Clever IT Sales Hack for Asking AMAZING Probing Questions Blog Feature
Dan Fisher

By: Dan Fisher on July 12th, 2019

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Clever IT Sales Hack for Asking AMAZING Probing Questions

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If you're like most sales professionals then you read industry publications to stay on top of the trends, challenges and news taking place within your given industry. In our case that industry is the information technology industry.  And if you're a top performing sales professional than you read what your customers read to stay connected with those Clever IT Sales Hack for Asking AMAZING Probing Questionstrends and challenges.  If you are not currently doing this than I strongly encourage you to quickly adopt this best practice into your daily or weekly routine.

The ability to talk intelligently about the events, challenges and industry drivers taking place in the information technology industry including your customer’s industry and/or product space is one sure way to help you build credibility. And we all need credibility in order to sell value.

I did this throughout my career of selling IT services.  Early on while reading industry publications I learned a clever IT staffing sales hack for asking amazing probing questions.  I'm going to share that hack with you in this post.

Relevant Industry Publications

For sales and recruiting professionals in the IT staffing and consulting space, relevant industry publications include Computer World, NetworkingWorld, CIO Magazine or eWeek among many others. 

IT staffing sales and recruiting professionals should read these on a daily or weekly basis to self-educate and improve their knowledge.  Reading industry publications first and foremost will improve the quality and productivity of both customer and candidate conversations.

Who These Articles are Written For

Keep in mind that these articles are written for IT practitioners, the very IT hiring managers and IT leaders that IT staffing sales professionals are calling on and selling to everyday.  

Why do IT hiring managers and IT leaders read these publications? They read these articles for a few reasons including:

  • Staying abreast of the latest trends, best practices and industry news
  • To gain fresh ideas and insights 
  • To learn from others how to solve their own IT challenges
  • To learn from others how to achieve the same or similar goals
  • To learn from others what pitfalls to avoid

Yes, there is a reason the last three bullet points are in red italics.  Most if not all of the featured articles in these weekly or monthly publications are case studies.  Each case study highlight a specific challenge or challenges a company was having and how they implemented technology and a supporting strategy to resolve the challenge(s).  The case studies always include interviews with the CIO and/or other IT managers talking about their challenges and the steps they took to overcome them.  IT hiring managers and IT leaders read these articles to see what they can learn and apply to their own situation including their team, department or project(s).

One month, on the cover of CIO magazine in big bold letters read: YOUR M&A SURVIVAL PLAYBOOK: Whether it’s a shotgun merger or a planned acquisition, IT can help make it work. Here’s how. The featured article in this months issue went on to explain how IT supports the business during a merger or acquisition.

How many of you are calling on accounts today (prospects or customers) who have gone through, or are about to go through a merger or acquisition?  I think we all have.  Certainly we’ve all heard “I’m really tied up with the acquisition, please call me back in six months.” Haven’t you always wondered exactly what work keeps IT people so busy during an acquisition? 

This article chronicles the “best in class practices” for going through a merger and acquisition and the common pitfalls to avoid. CIO Magazine interviewed several IT executives for their input on how to successfully navigate a merger. They explained the challenges that they had to overcome to complete their own mergers & acquisitions and how they accomplished it.  Here is one sample statement from the article:

CIOs stressed here that avoiding technical obstacles requires clear goals for the combined entity post M&A. CIOs said, for example, old organizations can tree-hug and not want to let go of their favorite system. 

To fix this, CIOs said it is important to set proper expectations with user communities as to what is changing and why ahead of time this is taking place. 

My Sales Hack

When calling on an IT leader in which I know their company is going through a merger & acquisition I can leverage what I read from the industry publication, in this case the CIO.com article and incorporate it into a well designed consultative pain probing question.  My question might sound something like this.

"Mr. customer, we are working with other IT executives who like yourself, are also responsible for leading their IT organization through a merger.  One of the challenges that they're facing is getting their users to let go of their old legacy systems and embrace the future.  What sort of plan do you have in place for addressing this within your organization?"

This question makes me look like an authoritative thought leader.  Yet it was real simple to construct, all I had to do was read the article and convert a couple of statements from the article into the form of an open-ended question. 

This level of questioning gives me credibility and differentiates me from all of my competitors because I can both empathize with my customer’s current situation and I have demonstrated that I understand their critical business issues.  Combining this information (what I learned from reading the article) and this line of questioning opens up sales opportunities that I never even knew existed. 

This my friends, is selling.

Replicate the Sales Hack

Suppose you're calling into “ABC Company” and you know they're implementing Microsoft SharePoint. Do some searches on Google for articles or blogs that discuss "SharePoint implementation" or "challenges implementing SharePoint." In your search results, find a blog that simply lists out one by one the top challenges. Then, highlight the sentences that explains the issues that customers have to overcome when implementing SharePoint.  Next, translate those statements into open-ended questions such as this. Clever IT Sales Hack for Asking AMAZING Probing Questions

Here is an Example: Notice the inset image to the right. This is from a blog post that discusses challenges with implementing SharePoint. Here is how I might leverage that short paragraph into an insightful, thought-provoking pain probing question to uncover a sales opportunity and position myself as a thought leader.

"Jim, one of the trends we're seeing with our other customers who are implementing SharePoint is around data tagging and metadata management.  While the product offers some great features for metadata management including team store and managed navigation, they don't have much effect when users fail to tag data assets. What are your plans for data governance and ensuring users are properly tagging their data?  Perhaps we should get together and brainstorm some ideas on how we could assist you?"

As you can see, you can easily duplicate this method. Remember, the heart and soul of prospecting is not simply the act of making calls, it is the salesperson's ability to identify pain points with their customers to fill the top of their sales funnel with new sales opportunities.  That requires asking thought-provoking probing questions.   Try applying my little sales hack and I think you will find your prospecting to be more productive.

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About Dan Fisher

Dan Fisher is founder and owner of Menemsha Group, a provider of sales enablement solutions dedicated to helping IT staffing firms improve win rates, shorten their sales cycle, and increase revenue per sales rep. Since launching Menemsha Group in 2008, Dan has consulted with over 200 IT staffing firms and has invested over 5000 hours coaching IT staffing sales reps. He’s authored is his own proprietary sales methodology and has previously spoken at Staffing World, TechServe Alliance and Bullhorn Live 2012. Prior to launching Menemsha Group, Dan spent 16 years in the IT industry running local, regional and national sales teams. Dan worked for Kelly Services, Oracle Corporation and Alliance Consulting. Dan currently resides in Boston, Ma.

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