The Top 5 Sales Process Fails that Kill Million Dollar Deals

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According to Gartner, 88% of salespeople are faced with unexpected events or situations that aren’t covered by their sales process. Meanwhile, 77% of buyers found their last B2B purchase to be highly complex or difficult.

So, it’s not surprising that sales forecasting feels like a guessing game for many sales leaders in B2B – especially on larger, complex deals.

With 2022 almost done, it’s worthwhile to take a look at the big deals in the pipeline and how your team performed.

When you look back on the year, what were the key reasons cited as the root cause for deal losses in 2022?

My guess is that the types of issues that are cited for losses can be categorized into the following problem areas:

Product functionality gaps

“The winning vendor’s solution included critical functionality that we don’t have. We were weak on some key functionality areas where the winning vendor was strong.”

Price gap

“We were too expensive. The winning vendor came in at a much lower price. The gap was too big to bridge. The customer didn’t even think it was worth negotiating.”

Company capability gap

“We are a smaller player. The buyer chose to go with a bigger company with more credibility (less risk), more service coverage etc. We also came across the ‘800 pound gorilla’. That is, the customer was super keen to go with us, but at the end of the day, it was too big an ask to switch vendors from the 800-pound gorilla to the challenger.”

Bad news from left field

“There was a change in company direction ;procurement weighed in late, our ‘champion’ was laid off, etc”

Five reasons why big deals are lost

I was having an end of year beer with a VP in the Enterprise Sales space and he neatly described all of the above as “folklore”. They are not ‘root causes.’

Let’s take a look at the five key ‘root cause’ drivers. The real reasons why deals are lost or go dormant. They are listed below in no particular order:

#1 Qualification process

We didn’t qualify the opportunity fully and continuously throughout the deal cycle.

#2 Discovery process

We didn’t dig deep enough in the discovery process

#3 Mutual action plan

We didn’t secure customer commitment to a timeline to design, approve and implement the solution

#4 Communication execution

We didn’t deliver persuasive communications at crucial moments in the buying process. This could have been the final demo, a presentation to the vendor selection team or it could have been the accumulation of smaller sales moments throughout the process or even a failure to respond clearly to some key customer information requests.

#5 Buyer-seller relationship

The relationship didn’t ‘gel’. The customer wasn’t super responsive. There was a lack of trust between both parties. Perhaps the customer never liked the Account Executive.

Note that the ‘folklore’ reasons cited previously were all issues that are largely external or outside the field of influence of the sales team. They fit in the “not our fault” category….

Winning sales leaders fully own the outcome.

These five root causes are ultimately failures of the sales process and sit within the field of control of the sales team.

For example, “our price was too high” could be the result of

  • an ineffective Discovery process that didn’t uncover enough ‘pain’ to justify the price tag for our solution
  • maybe the deal was never on and should have been ‘qualified out’ earlier
  • maybe a mutual action plan with the customer would have flagged issues around the need for a business case that was suitable for the CFO

What to do about it

It’s all about the process. Not the personalities.

We are going to lose deals.

We are going to have deals that go dormant.

A deal review is not a blame game. It’s an opportunity to learn.

You can focus on continuous improvement precisely because these five areas of the sales process are within the sales team’s circle of influence.

Recommended actions on Deal Reviews

The five areas provide a framework for digging deeper into potential red flags and opportunities on deals

#1 Qualification

How does the deal measure up using our qualification methodology now? Not just when we first met the customer. What does this measurement tell

us about our strengths and weaknesses in the account and likely actions to take.

#2 Discovery

Review the discovery documentation. Are we uncovering real insight that allows us to differentiate and create superior value – or are we going through the motions. Has the customer (all relevant stakeholders – not just one person) validated and agreed to the findings in our discovery?

#3 Mutual Action Plan

Do we have one and is it comprehensive? Is the customer demonstrably committed to it? Or are they missing key dates and deliverables?

#4 Communication Execution

Are our communications on brand and persuasive? Are we quality checking all content shared with the customer? Are we diligently role playing and rehearsing for the big moments?

#5 Buyer-Seller Relationship

Where is the customer relationship at? Are there any personality clashes to be addressed? Do we need to make tactical changes to the team players and roles? Are there issues on the buyer side that need to be addressed?

Recommended actions for continuous improvement

You should be striving to develop a culture of excellence in these five areas that will make or break your big deals in 2023.

The way to do this is to develop a “playbook” or “sales play” for each key area of the sales process and enable your sales team with easy access to the playbook, customer content, ongoing training, micro learning and sales coaching.

What is a Playbook?

This term gets thrown around a lot. People have different definitions ranging from something as tactical as a Phone Script through to a full “end-to-end system” for converting leads to Close / Won.

My view is that a Playbook sits in the middle. A Playbook is a combination of a set of “plays” to achieve an important outcome or milestone as part of the sales process.

A “play” is a discrete action such as a meeting, a phone call, an email or some other task.

A single Play should detail what needs to be done and why the Play is important to advance the sales and buying process. The Play should also include, where applicable, sales assets that are required to execute the Play. For example:

  • Buyer engagement content such as slides, case studies, ebooks etc
  • Sales support content such as scripts, templates, tools, micro training content, video examples etc

The Plays are ordered in sequence to form a Playbook. To drive continuous improvement, you need to be continually developing and reviewing Playbooks in each of the five areas.

Below, I have provided a detailed example for the Qualification playbook and guidance for what would go into other playbooks. Qualification Playbook The example below is based on using the MEDDICC qualification methodology.

