How AI fits into your prospecting now

“The future is already here, it
’s just not evenly distributed.”
—William Gibson

Forward-thinking sales professionals today are quickly embracing AI-powered tools to turbocharge their prospecting. These tools are chatbots designed to produce human-like conversations in which the results can improve with the number of questions you throw at them. For multipurpose use, there’s Chat GPT and Bard. There are also more specific tools (I’ll talk more about them below).

First, let’s talk about the challenge at hand: because all this consumer-focused AI technology is still so new, everyone’s still in learning mode trying to figure out how to get started and how to fully optimize these powerful tools. That’s why I recently reached out to Douglas Squirrel: he helps scale-up companies worldwide by showing them how to make smarter use of IT in their work.

From our conversation on LinkedIn Live, here are valuable takeaways about why you must make AI fit into your prospecting…and how to do it right.


As you know with dealing with people, successful prospecting is determined by the quality of the questions you ask. That same reasoning applies to AI-powered prospecting. You must further refine how you ask probing questions, much the way you already do every day when talking to people. For an-in-depth example of probing questions, I just happen to have an AI bot on my own website that’s waiting to help you. Go there now, click on the three dots in the bottom-right of the screen and ask it: “What examples does Colleen have about asking probing questions?” Apply that same approach to the prompts you give to AI tools. Begin by drilling in the right place and then see how deep you can go.


Technology—including AI—helps us be more productive because it’s able to perform many tasks incredibly fast. When it’s used right, it frees us up to do what people do best, which is to be creative: to connect things in new and unexpected ways. That’s the hidden edge that AI-powered prospecting gives you. Be deliberate and strategic in your creativity there. With AI, there’s no point in prompting it to “show me everyone in my country who might buy my product.” But there’s tremendous value in asking: “show me the places in my city where my existing customers gather regularly to talk about this unique sales problem they have.” Then keep tightening your probing questions with each subsequent prompt.


In addition to the general AI tools I mentioned in the introduction of this article, there’s also a wide range of more focused ones, such as:

  •—helps improve your marketing copy and quickly distils longer-form pieces into shorter social media posts.
  • Einstein—use it within a Salesforce account to anticipate sales, marketing opportunities and customer service challenges and then consider recommended solutions.
  • Fathom—summarizes your video calls into succinct reports.
  • Website chatbots—use these to quickly get detailed answers to challenges that are specific to a particular website (includes the one we use here at Engage – try it out for yourself at the bottom right of our page!).
  • Wordtune—helps improve the tone of your written material, adjusting it for greater diplomacy, clarity and empathy.
  •—get answers to questions provided by a character-developed AI ChatBot, including those of famous historical figures and celebrities.


An AI prospecting tool is never the subject matter expert: you are. Think of it instead as—and this is how Douglas Squirrel puts it—“a not very knowledgeable research assistant.” Volume is its expertise. Your job is to sift through the raw data and find meaning. That involves a lot of experimentation. “I learn how to use these tools much the way I go about making sense of the controls on a new car,” Squirrel explains. “A lot of trial and error.” That route is wiser than paying someone to provide you with—what they claim to be—engineered prompts. Learn faster by doing it yourself.


Beware of hallucinations (that’s what people in the AI business call them). These are falsehoods and wrong answers that AI tools mistakenly give you sometimes with seemingly high confidence. They happen. Similarly, you must remember that some of the search results you’ll be provided with today may be dated from a couple of years ago, because these tools are not yet capable of fully drawing on real-time data. Such are the limitations of using a brand-new technology. So if you ask an AI tool to produce a list of potential contacts, assume there are going to be people on that list who have since moved on to other jobs.


Never use AI tools to write proposals or to draft original articles for publication! Despite  their powerful benefits, AI tools write boring content. That kind of technology still lacks the humanity and creativity that only you can bring to your message that connects with readers. Instead, use these tools to vastly improve the depth and impact of your message…and do a lot more in less time with the amount of information this technology provides. It’s always up to you to apply critical thinking skills: you create knowledge, meaning and insight out of all that data.


In making the case for why AI is a must-have in your prospecting, always remember that  every new technology tends to be greeted warily at first. “Is this thing going to put me out of a job?” That’s often at the root of peoples’ fears. Well…fear not! If you’re a dedicated sales professional, these new tools aren’t going to replace you. Rather they’re going to make you more valuable…but only if you learn to use them well.

By bringing your critical thinking and creativity skills to the forefront, AI-powered prospecting tools will help give you a deeper understanding of your customer and equip you with insights about where to focus to your efforts. This technology can turn great sellers into superstar sellers.

Will you be among them?

One response to “How AI fits into your prospecting now

  1. This was very helpful. And, you were in my fair city. I hope your time in Seattle was productive.

    Lead Boldly!

Comments are closed.