Why Failure Is a Leadership Skill, and How to Get Better at It
Written by Tara Polley, Realtor and Television Host
Tara Polley is a Telly Award-winning TV host, media strategist, and national speaker with 25+ years of experience in luxury real estate, branding, and storytelling. She helps professionals grow their visibility with clarity, creativity, and an upcoming TedX Talk on purposeful leadership.
Failure isn’t a flaw in your leadership journey; it is the leadership journey. What if your biggest credibility builder isn’t your success, but your stumbles? Let’s talk about how to reframe failure as a skillset, not a scarlet letter, and why your team, brand, and future self will thank you for it.
1. What failure really means in business
Most people treat failure like an off-ramp. In reality, it’s a roundabout—annoying, but it keeps you moving if you know how to navigate it. In real estate, media, and public speaking, I’ve failed publicly, privately, and sometimes in a room full of cameras. It wasn’t a detour—it was data.
Failure, when properly framed, reveals:
What are your values?
How you lead under pressure
What not to do again
Who’s actually in your corner
In fact, research from Harvard Business School shows that leaders who openly discuss failure are perceived as more trustworthy and emotionally intelligent than those who hide it.
2. The hidden ROI of getting it wrong
I once lost a six-figure deal because I ignored my intuition in favor of “playing it safe.” But the lesson? Priceless. It recalibrated how I vet opportunities, and the insight became one of my most impactful keynote stories.
When we talk about ROI, we usually mean revenue. But what about:
Resilience
Insight
Opportunity
These aren’t just soft skills, they’re strategic advantages. And they’re earned, not taught.
3. Teaching others how to fail forward
As a speaker and coach, I’ve watched clients try to perfect their way into influence. But perfection doesn’t scale; honesty does. The leaders I admire most aren’t the ones who’ve never missed; they’re the ones who missed, learned, and still showed up the next day.
Want to lead better? Normalize failure in your culture. Ask:
What did we learn?
What systems failed, not just which people?
How can we turn this into a story worth telling?
4. When failure hurts more than it teaches
Let’s be real: not every failure feels noble. Sometimes, it just sucks. Maybe you trusted the wrong partner. Maybe you lost momentum. Maybe you burned out because you believed you weren’t allowed to slow down.
This is where grit with grace comes in. Leadership isn’t bulldozing through disappointment. It’s making space for it, integrating it, and returning stronger, not shinier. Stronger.
5. Make failure part of your brand (no, really)
Your audience doesn’t connect with your wins. They connect with the moment you almost gave up. With the deal that fell apart. With the mistake that made you more human.
So tell the truth. Not all of it, not all the time, but enough to remind people that growth isn’t a filtered reel. It’s a cycle. One that great leaders keep walking.
Read more from Tara Polley
Tara Polley, Realtor and Television Host
Tara Polley is a Telly Award-winning television host, media strategist, and national speaker with over 25 years of experience in storytelling, branding, and luxury real estate. As a host on The American Dream TV, an Emmy-nominated lifestyle show, she brings California Wine Country to a national audience through cinematic, narrative-driven content. Tara has a TedX Talk upcoming and is known for her dynamic keynote appearances that blend emotional intelligence with actionable strategy. As a proven thought-leader, she helps professionals amplify their message, lead with integrity and authenticity, and build meaningful visibility across media platforms.
