Is Shadow IT George Washington or is it Donald Trump?

27 Mar

In U.S. history, it’s fairly well recorded that George Washington neither sought nor wanted the office of president.  He reluctantly served a second term and refused the third.  The nature of Washington is considerably different from the majority of the rest of us, and certainly far different than that of Donald Trump. Trump made it very clear that he’s sticking to his guns, even when the effort to discover President Obama’s foreign birth was proven futile. In fact The Donald misses very few opportunities to let the public know he’s the man.  How does this relate to Shadow IT, read on.

Hasn’t Shadow IT been talked about enough?

The discussion around the good, the bad, and the ugly of SIT has raged for several years. However, I’m hoping that taking a non-traditional look at one of the critical underlying issues traditional IT and SIT commonly face when dealing with each other will give the leadership of each group new food for thought.

If you’re not familiar with the risks and rewards associated with the competition between SIT and the IT organization, I urge you to find some good articles* to give you more background. On the other hand, if you’re familiar and or struggling with the issue right now, then please, read on.  I’m not going to say whether SIT is good or bad, but I will attempt to shed some light on the “human” part of the equation.

I’ve been on both sides of this equation as and feel I understand fairly well why SIT (alternative) organizations are initiated. This blog isn’t an effort to say whether SIT is good or bad, but rather to shine a light on how the relationship with IT and the original goals can go wrong.

The battle between Shadow IT and the IT organization

As with most situations that involve humans, the “human” part of the equation must be taken into account if you wish to have any hope of getting to a satisfactory resolution. If you aren’t considering the human equation when dealing with a human problem, you’re missing the most critical aspect of the issue. It would be like ignoring the fact that you are driving a gasoline powered car and when it runs out of gas you put water in the tank and then yell at it when it won’t start.  What makes a mechanical device or a human tick is crucial to understanding how to deal with it. The easy problems to point at when SIT and IT are bickering are the “symptoms,” not the underlying dynamics that make the symptoms persist.  One could argue that the underlying dynamic is the perceived or real failure of IT to deliver, which then creates a space for SIT to fill. In many cases, you would be correct as to what “appears” to create the situation.  However, I would argue that in most cases it’s not the spark, and in many cases it’s not IT’s on-going delivery problems that keep SIT alive or make it thrive.

Why is Shadow IT often like Mr. Trump and less like George Washington?

When a cause is created the creator has a tie to it that is tough to break (President Obama’s Long Form Birth Certificate). In many cases, humans who have started a cause will continue to pursue the original aims of the cause long after the benefit or need ceases to exist (I’m sure Trump really believed that Mr. Obama wasn’t born in the US). When the need subsided Trump couldn’t let the issue go.  As humans we associate ourselves with our causes; for many of us, the “cause” is the work function we’re responsible for, and this association is what makes us who we are, right or wrong.

As the leader of a SIT group, you are by nature (in the majority of cases) at odds with the status quo (IT).  You’ve made them the enemy and as such, must defeat them through any means possible. Yes, that’s right, I said “any means possible.”  When you need to prove your value in the workplace, you generally have two avenues to pursue: work better and harder than everyone else or make the other guy look bad.  When it comes to dealing with traditional IT, you probably started your SIT group under the assumption that IT already looks bad.  What happens if IT does well? What happens if the real need for SIT seems to be diminishing? When IT starts to do well, your first reaction is likely to be, “I’ll ignore them,” and if they continue to do well, your next action is likely to be the initiation of the passive aggressive (PA) phase of the relationship.  In the early days of the PA phase you are anxious to point out perceived failures of delivery more aggressively; you might even try spreading doubt in the minds of your business leaders about the ability of IT leadership to succeed.  In the case of Washington, he “needed” to do a job that the people demanded of him, but his goal was “solve the problem,” rather than create an empire.  What do most leaders want to do? You guessed it—they want to build an empire. If they feel someone is threatening their empire, do they ask themselves, “I wonder if my opponents arguments are correct or if their services are actually better now,” or do they close the drawbridge and man the battlements?

No easy answers

  • Unfortunately, there’s no easy button for solving the SIT / IT death match, but there are some things that are worth trying.  Mind you, I’ve tried some of the very advice I’m offering, and if you don’t have the right leadership in place above SIT and IT, then it likely won’t work, but it’s the best I’ve got:
  • Develop strong communication channels between the two groups. As the old saying goes, “Keep your friends close and your enemies closer.”
  • Ensure regular dialog between members of executive team above each group. If they’re aware of what each group is doing, they are less likely to make a rash decision about the future of either group.
  • Find a way to develop a partnership. There’s usually enough opportunity (read: hard work) to go around for everyone.  Find projects that both teams can work on together and or give the other group a project that they might have better skills to handle or maybe they have more time and better funding.  In the end, leadership is about getting stuff done. If you’re getting stuff done, no one really cares how it happed or who did the work.
  • Look for opportunities to help the other in a time of need, but ensure everyone knows about the arrangement.
  • Make sure your counterpart is fully aware of the limitations you’re working with. You might be able to develop an ally from an enemy.

