comment 0

From Introvert to Rainmaker in 10 Steps

Most people feel selling is a god given skill.

It’s not, it can be developed.  Anyone can get better at selling; it just takes work – and time. 

You may never achieve rainmaker status at the highest level, but you can develop selling skills that will help you immensely in life, in business, and even in finding a mate.  And I hope my story helps you. 

The greatest benefit to having some selling ability is it distinguishes you from the majority of the workforce.

It’s an extra arrow in your quiver of arrows making you more marketable to prospective employers.  And if you dream of owning your own business, you’ll need to know how to sell.   

I find many people are afraid of selling for or one or more of the following reasons:

  1. Their personal appearance is less than flattering; overweight, bad teeth, out of shape, bald or balding etc.
  2. Introverted personality, shyness
  3. Lack of knowledge and/or respect about the importance of the sales process in any business
  4. Feel their advanced degree and education (doctors and lawyers for example) make them exempt from selling

Here’s some truth.  If you send two women, one stunningly beautiful and the other of average beauty (both with equal selling skills) to sell the same product to a man, the beautiful woman will win that sales contest 100% of the time.

Here’s more truth, good looking men can more easily sell to women … than other women. 

Beautiful people have advantages over average looking people.  But looks are a very small part of effective selling.  Looks may get you in the door faster – but skill is what closes a sale.  Skill that you can develop.

Why? Because ultimately – decision makers value solutions to their problems.  And if you can get their attention, uncover their pain, and provide a solution, it won’t matter what you look like. 

I personally struggle with my introverted tendencies. I’d rather stay in the comfort of my own home or enjoy the solitude of a golf course than do any anything social. 

But social shyness and business shyness are two very different animals.

It’s OK to be socially shy, but when it comes to business, it’s about your survival. 

And if eating and supporting your family isn’t motivation enough to break out of your shell – then nobody can help you. 

You have to help yourself in this instance.  The motivation to survive – and thrive – should trump all shyness in the business jungle.   

How do you do it?  By assuming a different identity for your social life and business life. 

Christopher Reeves as Clark Kent

Being shy and awkward at home like Clark Kent is fine, but when you dress for work you must turn into Superman – or Wonder Woman – a fearless version of yourself ready to do battle in a fierce competition for clients. 

Christopher Reeves as Superman – who would you prefer to buy from?

I find that many professionals like lawyers, doctors, and accountants dismiss the idea they need to sell.  Why else did they spend all those years in school studying? 

But the most successful and wealthy professionals develop a healthy respect for the selling process. 

Professionals have to become sellers and win clients before they can attain partnership status or build their own practice.

Find me the partner in a successful professional services or medical practice that doesn’t bring in new clients and I’ll show you my winning power ball ticket.   

The Importance of Selling

There are three foundational marketing principles underlying any successful business:

  1. Continued customer acquisition
  2. Conversion and Sales Optimization
  3. Customer Retention and Referrals

The most important, difficult and expensive of the three is customer acquisition.


Because … until someone, somehow, in some way – convinces a business, government, non-profit organization or person to part with their money – absolutely nothing would transpire in business.    

And because the selling process takes time, and customers are finicky, there’s endless competition, habits and trends change, leadership changes, governments and laws change. 

It takes patience to develop a relationship, to win trust, and deliver a solution.  It takes persistence, drive, skill and psychology. 

The Indians tried to create rain through rituals and prayer.  Man tried to create rain through scientific methods. In the business world, rain is made through methodical and strategic effort. 

And for those who can consistently sell at the highest levels, they are the true rainmakers. 

Rainmakers and Fulfillers

Very generally, there are two kinds of people in this world, rainmakers and fulfillers.  Those who can sell, and those who can’t – or don’t want to, for a variety of reasons, I call them the fulfillers. 

The vast majority of our planet is on the fulfillment side. They are the specialists, or subject matter experts, or number crunchers, and managers.  Their jobs are to fulfill and manage the obligations of the sale. 

Fulfillment of a sale is vitally important because it’s what retains and grows clients.  But the selling part is much more difficult.   

