Letter to a CIO — Understanding your dilemma and how to move forward. Part 1

9 min readJul 12, 2021

This article represents the first part of a series called “Letter to a CIO”, which reports the discussions between the author of the letter, dr. Domenico Lepore Founder Intelligent Managemnt Inc. and several Chief Information Officers, with the aim of providing them with an effective methodology to address and successfully solve common problems that CIOs face in the Digital Age.

The result of this series of interviews helped dr. Domenico Lepore crystallize the scheme for his last book “Moving the Chains — an operational solution for embracing complexity in the Digital Age”

Dear Bob,

You have asked me to guide you now that you have become the leader of your IT organization. You deserve this position, but the challenges are great. This is not because you are any less qualified than the best of your peers. It’s because the complexity that governs our world today requires a different kind of knowledge and new skills. I appreciate your courage and I want to reassure you that everything you need already exists. In this letter, I would like to offer an analysis of your current reality. What you then decide to do with this knowledge is ultimately your choice.

First, narrative helps. Let’s frame your situation as a story.

Phil is the CEO of a large financial conglomerate and Bob is the group CIO, with hundreds of people in different countries reporting to him. Phil wants to see a Strategy in place to ensure that the megabucks the company is spending in technology will bear fruit. Phil is convinced that Big Name Consulting Firms have the solution… well, he hopes they have it, and asks Bob to summon Big Name Firm and, er…. Strategize. He is the Boss, He demands results.

Bob is perplexed; not that he would ever dare to contradict Phil, he believes in CYA, but he knows, deep inside, that Big Name Firm will only rehash old platitudes whereas his own team, instead, has all the answers. He just does not know how to fish them out, how to harness the professional and intellectual power of his people. Team building exercises have only got him so far….

And why should he know? He ain’t no visionary leader, no strategist, no shrink. He is a guy with a Ph.D. in Engineering, a knack for science and technology, works hard and toes the party line. This is all new to him.

My message to you and all the Bobs, big and small out there is: Guys, there is light at the end of the tunnel. There is a why and there is a how.

Let’s start with the why

Bob, your life as CIO is captured by what in the Theory of Constraints (TOC) is called an “inherent conflict”, in other words, a situation of blockage. This blockage is determined by the dilemma generated by attempting to simultaneously satisfy two fundamental needs. Let’s take a look at the CIO dilemma.

On one side, your legacy role is to ensure the subordination of the IT infrastructure to the business; as such, you should not interfere with how business processes are designed and operated. Your job is to support them. The need you are protecting here is one of “stability” and it is driven, essentially, by fear (in this case, “fear” of not being compliant with your role).

On the other hand, you are asked by Phil to provide an input with clearly measurable business results; in other words, Phil wants you to be accountable for company performance, not tech mumbo jumbo. You know that many of the current business processes are either poorly designed by their leaders or, well… borderline lunacy. Hence, you feel you should act on them decisively. In doing so, besides being responsive to your Boss’s request, you are addressing a very legitimate need for “growth”, driven, more often than not, by desire (in this case, “desire” to see your company succeed).

What is common to these two needs, one connected with “stability” and the other with “desire”, is a genuine, attainable goal, NOT slogans –

Let’s map it out:

(See also short article ‘Building the Core Conflict)

Now, Bob you have been asked to call in a Big Name Firm, to strategize. For guys who live their lives trapped in this conflict, what the heck does “Strategy” mean? Please, bear with me.

One of the many mistakes that Big Name Pundits make is to purport that a Strategy can exist in isolation; it is something that can be designed behind closed doors and then handed off to a team of implementers. Such strategies are normally based on some ill-defined set of benchmarks, blessed by subject matter experts, and sanctified on the shrine of Best Practices.

Despite the glaring and systematic failure of this Paleo-Newtonian, mechanistic, clockwork view of the world, Big Name Firms remain unflappable and Teflon-sealed to any form of understanding. And, for the most part, they get away with it because CEOs do not often know any better and, in their world, are mostly concerned with even less knowledgeable Board Members and the intricacies of corporate governance. Simply, CEOs do not know which question to ask their CIOs, are ill-equipped to understand the answer and their MBA education does not help.

So, this is the situation many “Bobs” are in: a tech guy/gal, very happy to pull all-nighters but not very adept in the vagaries of human behavior, who needs to develop a “Strategy” that impacts, measurably, business results. Oivey!

Let’s go back to the conflict, there is some solace in robust thinking.

