Learn Your Lessons

Article published in Institute of Sales and Marketing Management "Winning Edge"

Let’s face it, if you win a contract, you just want to pop the champagne cork and walk into the sunset with your new client. And if you lose, you probably just want to forget about it. Nobody enjoys a ghastly post mortem. What’s done is done. But hold on, taking time to understand why your proposal was successful or not can make a remarkable difference to your future performance. In fact, I recently met a former student of mine and he was thrilled that introducing a ‘lessons learned’ process had transformed his team’s results. So, let’s delve a little deeper.


A positive mindset


It’s not about blame or ego-stroking. It’s about being positive and constructive for the benefit of all. And it’s important to acknowledge that not all winning proposals are all good and not all losing proposals are all bad. You may have done some excellent things even though you lost, and you may have done some poor things even though you won. The purpose of reviewing each win or loss is to identify the good and the bad in every case.

But there’s no point identifying the good and the bad if you simply record it for posterity and momentary congratulation or criticism. Lessons are only learned if behaviour changes. There must be a watertight way of embedding good practice and eradicating bad practice. This will usually be through a continuous improvement programme championed by senior management; and by championed, I mean a genuine commitment to allow time to design and effect change, and to support its implementation.

If you feel comfortable that you have the right mindset and environment, and that you understand why learning lessons is worthwhile, let’s explore timing.


All in good time


The most valuable improvements come from combined feedback from inside and outside your organisation – seeks views from the proposal team and from the client[i].  However, it’s not practical to hold just one review because:

  • There may be a delay (and possibly a long one) between submitting your proposal and learning the outcome.
  • The internal review will touch on aspects of your organisation you may not wish to share with your client – avoid airing your dirty laundry in public.   

So, as soon as possible after submitting your proposal, get together as a team while events are fresh in your minds. Then, when you know the outcome, arrange a de-brief with the client. Then, bring the client’s comments back to the ranch to compare with the team’s views. Both internal and external feedback then form the basis of the continuous improvement actions as shown in Figure 1.  

Figure 1: Consolidate, compare and act upon internal and external feedback. An integrated view of the good and the bad brings the greatest benefit

The right process


To get the most out of each lesson learnt review, create a routine agenda. Figure 1 works well – it gives enough structure to stay on track without constraining the participants’ input. Looking at the good points first encourages a positive tone.

Develop a checklist of the areas you want people to consider. For example, the planning, the people, the technology, the communication and the governance. These can be useful prompts during the session and can vary for the internal and external versions of the review.

Timebox each session and allocate the time evenly across the agenda points. Plan on thirty or sixty minutes depending on the size and importance of the deal.

Choose the session leader carefully. Whether for the internal or external session, the proposal manager may seem the obvious candidate, but remember (s)he has been heavily involved and emotionally connected. You also need his or her input. A neutral lead may be a more sensitive and effective option. The session leader will follow the agenda, manage time, and ensure each participant has the chance to contribute.

Organise the session to be in person if possible, or use effective communication and collaboration tools if the session is remote. For the internal review, invite everyone that has contributed, whether they co-ordinated, created content, reviewed or approved. For the external review, cast the net as wide as you can.

Remember to take notes and distribute the decisions and recommended actions afterwards. If the actions feed into an established continuous improvement programme, they will be executed and monitored via that process. If not, identify an owner to drive through the changes.

Ideally, you will repeat this for every proposal you submit – win or lose. Which brings us to the nuances of holding lessons learned reviews with your clients in each situation.

Figure 2: A six-step lessons learned agenda. Starting with the positive sets the tone for a constructive session

You cannot be serious!


Although you may just want to forget about a deal you just lost, most of us go through a short adjustment cycle – we experience denial, anger, questioning, despondence and acceptance before we can move on. Getting some answers from your prospect about where you went wrong can help this process as well as improve your future chances.

Think about using the lessons learned review as the first step in winning the next deal, not the last step of a failure. Explain to your prospect that continuous improvement is part of your company philosophy, so their feedback is critical. Set up a formal meeting with a structured agenda, and accept what they say without argument – remember, “perception is reality.” Being defensive or accusatory won’t help. A professional and dispassionate approach will give a positive impression. Aim to conclude with an enquiry about the next opportunity.

Whether or not your prospect grants you a debrief, and the time and way in which they do so, can tell you volumes. A five-minute phone call telling you your price was too high is palming you off. I’ve had many of those, but I also recall being given a whole hour with three senior buyers who provided insightful feedback because they genuinely wanted us to do better next time.  

Don’t forget that your prospect may be emotional about their decision not to select you. They may be embarrassed, in which case making it formal can help. They may be disinterested, which may indicate you have a big hill to climb for next time. Read the signs carefully and you should be better prepared to qualify and win your next campaign.


Hurrah, we won!


It may feel counter-intuitive to start dissecting why you won, but you can find hidden gems in these situations. When you have won, your client feels positive towards you and will want to start the relationship strongly.

Avoid subverting a formal lessons learned session into an informal chat or an agenda item in your project kick-off meeting – this dilutes the importance and detracts from it being a step in your continuous improvement process.

Stick to running a formal review following the formula of what you did well and what you could have done better. Ask them also if there was anything they particularly liked about the competition, or not. This is a perfect time to get that essential competitor feedback.

Whilst it’s entirely appropriate to be delighted and excited to have won, avoid appearing surprised by the decision. Strike a balanced and professional tone: pleased to have won and confident that you should have won, but with the humility to accept that no-one’s perfect.


School’s out


So, we’ve taken the time to understand the value of gathering feedback both inside our organisation and with our clients. We’ve thought about how to get the best out of a lessons learned review and how to make it stick. We’ve considered appropriate action and behaviour as victor and runner-up. And although I have focused on lessons learned as part of a proposal process, it applies equally to any sale you close, any process you follow.

I always counsel that best practice positions you to do your best every time. Life, however, will always conspire to tilt you off course. You will find time and co-operation can run short. Aim to spend time and effort learning your lessons as appropriate to the value of the contract. And if you sometimes miss it altogether, don’t be too hard on yourself, but getting into the habit and staying in the habit will definitely reap rewards. Happy learning.



[1] The term proposal means any formal written offer to a prospect or client. Alternatives names include bid, tender response and quote/quotation.

[2] The term client is used to denote a prospective client, whether you are selling to a new organisation or an existing client.  

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