Ask Your IT Prospects These Simple Questions

When it comes to social selling and cold prospecting, it is now somewhat common knowledge that taking it slow is actually the faster route to conversation. If you were at an in-person networking event, you wouldn’t walk up to someone and immediately start pitching them your services without some way to break the ice first. You may talk about the weather that day, a local sports team’s result, or some other form of “chit-chat” as a way of finding a common ground between you and your prospect. There is a reason why this is the way the vast majority of real-life conversations start and it has everything to do with picking up social queues that help to establish some form of trust between you and the other person.

When it comes to digital communications via phone, email, or messaging, this warm-up dialogue is much harder to achieve,=. This is primarily because proximity is no longer a common factor. You must have a reason for reaching out and interrupting whatever it is your prospect is doing, otherwise it may appear as though you are not considerate of their valuable time. The key to a successful “cold-opener” is offering something that may help them more than it helps you in genuine and selfless way.

Fellow MSP Marketer, Paul Green and I recently discussed this exact topic and talked about a few strategies we are refining with our clients to help them have more engaged conversations.

Here are some of our favorite ways to strike up a conversation with a cold IT prospect that may be worth trying for your next IT sales campaign:

Attend/promote their upcoming events

The rise in popularity of virtual events has led many businesses to begin hosting webinars, workshops, or peer networking events online as a way of staying in front of the customers and prospects. While this worked very well within the first few months of the pandemic, it appears that this tactic may have reached its saturation point. After all, there are only so many hours in a week and most events tend to be hosted in overlapping time slots (Wednesday / Thursday afternoons).

That being said, this now creates a very obvious need that you can provide as a relatively simple “favor” for your prospects who appear to be hosting regular events. Reaching out to them to show interest, asking how you can get involved, or even helping them promote the event to your audience are all great ways to open up conversation. At a minimum, complementing them on the quality of their content will go a long way, especially for those who are obviously putting a lot of thought and effort into it.

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Ask to collaborate on vertical specific content

In my book, I mentioned a tactic that I identified as an early trend the last few years that is now growing exponentially. Podcasting is now a common type of “business development tool” that allows you to reach out to just about anyone to offer them your “platform.” Curating your guests and focusing on a specific vertical will not only help them build thought leadership in their industry, but it will also increase their likelihood of engaging in your cold outreach.

An additional benefit beyond the warm connection is that this can often lead to inbound communication as well. For example, if you interviewed 10 different Insurance Agents all within the same area and each of them cross-promoted the content, you are almost guaranteed to get at least one inquiry from a competitor asking to be included as well.

Send and follow-up on a physical gift

Sending some kind of physical offering that has tangible value is one of the most time-tested ways of breaking the ice. As Paul mentioned in our conversation, having that gift be something that helps to establish trust (like his example of a book) not only gives you something to follow-up on, but it will help to reinforce your subject matter expertise as well.

I don’t know about you, but I find it incredibly difficult to dispose of books, whether I liked the contents of them or not. People generally do not throw books in the trash after they read them, making this a guaranteed way to take up residence somewhere on your prospect’s desk (rent-free), hopefully until the next time they are looking to purchase IT services.

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Give them unique insight about their competitors

While asking a prospect to complete a survey is not exactly a way of extending them value, including high level insight into their industry is. Business Decision Makers often jump at the opportunity to learn more about the successes and failures of their peers. This is primarily because they can’t call up their competitors and ask these questions on their own, as it could be quite embarrassing if they ever got caught.

Try researching a specific vertical market (either on your own or through surveys) and then use the information as leverage to spark as many conversations as possible. Think about what the largest measuring sticks are for the vertical you are targeting (size of customer-base, costs of specific services, exclusive pricing models, etc.) and learn what the major trends are outside of just the technology that you manage. This level of insight should be well received and an offer to email the report is a great way to move a conversation off of LinkedIn and into the prospect’s inbox.

Offer your time and expertise for free

One of the early articles on this site that helped to build our audience in its infancy was a series of screenshots that I took directly from a LinkedIn conversation I had with a net-new MSP prospect. The conversation itself occurred sometime in early 2018, a far different social selling landscape than we are witnessing today. Regardless of these differences, MSPs are still having success offering their time and asking for nothing in return (as I did in this scenario).

If you are wondering if this sets the wrong expectation for when you do eventually sign the customer, then you are not wrong to question this. However I have found that expediting the sales cycle by extending this value up-front is well worth the effort it will take to realign expectations after-the-fact. Sometimes it can mean the difference of whether or not they reply to your message altogether.