Mental models (assumptions)

What is this conflict underpinned by? Why do we believe in the alleged, unsolvable duality of this conflict? You know, there are things we say and things we don’t; and just because we don’t say something doesn’t mean that we don’t subliminally believe in it. Well, these spoken and unspoken beliefs have a name, they are called “assumptions” or, in contemporary PsychoSpeak, “Mental Models”.

Assumptions are “images”; world-views that shape how we perceive what we experience. They are a lens through which we see the world and, for the most part, they are the result of past experiences and our genetic neural endowment. Thank goodness we have them; without them we would have to re-invent ourselves every day, just like Drew Barrymore in “50 first dates”.

What is critical here is to understand that these images sometimes can produce misleading, dysfunctional perceptions. They can be, and often represent, a “Cognitive Constraint”, an inability to translate what we know is valid into coherent actions. They are what keeps us stuck and make “change” complicated. If you need a tragic reminder of where these altered perceptions can lead to, look no further than any of the violent conflicts taking place in the world right now.

So, which assumptions are sustaining this conflict and why do we need to unveil them? Because, wittingly or unwittingly, they represent the cognitive cage that keeps us trapped and forces us to reiterate well documented mistakes. By taking a hard look at them we can begin to understand how to challenge them. Yes, we all live in the Yellow Submarine of our mental models and sooner or later we need to resurface and breathe fresh air.

Three categories of assumptions keep this CIO conflict alive and kicking and provide a source of ever-multiplying assignments for Big Name Pundits:

Organizational design is separate from IT
Business strategy does not require input from IT
Organizational design and information flows are independent of each other

The full schematic including assumptions is then the following — you can read it through by following the numbers in red:

Yes: we experience the duality of this dilemma because we believe these assumptions are “true” (or, at least “valid”, a big difference…) and hence our life as CIOs can only unfold in its present misery and be driven by the platitudes of the Pundits.

Alternatively, we can decide that we are better than dolphins and horses (wonderful Godly creatures but with a limited development of their prefrontal cortex and bound to non-modifiable instincts). In the words of Al Pacino in ‘Any given Sunday’: “This is the most important battle of our professional life and it all comes down to today; we can get the shit kicked out of us OR we can fight our way back, into the light, one inch at a time”. (It is NFL Draft time, I could not resist…).

In light of this conflict and the blocking power of its assumptions, what does “Strategy” mean for a CIO?

A Strategy (aimed at a well-defined goal) links a thought process to coherent and implementable actions

If the thought process is flawed, the ensuing actions will not achieve the goal. And the thought process is driven by the assumptions in the conflict.

So, let’s look at the assumptions. Do we really believe they are valid? Of course not! They are just the remnants of a totally outdated silo-view of the world, the cultural dregs of the first industrial revolution, the last bastion of the all human tendency to avoid the pain of challenging deeply rooted yet completely outdated paradigms.

Reality is that “every organization is a technology organization” and the role of the CIO is to imbue this awareness into the life of the business. CIOs MUST become the engine that propels the business, NOT its butler. Every CIO knows it.

How can he/she do that?

Oh, well, let’s ask the relevant question then, one that far too often CIOs refuse to address: “What the heck is technology for? Why do we use cutlery and plates instead of biting meat off a bone?”

Technology’s only purpose, my dear friend, is to remove limitations, to facilitate tasks, to ease our efforts….. towards a Goal; and of course, in the realm of this conversation, what we are talking about is the Goal of the organization.

And what kind of limitations is our organization experiencing? Not enough sales? Too much inventory? Limited resources? Lack of human capital? Whatever the limitation is, the only meaningful “Strategy” is to gear our technology investments so they remove/alleviate that limitation. Anything else is (almost) irrelevant, and soon the role of the CIO will be irrelevant unless this concept is clearly understood. Bob -if you think this is too harsh, unfair or simply not true stop reading and go back to your router. But if you don’t, keep reading and listen up.

End of part 1.

Go to part 2

Further reading:

Here is a series of blog posts we wrote for CIOs.

You Say you Want a Revolution: Where Digital Transformation Is Taking You

Symptoms of Silo Sickness that CIOs Must Cure

Silos vs Systems: Solving the CIO Conflict

How to Grow the Whole Organization: Processes, Projects and the CIO are Key

How CIOs Can Break Free of the Silo Prison with Systemic Management

Digitalization Needs Cooperation: Start Transforming the Enterprise for the Digital Future

Digital Transformation and Systemic Change Management

How To Overcome Resistance To Change — a Systemic Approach