In his book Million Dollar Consulting, author Alan Weiss calls fulfillers – delivery people, and makes this point:  “If anyone tries to tell you … that delivery is the key to client success, I’d remind them that delivery people are more common than garden weeds, and rainmakers are rarer than Sasquatch.”

The process by which you are compelled to buy a McDonald’s cheeseburger and Coke has evolved from a sophisticated team of sales, marketing and merchandise folks – fulfillers trying to drive traffic into McDonald’s retail locations. 

The delivery of the meal is also fulfilled by the franchisor, who pays handsomely for the brand and system that delivers a Coke and cheeseburger to her customers.

The one who developed the idea, licensed it, financed it, and sold it to the masses was Ray Kroc, the rainmaker in this scenario.    

The car salesperson – or realtor – who start with nothing – and go on to build successful careers must develop rainmaking skills to succeed.

The finance person at the dealership, or the title agent at the title company, are the fulfillers of their sales.  The realtor and car salesperson generated the rain.  

While working in sponsorship sales at a division one collegiate athletics program I witnessed true rainmaking from our athletics director – Beth.  You’d think an A.D. would be consumed with wins and losses; she wasn’t.  Her mission is fundraising. 

Her focus was on raising money to fun scholarships and build state-of-the-art athletics facilities designed to attract recruits and coaching talent. Which in the long term will lead to more success for the program.

My Path to Making Rain

I’ve been in sales and business development my entire professional life.  And after 20 + years of selling I am now only approaching rainmaker territory.

I never had the desire, academic chops, or patience to become a doctor, lawyer or accountant. 

Even though I was shy and introverted, I had a good personality, a full head of hair, and good manners. And selling was the best path for me to earn a good income.

Now I’ll share how an introvert like me ascended from timid seller to rainmaker, and what I believe to be the 10 most important principles of succeeding in sales.   

#1:  Sell Something You Love or Believe In

In college, needing to make money, my interest in advertising and newspapers led me to sell ads for my school newspaper – The Ball State Daily News.  And it may have been the worst way to start my sales career.

Why?  Because newspapers (at this time in the early 1990’s) were still the dominant advertising tool for local businesses.  This was before Craigslist, Facebook, and digital media decimated print advertising.

So, selling ads in a college newspaper – to a business in a college town – wasn’t exactly difficult.  We had a virtual monopoly on our campus audience.  And I exploited this dominance.

The key here, I loved the product.  I devoured a newspaper every morning since I was a kid eating bowls of sugary cereal. 

Secretly, I wanted to be a journalist.  But there was too much competition for editorial jobs, and I was afraid to pursue a career with such low pay.

So, I sold ads, and discovered it was the highest paying student job on campus.  To me I was not only supporting journalism, I was also supporting students learning how to be journalists.  And I was making great money!

This made selling more of a mission, and it didn’t feel like a job, it felt like I was serving. 

Contrast this with selling something I wasn’t interested in, like corrugated boxes, or industrial widgets, or medical devices – selling something I didn’t have a passion for would have made it more difficult to overcome my shyness and call on strangers.     

#2. Embrace the Power of The Hustle

Selling newspaper advertising was easy, we were a monopoly. I just had to hustle, and call on as many businesses as possible.

Making calls every day, whether it’s on the phone, or in person is a fundamental part of the sales process, and a lack of activity is often the root cause of poor sales performance.

Making that extra phone call, or stopping by a business one more time, regardless of the outcome … is the core to success in selling. Whether it’s a no or a yes, making the call is the most important step. It’s the foundation of your selling house.

Over the years I developed a philosophy on how much activity I needed each day to be successful; I call it my Power of Ten system, and I’ll share more detail in a later post.    

Selling ads in my college paper wasn’t rainmaking, it was more of a transactional sale.  There was intrinsic demand for newspaper advertising, because they held a monopolistic advantage.  It was almost easy. 

That’s why after college I stayed in the ad selling business and took a job with The Indianapolis Star, the largest daily newspaper in Indiana. 

The hustle ethic I developed in college served me well because nobody at The Star worked very hard.  It was like unionized labor for salespeople.  They were all fat and happy with accounts who regularly spent gobs of money.

