How to Drive Digital Transformation and Survive as Your Company’s First CIO

I’ve spoken with several CIOs who were the first to hold the role and title at their organizations. It’s a unique experience, so I thought I’d share some thoughts.

When a new CIO comes on board, there’s often a mix of excitement and angst among the leadership and staff. Leadership wants to believe that what drove the need to hire a CIO materializes without too much time,  cost, and disruptive changes. The staff wonders who this new leader is and what they will ask of them.

These are all true for any new CIOs joining an organization, and the recommendations I share in this post are for all CIOs leading digital transformation.

But when it’s the company’s first CIO, there’s no benchmark to compare, and more importantly, few people truly understand the CIO’s primary responsibilities. Gaps in understanding, communication, and priorities often lead to unfulfilled expectations and vocal detractors, so first-company CIOs must move quickly to learn business needs, build executive relationships, set a course employees understand, and overly communicate progress.

Why companies hire their first CIO

You might think it doesn’t happen that often – that by now, companies should have woken up and realized the importance of having a CIO lead technology, data, and other operational responsibilities. However, many circumstances can drive the shift from having no CIO to requiring one. Here are several scenarios.

• A growing company – Technology, data, customer/employee experiences, security/compliance, and other operational factors require a CIO’s strategy and leadership.
• A struggling IT function – The company is struggling with its current IT operating model, and it’s underperforming; sometimes, because IT is outsourced and there are issues with the service provider, and other times, the workload is overwhelming the internal IT team.
• Prioritizing digital transformation – The business might have new competitors, changes in customer expectations, and technology-driven disruptions, forcing the Board and executive committee to hire a CIO who can lead digital transformation.  
• Promoting an IT Director – Sometimes, the IT director is promoted to CIO, with the expectation that they will take on greater responsibilities.
• M&A driven – When many acquisitions or mergers are completed over a short period, the Board and executive group often recognize the need for a CIO to lead consolidation and develop an IT operating model.
• Responding or recovering from major risks – The business may have security, compliance, and other material risks, and the executive committee hires a CIO to address them.

Understanding the underlying circumstances that led to hiring a first CIO is an important starting point, but CIOs taking this role will likely hear mixed messages on goals and priorities from the executives. Here are three recommendations for new CIOs, with more details below.

• Drive digital transformation, but take sufficient time to learn the organization’s true priorities.
• Survive because you won’t be able to make everyone happy while driving change.
• Thrive because getting past the first 100 days and the next two years is just the start of developing an IT operating model and digital transformation core competencies.    

Drive by digging into the why behind the need for digital transformation

I opened my first book, Driving Digital, with this key advice for any CIO assigned to lead digital transformation. “Look at your company as if it were your first day on the job. What would your first impressions be of how your business is operating?”

The first CIO at the company must often dig wide and deep to learn about the business opportunities and risks where technology, data, and AI can provide value. With every executive meeting, the CIO will learn priorities through a narrow lens; some want innovation, others efficiency and automation, and many will just want IT services running with fewer incidents.

“First-time CIOs must navigate the delicate balance between innovation and stability,” says Dr. Mahesh Juttiyavar, Chief Information Officer of Mastek.  “To succeed, they must understand the organizational culture and structure, foster open communication, and promote continuous learning within the IT department.”

Avoid succumbing to the mile-long to-do list. Instead, learn about opportunities and problems and categorize them through a digital transformation lens. Consider dimensionalizing:

• What are the game-changing opportunities where there is executive consensus
• What are the critical operational priorities that address recurring system performance issues, significant compliance gaps, or other material security risks?

• What agile programs belong on the longer list of priorities needing vision statements and aligned objectives?

Another key consideration to review is the talent and skill level of the IT staff, especially the Digital Trailblazers needed to lead digital transformation initiatives.

Survive by developing your EQ and change management practices

It’s not easy to identify a change velocity that the organization can execute and deliver results.

CIOs who don’t prioritize will fail because of too much work in progress that materializes too slowly or misses expectations. CIOs who prioritize will have supporters in some areas of the business and detractors in others where executives aren’t getting what they want. In digital transformation programs, all CIOs need change management practices, and they will feel the spectrum of employee responses, with some enthusiastic early adopters and many others who resist change.   

“An accurate CIO job description should list two core attributes: thick skin and excellent listening skills,” says Ross Meyercord, CEO of Propel Software. “Without these, no CIO or CEO could succeed or even survive. CIOs must listen attentively and carefully to users to identify root problems as quickly as possible to take action and deliver demonstrable improvement.”

Surviving means that transformation doesn’t come easy, especially for CIOs, who are often introverted and more technically oriented than people-centric. In a recent post on selling innovation to executives, I used a skiing analogy, suggesting that CIOs “keep their ski tips up” to actively listen and respond before driving actions. In another post, I recommend Digital Trailblazers, CIOs, and other leading digital transformation initiatives to balance their drive with empathy to develop their emotional intelligence and change the culture.  

Thrive by developing digital transformation core competencies

Unfortunately, while Boards hire CIOs to drive digital transformation, many are thrust into firefighting mode because of the underlying operational issues, security gaps, and risk driven by technical debt.

More unfortunate is that CIOs who stick to firefighting end up with a team that follows these behaviors. And it’s really hard to drive transformation when 40-60% of everyone’s time is spent chasing incidents and urgent requests.

The bottom line is that CIOs who don’t develop an IT operating model and digital transformation core competencies struggle to survive and last in their jobs beyond their third year.

I mentioned change management as one transformational core competency, and others all CIOs should establish include agile planning, data-driven organizational practices, and no-code / low-code application development. Companies developing customer-facing technologies also need product management, while others supporting many cloud and legacy applications should invest in DevSecOps and ITSM.

A company’s first CIO often walks in with mile-high expectations – unlike any new CIO walking into a new job. My three recommendations apply to all CIOs leading digital transformation, but first-timers have the added pressures of learning and setting precedences, especially when the organization knows less about the CIO’s role and responsibilities.

StarCIO Digital Transformation Core Competencies

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