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.


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. 

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 usthat 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.

by Rick Maack – Be!


You are the leader of your team most likely because at one point you did the work they are doing and you did it well.  When was the last time you sat down with your team and got in the weeds with the work they do? Not in your office or some other lonely place but on the floor or at their desks with them in the trenches understanding the issues they deal with on a daily basis.  Hearing the conversations they have.


The team probably will not like that you want to work next to them.  They may think you do not trust them. So, you have to communicate that you want to do this to stay current and understand the work at a granular level.  Tell them that the time you spend will not be evaluating but learning and helping get the job done.

Lead from within the team and behind the team.  Pick a day each week and for an hour or two assist with a project.  Ask the team where you might be able to help let them choose the tasks for you.  Let them lead you.

Stephen Covey calls Habit 5: Seek first to understand, then to be understood.  As experienced as you might think you are, there is no substitute for getting a real-time on-the-ground look at what goes on with the team.  And there’s no better way to do that than to go where they are and do what they do.

In the military, it is axiomatic that there is no substitute for personal reconnaissance.  The best leaders make good decisions because they go and see for themselves what is happening.  This means getting down in the trenches.  

Here are six reasons why doing this is a good idea.

Lead by Example.  Seeing the boss mopping a floor sets a powerful example; if it’s important enough for the boss to be doing it, then it must be important for the team as well.  Getting down in the trenches gives you a great opportunity to set a personal example.

Get the Team’s Perspective.  Get to see the world the way your team sees it.  This does three things for you:

  • You learn what life is like for them.  By doing what they do, you will quickly see what the challenges are, what works well, what doesn’t, and what processes might need to be reviewed and improved.
  • You learn what they know (and don’t know).  See how they use the equipment, ask questions about how they do things, have them show you what to do (even if you think you already know).  Either you will learn something you need to know, or you will find out that there’s more they need to know.
  • You connect with them.  And in working with them, you will also get to know them and can begin to connect with them on a personal level.


Get to Know the Managers.  Putting yourself under the direction of your front line managers does many good things for you.  First you get to see how they operate, their leadership styles, how they interact with customers and other employees.  Second, if you ask them to train you on something, you will quickly learn how much they know about their job. Third, you can get their first-hand input on ways things could be done better.


Get to Know the Customers.  If you place yourself on the front lines than you’ll have a chance to interact with the customers, too.  What questions do they ask? What are they interested in? What else could you provide that fits their needs?  And you have the opportunity to observe what they do, where they go, how they act. All this will be useful to you as you work to establish the direction of your team and business.


Learn the Systems.  How does the team communicate?  How do different jobs interrelate?  Is it clear who is supposed to do what?  What happens when opening and closing the store?  What happens when something stops working? What seems inefficient?  As you work, think about the flow of the operation, the physical structure, the communications.  If something doesn’t make sense, ask your teammates about it and get their perspective.


Get Feedback on Your Ideas.  One great way to get a sense of whether or not your ideas will work is to ask the people who would have to implement them.  You may be bringing useful big-picture perspective to the equation, but they can contribute on-the-ground feedback on how it might turn out, or how to adjust your idea to make it more effective.


The greatest thing that a manager can do is understand the impact they have on the people working for them. Empathize with the realities of the job and support those doing it – and maybe you’ll spare someone a sleepless night.



I have been working with several clients over the past few years with Workday solutions.  Robert Half partners with clients of all sizes and industries to help you realize the full power and potential of Workday. We provide expertise to set your cloud deployment on a smooth course. And once live, our application management services and ongoing administration solutions will help your platform operate at peak performance.

Rick maack is a leading finance and technology talent expert.  Robert Half focuses on the staffing solutions you need. No matter the challenge you’re facing, we have the staffing experts and proven methodology to solve it. By integrating Protiviti’s accounting, audit, technology and consulting expertise, we provide project management through your transition, including performance-gap assessments, system implementation, process and reporting optimization, and control and process documentation updates.

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