I once overheard the Director of Sales proclaim if we just answered the telephone – and made no outside sales efforts – the paper would take in over $100 million dollars per year. 

I was not deterred, and spent each day calling as many people as possible.  By sheer volume I was guaranteed to outsell everyone else.  And this rang true when I won salesperson of the year in my second and third year on the job.   

The problem with being in transactional sales is it doesn’t pay well.  I was managing millions of dollars in revenue for the paper, but my compensation maxed out at around $60,000. 

And, I wasn’t learning how to be a true salesperson, or a rainmaker.  I was propped up by a monopolistic advantage – so my education (along with my pay) – stagnated.        

Eager to learn (and earn) more, I noticed the radio salespeople were all driving nice cars and having a lot of fun.  Radio was at its peak in terms of its influence and revenue.  But the model of selling radio was different than newspapers. 

Radio didn’t have the same competitive advantage as a lone daily paper like The Indy Star. There were more than a dozen stations all competing for the same piece of radio advertising pie.   

This was my first exposure to 100% commission sales.  I had to learn to kill for my supper.  Working for straight commission is an experience I would recommend everyone try, preferably while you’re young. 

Because earning money only when I sold something sharpened my focus like nothing else.  Once I kissed the cushy salary goodbye my whole mental state took a sharp right turn towards calculated efficiency. 

#3.  Learn more By Being Dumb

Everyone has a huge advantage early in their sales careers. 

It’s before we become experts in our own product, and by default listen more to our clients.   

I remember a story from sales training.  A department store hires a young sales trainee and assigns him to the section selling portable heaters and other hardware.  

It happened to be a very frigid winter and sales were poised to go through the roof.  The kid was far from an expert on heaters.  He simply listened to what customers needed and responded to that need.

His sales were so good the store manager sent him to the management trainee program where he became an expert in all of the department store’s products, especially portable heaters. 

And next winter, another cold snap, and our new management trainee was ready to sell.  Nobody knew more about the technical specifications of portable heaters than this kid.

But a funny thing happened, instead of listening to his customers, he spent more time talking about all of the useful knowledge he learned in training.  

His sales cratered, even in a record cold winter.  Why?  By complicating a simple process. People were cold, and each had a different number of rooms to heat, and only so much money to fix it. 

They weren’t interested in the technical wizardry of each portable heater.  They just wanted to get warm, affordably, and fast. 

The toughest thing I’ve learned is that acting dumb sells more.         

That’s right, in order to help clients – you have to play dumb, exactly like Detective Columbo. 

You have to swallow your ego and allow them to be the big shot in your conversation.  Because they are, it’s their money.

Why?  Because they’ll let their guard down.   

This is how you truly uncover pain and learn what solutions are needed to close a sale.

Nobody was threatened by Columbo, and when their guard was down, suspects would willingly share information, secretly thinking there’s no way this dumb detective will ever figure it out, and then he’d put the pieces together and arrest them.      

Acting as if you’re there to learn, instead of teaching (and avoid industry lingo and product language they won’t understand) enables your prospect to drop their guard and not feel threatened.   

This is still tough for me to do, it’s tough for anyone to do because psychologically it feels so wrong. But it works, and Detective Columbo always closes his cases.   

#4.  Qualifying

Now that I was earning 100% commission, I had to get much more precise in qualifying my prospects. 

It wasn’t efficient for me to call on everyone.  My radio stations appealed to a more targeted audience.

I discovered the best place to prospect wasn’t the newspaper, or TV, it was the other radio stations.

This was more efficient because these clients were sold on radio, and they already had radio commercials produced.

Only after I exhausted these prospects was it efficient to move on to other non-radio prospects – which took twice as much time to develop. 

In every sales situation, identifying your best prospects is the most important factor in becoming a successful salesperson.

I’ll share with you how you can maximize your selling time by identifying the best type of prospect to call on regardless of what you are selling. 

While I was selling radio and honing my skills as a commissioned salesperson, something became very clear to me; Local Network TV was taking in an increasingly large amount of advertising dollars. 

