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Learn from Losing

5/9/2026

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Last weekend I played, and lost, a tennis match. It was only a club handicap tournament so hardly Wimbledon and the other pair were better, so we deserved to be defeated. Nevertheless, losing any game in sport still rankles a bit. However, it made me think of the parallels with professional life. For example, a significant part of my work as a lawyer is acting for clients in-house or in private practice during the process of bidding as a potential supplier for an IT outsourcing service contract. These can be very intense periods in our work preparing for the process, submitting several offers, participating in extensive negotiations, refining the draft contract and creating and delivering a final tender. This can go on for 6 to 18 months and during this time subsume a large part of our working lives. We typically become, or certainly should, as lawyers and commercial or procurement advisers, critical members of the bid team often working long hours in client offices or at customer premises. Close working relationships are established with others at your client and indeed the customer. Statistically however, whoever our client may be and no matter how experienced and competent the team no business can win all of the bids it competes for. So, when you get that dreaded letter saying you have not been down selected for whatever reason it is to say the least an anti-climax and a failure and all the hard work appears at first sight to be wasted.
 
However, I suggest this is the wrong way to look at it. In sport at any level if you lose you try to work out why and strive to play better next time. In business valuable lessons can be learned from a failed bid to enhance the chances of future success. Instead of despair we should rather find ways to learn from losing. Key relationships in your organisation created during the process can be fostered and improved for next time. Analysis of the process including seeking honest and open feedback from the would-be customer improve the chances of success on the next bid. For example, sometimes you lose because your bid price is too high, sometimes because your technical solution is not considered viable, but also perhaps because the customer decides not to take any risk and stay with an incumbent supplier. Each can be considered in the context of continuous improvement.
 
AI suggests that “Key lessons include securing detailed, honest feedback, analysing competitor pricing and strategy, and ensuring the submission focused on solving the client's problems rather than just listing company features.” This last is really important. I have seen clients convinced their “standard” solution was what a customer wanted, when in reality it was far from meeting expectations. See this short but to the point blog  Win-Loss Analysis: How to Learn from Every Tender Outcome which observes “Understanding the outcome of a tender—whether a win or a loss—can be one of the most powerful tools in your bidding strategy. Yet, many organisations move on too quickly, failing to extract the valuable insights that come with a structured post-bid analysis.” It proposes a post bid audit including an internal debrief and seeking client feedback.
 
While this more detailed Harvard Business Review article How to Learn from a Failed Negotiation suggests we should avoid protecting egos and reputations, blaming others, (does that resonate!) and instead “step back, take ownership, and invest time and energy in understanding what went wrong so they can do better in the future.” It cites a book on the topic Getting Back to the Table and proposes you should first understand the reasons for failure which could include:
 
  • Failure by design – expecting to fail.
 
  • Not reaching agreement when it was possible.
 
It then proposes Five Steps to Improvement such as:
 
  • conduct a deep dive and analyse what happened and why
 
  • pinpoint and fix your weaknesses that contributed to the failure
 
  • come back to the table with confidence.
 
See also this Forbes article How To Reflect, Learn And Win After Losing A Contract which sagely observes that “Losing contracts is part of doing business. And, unfortunately, most organizations lose more contracts than they win.” It proposes three steps to improve performance and answer the question “Where did we go wrong?”
 
1 Politely request a debrief from the client to see what you could have done differently, or better, to win the contract.
 
2. Rereview your proposal through the eyes of the client.
 
3. Schedule a postmortem meeting with your team. 
 
I think we often forget that it is very much in our would-be customer’s interest to provide effective and meaningful feedback as this enhances the chance of improving competition in the market for future bids. I would recommend perhaps using somebody in your business not involved with the bid as this removes any lingering emotions and enhances the opportunity for full and frank feedback. 
 
I would also add that winning is not necessarily a recipe for success. I recall some successful bids where our clients won but then really struggled to deliver, especially in IT projects intended to transform existing services. Believe me there is more pressure on a team that fails to deliver what transpires to be an onerous contract than one which loses a bid. There are lessons to be learned here like listening to doubts about the viability of the solution expressed during the final contract governance process, but ignored in the excitement of the bid process and the momentum built up in favour of submitting without any qualifications.
 
As we rightly applaud winning, we should also celebrate the successful conclusion of a bid process, even if not down selected. It is obviously not the desired outcome, but the experience and lessons learned are valuable and should be recognised and applauded. When I managed my son’s youth football team some years ago, we went a whole season without winning BUT the team learnt, got fitter and better – and next season we started winning. It is as the saying goes as much about the journey as reaching your destination.
 
Nick Saban, the US college football coach said, “Never waste a failure.”
 
While Bill Gates observed “Success is a lousy teacher. It seduces smart people into thinking they can’t lose.”
 
And returning to tennis and a great quote from Venus Williams, one of the most successful tennis players of all time. “Losses have propelled me to even bigger places, so I understand the importance of losing. You can never get complacent because a loss is always around the corner. It’s in any game that you’re in – a business game or whatever – you can’t get complacent.”

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