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The Corporate Crips vs. the Pinstripe Suited Bloods. The C-Suite Angels vs. the Organizational Banditos.

These functional gangs are all scrapping for their share of turf in the “digital transformation” war. CEOs, CIOs, CMOs and a new entrant to the transformation ring CDOs (short for Chief Digital Officers) are fighting for their fair share of real estate. Digital and organizational blood is being spilled.

Okay, maybe a little over-dramatic, but the inability to get people to effectively lead digital transformation is holding companies back. Attached is our reference file pointing to nearly every company wanting transformation, but not many of them getting it. The gap between desire and reality is wide. It’s tough enough winning against disruptive competition, disloyal customers and demanding employees in a digital era, just getting beyond your own C-suite is proving even more challenging. Want proof?

Here’s some recent headlines reporting back from the battlefield:

Some CEOs Drive Digital Transformation Even Faster Than IT: “When it comes to understanding digital transformation the CEO is now at par with the IT department, and in some cases has pulled ahead.” Wall Street Journal

CIOs Should Lead Digital Transformation: “The CIO has to maintain a leadership position in this digital age. They should be at the table of every executive meeting when discussing strategy and tactics.” Lundberg Media

CMOs Must Drive Digital Transformation: “The future of digital business models should be coming from the marketing department. Where else should it come from?” Digitalist Magazine

‘Transformer in Chief’: The new Chief Digital Officer: “The CDO is now a “transformer in chief,” charged with coordinating and managing comprehensive changes that address everything from updating how a company works to building out entirely new businesses.” McKinsey

We’ve even had calls to a lesser extent for the CHRO to lead (Transforming the Future: the CHRO as Chief Change Officer), the CFO to lead (Finance Teams Should lead the League in Digital Transformation) and the COO to lead (The Chief Operating Officer Overseeing Technology as CIOs). That’s a lot of cramped quarters in the executive boardroom!

We’re tempted to say, “who cares, just get it done – most of you are failing while you are trying to decide”. But that would be callous.

So, we’ve tried to take an objective view here with a focus on who is the right person to lead digital change for YOUR organization. We’ve looked at the candidates from 5 different factors:

  • how much change is required?
  • what is the core transformation driver?
  • what are the actual demands for the transformation effort?
  • what skills will be put at a premium?
  • and what handicaps and blind spots will be tough to overcome?

 Caveats also exists for what I am about to advise:

  • any transformation leader and organizational set up might be successful given the right mindset and leader’s hard and soft skill sets
  • any transformational leader and organizational set up might be a failure given poor leadership, unclear mandate, organizational misalignment and tepid or antagonistic functional support
  • as alluded to in section 1 below, the right leader choice today may not be right tomorrow
  • the size and newness of company, expectations of customers, industry vertical, corporate culture and  leader bandwidth and knowledge all have strong influences on transformation success or failure, regardless of calibre of transformational leadership.

I) The Amount of Change Required

If you look at the following graphic as a time scale, there is a good argument to be made that functional leadership of digital transformation may not be a point-to-point effort but a progression of phases.

When starting out – at the start of any change, strong CEOs are most capable of winning over converts through positional authority, hard incentives and access across the organization and externally to generate the interest and champion mandate to pursue further structural change and investment.

When pivoting to becoming a digital company – in this era of massive change and expectation setting, CDOs are most likely to tackle efforts given their balanced skill sets, innovation agenda, large capacity (digital change is their only job) and single point of accountability.

When digital organizational mindset can translate across the customer experience – once the digital table stakes are in place, it’s much easier for CMOs (chief marketing officers) to swoop in and translate better digital organizational capabilities into an optimized customer experience across all touch points.

When digital orientation can deliver digitalization of operations – once enough organizational momentum has been established and progress made in delivering digital strategy, customer experience and talent transformation, CIOs are most effective at optimizing supporting technology, stewarding  systems and platforms and holding the rudder straight for platform interoperability, security and servicing functional needs.


II What is the Core Transformation Driver?

At its highest level;, we can identify 4 types of change being delivered in a digital transformation –  they all require different functional orientations.

CEOs are best at delivering alignment to a new strategic agenda that often requires a fundamental rethinking of the business and where the organization competes. Their background and position allows them to more effectively to bulldoze through obstacles and get key stakeholders onside.

CIOs/CTOs tend to be the most technology adept people in organizations. So when the transformation has a premium on getting technology to actually work and drive progress, they are the best positioned to deliver technology-led capability.

CDOs have become more popular in recent years as a transitional role that gets companies over the digital cultural hump by providing added bandwidth, balanced functional perspective, galvanizing digital enthusiasm and centralizing transformation  efforts for clarity and efficiency.

CMOs are the C-Suiters most intimate with their customer base and the marketplace. Given the digital disruption companies are facing frequently  outside their traditional industry marketplace segments and the increasing demands of a customer base desiring, not just products and services, but a positive and consistent experience, CMOs are best positioned to deliver customer-led transformations.

2x2 digital transformation

III) What are the Deliverables & Demands for Transformation?

As we have shown by the 40 boxes below, there are a lot of reasons to tackle digital transformation. Where the highest priority transformation deliverables fall may determine who is best to lead the overall effort.

transformation deliverables

IV) What Skills Does the Transformation Leader Need to Have?

Less than 1/2 of digital transformation projects succeed. And the findings are that “skilled leadership” of transformation projects is crucial as entrenched culture, practices and processes will naturally resist change. The core question of who the best leader is may be answered by “who is most skilled at overcoming these obstacles?”

transformation skills

V) What Blind Spots are you Most Fearful of your Transformation Leaders?

Talk about transformation projects that didn’t work and people will happily wax poetic about the irritating, maddening things that the transformation leaders did to throw projects off the rails before they even had a chance to succeed. We’ve identified the 7 classical ones that get tied (wrongly or rightly) to each function head. if you have a heightened fear of missteps (perhaps coming out of an already failed transformation project), you might choose transformation leadership to compensate against the following hyper-sensitive blind spots.

transformation blind spots

As mentioned by some of my peers in my beta post, letting digital transformation leaders fail on their own helps nobody. Without exception, the effort needs to be a collaborative, organization-wide one. Bury your egos, be willing to help, grab an oar, start paddling and help your transformation leader get digital change to work and stick. Business in a digital age is like travelling by river in whitewater. The marketplace is surging, and if not enough people are paddling, you either get stuck or tip over. If you don’t like suffering through a little change and extra effort, you will hate failure (and company death) even more.

Precog Digital ( offers interim digital transformation leadership for companies embarking on sweeping digital effort. We work as embedded partners to catalyze, diagnose, strategize, align, develop and deliver digital-led change as neutral, experienced and technology-adept change agents. Frequently, this will involve special project leadership in large companies, org. wide transformation leadership in small-mid-size enterprises and audits, roadmaps, keynotes, workshops, executive counsel and thought leadership for other organizations.