And at the time the four broadcast networks were at their peak in terms of reach and popularity – ABC, CBS, FOX, and NBC.  And cable TV (ESPN, TBS, TNT, CNN) was still in its infancy. 

Only four TV stations gobbled up most of the television advertising revenue.  And those four stations took in more money than all of the radio stations combined.    

So, after three years of honing my craft in radio advertising sales, I landed a job at the Indianapolis CBS station WISH-TV.

#5.  Invest in Training and Education

As I ascended into the big leagues of television ad sales, I realized there was a great income opportunity in front of me. 

I was getting paid 100% commission to sell a monopolistic product with an average sale of about $20,000. 

So, I decided to step up my selling game and invested in sales training – with my own money. 

It’s different investing your own money in education, much different from your parents paying for your college. It means you actually pay attention, attend class, study, and learn. 

The most transformational training I invested in cost me $11,000.  And I didn’t have the money, in fact, I was deeply in debt.  I put it on my credit card, and they billed me in installments.  I never learned more in my life.

In addition to my investments in training, another transformational habit I developed was reading a book in the morning with my coffee.  Usually a self-help or non-fiction book about sales, marketing, or investing.

I used to start every morning reading the news, but I quickly realized it’s all the same crap every day.  Even a chapter or two of a good book allows me to learn something, and start the day off on a positive note.

I’ll share with you the key takeaways from my training and provide you a list of training programs you might consider.    

I’ll also provide you a list of the books and audio programs that have helped me the most in my sales career.  A list that keeps growing.   

#6.  Proposals and Presentations

My investment in training helped me become the #1 salesperson at the TV station within two years.

Eventually I was asked to manage larger accounts with huge revenue responsibility.  All of a sudden, I’m making presentations and asking clients to spend hundreds of thousands of dollars.

Instead of presenting to mom and pop retail stores, I’m now in rooms full of corporate executives, owners of large retail enterprises, and media buyers – so my proposals HAD to get better. 

They had to address pain, provide rationale to resolve that pain, then sell. 

Most salespeople still use PowerPoint and build text-heavy slides – AND PROCEED TO READ what’s on each slide DURING THEIR PRESENTATIONS!!!!! 


There is a better way, and my style of presenting has worked for me at the highest levels of corporate America.  For example – one of the highlights of my selling career was an opportunity to present to the marketing leadership of Coca-Cola in Atlanta, GA. 

I’ll share with you all of my tools and tips on building presentations that sell along with actual examples of presentations.

#7.  Building and Nurturing Your Network of Personal and Business Relationships

After seven lucrative years in television a newspaper colleague recruited me to work for an advertising agency in Dallas, Texas. 

And I was given responsibility over some regional grocery chain accounts.  My job was two-fold:  First, make sure our team of fulfillers (creative/production/copy/media) were exceeding client expectations

Second, grow and find new business.

Guess which one was more praised by my leadership?  That’s right, growing and finding new business. 

I had to climb a very steep learning curve professional services are intangible, and it’s different than selling a quantifiable product. With professional services your clients area asked to take a bigger leap of faith.

Selling services, like legal, accounting or marketing services – is all about relationships, and it takes time and skill to build this type of trust. 

This is when I realized how important it is to build and maintain a network of personal and professional relationships. 

Because 100% of our agency clients were from relationships built over the years by our executive leadership

Our relationships were so strong our clients would bring us along if they took a job at another company.

The foundation of the agency became a single relationship our founder Warren had with a young grocery executive, who went on to become the CEO of Albertsons, one of the largest grocery chains in the U.S.  This relationship blossomed into a $250+ million-dollar account. 

I also learned the importance of developing conversational skills with executives, who aren’t interested in small talk, and grow weary of people kissing their ass.

If you can spark up an engaging conversation – cold – with a Fortune 500 corporate executive, you have acquired a rainmaking skill that 90% of salespeople don’t have. 

In the services world, new relationships are often built through referrals – which I’ll address later – but solidified in social or quasi-social settings like lunches, dinners, golf outings, and seminars. 

I’ll share with you how I continue to develop and maintain my own network, and how I successfully engage executive level prospective clients in social settings so they can turn into lasting relationships. 

