The 5 Questions Every IT Buyer Asks Before They Shortlist a Vendor

Let’s look at a typical scenario in IT sales. 

A potential buyer is evaluating vendors for a significant engagement. Your company is on the initial list – maybe through a referral, maybe through a LinkedIn search, maybe because someone in their team came across your content. The buyer’s team spends 20 to 30 minutes researching you online. They look at your website, check your LinkedIn, and read whatever they can find about you.

And then they decide to move on. They don’t share a specific “feedback” or email with you. 

The result? Your company never even made it to the conversation stage.

What happened in those 20 to 30 minutes? What were they looking for? What did they not find?

In our experience at Midas Touch, working with 250+ IT services companies, the answer mostly  traces back to five questions. These are the questions every serious IT buyer asks before they decide whether a vendor is worth a conversation. They may not always ask them out loud, but they are always looking for the answers.

Question 1: “Have You Done This Before for Someone Like Me?”

Before a buyer thinks about your team size, your technology capabilities, or your pricing, they want to know one thing: have you solved this specific problem for a company that looks like mine?

Not a similar problem or a related engagement in a different industry. This specific problem, for this type of company, and with measurable results.

This is why generic positioning tends to damage IT services companies. When your website says “we help enterprises with digital transformation,” you are speaking to everyone and convincing no one. 

If the buyer reading your website is a CFO at a mid-size manufacturing company looking for a partner to modernise their ERP, they are not looking for a company that does everything for everyone. They are looking for a company that has clearly done this before for someone like them.

The companies that consistently make shortlists are the ones that have documented proof -real case studies with named problems, specific approaches, and real outcomes. Not vague testimonials. Not client logo strips without context. 

So, ask yourself honestly: If an IT buyer in your target segment visited your website right now, would they find a clear answer to “have you done this before for someone like me?” If the answer is no, that is the first thing to fix.

Question 2: “Can I Trust These People?”

Shortlisting a vendor is a professional risk. The person championing a vendor internally is putting their judgment and their reputation on the line. If the engagement goes wrong, they will answer for it. 

So before a buyer goes to bat for you internally, they are looking for trust signals. And trust in B2B is not built through advertising or clever messaging. It is built through evidence of consistent, credible expertise over time.

What does that evidence look like in practice?

It is the founder who posts regularly on LinkedIn with genuine insights. They don’t care so much about promotional content or shared articles. They look for original perspectives on problems their buyers are actually grappling with. It is the company blog that publishes educational content that helps buyers think more clearly, even if they never hire you. It is the case study that is honest about what was difficult, not just what went well. 

The question a buyer is asking is not “Does this company seem trustworthy?” The question is “Can I find enough evidence of their competence and integrity to justify recommending them to my leadership team?”

Question 3: “Are They Talking to the Right People in My Company?”

As we know, the average B2B technology purchase involves 13 people across the organisation. The IT Head who is evaluating you has peers, a CFO, business unit leaders, and a management team who will all form views about your company. When your positioning, your content, and your proposals speak only to the technical decision maker, the other twelve stakeholders in the buying group have nothing from you to work with.

Buyers shortlist vendors whose communication is mature enough to speak to multiple audiences. The CFO needs to understand the business case. The procurement team needs to understand your vendor credentials and stability. The business unit leader needs to understand the implementation impact. When your company’s public presence – website, content, LinkedIn only speaks the language of IT, you are leaving the rest of the buying group to form their own impressions without your input.

The best IT services companies we have worked with understand this instinctively. Their case studies have a business outcomes section, not just a technical summary. Their founder’s LinkedIn content occasionally addresses business leaders, not just technologists. Their website has a page or a section that speaks to the business value of what they do, not just the technical features.

It is a small shift in perspective. The impact on shortlisting is significant.

Question 4: “What Makes Them Different From the Other Five Vendors I Am Looking At?”

Think about what a buyer sees when they research five IT services vendors in a single afternoon. Five websites that all say cloud, digital transformation, cybersecurity, agile delivery, customer-centric. Five LinkedIn company pages with similar follower counts and similar content. Five “About Us” pages with nearly identical language about passionate teams and innovative solutions.

How do they choose? Often, they default to the vendor they have heard of most, the one with the most recognisable client names, or the one that a peer recommended most strongly. In other words, whoever has the strongest market presence wins.

Differentiation in IT services is genuinely hard. But it is not impossible. The companies that answer this question well have usually done one of three things. 

  • They have gone deep in a specific industry – becoming the obvious choice for, say, mid-size pharmaceutical companies or export-oriented manufacturers. 
  • They have built a strong point of view on a specific problem – becoming known as the company that has thought most rigorously about a particular challenge their buyers face. 
  • They have a founder with a public voice whose perspective is distinctive enough that buyers feel they know them before the first conversation.

All these things are a result of deliberate positioning decisions, sustained over time.

Question 5: “What Happens If This Goes Wrong?”

IT projects have a well-documented history of running over budget, over timeline, and under-delivering on the original promise. Buyers know this. They have read the reports, heard the anecdotes, and in many cases, lived through a failed engagement themselves. When they are evaluating a new vendor, they are not just thinking about the upside. They are thinking about the downside and who they will be accountable to if things go wrong.

The vendors that answer this question well are the ones that acknowledge the reality of implementation risk honestly in their communication. 

  • They publish content about what makes IT projects fail. 
  • They are transparent in their case studies about challenges they encountered and how they handled them. 
  • Their proposals include a clear section on risk management and escalation processes.
  • Their founder or senior leadership talks openly on LinkedIn about the lessons they have learned from difficult engagements.

In experienced buyers, it builds confidence. There is a significant difference between a vendor who says “our projects always succeed” and one who says “here is how we identify and manage risk, and here is what we did when something did not go to plan.” The second vendor sounds like someone you can actually trust with a high-stakes engagement.

What This Means for Your Company Right Now

Let us connect these five questions to a practical reality.

If a serious IT buyer researched your company today – spent 30 minutes on your website, your LinkedIn, and whatever they could find through a Google search – would they find clear answers to all five?

Would they find evidence that you have done this before for companies like theirs? Would they find enough trust signals to feel confident recommending you internally? Would they find content that speaks to different stakeholders in their buying group? Would they find something distinctive that sets you apart from the five other vendors on their list? And would they find enough honesty and transparency to feel comfortable with the risk of shortlisting you?

For most IT services companies, the honest answer is unfortunately no. 

Your buyers might be asking you for proposals, pricing, and references. But they also need enough confidence to put your name forward in a room full of people who will challenge their recommendation.

Building that confidence is a marketing job. Not a sales job.

At Midas Touch, we have spent 15+ years helping 250+ IT services companies answer these five questions – in every touchpoint a buyer encounters before that conversation even begins. If your company is strong on delivery but struggling to make shortlists, chances are the answers to one or more of these questions are not visible enough yet.

That is a solvable problem. And the good news is, solving it does not require a big budget. It requires clarity, consistency, and the willingness to show your expertise openly. 

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