Jay Spielvogel Most sales teams think they’re trying to win deals, to close.
Unfortunately, the reality is they’re coached by management to win prospects over, and it costs them.
A win-over or chase strategy is built around responsiveness and persuasion. The salesperson tries to prove their value at every step, rushing to provide demos, presentations, samples, and proposals.
It feels right. It feels like progress.
But it’s not.
Because it’s built on a flawed assumption:
If we show enough value, the customer will choose us.
Showing value and being responsive are activities that are important, but they don’t win deals. Deals aren’t won by the most “helpful” vendor, they’re won by the team that best navigates the decision process and political landscape.
That’s the difference between winning someone over and winning the deal.
A win strategy requires a different mindset. It’s not just about what the prospect asks for, it’s about what’s required to get to a decision.
This is where most salespeople break down.
- They present before they clarify the impact of the issues.
- They quote before they qualify for the opportunity.
- They propose before understanding the decision-making process.
At Venator Sales Group, we call this “interrogating deal reality”. When this isn’t done, opportunities slip through because the deal wasn’t properly controlled or qualified.
To get your team operating with a win strategy, you must coach it deliberately. Here’s a simple three-part framework:
1. Diagnose Before You Deliver
Win-over salespeople react to requests; they focus on making the prospect happy right now.
Win-strategy salespeople diagnose the entire situation behind the request.
A demo request is not a signal to present; it’s a signal to understand:
- What issues and concerns are driving this?
- Why now?
- What pressure exists from other stakeholders?
- What’s on the line if nothing changes?
At Venator, we emphasize deep qualification before any real “give.” If your team is presenting before they’ve established clear issues, concerns, impact, and urgency, they’re not advancing the deal, they’re just performing.
Manager coaching focus:
Don’t ask, “Did you give the demo, sample or an initial quote?”
Ask, “What did you learn that changes how you’ll win this deal?”
2. Control the Process, Don’t Follow It
Win-over salespeople follow the buyer, providing information as a ‘trusted resource.’
Win-strategy salespeople lead the buyer, shaping the path as a ‘trusted advisor.’
When a rep agrees to “just send a proposal,” they’ve lost leverage. They’ve allowed the deal to move forward without clarity on who will be involved, what are the steps to approval and what roadblocks might derail the deal.
A win strategy requires intentional friction:
- Who else is involved in the evaluation?
- What criteria will be used to determine the decision?
- How do your approval and budget processes work?
- What alternative solutions are being considered?
At Venator Sales Group we teach this principle: every step in the sales process should earn a corresponding commitment from the buyer. No free progression, no exceptions.
Manager coaching focus:
At every stage, ask: “What commitment did you secure in exchange for what you delivered?”
3. Drive a Decision, Not Just Activity
Win-over salespeople optimize for momentum: more demos, more free trials, more proposals.
Win-strategy salespeople optimize for progress: information, access and a decision.
Activity is not progress. Deals only move forward when the likelihood of a decision increases.
That means:
- Challenging unclear next steps
- Questioning the process and timelines
- Disqualifying when necessary
This is where most reps hesitate. Asking tough questions and negotiating the process carries risk. It may create tension; it may even stall the deal.
But that’s exactly the point.
The core Venator principle is that if a deal can’t survive tension and clarity, it was never truly qualified to close.
Manager coaching focus:
Stop tracking output. Start tracking change:
- Is the decision process clearer?
- Is access to power improving?
- Is there a defined path to close?
Teams trapped in win-over mode will stay busy, but inconsistent.
If you coach them to execute a win strategy, you’ll see fewer “great calls” that go nowhere and more deals that close.
Sales Management
