IT Leadership

The IT Leader’s Guide to Navigating Failure

As IT leaders, we’re expected to be omnipotent and omnipresent, with answers to every problem and solutions for every scenario. The reality is often very different. Despite our best efforts, projects sometimes fail, and when they do, it can be difficult to see any upside or opportunity for growth. In this chapter, we’ll explore how shifting your perspective onto failure can fuel personal growth and make you a more resilient and effective IT leader. Let’s begin by understanding how to reframe failure.

Reframing Failure

Failure is often viewed as an end state, a negative outcome that’s to be avoided at all costs. In reality, failure is more like a data point on a continuum of information and feedback that helps us make better decisions. Just like a scientist who adjusts a hypothesis based on experimental results, failing forward is a mechanism for iterating and improving your approach to leadership.

This doesn’t mean ignoring or downplaying the negative emotions that come with failure. It’s natural and healthy to feel disappointment, frustration, or even anger when something you’ve worked hard on doesn’t go as planned. Allowing yourself to feel these emotions and experiencing them fully can help you work through them and maintain a healthy perspective.

It can be helpful to think of failure as an investment in your personal growth. It provides you with valuable information and experiences that can serve as a foundation for future success. Similar to how a vaccine introduces a harmless version of a pathogen to train the body’s immune system, failure can train your leadership instincts to succeed better next time. You develop grit, perseverance, and a more realistic outlook on what it takes to succeed.

This mindset can help you embrace failure as a learning opportunity and catalyst for growth, rather than a defining moment or cause for self-doubt. The next section will delve into specific strategies for leveraging these opportunities.

Strategies for Learning from Failure

IT leaders are often the architects of grand plans that require many moving parts to collaborate seamlessly. When one of these plans falls short, it can be difficult to pinpoint why. Going issue by issue to find the root cause is an exhaustive task, but it’s necessary to improve. Let’s look at some strategies to do this effectively and efficiently.

Start with Empathy

When projects or initiatives fall short, it’s easy to point fingers and assign blame. Focusing on blame, however, distracts from the real goal of learning from failure. Instead, empathize with everyone involved, including yourself. Failure is a collective experience, and empathizing with everyone who contributed to the outcome helps you understand the bigger picture.

This doesn’t mean ignoring accountability or allowing blame to fall solely on others. It’s important to be accountable and to hold others accountable when necessary. But focusing on empathy first can help you avoid making the same mistakes others made and better understand how everyone’s contributions led to the outcome.

This empathy-based approach to leadership, especially when facing challenges, can help you build trust and cultivate a culture of learning from failures rather than fearing them. This will empower team members to be more innovative, make calculated risks, and be comfortable communicating when things go wrong. As mentioned earlier, failure is more about learning and course-correction, rather than indictment or final judgment.

Conduct a Blameless Post-Mortem

Post-mortems are examinations of failures or unexpected events to determine what went wrong and how future incidents might be avoided. The goal is to identify root causes, determine responsible parties if applicable, and define preventive measures for the future. The trick here is to conduct this investigation without blame so that everyone involved feels safe to participate fully and candidly.

Start by defining the problem as objectively as possible. Use data, observations, and insights to paint a clear picture of what happened and when, as well as how it exceeded beyond the scope of acceptable limits or expectations. You should also define what success would have looked like to clarify your goals.

Next, generate potential root causes that you and your team can brainstorm and analyze in a focused, constructive fashion. Aim to identify the root cause rather than getting stuck on symptoms to prevent the same mistakes going forward. From there, determine who was involved and what their responsibilities were.

Once you’ve identified the contributing factors, develop a plan to address and mitigate future occurrences. Determine the actions and steps that should be taken to prevent the failure from recurring and outline a clear path forward.

Leverage the Power of Reflection

Reflection is a powerful tool for processing and learning from failure. It helps you make sense of what happened, identify any patterns, and gain insights into your own thoughts and behaviors. At a minimum, reflect on the following:

• What did I learn from this experience?
• What could I have done differently?
• How has this experience changed the way I think or approach similar situations?
• What would I do differently if I could do it all again?

Set aside regular time for personal reflection and keep a journal to help you track your thoughts and insights. Reflecting on failure helps you clarify what went wrong, why you think it went wrong, and what you could do differently in the future. It also helps you identify any patterns or common themes in your behavior or approach.

If reflecting alone feels challenging, consider enlisting a coach or mentor to help you work through your thoughts. Sometimes an outside perspective is all you need to see things differently.

Overcome Cognitive Bias

Cognitive biases are based on your beliefs and experiences, and they affect the way you view yourself and the world around you. When it comes to failure, many people suffer from cognitive bias, which causes them to view failure disproportionately to its actual impact. Common examples include the negativity bias (giving more weight to negative experiences than positive ones) and the imposter syndrome (feeling like a failure despite evidence to the contrary).

