Stop Blaming the Proposal for a Loss the Relationship Already Decided

Read time: 2 Minutes

Bad news is bad news.

You lost a contract. Unfortunate news.

All the time, energy, and effort that went into delivering the proposal to the customer takes a lot from a company, regardless of your size.

If you did not half-ass the proposal (i.e., throw it together last minute, didn’t know the customer and the customer didn’t know you, had ChatGPT do the whole thing, etc.), you should always know where you went wrong.

It sucks.

Embrace the suck and learn from it.

How you lost it is the more important thing to do when reviewing your losses.

It’s not just reviewing the last step either. Not just what was in the proposal and what was written down and what you can visually see on a piece of paper.

That’s the easy review.

Was this newsletter forwarded to you?

I have sat in more proposal lessons learned (or post-proposal, post-mortem, after-action) reviews than I can count.

And many of them looked the same.

The proposal gets printed out or pulled up on the screen. Someone reads the executive summary out loud. The team goes through the pricing breakdown. The compliance matrix gets marked up. People talk about what they would write differently, what sections were stronger than others, where the technical approach could have been sharper.

And then the next opportunity is already waiting, and everyone moves on.

Everything we just spent two hours reviewing was the last step before we hit submit. We just spent two hours on the last five percent of the lifecycle and called it a loss review.

The real review had not even started.

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Where

A few years ago, my team went after a significant infrastructure project in Northern California.

We lost. On price and on technical acceptance.

We did exactly what every team does after a loss. We pulled the bid document. We broke down the areas where we were noncompliant. We identified where pricing had gotten away from us. It was a thorough, honest review of the document.

I knew we were being too short-sighted. Something was off about this one, and the proposal debrief was not surfacing it.

So I pushed the conversation backward. Not into the proposal.

Into the relationships.

So looking into:

When did we first engage this customer?
Were we on a first-name basis with the right people?
Did the customer want us for this project?
How often were we actually meeting with them before the solicitation dropped?
Did the customer tell us to bid on this project just to tell us to bid on this project, with no real intention behind it?
When did our account plan actually look strong for this project?
Who were our partners on the ground, and were they the right ones?

The room got uncomfortable fast. It’s not personal.

It sure feels personal.

And it should have.

Because what we were doing to the BD team was exactly what the proposal team goes through on every single review.

The gauntlet.

The moment where every decision gets examined and every assumption gets questioned. BD teams are rarely asked to sit in that seat.

The decisions that determined the outcome of that pursuit were almost entirely BD decisions made months before anyone wrote a single word of the proposal.

What surfaced when we went back to the beginning changed how I think about loss reviews permanently.

There were customer gaps we had not addressed. Relationship gaps that, in hindsight, we should have caught and corrected much earlier. Partner relationships in the region that were not as strong as we had assumed. Pricing signals from the customer that we had not acted on when there was still time to adjust.

None of that was in the proposal document. All of it determined the outcome.

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Early

When a gap surfaces early in the lifecycle of an opportunity, you have options. You can pivot the strategy. You can bring in a stronger partner. You can adjust pricing before it becomes embedded in a bid structure. You can have a direct conversation with the customer about where you actually stand before the solicitation process makes that conversation inappropriate.

You can fix the thing while it is still fixable.

When the gap surfaces at the proposal stage, your options have collapsed to almost nothing. You are heads down under a timeline. The team is focused entirely on getting the document out the door. The relationship is locked into a formal procurement process. The partner you should have swapped out six months ago is now baked into your teaming structure. The pricing that the customer signaled concern about in a conversation nobody documented is now on the cover sheet.

The proposal stage is where gaps become permanent. The lifecycle is where they could have been closed.

That realization led us to build a much more structured approach to gate reviews, the checkpoints that happen before an opportunity moves forward at each stage of its lifecycle. Not just reviews of where we were in the pursuit. Honest examinations of whether the relationship foundation, the partner structure, and the competitive position were actually what we assumed they were.

And it created something else that is harder to build but more valuable. A culture where those “I knew I missed something” moments get named out loud before they become a loss debrief.

Gap

Real improvement does not start with the proposal. It starts with day one.

The most emphasis and scrutiny is around the proposal submission, but we cannot forget what was built leading up to this.

This doesn’t just have to be on a proposal; it can be in an environment that leads up to a heavily scrutinized event or opportunity.

I also did this with the professional rugby club here in DC. The most eyeballs were on match day and making sure things went off without a hitch. But the lead-up to the match that week was constantly reviewed by senior management each week.

Ticket sales, sponsorship sales, talking with the VIPs, fan engagement activities, coordinating with Operations, player appearances, media days, practice- the list goes on.

Match day took on a life of its own.

Post-match reviews were mandatory. In person, notes, senior manager had input and recommendations all around a conference table.

Where did we do well, where can we improve? Each week. Document and find areas to improve.

Discipline

Doesn’t matter if you operate at a week-by-week sales lifecycle or a long sales lifecycle; it is critical to review the overall process and not just focus on the one stage that gets the most scrutiny.

The moment this opportunity first appeared. Whether that was a conversation at a conference, a lead through your website, or a relationship that had been building for years before the solicitation dropped. That is where the review starts.

From that point, you map every meaningful touchpoint forward.

Every meeting.
Every demo.
Every person from your organization who interacted with the customer and what those interactions actually produced.
Every moment where your team assumed they had stronger positioning than the customer had ever confirmed.
Every point where the engagement went quiet, and something else filled that silence.

You are not looking for proposal errors. You are looking for the moment the gap opened.

Almost every loss that gets examined properly at the lifecycle level, the gap opened long before the proposal was written. The proposal just made it visible.

The questions that produce real answers are not about what should have been written differently. They are the ones that go back to the beginning.

When did we first engage this customer, and what did that engagement actually establish?
Who from the customer’s side knew us well enough to advocate for us when it mattered?
Where did our touchpoints go quiet, and what filled that silence?
What did the competitor understand about this customer that we did not, and when did they learn it?

Those answers do not live in the proposal document. They live in the full history of the opportunity and sales process. And most organizations never go looking for them there.

So…go look.

Now

The gaps that cost you the last contract did not appear for the first time on that pursuit. They are patterns.

Relationship assumptions that never get verified. Partner structures that get locked in before they are properly evaluated. Customer signals that get noted in a conversation and never acted on. Gate reviews that examine progress without examining foundation.

Those same patterns are present in your active pursuits right now. The lifecycle review of your last loss is not just a retrospective exercise. It is a diagnostic tool for everything currently in your pipeline. If the gap in Northern California opened at the relationship stage, you go look at your current opportunities and ask honestly whether the relationship foundation is actually what your team believes it is.

The loss that already happened is the one that can teach you how to protect the ones that have not been decided yet.

Take your most recent significant loss. Not the proposal debrief you already did. The full lifecycle.

Go back to day one of that opportunity and map every meaningful touchpoint forward to the loss notification. Then answer three questions honestly.

Where was the last moment you had genuine confirmed momentum with this customer, not assumed momentum, confirmed? What happened or did not happen between that moment and the proposal submission that you did not address in time? And what did the winner understand about this customer that your team either did not know or did not act on when there was still time to matter?

The answers will tell you more about why you lost than everything in the proposal debrief combined.

And more importantly, they will tell you exactly where to look on the pursuits you have not lost yet.

See you next week.

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