#8.  Stop Calling Cold

After several years at the advertising agency I grew weary of the travel and decided to move back home to Indianapolis. 

I took some time off, and eventually accepted a position with Ball State University to mange corporate sponsorship sales for athletics.

I returned to my roots of hustling and working harder than everyone else.  But it became clear to me that that calling people cold, for a variety of reasons, was less effective than it used to be.

For one, there are now more salespeople than ever calling on a shrinking number of business owners.  Never in our history has there been more “solutions” for business owners; software, marketing, accounting, digital, and more. 

Most business owners get 30 or more solicitations PER DAY from salespeople.   

Good news, most of the salespeople you compete against are lazy.  And they only use one tactic – email – and usually send one email and give up.  Few ever commit to the process needed to turn a stranger into an appointment. 

Fewer qualify and focus their time and energy on the right tactics and right prospects. 

So, again … I read several books and adopted some different and more effective methods of attracting new business. 

And I’ll share those with you along with examples of letters and emails and strategies guaranteed to get you an appointment. 

#9.  Becoming a Thought Leader

I also realized, one day – while listening to a business owner blab on about knowing everything about marketing – that I, in fact, knew a lot more about marketing than him, and most other people. 

I had worked in every advertising discipline known to man – from newspapers to radio to TV to digital media to sports marketing AND provided marketing strategy to some of the largest retailers in the U.S.

But even though I knew more, nobody cared.  I had no credibility … no 3rd party endorsement … nothing backing me up.  Sure, I had a resume, but so does everyone else.    

So, as part of my effort to establish my credibility I wrote a book, and then I started a blog (you’re reading it!). Eventually I submitted some of my blog posts to local media and a several have been published.    

I also started giving presentations and speeches to local civic and business groups.

And what did it to? 

It positioned me beyond just a salesperson, it positioned me as a thought leader, adding a layer of credibility. 

I’ll show you how you can take experience and knowledge you already have, something you probably take for granted, and use that to position yourself as an authority in your field.

This will result in greater client attraction, and you’ll hopefully transition from seller to adviser. 

#10.  Retention and Referrals

If you look at the 3 phases of marketing: 

  1. Customer Acquisition
  2. Conversion and Sales Optimization
  3. Client Retention/Referrals

The one we neglect the most is #3 – Retention and Referrals. 

Why?  Because it’s psychologically the toughest to tackle.  Most of us were raised to be polite and thankful for what we have … and not to be greedy and ask for more than our fill. 

And we all want to be liked and loved. 

But asking a client – who presumably just spent money with me – for another (perceived) favor – a personal referral mind you – after they just did me a (perceived) favor by purchasing my product or service, seems inappropriate or discomforting – for many of us.

So let me ask, is requesting this referral, from a presumably happy customer, someone I have a relationship with, worse than cold calling 10 new prospects? 

Nope, not even close. 

Again, this is a distinction between social life and business life.  In our social lives, it’s OK not ask anybody outside of your family or friends for help.      

But in business, you must don your Superman (or Wonder Woman) cape, because there is no room for introversion – YOU MUST ASK – or you will never get anything. 

And the people you ask – your clients – will understand because they have the same understanding about business. And they struggle with the same issues we do about asking for referrals.     

I’ve slowly developed the mindset that asking for referrals is more productive and efficient way of finding new clients vs. cold calling. 

I’ll share with you how I overcame my inner angst and now get more referrals than ever before. 

I’ll also describe the techniques I use to keep my clients engaged while also reminding and incentivizing them to send referrals my way. 


To summarize my ascension from introvert to seller to rainmaker, here are the 10 steps I took in over 20 + years of selling products and services. 

And in the next few months I’ll breakdown each step and hope my story – and the resources I share – help you ascend to becoming a better seller.    

10 Steps to Rainmaker Status

  1. Only sell what you feel passionate about
  2. Hustle
  3. Be dumb and sell more
  4. Qualifying
  5. Invest in training and education
  6. Propose and present better
  7. Building a network and relationships
  8. Stop cold calling
  9. Become magnetic
  10. Retention and referrals

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.