"Excuse Me Miss" Prospecting Only Works for Jay-Z

Courting, also known as courtship, is the pursuit of a thing one deeply desires. To be effective one must strategize and move to sway another person into one’s way of thinking.

The way we kick off a courtship is as unique as the person we’re courting. For some notable figures like Jay Z, courting may begin with a simple and respectful "excuse me, miss," which may lead to an initial conversation -- just like in Jay Z’s hit music video, "Excuse Me Miss."

And then, sometimes for others, it doesn’t work quite as easily and we have to be more tactical.


The thing is entrepreneurs can’t afford a hit or miss mentality when it comes to meeting and courting a prospect. This is because business growth and revenue generation depend on successfully meeting the prospect, understanding their pain points, and their pleasure points (some never consider the pleasure points), and then keep the prospect happy throughout the customer journey.

No matter what industry you’re in, entrepreneurs who excel in and enjoy cultivating relationships are usually adept at courting prospects.

Entrepreneurs who haven’t developed their relationship building muscle or skill set may not be as astute at courting prospects and creating messaging to reach them, but thankfully for those individuals, all hope is not lost.

A Good Marketer Comes In Handy

For the marketer and the founder who need to bootstrap these tasks themselves, segmenting potential customers is key. Researching and building detailed personas is essential, so one must look to segment potential customers by asking deeper questions that will really create the meaningful connections you may seek.

I know the intense benefit of segmenting audiences and building personas through asking questions, because I myself have gone and done this, with success, many times.

Tech Marketing

When I became a marketer in technology, I worked with senior level technologists. Based on my deep relationships and persona-based knowledge of that particular segment I thought I knew all the techies - from Heads of IT to software developers- pretty well.

I had certainly done my research, so why wouldn’t I know them? I’d interviewed Chief Tech Officers, joined forums on trends impacting IT leaders and subscribed to publications focused on the needs of Information Officers. I was consuming all of the information.

All Segmented Tech's 

The problem was, I only knew about issues facing technologists who were C-Suite decision makers and managers. I didn’t know a thing about those technologists who actually use platforms, data and APIs to build tools.

Two (of many) tech audience segments I quickly became acquainted with were web developers and app developers. The C-suite technologists I previously engaged with were focused on themes that impact their overall business such as meeting regulatory requirements, reducing hardware costs and maintaining compliance.

The Developer

When I shared these with my developer audience, they gave me a different set of concerns altogether.

Developers cited using multiple APIs when creating new tech tools as a primary pain point, and bringing their technologies to market quickly as a pleasure point. Developers were largely interested in creating efficiencies and ease of use in their workflow, whereas senior level officers focused on solving broader pain points that may impact business growth. Both segments are technologists, but with vastly different pain and pleasure points.

Unique Approach

I realized my approach towards these two diverse groups should be different when I asked questions such as these:

  1. Do they have different pain points?

  2. Do they use different tools?

  3. Are they solving for different things?

  4. What are their objectives and outcomes?

  5. How am I serving them?

It took me a while to absorb that not all technologists have identical pains, but when I did absorb and truly understand what was going on, I was able to create content that spoke to the needs of each segment. This increased my ability to generate high quality leads in each community.

Entrepreneurs and product owners can always enhance their segmenting efforts to better understand nuances in seemingly identical prospect groups. The key benefit I found in this type of outreach is it shows prospects you are committed to building an authentic relationship, not just pushing a product.

When I meet people, demonstrate curiosity about their lives and learn from them- over a cup of coffee or through social media- that leads to relationships. Relationships have the potential to lead to prospects who may become loyal customers.

Beyond The Sell

My challenge to you is to be willing to go beyond the sell and actually get to know prospects by asking these questions:

  • How will your needs change over time?

  • How will your industry change over time?

  • What do you need to make your job easier?

  • How do you manage and  influence your internal stakeholders?

  • How can I best serve you?

Asking my technology prospects more probing questions has helped me cultivate more positive relationships.

Courting prospects goes much deeper than an initial conversation.  Asking key questions to understand each segment’s pain and pleasure points, helps you create messaging that resonates and keeps them interested in getting to know your brand, product or service.

Do you have a phenomenal prospect segmenting courtship story? Would love to hear what has worked for you.