Deal or No Deal: Deal Reviews are the reality check you need

Time for a quick pop quiz. Please be honest:

When you hold a deal review with your seller, what is the purpose of this session?

Option A:  To make sure everything is right in the CRM 

Option B: To quiz the rep to make sure you have the info on the deal, so if
asked, you have an opinion and a roll up forecast.

Option C: To pressure test assumptions; determine gaps in
knowledge; figure out next steps and who needs to be involved; and
ensure that the deal has the right strategy and probability to win.

Sure, you're all savvy enough to pick Option C. So why do deal reviews often feel like a drill in Options A and B? 

💥So let’s discuss a framework to flip the script and make these sessions the secret weapon for success.💥

🤷 Who should be in the meeting:

Multi-threading isn't just for deals – it's for deal reviews too! Get diverse perspectives and open new lines of communication. 

The Sales Rep: Reps are notorious either for having happy ears (meaning any positive thing said means the deal ‘definitely is coming in’) or total sandbaggers so they push every deal to the next quarter so they don’t get caught out forecasting a deal that slips or is lost.  (Note to reps–you think you’re playing a good game but it will hurt you in the long run so quit it.)   

The Solutions Engineer (SE): I can’t tell you how many deals were won because the SE had really solid and separate conversations with their technical counterparts when “sales” wasn’t in the room. Or the SE knew from the offset this deal would never close but was never asked.  The proverbial “second set of eyes” is a massive value.

The Sales Development Rep (SDR): It’s important for an SDR’s learning to include them if possible.  Not only so they can start adjusting their initial outreach content based on how the deals are progressing, but also for their own development into a more senior role.

If you have:  

Sales Ops: Ultimately they work to ensure the forecasting is correct, whether reporting into the CRO or CFO

Others as needed: It may be that the AE knows a subject matter expert can help, marketing to work on stakeholder influence, a senior exec prepping to speak to a counterpart, etc.  

🗯️ What to Discuss:

No history lessons here. Deal reviews are about validating assumptions and planning next steps, not dwelling on the past. 

Before the session:  If you have a qualification framework you use, have details filled in before to guide the discussion. This can be MEDDPICC, SPORTSMAN, CHAMP—it doesn’t really matter.  The point is that the rep has updated it, and everyone attending has reviewed beforehand.


I like to open with the AE giving a brief summary:  

  • What challenge the customer is trying to solve
  • Why your company is best suited to help solve that problem 
  • A quantified view of how big that problem is 
  • When do they need to solve this problem

Also helpful: who they’ve spoken with and who still needs to be contacted. And most importantly, what their plan is with next steps to move this forward.

If there’s an SE, an update here on their view is helpful—additional context to the rep’s content, any additional conversations.

Please make sure to keep this punchy, this isn’t meant to be War and Peace.


Pressure test the assumptions made. For this post I’ll use the MEDDPICC framework but again—use whatever best suits your business.  Note, Enterprise deals are COMPLEX–they don’t often fall into a straight line sales process.  But that’s the point of this session—understand what you do know and feel confident about; find weaknesses in your narrative or deficiencies in who you have been speaking with; and plan for how to best position your company to move forward.

Obviously every part of a qualification methodology is important—but let’s deep dive on three here.

🦸 Champion. If you don’t have a champion in a deal, there’s almost no chance of closing this. Companies now are hyper aware of additional spend, of bringing on even more vendors, and the organisational impact bringing on your solution will entail. If your “champion” doesn’t have all three requirements:  a vested interest; power and influence; and is actively advocating internally for you, they aren’t a champion. They might be a coach–that’s great, you need those too. Champions act, coaches just tell you things. Make very sure you have a champion, and discuss how to test that. The last thing you want at the very end of the process, when you’re negotiating, is to find out you don’t actually have a champion, but your competitor does.

In this selling era, decisions to spend are made by consensus. You need a strong champion who will help you navigate the organisation, actively build support with key stakeholders and ensure you have the right people vocally advocating for your solution over any competition.  – Dave Harper, Sales Director, Celonis

📈 Metrics: Has the prospect qualified the size of the pain, and what the ROI of your solution can be? Hint, creating a business case without input and buy-in from the client isn’t a business case they’ll ever believe, so don’t. You have to work collaboratively with your Champion so they not only believe the numbers, but see the impact that advocating your solution can have.  If you don’t know the size of the pain, chances are the customer hasn’t fully recognised it either. A great sales rep will ask the right questions to highlight how impactful this pain is to the business.

✅ Decision Criteria: If the criteria your prospect is judging you on isn’t unique to you–it’s a commodity:  the whole deal then comes down to price. Enterprise deals are never about price. They are about solving the prospect’s challenge in the best way for them that provides the most value. This is your chance to ask sophisticated questions for them to value your differentiation. Plant landmines that your competition just can’t provide, or where you bring a far better approach. Decision criteria often change throughout the lifecycle of the deal–constantly evaluate and challenge what you think is the case. If you get complacent, a competitor can come in and totally change the game without you ever knowing.

Deal reviews should hone in on validating not just that you have the right assumptions but why—how did you get to them? Who did you speak to? Who might you not have spoken to yet that might have a differing viewpoint? Who might be actively championing your competition and why?  

Really hone in on asking if the rep is confident in their answers, assuming or just guessing. Many, many deals are lost based on assumptions, faulty or old information. Deals aren’t static –things change. 

A key attribute to deal reviews being productive is humility - on both your own part as well as the sales rep.  The rep needs to be humble enough to acknowledge what they’ve done as well as not done - which can include things that may not have been handled ideally.  Gaps in the deals should be welcomed, not hidden from.  Same goes for you - these sessions should not be about you demonstrating your brilliance but helping find ways to win as a team.  
If everyone goes into these sessions with an eye on what can be done to progress the deal (rather than looking back and criticising what hasn’t been done - or done poorly), you’ll find these are incredibly productive sessions.  - Chris Neenan, VP Sales, Civitas Learning

This is also where you can determine when it’s best to bring in other executives or subject matter experts from your side. Enterprise deals are a team sport–not a solo performance.

Deal reviews aren’t meant to be full coaching sessions—but neither are they for you to make all the decisions. Ask the rep about next steps, key contacts still needed, required information, and messaging.  This will also give you an idea of how well that rep is able to orchestrate sophisticated deals and where a proper coaching session might be needed.  Don’t just review–progress.


A deal review without agreed next steps is just ticking a box. These steps need to have dates to be completed with who is responsible, otherwise the same content gets rehashed at the next session.  This isn't a passive exercise; it's a roadmap for success.

🔮 In conclusion:

This framework can and should also be used for post mortems: if you lose a deal and don’t learn anything from that, it’s a double loss. Take the opportunity for your company and your team to understand what went wrong, where false assumptions were made, and where you can improve—sometimes a loss is the best thing that can happen to ensure you win more in the future.

Most of what I’ve written here seems quite obvious. But, oddly, though deal reviews are the area that can help drive momentum, they are usually not done, are done poorly, or are lumped into a full team pipeline review for a quick rehash (see options A&B above).  A great deal review helps move the deal forward, sometimes qualifies the deal out letting you focus your resources and time, and gives stronger predictability and accuracy in your forecast.

Give it a try and let me know how you get on, deal?

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