A former colleague called the other day and was utterly devastated over losing a big sale.  This was an important deal for him personally, and for his company. He was beating himself up over the loss and feeling like a failure.  No one wins every deal, so the best prevention against loss is to make sure you are paying attention to the details.
We did a little post-mortem analysis of this sale (an exercise that is both painful and highly valuable) and discovered several issues my friend failed to recognize in time to save the deal:

1.  There were more decision-makers in the cycle than my friend was aware of.  

This is extremely common reason complex sales fail to close.  As marketers, we spend a large amount of time understanding all the people might be in the buying cycle, and what their motivations might be.  We create content that aligns to their needs since people are incapable and unwilling of sorting through all of your content to find the one thing that applies to them.

In this case, the user buyer was influential and had budget, need and urgency, but did not have the economic buyer on board.  It's a red flag to me if the buyer is not willing to make introductions to other people who have influence or decision-making authority in the process.  Keep in mind how risk-adverse buyers are these days; they don't want to risk offering your solution to their company unless they have 100% confidence that it's necessary and beneficial.  Help the buyer build confidence with verifiable facts.  Offer guarantees if you can.  Offer free trials if your product offering supports that.  

Note on trials:  In a complex sale, never throw a trial over the wall with the hope the prospect will figure it out, see value, share results with their colleagues and drive your sales deal for you.  Assign someone to work with them, train them or provide whatever support is necessary for users to feel successful and come to their own conclusion that your product adds value. Make sure you go into a trial knowing how success will be measured.

2.  Several parallel efforts were underway in the prospect's organization to solve this problem.

The user buyer failed to understand that other people in his organization were also shopping for solutions.  This could have been avoided by involving the economic buyer early in the sales process to determine if it was possible to complete a sale, if the other vendors were offering something more compelling or if some creative packaging of the deal would have made it more appealing.

3.  The seller had failed to properly understand the use case the buyer had in mind.  

With a more complete understanding of the business and technical issues causing pain to the prospect the seller could have offered more relevant content related to the use case.  In this sale, the prospect saw a number of case studies how this product was used by other clients, which caused some confusion on the part of the buyer and the other people in the sales cycle.  The economic buyer ultimately thought the product would have to be "bent" to meet their needs.  Have the prospect walk you through their pain and processes.  Make sure the use case you offer deals with these issues, and only these issues.  More content is not better in this case.  You must offer specifics and resist the urge to pile extraneous content the prospect.

4.  A couple of strategic missteps.

Early in the sales cycle, the buyer was asking for references, use cases and documentation.  This is always a red flag that you are either not talking to the right person or that another agenda is afoot.  Sometimes the prospect is trying to learn as much as possible to educate themselves, sometimes they are looking for solutions to problems without having to buy anything.  These signals don't mean you can't make a sale, but they do indicate that you need to be strategic about how you manage the opportunity.  I'm all for buyers educating themselves, I just want salespeople to add value during this part of the cycle.

After this deal had been on the sales forecast for four months, the sales manager instructed my friend to try to motivate (bully) the prospect into an end-of-quarter close.  Nothing is more irritating to a buyer than a salesperson trying to push his own agenda.  Your prospect doesn't care if you need to meet quota, if it's the end of your quarter (unless you are offering a huge discount on something they've already decided to buy anyway.) Appearing desperate in sales is never a good idea; it undermines your credibility and puts you in a position of weakness.  Put more deals in your funnel and provide the support your prospect needs to close on their schedule.  In this case, the average sales cycle is nine months and pushing for a close before the prospect was fully engaged was a major strategic error.  It spooked the prospect and they ended up buying another vendor's product.

Post mortem exercises like this are valuable for training.  In a perfect world, this is an exercise that sales and marketing would conduct together.  It should be an experience of trust, looking for someone to blame is pointless since the entire company lost.  Looking for ways to do better is positive and motivating.  I know my friend will not make these mistakes again.  

What's happened in your sales life that you wish you had reacted to earlier?