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Winning mindset: Confronting failure in project management
By Tayyab Jamil

June 17, 2024 | 5 min read

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Written by

Tayyab Jamil

Managing Partner

Tayyab is the Founder and Managing Partner of Firewood. He brings a proven track record in leading large-scale transformation programmes, operating at CxO level. Projects led by Tayyab include a post-acquisition integration at London Stock Exchange Group and a large complex digital transformation at Cardif Pinnacle, part of the global banking group BNP Paribas. Tayyab is also a licensed P3M3 assessor and an associate lecturer at University College London. 

Success is the ultimate goal when managing projects. Obviously, the criteria for success must be defined as people can have different perspectives of success. I, for example, don’t agree that as long as you hit a deadline to a budget to what seems like a good requirement is necessarily a success, especially if you leave a trail of problems in your wake. I believe that what you set out to achieve, must be achieved and regardless of what that is; having a winning mindset is the key to success. 


There’s a lot of talk these days about failure, and how it’s part of success, and that it’s OK to fail, and “failing fast” is cool, etc, especially if you’re backed by billionaires or burn somebody else’s money. I don’t like that mentality. I know that an inevitable aspect of striving for success is confronting failure when it occurs but it’s important to recognise and address failure head-on, without sugar-coating it, or giving yourself a ‘participation prize’. 


Failure isn’t just a pathway to learning; it's a loss, distinct from success. When I play tennis with my friend Louis who I’ve known since secondary school, there's a winner and a loser at the end of our match. Not a winner and a learner. Yes, we both have fun playing the game, will shake hands and then grab a bite to eat, but somebody is hurting (inside and out) and thinking about every shot that should have gone in and what they need to fix, so that they get bragging rights next time! 


Being the greatest of friends, the winner will even share some of their tactics or point out flaws in the other’s game so that they can improve. Similarly in projects, acknowledging failure allows for a more realistic appraisal and handling of project outcomes. Nobody wants to call themselves a loser, in any setting, but I still see senior stakeholders not owning their mistakes and being OK with the loss, so long as it doesn’t look bad on them. This isn’t how winners behave. 


Success also demands identifying the real causes of setbacks. Project teams can fall prey to convenient but inaccurate conclusions, often swayed by internal politics or groupthink or both. True winners seek the underlying reasons for failure and ask challenging questions of themselves, and others, to prevent recurrence. I sometimes get irritated when I hear unfounded and immature analysis being thrown about by those that don’t have a Scooby-Doo about what it actually takes to deliver something. If I go back to my tennis match, it would be like blaming the loss on a gush of wind or an unexpected slip during one point. When in fact it’s more likely to do with fitness, tactics, technique, etc. Things that the individual should have done better. 


Obviously in tennis matches, and in project settings, there can be bad calls (decisions) by the umpire or players being put-off by a spectator or the crowd in general (stakeholder politics). In those cases, it’s important to call it out, either directly yourself or via a senior stakeholder that you know will be fair and tactful. You shouldn’t be a walk-over. I say this because a lot of project and programme managers are afraid to tell their boards what really went wrong because they worry about unfair consequences. In essence, they instinctively know that somebody very senior doesn’t want to hear the bad things that are probably related to their area of control. And I get that people don’t want to make ‘career limiting moves’ but if you’re working in an organisation that would punish you for saying how it really is – then your organisation is run by losers. 


The key distinction I’m making here is that failing is only acceptable if you’ve tried everything you could have, to make something a success. Otherwise, it’s not OK to fail. It’s a loss, and it has consequences and repercussions that you might not care about; and if you don’t care about these things then you’re not a winner. 


I have failed at times. Did I learn from those failures? Yes. Do I also learn from my successes? Yes. Do I treat losses and wins the same? Absolutely not! I hate failing and I love winning. Adopting a positive attitude towards inevitable setbacks is crucial if you work in high pressure, high profile settings. Dwelling on personal shortcomings can be cathartic for a little while and playing the blame game is just what losers do. You should always be learning, whether it’s a success or a failure and once you know what to do better next time, it’s also about letting go. You can’t go back and replay the match or redo the project, so just use these experiences to build resilience in yourself and your teams.

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