Losing Big Deals? Fix These 5 Sales Process Fails

Losing Big Deals? Fix These 5 Sales Process Fails

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.

And I see those same teams wrongly claiming, in deal reviews, that these are the things that killed their deals:

  • 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 less risk and more service coverage.
  • Bad news from left field
    • There was a change in company direction. Procurement weighed in late. Our ‘champion’ was laid off — etc.


All of these are excuses, not reasons. Winning sellers own the outcome. I’ll walk you through it — and how to change your processes to win your deals by focusing on the actions you control.

Table of contents

The 5 real reasons salespeople lose big deals

I have worked hundreds of major deal cycles in my B2B sales career across all the major industry verticals. In a 20-year career, you accumulate your share of losses along the way. The big ones stay with you.

In my experience, there are five key ‘root causes’ of why deals are lost or go dormant:

#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.

#5 Buyer-seller relationship 

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

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

For example, the excuse I shared in the intro, “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
  • the deal was never on, and should have been disqualified earlier
  • we failed to make a mutual action plan with the customer, which would have flagged issues around the need for a business case that was suitable for the CFO (Related: 7 Insider Tips for Selling to CFOs )

As they say: The buck stops here.

Related: Sales Managers: The Reason Reps Don’t Follow Your Sales Process is You

So you own your sales process: How do you fix these issues?

I recommend a two-pronged approach:

  1. A) For immediate impact, anchor your deal reviews in these five areas
  2. B) For long term gain, develop detailed playbooks for each of these five areas

Related: Enterprise Sales Process: Closing Deals In Niche Markets

A) Quick sales process fix: 5-step framework for deal reviews

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

In your deal reviews, ask the following questions:

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?

Related: 3 Discovery Call Questions that Unlock Amazing Potential

3. Mutual action plan

  • Do we have one?
  • Is it comprehensive?
  • Is the customer demonstrably committed to it?

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?

Related: Gathering the Right Win/Loss Data to Transform Your Team

B) Lasting sales process fix: Develop playbooks to drive continuous improvement

For a long-term solution, you should be striving to develop a culture of excellence in these five areas.

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 “playbook” gets thrown around a lot in sales. 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 of tactics and strategy. A playbook is a set of “plays” — discrete actions, such as meetings, phone calls, emails, or other tasks — to achieve an important outcome or milestone as part of the sales process.

A single play should detail:

  1. what needs to be done
  2. why the play is important to advance the sales and buying process
  3. any sales assets that are required to execute the play (e.g., case studies, ebooks, scripts, templates, tools)

Ordered in sequence, the plays form a playbook.

Bonus: Forget Sales Process Stages. Focus on Buyer Decision Points

Example: the qualification 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


Playbook Qualification

Continually track key qualification criteria throughout the sales process


All fields in Salesforce are completed and up to date and validated by the customer


Play # Action Content


Run initial customer call qualification

Phone script, MEDDICC training


Document the metrics

Metrics worksheet, Zoom recording snippets of effective Q&A on metrics


Identify the economic buyer and the champion

Questions to ask to probe for who is the EB. Identifying your champion.


Document the decision criteria

Decision matrix template, decision matrix examples per vertical.


Confirm the decision making process

Key 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)


Implicate the pain

Slide exhibits , video recordings


Confirm the paper process

When to ask. Key questions to ask. Ref Mutual Action Plan


Update MEDDICC fields in Opportunity record

Video 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 a specialist tool such as dock.us or recapped.io.


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.
    • Pro tip: Customers hate starting discovery calls with a “blank canvas.” If you are doing this, stop it now.
  • Running a discovery workshop.
  • 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 an RFP.
  • Curating the final discovery documentation.
  • Getting signoff from the customer.

Note: This is just a starting point. I hope you can see that, fully built out, a playbook provides real depth. (i.e., Your discovery playbook is not a Word doc that lists ten commonly asked questions in a requirements call.)

Related: Seven Process Steps For An Incredible Sales Discovery 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 (PoV) or PoC playbook
  • Final presentation playbook

The PoV is a favourite 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. We sales people love deal momentum and nothing shouts deal momentum like “the customer agreed to a PoC”.

But this is false momentum if we are pushing the project (and yes, a “PoV” is a serious project that demands serious resources) on the customer without clear understanding of the project scope, deliverables, timeline and acceptance criteria by the customer.

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
  • Memorialising the PoV // exhibits and a final report for the customer

Other communication plays you’ll cover in other playbooks

Of course, there are many other moments in the sales process where the customer will require information that needs to be communicated in a clear and persuasive way.

These moments could be covered as plays in other playbooks. For example, 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, and detailed documentation. 

Plus, it requires new players from both sides to get involved — like the CIO, tech analysts, engineers, and legal. This could do with its 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.

Exception! The buyer-seller relationship

The buyer-seller relationship is the one part of the sales process where you don’t need a dedicated playbook.

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. e.g.,

  • 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 introduction to other people in the organisation.

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.

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.


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.

My recommendation to sales leaders is to follow the playbook structure outlined above. Start with a Powerpoint (or Google Slide) deck for each playbook with clearly documented plays, embedded content 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.

Edited by Kendra Fortmeyer @ Sales Hacker 2023

Join Us Today

Insider access to the GTM network and the best minds in tech.

Join Us Today

Insider access to the GTM network and the best minds in tech.

Trending Now

You may also like...