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Inside the Mind of an Inside Sales Rep

Inside the Mind of an Inside Sales Rep


I’ve been in sales longer than some of my peers at Pragmatic Works have been alive. If there is one thing that I have learned in all these years, it’s that I am still learning. Before I share my top five tips for being successful, let me share a little about me, so you understand where I am coming from.

I started as a telemarketer in the early 1990’s where finding the right contact was the problem, not the message or elevator pitch. The internet was just beginning so applications like LinkedIn, Twitter, Hoovers and InfoUSA were not invented yet. Customer and prospect websites? You’re kidding right? Those were in their infancy and only the brave were trying to get on the bleeding edge of technology. Giving the pitch and closing the sale to me was obtaining a meeting for a real sales person to sell them something. Oh boy, have things changed since then. And so have I.

Gone are the days of rapid fire phone calls, where you used a real phone and manually dialed the number with a push button phone and a desktop computer that weighed about 20 pounds. Okay, well maybe not 20 pounds, but close. The tower sat on the floor and kept feet warm in the winter. Today, we use automatic dialers, VoIP and Bluetooth headsets to call and communicate with people.

For as much that has changed, much has remained the same. If you want to make your quota, you better make phone calls. Sales always has been and always will be, a numbers game. I remember early on, a manager teaching me how to start with my yearly quota and breaking it down backwards, into how many sales, proposals, presentations, demos, meetings and cold calls were going to be required in order to reach my quota. A quarter of a century later, I still use what that manager taught me at the beginning of every year.


I have learned many things in my career as a sales person. First, repetition is key. Doing the same task over and over again helps you to get better at it. This way, you can do “it” (e.g., presentation, cold call, elevator pitch, etc.) on command without even thinking about it.  For instance, I used to freeze when I was in a public setting, or out and about, not in a business setting and someone asked, “what does your company do’’ or “what do you sell”?


Blocking off time in my calendar on a daily or weekly basis for specific activities helps with the repetition. How do you deliver a good elevator pitch for cold-calling? I block off at least two hours a day, alternating mornings and afternoons and practice. I pick up the phone and call somebody; a prospect. This not only helps me in my delivery, but when I make enough calls, I invariably connect with a person who wants to talk to me and we schedule the next interaction (e.g., demo, presentation, technical discussion, etc.).


A skill that is a must for anyone that wants to be in sales is the art of listening. In order to find out what drives your prospect or what your customer really needs, you need to listen. You need to ask the right questions, but more importantly, you need to listen to their answers. Not only their words but their body language, their tone of voice and eye contact (or lack thereof). In my humble opinion, when my customers are doing 80% of the talking, I better be doing 80% of the listening.  My belief is that the better your skill at listening is, the better your sales conversations will be.  That leads to winning more deals. I mean, we have two ears and one mouth. What do you think?


Another daily useful block of time I use is for moving opportunities forward. Spending time every day looking at each opportunity, at whatever state it is at, and thoughtfully thinking about what can I do to get it to the next stage and who can I call or who should I ask for help in this? Doing this ensures several things. First, each opportunity gets a lot of my mindshare. Any time my manager or anyone else asks me about an opportunity, I know exactly where it stands, what is going on and what is next. I know the names of all the people involved and their titles. By spending all this time examining my opportunities, I should then know the organizational chart of the players involved.

This close involvement with each and every opportunity affords me close communication with my contacts. This way, when the opportunity closes, I already have a close connection and rapport with my client.  Asking for a reference,  referral (inside and outside the organization) and additional business (up-sell and cross-sell) comes easy and natural.


I have found that technology plays a role in my selling too. Over the past 10 years, that role has gotten bigger and bigger. Take LinkedIn for example. At first, I only used it to connect with my customers. Now, LinkedIn is a platform I use to not only connect with customers and prospects, but an avenue to promote, announce and leverage content to a mass audience to elicit a response; whether it is a like, share, comment or the best ones… a direct message or an invitation to connect.

Another example is Twitter. Five years ago, I had no idea what Twitter was and how to use it. Today, I have close to 250 followers and growing. To think, there are people out there that actually made a conscience decision to connect with me (LinkedIn and/or Twitter) to read what I have to say. Really?! Really! Technology helps me to communicate, stay in touch and learn, from both inside and outside my organization. Applications like Skype, Skype for Business, Yammer and Glip are a few of what I use on a daily basis.

The last 5-6 years of my selling have shown me many things. Skills that I learned early on are still applicable and can be utilized today. As technology expands and influences business, I use that technology in a way that serves a positive purpose for me.

Continually learning and adapting in sales is a key component of success. I hope that these lessons I've shared are something you can leverage in your own sales process. If you have any best practices for sales that you'd like to share, please leave them in the comments!


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