Don't Just Craft Your Success Stories, Get Comfortable Talking About Failures

The main objective when a company reaches out to a public relations firm is to build brand awareness and tell their company story. Business owners spend a lot of time telling the story of how they built the brand, what sparked their idea to start the company and interesting anecdotes and customer testimonials. One thing that many leaders don’t spend time on is telling the stories of what they did wrong — and that is a big mistake. 

I spent more than a decade in the world of journalism, specifically business journalism, covering entrepreneurs and the innovative companies they’ve built. Among the hundreds of leaders I have spoken to, I have asked nearly every single one of them to tell me about their successes as well as their failures. Almost to a person, these entrepreneurs were able to clearly tell me specific examples of success that they, or their company, experienced with colorful details and memorable quotes but when I ask about their biggest failure I was usually met with silence. Occasionally, I’d meet with an executive who was fairly certain they couldn’t think of a single failure either personally or from the perspective of the company — this is usually when I would start questioning the honesty or memory of the interviewee. 

While I understand the reticence to share mistakes, missteps, and even failures, not being prepared for that topic and trying to convince a reporter that your company is free of them draws more concern and criticism than disclosing past errors. And, frankly, a rosy profile about how great a company is just isn’t as impactful or memorable as one where an executive shares some of the chinks in the armor. This is true of all profiles. Flaws make a subject more relatable and believable. 

So, below I have included some guidance on how to prepare for questions about failure and even ways to use those past mistakes to help boost the clout of your leadership and your company.


Whether you have ever spoken with the media about your career or company, chances are you would be able to quickly respond to a lot of the basic media inquiries about how your company started, what problems you are solving for and what is next, but those are softballs. 

What about:

  • What is the hardest part of running this company?
  • How do you deal with customer complaints?
  • Was there a moment when you almost threw in the towel?
  • What is the biggest mistake you made?
  • Why aren’t you doing X anymore?

Those questions can be uncomfortable for those that aren’t prepared to answer them but everyone in business should expect to be asked these sooner or later. So there is no better time than the present to address them. 

Schedule some time alone or with a business partner to really talk about your company’s whole journey and the milestones (both good and bad) and how you would want that story to be told. Don’t shy away from the uncomfortable episodes: instead take the time to write about what went wrong, why you think it went wrong, what you learned from it, and how you are preventing something similar from happening in the future. Be thorough in your initial notes then circle back to them a little later using a public relations lens. Repeat these steps as you go through the whole timeline of your company until you hit present day.


Now that you have notes highlighting various highs and lows from your company’s history, start looking at those lows through a PR lens. Pick one or two easily-communicated scenarios and think about how you can tell a reporter about them. Bringing other people in to brainstorm is helpful here since a fresh perspective can help reframe what might, for you, be a sore subject. 

Think about Steve Jobs and Apple. Both are widely regarded as the pinnacles of success and innovation but have both had extremely public failures witnessed in real life, print, and several movies. 

The humor and hindsight when Jobs recounted in a 2005 commencement speech, “I didn’t see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me” made it far more memorable than if he had just told graduates that hard work leads to success. 

As you draft different ways to discuss past errors don’t forget to:

  • Think about your audience: If you are telling a story to business people, you can likely use business language and tie to larger trends going on at that same time. If you mostly talk to consumers, discuss your missteps in plain speak and with humility.
  • Don’t minimize failures: It may feel necessary to diminish bumps in the road but you run the risk of sounding dishonest or like you are hiding something. If you are going to talk about failures, speak plainly and honestly as you would to a mentee or fellow business owner and truly own those mistakes.
  • Attitude is everything: How you retell your failures is also critical. For some, they default with earnestness. For others humor comes naturally. A reporter writing about your company and the readers that will later read or listen to your responses are far more likely to endear themselves to you if you approach your responses with very human and relatable emotions.


Like any narrative, you will deliver your story more clearly each time you tell it so don’t expect that an hour of jotting down notes will be all you need to do, but it will help. In addition to building a more honest, complex narrative for consumers, you may also become known as a good interview subject which can help lead to more earned media and opportunities to tell your story. Good stories need to be told and, hopefully, these suggestions will help you get comfortable telling yours.

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Post Author

Krystal Peak
Krystal was a senior account executive at Gravitate PR. Prior to joining Gravitate, Krystal held various marketing/communications roles at startups. She started her career in journalism, working for publications including the San Francisco Business Times, Silicon Valley Business Journal, and many others.

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