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Star Leadership is also about Finessing Failure

Failing Intelligently and How it’s Better than Success
What can I do with my Failures at the Workplace?

In the endeavor for success, not failing is never an option. Success without even a bit of failure – if it would have existed at all, would have made that success taste so much less sweeter! Therefore, just like most things out there, failure is not just inevitable; it has a purpose, and is therefore valuable.

The word failure is one that carries automatic negative connotations, and does not really apply to what happens in real life. Generally, some events are regarded as failures, we figure out who or what to blame and then conclude what we should do differently from now on. As this HBR article mentions, IDEO, the design and consulting firm decided to see how they could potentially deliver the service of coming up with new lines of innovative products for their customers. Till then they were only involved in coming up with products in existing lines, but they tried their hand at this service with a mattress company on a small scale. After “failing”, they knew what they had to do for delivering the service and made new teams which involved managers from customer companies and their own employees. Today more than a third of IDEO’s revenues come from this strategic innovative service. This is because they gained the right insights from doing the right things and applied it!

What are You Really Failing at? 

One of the greatest truths of life has been very eloquently put down by Francis Chan – “Our greatest fear should not be of failure but of succeeding at things in life that don’t really matter.”

Before you fear failing and worship success, know what exactly you’d be failing or succeeding at. Is the task even worth it? Do you love what you do? Does the task matter to you, or is it just the concept of success or winning that you find alluring?

Leaders and executives may benefit from a competitive spirit but it’s not always exercised in the right direction. A good example of this is the sunk cost fallacy. We often keep spending more time and resources on projects that are not giving any good returns or even learning because we cannot accept that it failed and keep delaying shutting it down. We have to learn how to let go, be glad that we avoided a bullet and try other things which may be more prudent. Instead of giving into this insight, we keep doubling down on something that doesn’t work or can’t benefit us and feel like it’s doomed for failure. 

Failing vs. Failure

We differentiate between failure and failing. They say it’s the act of not getting up after failing that makes you a failure. It doesn’t matter how many times you fall – you fall seven times, make sure you get up eight!  Whether you think you’ve failed a couple of times, and you still have at least four more times to fail to be awarded the official title of a failure; or you think you’re never going to get yourself associated with the word ‘failure’ – the point is, it is okay. 

This Forbes Article reviews the process of design thinking: how instead of trying to come up with that one solution which turns a failure into a success, keep deviating from normal processes a bit more every time, fail continuously in small amounts but keep improving designs with the learning every time. This is how we can be okay with tolerating failure and encouraging innovation and end up gaining exponentially much more in the long term than we lose in the small failures along the way. 

The Awkward Failure Conversation

The problem with being okay with failures as most managers would expect is that they might okay problematic behaviours and encourage lax behaviours from employees. The way we approach failure itself is awkward and unhelpful to learning from it. Either we blame someone or something so that we can directly conclude how to not fail, or we feel uncomfortable talking about it and bringing it up. When failures are seen as inevitable and something as a part of the process, it enables a third option: admitting to mistakes, talking about it openly and understanding the layers of problems which occur. It’s not just the employee who maybe made a mistake in calculations, it’s also about the long hour-shifts that the manager put forth which made mistakes like this more possible. Insights are therefore not constrained to one thing or one person, it’s about how the system works and being cooperative in making it better, not just correcting one action. 

Impact on Leadership

Treating failure the right way is how you win the war by losing a few battles. By trying to avoid failure, companies often lose out on relevant information which can help them succeed better. One example of this is how pilot projects are often simulated with ideal customers, services and top-notch implementation. Obviously the project will have more chances of success, and we end up generalizing too much from that success which will not apply to real life. The pilot project should reflect real conditions: customers who will be confused about the product/service, demand for it in inaccessible places, basically difficult situations so that you learn what exactly to fix even if the pilot project goes wrong. That is how you lose out on the small scale to gain big when it’s time. 

Star Mindset

Leaders who are privy to this secret of failure-success dichotomy being false go beyond the immediate “cause” of failure such as procedural deviations and go for explanations which are more systemic. It’s not just about the one employee or group, it’s about how instructions are conveyed, how departments communicate and what are the different stages that small problems accumulate over before one big thing happens. Sadly, the dominant culture is to instead find one causative element and take decisive action against it. 

What you as a leader can do instead is to observe more and reflect over it. This helps avoiding a straightforward view of blame and instead learning what must be done for success. Often, the way to realize how you can produce such circumstances is to fail intelligently and fast. By doing the correct experiments and taking the right risks, your learning and therefore subsequent steps are better, rather than playing it safe and learning nothing. 

3 Immediate Actionable Steps

  1. To catch mistakes before they accumulate, you can make reports be colour coded in green, yellow and red. This is a common technique where green means there is nothing to worry about, yellow is caution and red means there are problems. 
  2. Rotate the responsibility of being the devil’s advocate in your team across different meetings. One person will be tasked with and praised for finding faults and deliberately going against what is being discussed.
  3. When a meeting reviews a failure, make a visualization of the narrative of failure. This should include what was the context, what were the sequence of events and what were the tipping points. 


Failure is an important concept – far too important for you to waste it on something that you don’t care for. And to do that, the only way is to not take it too seriously. Similarly, success is too happy a concept – almost a fleeting one. The way to enjoy it is to just let go of the fear of losing it. So take every success and every failure in your stride, and move on forward like the star you are! #BeTheStar


Do you think talking in terms of failures and success undermines the spirit of a team as well as leadership? I love learning from my readers. Please do share your thoughts!


  1. Edmondson, A. (2011, April). Strategies for Learning from Failure. Harvard Business Review. https://hbr.org/2011/04/strategies-for-learning-from-failure
  2. Whysel, B. (2019, January). Failing To Succeed: Use Design Thinking To Improve Your Strategy. Forbes. https://www.forbes.com/sites/brettwhysel/2019/01/22/failing-to-succeed/

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