Thinking of Becoming a Fractional CMO?

The Short Answer Most senior candidates can confidently talk about their successes. Growing revenue. Building brands. Leading teams. Delivering commercial results. But one of the questions that consistently catches people off guard is this: "Can you tell me about a time you failed?" The truth is, hiring managers aren't looking for perfection. They're looking for resilience, accountability and the ability to learn when things don't go to plan. Why Talking About Failure Matters in Executive Interviews Recently, I was supporting a Chief Marketing Officer through a series of final-stage interviews. They had all the credentials. Commercial growth. High-performing teams. Complex stakeholder management. Transformational leadership experience. Yet after making it down to the final two candidates several times, they kept missing out. The challenge wasn't talking about success. It was talking about failure. For many senior professionals, that's completely understandable. Years are spent building a track record of achievement, so it can feel counterintuitive to highlight setbacks. But experienced hiring managers know that careers are rarely linear. The campaigns that didn't land. The strategy that missed the mark. The hire that wasn't the right fit. The project that faced unexpected obstacles. These moments often reveal far more about a leader than a list of accomplishments ever could. What Hiring Managers Really Want to Know When interviewers ask about failure, they are usually assessing four key qualities: 1. Self-Awareness Can you objectively recognise when something didn't work? Strong leaders understand their role in both successes and setbacks. 2. Accountability Do you take ownership, or do you place blame elsewhere? The best candidates accept responsibility while demonstrating professionalism. 3. Problem Solving How did you respond once you realised there was an issue? Hiring managers want evidence of decisive action and commercial thinking. 4. Resilience Can you recover, adapt and move forward? The ability to navigate challenges is a critical leadership skill. How to Structure Your Answer A simple framework can help you deliver a clear and memorable response. Situation Briefly explain the context. Challenge What went wrong, and why was it significant? Action What did you do to address the problem? Learning What did you take away from the experience, and how has it influenced your leadership since? The focus should never be on the failure itself. It's about demonstrating growth. Examples of Professional Setbacks You Could Discuss Not every failure needs to be dramatic. Some of the strongest interview answers come from everyday leadership challenges, such as: A marketing campaign that underperformed. A strategic initiative that didn't achieve expected outcomes. A difficult stakeholder relationship. Hiring someone who ultimately wasn't the right fit. Managing organisational change that faced resistance. Missing a commercial target and adapting the approach. Authenticity matters more than trying to find the "perfect" example. Prepare Before Your Next Interview If you have an interview coming up, spend a few minutes reflecting on your career. Take out a pen and paper and write down three examples of setbacks or failures that have shaped your professional development. For each one, ask yourself: How did I recognise the issue? What action did I take? What did I learn? How did I improve because of it? These are the stories that often create the strongest connection with hiring managers. Failure Doesn't Define Your Career A successful career isn't built by avoiding failure. It's built by learning from it. The most effective leaders are rarely those who have never experienced setbacks. They are the ones who can reflect, adapt and lead with greater insight because of them. When an interviewer asks about failure, they aren't trying to catch you out. They're trying to understand how you'll perform when it matters most. And often, that's exactly what sets exceptional candidates apart. Frequently Asked Questions What is the best way to answer an interview question about failure? Use a structured approach that explains the situation, your actions, what you learned and how you applied those lessons moving forward. Should I admit to a real failure in an interview? Yes. Authenticity is important. Choose an example that demonstrates accountability, resilience and professional growth. What do hiring managers look for when discussing failure? Most employers want to see self-awareness, problem-solving ability, resilience and the capacity to learn from setbacks. Can talking about failure help you get hired? Absolutely. A thoughtful answer can showcase leadership qualities that achievements alone may not reveal.