How AI Is reshaping IT leadership and the modern CIO

In a volatile landscape, IT leadership development and succession planning are more important than ever.  

Without the right leadership pipeline, shifts in the workforce – such as executive leaders exiting the workforce and restructuring – can lead to real-world consequences for an organization. Leadership gaps, project disruptions and technical debt can all derail organizational plans and initiatives if they don't have a proper strategy in place. 

An effective future-forward IT strategy depends on finding IT leaders who can effectively handle these challenges. Creating an effective succession plan ensures that an organization can maintain a competitive advantage through workforce changes and disruptions. 

With a solid succession plan in place, organizations can stay ahead of the game and help mitigate organizational disruption even when unexpected workforce shifts occur.  

The importance of IT leadership pipeline 

A strong leadership pipeline in IT is crucial for ensuring smooth workforce transitions and navigating disruptions with minimal impact on operations and organizational health.  

“Internal talent development for future CIO roles is basically insurance for continuity,” said Jake Randall, co-founder of Modall. “You’ll have candidates perfectly suited for the role, already vetted and already trained.” 

It's especially crucial for organizations to have a pipeline for critical positions like CIOs in changing times. When leaders exit – whether expectedly or unexpectedly – the gap in leadership can cause negative effects on the organization, including disruptions to organizational culture, data vulnerabilities and operational disruptions.  

When an organization has a predetermined strategy that includes looking internally instead of externally to fill the CIO role, it can promote organizational continuity and benefit the organization through: 

• Reducing the time spent on integrating into the organization and adapting to the culture. 

• Emphasizing the importance of upskilling and the company’s commitment to advancement within the organization. 

• Reducing time and resources spent on internal knowledge building. 

External hires can be valuable, but internal successors already understand the organization's business model, customers, technical limitations and culture, said Tom Catchings, interim CIO at Cornerstone.  

“This institutional knowledge can only be learned with time in the seat," he said. "In a volatile, unpredictable and fast-moving business landscape, internal successors provide a head start that can be the difference between a smooth leadership transition and a stalled roadmap.” 

Identifying high-potential IT talent 

Developing future IT leaders starts with identifying high-potential employees who can be nurtured through development opportunities to become leadership-ready.  

As technology evolves, IT leaders who can solve problems by applying new relevant technologies will thrive, said Ajit Shah, managing director at Global Teams AI. 

 “The new-age CIOs will be articulate, empathetic and open to ideas,” he said. 

However, identifying CIO-specific talent involves more than just throwing any high-potential employee into the talent pool. Knowing what to look for can help narrow the pool of high-potential talent to pick the best-fit employees for the CIO talent pipeline. 

“The skill set for deep technical work and the skill set for leading at the CIO level overlap, but they are not the same,” said Randall. “You can absolutely make a strong external CIO hire, but the odds of a perfect fit on culture and communication are usually lower than developing someone from inside the company.” 

Future CIOs typically have leadership-ready skills and competencies such as: 

• Strategic vision 

• Cross-functional influence  

• Digital fluency 

• Financial acumen 

• Business-technology integration 

After identifying people that possess the core competencies that make them a good fit for a future CIO role, it’s essential to measure how they might fit into a leadership role. Although some high-potential employees may look good on paper, seeing how they would perform CIO duties is the true test for future CIO leaders.  

Organizations can assess the potential of chosen employees through evaluation methods such as: 

• 360-degree review 

• Leadership assessments 

• Stretch assignments 

Mentoring and coaching for IT leaders 

Hands-on experience and one-on-one sessions with individuals who are familiar with the roles and responsibilities of a CIO – especially with internal executives who also know the organizational ins-and-outs are invaluable.  

Structured mentoring programs can provide regular support and coaching for emerging leaders. These give high-potential employees a space to discuss leadership challenges and get advice from mentors. Regular mentoring sessions promote a consistent focus on leadership development, which can help high-potential talent develop faster and keep them equipped to step into new roles when possible.  

Executive mentoring in tech roles can provide potential future CIOs with a clear path forward within the organization and help develop strategic thinking skills through open discussions with current organizational leaders.  