Happily ever after?

If you’re lucky, the two groups will learn to trust each other and stick up for each other during debates over issues and or funding.  If you’re really lucky, one of the two leaders will show their true leadership abilities by convincing their counterpart that a merger is the right approach. The only way to succeed is by keeping the human equation in the back of your mind during every debate, argument, or struggle for shared funding.  The reason for your counterpart’s position isn’t important—what’s important is that you deal with it in a way that’s likely to show results.  As evidenced in the news, you can throw rocks and yell all you want, but many leaders would rather lose everything than give up their failed cause.  Take a long look in the mirror and be honest…am I George Washington just trying to do the right thing or am I Donald (a fool for all seasons) Trump?


A cherry picked “Rogue IT” blog by @jeffsussna

Blog copy edited by Kestine Thiele (ImKestinaMarie). I made some updates after Kestine finished editing, which likely ruined some of her perfectly good work. 


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  1. Jeff Sussna

    March 30, 2014 at 12:38 pm

    In my experience there is no monolithic SIT group to square off against IT. If there were it woundnt be “in the shadows”. Instead there are individual teams making decentralized decisions. They make those decisions because they want to get work done. They have no vested interest in the chosen technology, or even in the technology management process. They quickly forget about the (S)IT process and get on with their lives.

    Yes, they often display skepticism and resistance when “asked” to “relinquish” control of their tools back to IT. But again in my experience, they do it for the same reasons they pursued an SIT solution in the first place, not out of any corporate politics.

    • Mark Thiele

      March 30, 2014 at 5:46 pm


      I’m glad you’ve had better experience in the relationship and organizational models of SIT and IT. I’ve had good and bad experiences on both sides as I’ve been a part of SIT and IT off and on for 25 years. Where I’ve run in to the most serious problems with the relationship between SIT and IT was when it involved “mini-IT” organizations. These SIT groups had several layers of staffing that mirrored a small traditional IT group and in both cases over time the “owner” of the SIT group became a major thorn in our side. The real reason for being a thorn was the effort to try and prove that IT could never be good enough to take over what they had been doing. I accept and have seen that this problem doesn’t apply to all SIT groups, and I’ve certainly seen and been involved in my fair share of dysfunctional IT organizations. However, it doesn’t change the risk that the longer you allow something to grow, the deeper the roots become. This principle is also repeated over and over when two companies merge and there is a failure to effectively consolidate and incorporate infrastructure and applications.

      Thanks for the comment!

      • Jeff Sussna

        March 30, 2014 at 6:49 pm

        I’ve seen similar situations in the past. I think that cloud is dramatically changing the dynamic. Non-IT groups are gaining the ability to fulfill their needs without investing in significant “mini-IT empires”.

        • Mark Thiele

          March 31, 2014 at 4:26 am

          I tend to agree. However, with great power comes great responsibility. While there is the opportunity to be more agile, there’s also the risk of introducing risk. Best if the two groups cooperation.

          Thanks again for taking the time to comment.

          • Rich Hintz

            April 1, 2014 at 4:29 pm

            I’ve seen both micro shadow IT with single developers and mini shadow IT. In my experience, micro shadow IT are formed in departments that can’t get their work done with the central IT systems they’re given, which are generally inflexible ERP systems with close to useless interfaces. Central IT development cycles are usually years and the product often is a failure.

            Mini shadow IT seem formed when there’s political contention between central IT and well funded departments and weak overarching governance. Again, though, the central IT organization can’t deliver the business data, analysis, modeling that the departments need.

            In the micro case, central IT seems to at least countenance shadow IT since central IT knows that central IT can’t deliver. Business continuity, audit, and even knowing where the authoritative data is are all problems.

            In the mini case, the lines of communication with central IT are already broken, there are often personality issues, and things generally won’t get better without changes in personalities. Even then nothing much will change because the mini shadow IT group has been institutionalized.

            There may be stronger or weaker partnerships among lower level staff, but, especially in the mini shadow IT cases, the overall goals of the organization end up taking a back seat to tribal goals.

          • Mark Thiele

            April 1, 2014 at 4:42 pm

            Rich, thanks for the comment. Excellent points.