How to Create a Winning Sales Playbook for Your Team
- Matthew Earle
- Feb 28
- 2 min read
Updated: Aug 20
Your IT Sales Team Need Help Closing
Why IT Sales Teams Struggle to Close Deals (And How to Fix It)
Your IT sales team need help closing. In the fast-moving world of IT sales, many teams find themselves stuck in the same frustrating cycle—engaging prospects, running solid demos, sending proposals… and then silence. No response. No deal.
Why does this happen? And more importantly, how can you break the cycle?
The Real Reason Deals Stall in IT Sales
Many IT sales teams assume deals are lost due to price, competition, or bad timing. While those factors play a role, the real problem is often a lack of urgency from the buyer’s side.
In B2B IT sales, decision-making is complex. Multiple stakeholders, long procurement cycles, and competing priorities make it easy for deals to slip into the abyss. If there’s no compelling problem driving immediate action, your solution—no matter how great—gets deprioritized.
3 Common Mistakes IT Sales Teams Make
Focusing Too Much on Features IT sales reps love to talk about cutting-edge features, integrations, and technical capabilities. But buyers don’t buy features—they buy solutions to problems. If you’re not tying your offering to a business-critical issue, you’re giving them no reason to act now.
Assuming the Buyer Sees the Problem Just because a prospect takes your meeting doesn’t mean they recognize the full impact of their problem. If you’re not helping them quantify the cost of inaction, you’re making it easy for them to do nothing.
Selling to the Wrong Stakeholders IT decision-makers are rarely the final say in major purchases. If you’re only engaging with technical buyers and not influencing finance, operations, or leadership, you’re missing a key part of the deal-making process.
How to Fix It: Problem-Centred Selling
Instead of leading with your product, shift the conversation to the problem. Here’s how:
Diagnose the real issue – Before pitching, ask deeper questions: “What’s the impact of this on your business?” “What happens if this isn’t solved?”
Quantify the cost of inaction – Show them what staying the same will cost in wasted resources, lost revenue, or increased risk.
Get to the right people early – Engage not just IT, but also business decision-makers who feel the pain in their budgets and KPIs.
Shift from vendor to trusted advisor – Stop selling a solution, start helping them solve a problem. Position yourself as the expert who can guide them through the decision.
Final Thought
In IT sales, no problem = no sale. If your deals keep stalling, take a step back and ask: Are we really uncovering the urgent problems that drive action?
Ready to stop chasing deals and start closing them? Let’s talk. [Book a call with The Selling Collective today.]
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