“Nurturing the next generation of CIO talent means ensuring access to deep in-house knowledge and awareness of ongoing internal and external technology evolution,” said Shah. “This coupled with the ability to work effectively with talent across geographical boundaries will help facilitate seamless digital workflows.” 

Organizations should prioritize valuable, holistic mentorship opportunities like cross-generational programs and reverse mentoring, according to Drew Firment, vice president of global partnerships at Pluralsight.  

“As new leaders are appointed, reverse mentoring can aid senior leadership in understanding the tools and cultural shifts that are going to be influencing their industry in the years ahead,” he said.  

Creating experiential learning opportunities 

It's important to find ways to give potential future leaders hands-on learning experiences to improve their leadership skillset and deepen their understanding of the organization’s operations and services.  

For example, Randall advises organizations to let IT leadership candidates lead client calls, own cross-functional projects or run small teams, and note how they communicate, handle pushback and follow through. 

“Pay close attention to who fixes problems that nobody formally assigned to them, and how their peers describe working with them," he said. "That pattern tells you a lot about whether they can grow into a CIO-type role.” 

Pay close attention to who fixes problems nobody formally assigned to them, and how their peers describe working with them. That pattern tells you a lot about whether they can grow into a CIO-type role.

Integrating experiential learning wherever possible can help develop high-potential employees and improve their leadership readiness. Rotational programs can help give employees a more rounded view of critical IT functions, such as security, cloud, data and operations.  

Future leaders should have the chance to interact with and be exposed to critical leadership elements such as business strategy, vendor management and enterprise architecture. The more an employee is exposed to these areas, the more their leadership skills and internal knowledge on the business grows. 

Succession planning best practices 

“Effective succession planning outlines clear answers to what an organization is trying to accomplish in terms of its OKRs (objectives and key results), tech roadmap and required maturity,” said Firment.  

There are some frameworks and strategies that can ensure that future IT leaders are prepared to step into these critical roles: 

• Ensure alignment. Before beginning the action steps for succession planning, it’s critical to define the reasons for succession planning and ensure that it aligns with the larger organizational strategy.  

• Use a step-by-step approach. A simple four-step approach can simplify the succession planning process: identify, develop, evaluate and promote. 

• Utilize technology. Organizations can invest in software and tools to gauge employees’ readiness for leadership positions, skill gaps and relevant career advancements to help evaluate and track employee progress. 

Challenges and pitfalls in IT succession planning 

Just like there are best practices to succession planning, there are also pitfalls that organizations should avoid to ensure succession planning is fair and valuable: 

• Avoid bias. Making decisions about who is an ideal succession candidate should be objective and neutral. Having a standard set of traits and behaviors to look for, as well as a defined scoring system for employees, help keep the process as unbiased as possible. 

• Focus on retention. Developing top talent is crucial but so is ensuring that top talent stays with the company long-term. It's critical to manage retention risks for high-potential employees, who are less engaged than underperforming employees, according to a Leadership IQ study.  

• Balance short-term and long-term needs. Finding a balance between focusing on short-term operational needs with long-term leadership development ensures that succession planning doesn’t take a backseat to short-term needs but is still kept a top priority. 

Measuring success and adjusting the program 

Succession planning should be a continuous initiative, not a one-time project. Measuring how effective a succession strategy is – as well as how succession and employee development is viewed across the organization – can reveal what succession initiatives are successful and where there is room for improvement, as well as how employees feel about succession efforts.  

“Failing to measure progress against business results derails accountability, so succession can’t just be determined by the number of hours put in; ROI has to be a core part of the process,” Firment said. 

Organizations should identify and monitor key performance indicators (KPIs) surrounding succession, such as: 

• Internal advancement rate 

• Employee participation in development opportunities 

• Time-to-fill executive positions 

Executive call to action 

CIOs need to proactively invest in succession planning to help ensure business continuity and innovation readiness. Plus, leadership development and succession planning can cause ripple effects across the business that promote growth and engagement.  

Employees are more motivated to go above and beyond when they know there's a genuine chance to move up the company ranks, according to Randall. 

 “They start expanding their skills and behaving like leaders before they have the title," he said. "That creates a healthier culture, more engagement, and better outcomes for the company.” 

Alison Roller is a freelance writer with experience in tech, HR and marketing.