If you’ve struggled with these feelings, it may be helpful to seek feedback from a trusted colleague or mentor. They can offer you a more balanced perspective on your performance and help you identify any patterns that may be impacting your ability to learn from failure.

Seek Help and Support

IT leaders can’t succeed in isolation. When you’re overwhelmed or stuck, it’s okay to ask for help. This could mean seeking guidance from a mentor, admitting that you don’t have all the answers, or even asking for help in identifying potential opportunities for growth. Help can come from many places, including your peers, your team, or even through therapy.

Therapy has increasingly entered the mainstream as a tool to facilitate leadership growth. It can help you overcome mental roadblocks, such as anxiety or depression, that may be inhibiting your ability to see failure for its true value. It can also provide a safe space to work through your emotions and experiences, particularly those related to past failures that may still be affecting you.

Developing an Emotionally Resilient Mindset

Building emotional resilience is a key aspect of embracing failure as a catalyst for growth. Emotional resilience is the ability to manage your emotions and maintain personal balance, even under pressure or after experiencing a setback. By developing this skill, you’ll be better equipped to weather the storms of leadership and leverage failure to propel you forward.

There are many ways to build emotional resilience, including:

• Keeping a positive outlook. This doesn’t mean ignoring negative emotions but rather learning to balance them with positive ones. Emphasize the positive aspects of your work and the potential for growth.
• Practicing mindfulness. Being fully present in the moment can help you navigate failure more effectively. Mindfulness techniques, such as meditation, help you clear your mind of clutter and distractions so you can better process your emotions and reactions.
• Setting realistic expectations. Having realistic expectations for yourself and others will prevent feelings of defeat or disappointment when things don’t go perfectly. Hold yourself to high standards, but also recognize the complexity of your work and what’s possible within the context of your resources.
• Maintaining a growth mindset. Those with a growth mindset believe their skills and abilities can be developed through hard work, learning, and resilience. This allows them to see failure as a natural (and expected) part of the growth process.

Seek Opportunities to Fail Faster

To fail faster, you must be willing to take risks and try new things. This also means recognizing when you’ve failed and learning from your mistakes before they have a chance to fester. Experimentation and innovation are key components of failing faster and leveraging failure to your advantage.

This may involve pushing yourself outside of your comfort zone, taking on new challenges, or trying unconventional approaches to problem-solving. It also means being open to feedback and constructive criticism, as well as proactive in seeking it out.

Navigating the Mental Health Impact of Failure

Leading an IT organization can be mentally and emotionally exhausting. It’s easy to dismiss the effects that negative emotions have on your mental health, but long-term stress can lead to burnout and other mental health issues. It is imperative that you prioritize your own well-being, especially when facing difficult circumstances.

When you’re in the thick of things, it’s easy to dismiss the signs of mental or emotional strain. Some common symptoms to watch for include:

• Feeling overwhelmed or unable to cope with responsibilities
• Increased irritability or moodiness
• Feeling emotionally drained or depleted
• Withdrawing from friends, family, or activities
• Lack of interest in things once pleasurable
• Difficulty focusing or making decisions
• Feeling like you’ve failed or let others down

If you experience any of these symptoms for an extended period, it may be a sign that you’re struggling to process the mental impact of failure. This can also lead to behaviors, such as:

• Blaming others or taking out your frustrations on them
• Using substances to cope
• Stepping away from your responsibilities
• Lashing out at others

It’s important to prioritize your mental health and well-being, especially when facing difficult circumstances. Here are some strategies to cope when the going gets tough:

• Take breaks and prioritize self-care. Taking breaks is an important part of avoiding burnout and staying fresh and focused. Take a few minutes each day to practice self-care, whether it’s taking a walk, doing some meditation, or simply spending time with loved ones.
• Stay connected. Isolation is common when emotions are running high, but having a supportive network of colleagues, friends, and family can help you stay grounded. Leaning on them during tough times can remind you that you’re not alone in facing challenges.
• Keep a healthy lifestyle. Exercise, a balanced diet, and sufficient sleep will help you manage your emotions and mental fatigue.

Summary

Failure is a natural part of the IT leader’s journey, and it can be a powerful catalyst for growth if you view it through the right lens. The first step in embracing failure is to reframe it as a learning opportunity and a stepping stone to future success. Using the strategies outlined above, you can implement blameless post-mortems, leverage the power of reflection, overcome cognitive bias, seek help and support, build emotional resilience, and navigate the mental health impact of failure. By doing so, you’ll be able to fail faster and with less friction, paving the way for faster progress and growth.