Selling Managed IT Services? These Three Questions Will Tank Your Credibility Blog Feature

Office Technology

By: GreatAmerica on July 7th, 2022

Selling Managed IT Services? These Three Questions Will Tank Your Credibility

Updated 7/7/22. Originally published 12/12/19.

We attended a Sales Simplicity Seminar presented by Alex Rogers, CEO of CharTec, back in 2017.  Gaining a better understanding of our customers’ experience when they sell Managed IT services motivated us to attend this two-day training session. Initially, we expected the training to bear similarities to our GreatAmerica sales training and were looking forward to getting first-hand knowledge from Alex, who is widely considered one of the best consultants in the industry. But we learned so much more than we anticipated. Alex is energetic and extremely passionate about helping solution providers be more successful. As CEO of his own technology company, Alex has faced many of the same problems as his peers – that's why the two-day seminar was developed by a technology company for technology companies. He is quick to challenge solutions providers to grow beyond a commodities-based seller and become a trusted advisor who can help their customers think critically about their businesses. 

One of the first steps in building trust is to improve the way you ask questions.  

Alex’s training suggests making some small but impactful tweaks to the way you ask questions in your discovery process for better results. Below are three example questions that your sales reps may be asking your customers and some suggested improvements that help you better understand needs and build credibility: 

Question #1 - How Old Is Your Equipment? 

The first thing Alex teaches is to identify and understand what your customer needs. You may want to sell the latest and greatest technology to your customers, but it may not be right for them. 
Better Phrasing: How are you currently using your equipment? 
Alternates: Are there any issues with the technology? Is there something you wish your technology could do? 

Question #2 – Do You Have Anti-Virus? 

With high profile cyber security breaches on everyone’s mind, you need to dig into the current status of their IT security is and how big of a concern it is to them. With some simple phrasing tweaks, you can instead ask a question that may help you uncover vulnerabilities in your prospect’s technology environment that they aren’t even aware of. 
Better Phrasing: How much emphasis does your business place on security? 
Alternates: Do your partners see you as a security risk? Do you have a current process that could be a security risk? What measures are you taking to ensure cyber security? 

Question #3 - Are You Happy with Your IT Person/Provider? 

Sure, they might be happy with them—they might even be friends. What you need to understand is whether the IT solutions they have in place are working.  
Better Phrasing: Is your current IT provider accomplishing what you need? 
Alternates: Is there something you wish your technology provider offered? How often are you in contact with your technology provider? 

RELATED: 3 Signs It’s Time to Outsource Your Managed IT 
You may have noticed a pattern here – the original questions can be answered in one or two words, whereas the suggested phrasing and alternate options prompt deeper conversation. Check out this video from Alex where he explains how to ask questions that build your credibility as you’re selling managed IT. 


Solution providers who have attended this training have found greater success closing deals and building their recurring revenue. By attending the Sales Simplicity Seminar, you gain a proven process for closing As-A-Service business and the confidence to be a trusted resource for your customers.

Register for the July 2022 Sales Simplicity Seminar 

Interested in attending one of these sessions for yourself? If you desire higher closing ratios and more recurring revenue, I highly recommend attending this training. Our next Sales Simplicity Seminar, led by CharTec, will be held in July 2022. To learn more about this exclusive sales training and to reserve your seat, click the button below!  

Register Now


GreatAmerica is the largest independent, family-owned national commercial equipment finance company in the U.S. and is dedicated to helping manufacturers, vendors, and dealers be more successful and keep their customers for a lifetime. A $2.4 Billion company, GreatAmerica was established in Cedar Rapids, Iowa in 1992 and has a staff of over 600 employees with offices in Iowa, Georgia, Minnesota, and Illinois. In addition to financing, GreatAmerica offers innovative non-financial services to help our customers grow.

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