Discovery: Stop What Stops your Deal
~ Guest blog by Mike Slater, Growth Partner at Carlyle Group
If you could have a word with your future self, what would you do in discovery to qualify in or qualify out faster? What would you do to ensure the things that stop your deal from happening are less likely to happen?
This blog is here to give you some tips on what could go wrong and why. The more you explore these in discovery so that you can move on, one way or another, the better. Your future self will thank you.
Jump to section:
- Complex Deals Rarely Follow a Straight Line
- The Question That Surfaces Hidden Risk
- Ask the Whole Buying Group
- Turning Obstacles into a Deal Plan
- Why Sellers Still Skip This Step
- A Practical Habit for Better Deals
Salespeople like momentum.
A meeting goes well, the customer is engaged, next steps are agreed, and another meeting is booked. The opportunity moves forward in the CRM, and everything appears to be progressing as planned.
But moving forward is not the same as being in control.
In many cases, what looks like progress is simply a strategy of hope. Hope that procurement won’t delay things. Hope that budgets remain available. Hope that internal stakeholders stay aligned.
Even very organised salespeople who carefully agree on next steps and even qualify the entire Decision process with the customer often fall into the same pattern. The deal progresses stage by stage, but no one stops to ask a critical question…
“What could stop this deal from happening?”
In complex sales with multiple stakeholders involved, obstacles are not the exception; they are the norm. And the sellers who consistently close large deals are not the ones who hope for a smooth path; they are the ones who actively identify and manage the bumps along the way through constant discovery.
Complex Deals Rarely Follow a Straight Line
Anyone who has worked on large or strategic opportunities knows that deals rarely move in a perfectly predictable way.
- Stakeholders change
- Priorities shift
- Procurement requirements appear late
- Legal or compliance reviews slow things down
In my experience, complex deals, even when successful, often look dead at some point before they eventually close.
Momentum stalls. Communication goes quiet. A new concern surfaces. Something unexpected happens internally on the customer side.
This is not unusual. It is simply how complex buying decisions work.
Salespeople experience these disruptions all the time. Yet many still approach deals as if everything will move smoothly from one stage to the next. They plan the next meeting, but rarely plan for the potential obstacles.
That is where opportunities start to slip or never close at all.
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The Question That Surfaces Hidden Risk
One of the most useful questions a salesperson can ask is also one of the least commonly asked:
“What could stop this deal from happening?”
It is a simple question, but it often opens a far more realistic conversation about the buying process.
Many sellers hesitate to ask it because it sounds negative. They worry it might introduce doubt or slow momentum.
In practice, the opposite tends to happen.
Experienced buyers recognise that complex decisions involve internal hurdles. When a salesperson asks about them directly, it demonstrates awareness and professionalism rather than pessimism.
It also helps the customer think through their own internal process more clearly.
For example, the answer might reveal issues such as:
- Procurement requiring a formal tender process
- Security or compliance reviews
- Budget approvals still needing sign-off
- Internal stakeholders who may challenge the project
None of these necessarily stops the deal. But if they surface late, they can easily delay or derail the deal altogether.
Ask the Whole Buying Group
Another common mistake is asking this question only once, or only to a single contact.
Most sellers rely heavily on their Champion to understand what is happening inside the account. Champions are incredibly valuable, but they don’t always see every risk.
Different stakeholders have different perspectives:
- A Champion may focus on solving the operational problem
- An Economic buyer may focus on financial justification
- Technical stakeholders may focus on security or integration concerns
- Procurement may focus on process and contractual terms
This is where frameworks like MEDDIC or MEDDPICC help. They encourage sellers to validate multiple perspectives, not just one.
When the question “What could stop this deal from happening?” is asked across the buying group, sellers gain a much clearer picture of the opportunity.
Risks become visible earlier, and the deal plan becomes more realistic.
Turning Obstacles into a Deal Plan
Identifying potential obstacles is only the first step. The real value comes from working with the customer to proactively manage them.
For example:
- If procurement will require a competitive process, the salesperson can clarify what that process looks like and how long it typically takes.
- If a security review is likely, technical teams can be introduced early to avoid delays later.
- If executive approval will be needed, the salesperson can help the Champion prepare a stronger business case supported by clear Metrics.
These actions shift the conversation from reactive problem-solving to proactive deal management.
Instead of being surprised by obstacles, the sales team works with the customer to remove them before they disrupt momentum.
This is a key factor in improving deal quality, forecast accuracy and ultimately the likelihood of winning.
Why Sellers Still Skip This Step
Given how often deals encounter obstacles, it is surprising how rarely sellers plan for them.
Part of the reason is cultural. Sales teams are often encouraged to move on - to focus on positive momentum and next steps. Raising potential problems can feel counterintuitive.
But experienced sales professionals know that ignoring risk does not remove it. It simply delays the moment when it becomes visible.
In many slipping deals, the issue was not that the customer changed their mind. It was that an internal hurdle appeared late, and no one had anticipated it.
When risks are surfaced early, they are usually manageable. When they appear late, they often disrupt the entire timeline.
A Practical Habit for Better Deals
Strong sales execution often comes down to simple habits. Before moving a deal forward, take a moment to ask:
What could realistically slow this down or stop it from happening?
Ask your Champion. Ask other stakeholders involved in the decision. Revisit the question as the deal progresses, because risks evolve as the buying process moves forward.
This habit aligns naturally with MEDDIC and MEDDPICC thinking. It strengthens discovery, clarifies the Decision process, and improves deal quality.
Most importantly, it helps salespeople replace hope with informed action.
Because in complex sales environments, success rarely comes from a perfectly smooth journey. It comes from recognising that obstacles will appear, and helping the customer navigate them before they become deal-breaking surprises.
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