diffuse his energy by letting him connect to other Tobys outside the organization – he may bring back some interesting learning from networks of passionate folks far outside your walls. 

Character: Burnout Bob

What you experience: Of the four characters in this article, Burnout Bob can be the hardest to identify. Bob may initially present as a Suzy Skeptic, putting in a few seemingly thoughtful criticisms here and there – but more often, he seems on board with the digital transformation agenda. You’ll only notice that something’s amiss when you start seeing tepidly worded communications or anemic progress on key projects. Maybe an email comes back into your inbox with Bob quietly undermining the ideas behind a central initiative somewhere down the chain. What’s going on? Bob is quietly exhausted – he has no more transformation energy left, and trying to subtly slow down the world around him has become his way of making work palatable.

What to do: There are two kinds of Bobs, and it’s critical to figure out which one you’re dealing with. Blah Burnout Bob never fully invested himself in technological transformation at any point in his career, and years of dealing with enthusiastic people around him have taken him to a dark and grouchy place from which he will not recover. Encourage Blah Burnout Bob to consider a new role (internally or externally) – it’s in everyone’s best interests. 

Bob is quietly exhausted – he has no more transformation energy left.

But a better Bob does exist: Banged-Up Burnout Bob. This Bob was passionate about the possibilities of technology at one point in his career – and suffered such grave disappointments that he burned out. If you can honestly offer Banged-Up Burnout Bob a clear path to success (and maybe some resources to help accomplish his goals), you may be able to re-activate his former passion, turning him into a real asset. 

Knowing is half the battle

Knowing what to do about Suzy, Hank, Toby, and the Bobs can be the difference between digital transformation success and failure.

But remember – just as "The Breakfast Club" teaches us that each one of us is a brain, and an athlete, and a basket case, a princess, and a criminal – no one at your organization is just a skeptic, or full of hot air, or a true believer, or a burnout. As we noted at the beginning, you need to look in the mirror and acknowledge the aspects of all the characters you see.

[ Is your digital strategy up to date? Read also: 8 digital transformation trends for 2020. ]

Melissa Swift is the U.S. Transformation Leader at Mercer, the consultancy helping redefine the world of work. In this role, Melissa is responsible for the firm’s efforts in the areas of workforce transformation, HR transformation, HR digitization, diversity equity and inclusion, and workforce analytics.