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Preparing for Success: Practicing for Failure in IT Leadership


Daniel Elacqua


In the fast-paced and ever-evolving world of technology, IT Directors and Chief Information Officers (CIOs) are constantly faced with new challenges and opportunities. To truly succeed in these roles, it's essential to prepare not only for success but also for the inevitable failures that come with the territory. In this blog post, we will explore the concept of preparing for failure by practicing for what could go wrong and how this proactive approach can better equip IT leaders for success.

Embrace the Reality of Failure

We all fail, it’s how we learn!  It is essential to recognize that failure is not a sign of incompetence but rather an integral part of the learning process. In the world of IT leadership, things don't always go as planned, and technology can be unpredictable. Rather than fearing failure, we should embrace it as an opportunity for growth and improvement.

Identify Potential Weak Points

To effectively prepare for failure, start by first identify potential weak points in our project plans, processes, or strategies. Ask questions like: do we have the right skills with current staffing to complete this project? And is the scope clearly understood?  Consider scenarios that could lead to failure, such as scope creep, resource shortages, or communication breakdowns. By recognizing these vulnerabilities, we can proactively take steps to address them.

Develop Contingency Plans

Once you've identified potential weak points, it's time to develop contingency plans. These plans should outline specific steps to take in case of failure, allowing you to react swiftly and minimize the impact. For example, in the event of a data breach, you should have a well-defined incident response plan in place to contain the breach, notify stakeholders, and restore normal operations.

Practice Leads to Excellence: Simulating Failure Scenarios for IT Leaders

My grandfather had a saying: "Practice makes perfect." As an IT leader, I've come to realize just how accurate this adage is. One of the most effective methods of preparing for failure is by simulating failure scenarios. This can encompass various activities such as tabletop exercises, penetration testing, or disaster recovery drills. Simulating failure enables you to evaluate your contingency plans in a controlled environment, allowing you to uncover any vulnerabilities before they can cause a real crisis. Furthermore, it offers your IT team a valuable opportunity to gain experience in navigating challenging situations.

Cultivate a Learning-Oriented Environment and Skill Development

In the realm of IT leadership, fostering a culture of continuous learning is paramount. Encourage your team to derive valuable lessons from both successes and failures. When setbacks occur, initiate a post-mortem analysis to comprehensively understand what transpired, why it unfolded as it did, and how to proactively prevent similar occurrences in the future. This approach not only facilitates learning from mistakes but also instills a sense of accountability and drives continuous improvement.

Simultaneously, as part of your preparation for potential failures, invest in the training and skill development of your IT team. Guarantee that each team member possesses the requisite knowledge and expertise to effectively navigate prospective failure scenarios. Provide them with opportunities for skill augmentation through comprehensive training programs, industry-recognized certifications, and hands-on workshops. This investment not only enhances individual capabilities but also reinforces your team's overall resilience and readiness for adversity.

Stay Informed and Adapt

The IT landscape is constantly evolving, with new threats and challenges emerging regularly. To stay prepared, IT leaders must stay informed about industry trends and emerging technologies. Being aware of potential disruptions and adapting your strategies accordingly is a key aspect of failure preparation.


In the world of IT leadership, preparing for failure by practicing for what could go wrong is not a sign of pessimism but a proactive approach to ensuring success. By embracing failure as an opportunity for growth, identifying weak points, developing contingency plans, simulating failure scenarios, and fostering a culture of learning, IT leaders can navigate the complex and dynamic IT landscape with confidence. Remember, success in IT leadership is not about avoiding failure altogether but about how effectively you respond and learn from it.

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