You can build out your own unique playbook depending on what works for your business. The key point here is to enable your team with:

  • Clear goal and KPIs
  • Clearly actionable tasks to perform throughout the sales process
  • Useful content that will assist the sales team
GoalTo continually track the key qualification criteria throughout the sales process.
CriteriaAll fields in Salesforce are completed and up to date and validated by the customer.
Play #ActionContent
1Run initial customer call qualificationPhone Script, MEDDICC Training.
2Document the metricsMetrics worksheet, Zoom recording snippets of effective Q&A on metrics.
3Identify the economic buyer and the championQuestions to ask to probe for who is the EB. Identifying your Champion.
4Document the decision criteriaDecision matrix template, Decision matrix examples per vertical.
5Confirm the decision-making processKey questions to ask, What to say when the customer says they “don’t” know, Mutual Action Plan, Questions to flesh out special compliance criteria (eg SOC2).
6Implicate the painSlide exhibits, Video recordings.
7Confirm the paper processWhen to ask. Key questions to ask. Ref Mutual Action Plan.
8Update MEDDICC fields in the Opportunity recordVideo run thru of using Salesforce re MEDDICC.

Mutual Action Plans

An effective playbook for Mutual Actions Plans should cover these plays (at a minimum)

  1. Understanding the importance of Mutual Action Plans in the buying process
  2. Pitching the MAP to the customer early & at the right time in the process
  3. What to do if they say no or aren’t engaged
  4. Set up the Mutual Action Plan
  5. Tips for running the MAP

The Playbook will reference the MAP template, a Go Live plan and ideally a tool for housing your MAP so that the customer has live access. This could be Google Drive or maybe you are using a specialist tool such as or


The Discovery playbook and the Qualification playbook will necessarily reference each other. A solid Discovery playbook will dig into plays such as:

  • Leading the customer during the Discovery process (customer’s hate starting discovery calls with a ‘blank canvas’; if you are doing this – stop it now)
  • Running a discovery workshop, agenda template, Discovery slide deck
  • Open questioning techniques to dig deeper on the broader business drivers that might impact the buying process and the solution design
  • A worksheet for running discovery on functional requirements
  • Managing technical requirements and meetings with their technical buyers – Managing a RFP
  • Curating the final discovery documentation
  • Getting sign off from the customer

This is just a starting point. I hope you can see that a Playbook provides real depth. Your Discovery playbook is not a Word doc that lists ten commonly asked questions in a requirements call.

Persuasive communication

This might be split into a number of core playbooks that cover the “high stakes” moments in your sales process. For example:

  • Product Demonstration Playbook
  • Proof of Value Playbook
  • Final Presentation Playbook

“PoV” is a favorite of mine and a good case for why a robust playbook is crucial. In my experience, there is a natural tendency for PoVs (or POCs) to be ‘pushed’ on customers. They become an exercise in “throwing darts” with ongoing demo configurations. This is done in the hope the customer will be persuaded due to the sheer weight of effort by the vendor.

A robust playbook enables the sales team with clarity on:

  • When to do a PoV and why it’s important
  • How the PoV links into the Discovery playbook & MAP
  • Actions to properly scope a PoV
  • Actions to engage your champion during the PoV
  • Demonstrating the PoV
  • Memorializing the PoV // exhibits and a final report for the customer

Other Communication Plays

Of course, there are many other moments in the sales process where the customer will require information and it needs to be communicated in a clear and persuasive way. These moments could be covered as Plays in other Playbooks eg. “FAQ during a Discovery meeting” would be a Play in the Discovery playbook..

Think about the high leverage aspects of your sales process. Maybe you sell a SaaS where technical compliance is an absolute make or break item of the decision criteria. It’s a process that typically requires multiple meetings, significant Q&A, detailed documentation and requires new players from both sides to get involved (eg CIO, tech analysts, engineers, legal).

This could do with it’s own unique Playbook. Finally, think of each Playbook as a core competency where your sales team needs to strive for excellence. Each stage in your sales process should detail at least one Playbook (in my experience 1-3 seems about the right number).

The Buyer Seller Relationship This area of the sales process is the one case where you don’t have a playbook(s). But you should be ensuring the sales process details various plays throughout. For example, on the introduction call as part of the Qualification playbook, you need a Play that is focused solely on the customer(s) on the phone / Zoom call.

Researching their profile and socials prior to the call. Studying their buyer persona. Giving yourself the best opportunity to make a connection with this person(s) and to be able to seek an introduction to other people in the organization.

The Discovery playbook should also include a Play for making sure that new people on both sides are properly introduced and connected into the process.


Too often, I see sales teams thinking of their “sales process” as a set of Stages in their pipeline and maybe a bunch of fields to complete at each stage.

Likewise, there might be a slide deck or word document that provides more detail on how the process should work. And there’s a bunch of content files on Gdrive or Sharepoint.

My recommendation to sales leaders is to follow the Playbook structure outlined above. Start with a Powerpoint (or GoogleSlide) deck for each Playbook with clearly documented plays, embedded cogent and links to Content and buyer engagement assets as needed.

There are some inherent risks and constraints with taking this approach if you are serious about driving for best practice in this space.

There is now an extensive category of Sales Enablement tools that provide deep capability in the area of content management. Products such as Highpot, Seismic, Showpad, Mindtickle, Brainshark and more.

My company SalesGRID aims to bring Content enablement and Process enablement together so that you can codify and collaborate on the key Playbooks and content in your sales process.

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