Episode #275 – Tom Pisello

Identify and Overcome Your Gaps To Succeed with Virtual Selling

Tom Pisello


Tom Pisello

Tom Pisello is a thought leader and author on sales and marketing effectiveness, as well as a serial entrepreneur. He’s well known from his videos, blog, and newsletter as “The ROI Guy.” He is the Founder of the Evolved Selling Institute and currently Chief Evangelist for Mediafly.

Salespeople are still struggling to adapt to all of the changes that the Covid pandemic has brought about. Virtual selling is still largely at play, with some in-person interaction still sprinkled in. Tom Pisello believes that to adapt, you need to become laser-focused on helping prospects become aware of and solve their problems. To do that, you have to identify your own struggles to become more effective. Tom shares insight into this process in this episode of Sales Reinvented!

Salespeople need to identify where their gaps are and overcome them to succeed with #VirtualSales. Learn more about the process from @tpisello in this episode of @SalesReinvented! #Sales #SalesReinvented #Mindset #DiscoveryClick To Tweet

Outline of This Episode

  • [0:49] The difference between digital and social selling
  • [3:21] How to succeed with virtual selling
  • [9:32] Tom’s virtual selling strategies
  • [10:59] Attributes and characteristics of a great seller
  • [12:04] Tools, techniques, or strategies to improve virtual sales
  • [14:15] Top 3 virtual selling dos and don’ts
  • [15:17] Foster engagement in virtual sales presentations

How to succeed with virtual selling: identify your gaps

Sellers are frustrated with how much longer purchasing decisions are taking and how many people are involved in the process. It can be difficult for them to manage. But Tom emphasizes that if you look for what buyers are saying their challenges are, it can be a turning point. When the Rain Group surveyed buyers on what they thought of sellers in the digital environment, four gaps that were recognized:

  1. Leading a prospect through a thorough discovery: Don’t just show up and throw up and make discovery as part of the process. Give a presentation with an interactive demo.
  2. Mapping solutions to the problems that were identified: Do your best to address the root cause problems that the buyer is facing.
  3. Listening skills: Many sellers don’t stop talking. There’s a loss of eye contact, talking over the other person, etc. You have to slow your roll in virtual meetings. Don’t be afraid to stop early and leave a cliffhanger and time to talk next steps.
  4. Making the ROI clear to the buyer: Tom’s nickname is “The ROI Guy.” Buyers care about the problem they’re solving and the business outcomes you can assure they get. Focus on the outcome you’ll give them—not what you’re selling. What can your product solve? What can it deliver in terms of quantifiable business value? Make it clear.

How to succeed as a virtual seller

How do you present your sellers with discovery guides and interactive presentations? Can you provide your sellers with an interactive diagnostic assessment or a problem/solution guide to use with customers? You have to provide an interactive value assessment tool so sellers can collect data from the customer and do the number crunching to make a business case. 

Make sure you’re implementing conversational intelligence tools so you don’t have to have your head down to take notes. You need a good video presence and the ability to listen more than they talk. So learn how to maintain eye contact on video calls.

When you do talk, you need to ask good in-depth discovery questions that help buyers be introspective. A good seller is armed with good content and tools. They’re leveraging dynamic presentations and assessment tools to add value, insight, and guidance.

How do you succeed as a virtual seller? @tpisello shares his thoughts in this episode of @SalesReinvented! #Sales #SalesReinvented #Mindset #Discovery #VirtualSales #SuccessClick To Tweet

Tools, techniques, and strategies to improve virtual sales

Tom recommends that content enablement groups work to examine PDFs, videos, guides, etc, that are being provided to their salespeople and think about retooling them. Can you make them interactive? Can you click on elements? Customers don’t have the patience to sit through a deck. You have to be able to pivot the conversation to what the customer wants to talk about and have content to support it.

Tom loves doing diagnostic assessments to assess a company’s maturity and where they are in the journey. You can map out improvements that they’d like to make and give intelligent recommendations. You can benchmark them against peers.

What about business value assessments? What challenges are they facing? What is it costing them? What’s the value potential of implementing a solution? What evidence can you share that you can deliver on this? The right tools can make a difference.

What are Tom’s virtual selling dos and don’ts? Listen to learn more!

Foster engagement in virtual sales presentations

Tom once had 16 people in a company’s buying committee in a virtual meeting. With a crowd that large, you want to be mindful of who is paying attention. What does everyone care about? The customer was early in their decision-making process. So instead of talking about the solution, Tom mapped a day in the life of their customer’s customer and how they helped to overcome their problems. They went into how they could help address the friction this prospect was dealing with in their selling process.

As they walked through the pieces of their sales process with the customer, he got almost everyone on the call to participate. Tom made sure he got input from everyone to make sure everyone was engaged. They took notes on what was important. When they went into the solutions part of the call, they tied back to specific people and pain points.

Tom notes that people can be afraid to speak up in front of their CEO and other executives, so you have to be conscious of the political dynamics within the environment. You can overcome that by calling on specific people to contribute to the conversation and be heard. Above all, spend time walking through discovery with the group and make sure everyone is engaged in the pain-point portion. Be aware of the dynamics that occur and be ready with strategies to engage everyone.

Why is it important to foster engagement in virtual sales presentations? Find out from @tpisello in this episode of @SalesReinvented! #Sales #SalesReinvented #Mindset #Discovery #VirtualSales #SuccessClick To Tweet

Resources & People Mentioned

Connect with Tom Pisello

Connect With Paul Watts


Audio Production and Show notes by

Tom Pisello

Are there any great Digital or Social Selling books that you highly recommend? The Transparency Sale – Todd Caponi, Virtual Selling – https://www.rainsalestraining.com/resources/books/virtual-selling

What do you most admire in the sphere of Digital or Social Selling and why? Daniel Khaneman – behavioral neuroscience and bias / noise research on decision making. Todd Caponi – his work and writings on Trust

Are there any aspects of your own Digital or Social Selling skills that you are working on improving at the moment? Yes, not over-scheduling what has do be done in each virtual call and slowing down in all digital calls / demos and presentations, to make sure buyers have time to jump in.

Hobbies, Interests? I play Piano (ex-Wedding Band player), spin and workout every day. Growth mindset and Neuroscience junkie.

How can our listeners contact with you? Evolved Selling Institute is where I post all my podcasts, articles and access to book / tools. LinkedIn is good as well.