How to Talk About Failure in an Interview (And Why It Could Be the Answer That Gets You Hired)

There’s something I’ve noticed more and more lately when speaking with hiring managers. People are trying so hard to present the “perfect” opportunity that they end up avoiding the reality of the role altogether. And I understand why. No one wants to admit their team is stretched. Or that stakeholder alignment is messy. Or that the business is under pressure. Or that the role they’re hiring for exists because things haven’t quite worked the way they hoped. But here’s the thing I always tell clients: The right marketers are not scared of challenges. What they are scared of is being blindsided. The Problem Isn’t the Challenge — It’s the Surprise I’ve worked in marketing recruitment for more than 20 years now, and one pattern has stayed remarkably consistent. Most experienced marketers actually want to solve problems. They want to lead transformation. They want influence. They want complexity. They want to build things properly. What they don’t want is to walk into a role expecting one thing and discovering a completely different reality three weeks in. That’s where trust breaks down early. And once trust is gone, retention becomes very difficult. Why Hiring Managers Hold Back A lot of hiring managers worry that honesty will scare good people away. So instead of saying: “The team needs rebuilding” “The culture has become fragmented” “The business is going through change” “There’s still confusion around marketing’s role internally” …they soften the edges. The job ad becomes polished. The interview process becomes overly optimistic. The challenges get wrapped up in vague corporate language that nobody really understands anyway. But strong marketers can usually sense when something’s being left unsaid. The irony is that trying to make a role sound “safe” often creates more hesitation than simply being upfront. The Best Candidates Lean Into Transparency Some of the best placements I’ve made over the years started with incredibly honest conversations. I’ve had clients say things like: “We’ve had high turnover because the structure hasn’t been right.” Or: “Marketing hasn’t had a strong voice internally, and we need someone who can help shift that.” Or even: “The business is under pressure, but leadership is committed to investing properly now.” That level of honesty doesn’t repel great candidates. It attracts the right ones. Because senior marketers aren’t looking for fantasy-land businesses where everything runs perfectly. They know that doesn’t exist. What they’re looking for is clarity. They want to understand: What they’re walking into What success actually looks like Where the friction points are Whether leadership genuinely supports change And whether they’ll be set up to succeed Those conversations build credibility immediately. Transparency Creates Better Long-Term Hires One of the biggest reasons hires fail isn’t capability. It’s misalignment. Misaligned expectations. Misaligned culture. Misaligned understanding of the role. When businesses aren’t transparent during the hiring process, candidates end up making decisions based on incomplete information. And eventually reality catches up. That’s usually when I get the phone call six months later. The strongest hiring processes create alignment from day one. That means being honest about both the opportunities and the challenges. Especially in marketing, where so many roles today involve transformation, change management, commercial pressure, stakeholder complexity, or rebuilding trust internally. None of those things are red flags on their own. But hiding them can become one. Good Recruitment Should Create Honest Conversations This is actually a huge part of how we work at New Chapter Talent . When I started the business, I wanted it to feel far more human and personalised than traditional recruitment often does. Not transactional. Not overly scripted. We spend a lot of time understanding the real dynamics of a business — the personalities, leadership styles, team culture, internal pressures, and growth ambitions — because that context matters just as much as the role itself. A position description alone rarely tells the full story. And honestly, the more open clients are with us, the better outcomes we can create for everyone involved. That transparency also underpins the broader community work we do through initiatives like the CMO Chapters Podcast , Marketing Leadership Awards, CMO Collective Lunch Club, and the Marketing Mentorship Program. The conversations that matter most in this industry are usually the honest ones. The Employers Winning Great Talent Right Now The businesses attracting strong marketing talent right now are not necessarily the ones with the biggest budgets or the slickest employer branding. They’re the ones communicating clearly. They’re realistic about where they are. They’re transparent about expectations. And they treat candidates like adults throughout the process. That approach creates trust early — and trust is still one of the strongest predictors of long-term retention I’ve seen. Especially in this market. A Final Thought for Hiring Managers If you’re hiring right now, don’t feel like you need to present a perfectly polished version of the role. You don’t need to hide the challenges to attract good people. In many cases, the challenges are the opportunity. The key is being honest enough for the right person to recognise themselves in the role. That’s what creates alignment. That’s what builds trust. And ultimately, that’s what creates longevity. If you’re navigating a marketing or sales hire and want a more transparent, human approach to recruitment, I’m always happy to have a conversation. You can connect with me via New Chapter Talent or reach out directly on LinkedIn .