I want to open this segment by letting you know that the ins and outs of sales could be a full-on stand alone multi-week/multi-class course.

I don’t say that to frighten you just to let you know that if you’re in business, becoming a great salesperson should be one of your top priorities (outside of delivering impeccable service).

And becoming a good salesperson requires taking pride in your craft, understanding that sales is service, and continued incremental improvement (largely from study and then practice).


Sales drives business. You must master the process so that you close business and have clients.

No doubt you’ve heard some axioms about sales:

“Sales is a numbers games.”

“Sales is based on relationships.”

“Sales is hard.”

“You are either born good at sales or not.”

“You have to be aggressive to close sales.”

Umpteen best selling books try to deconstruct the sales process and put their own spin on how to be successful. If you crack the sales process and make it repeatable, then your profits will increase.

Now, don’t go buy out all the sales titles in the business books section.

A ton of those books have maybe five nuggets of information and others are worthless.

I read my first sales book (Jeffrey Gitomer’s Little Red Book of Sales) when I started selling wholesale fashion. It’s a good read. If you’ve never read a book on sales it’s a great intro too.

But that book is the equivalent of sales kindergarten.

Still, you need to start somewhere!

So go order it on Amazon or buy from your local bookstore. I recommend the hard copy because you’ll want to return to these kinds of books over and over again.

Here’s what I believe about sales:

Selling to businesses is simultaneously easier and more complex than selling to individuals.

It’s easier because you’re asking someone to part with OPM (other people’s money). It’s much less emotional than asking a small biz owner to part with the same amount of cash.

It’s more complex because you most likely have to navigate a host of personalities and agendas, politics and committees. (There are ways to circumvent those intricate webs; however you mustn’t ignore them outright.)

Selling requires a strategy and skill set that many people do not naturally have.

This does not mean that you are either born with the sales gene or not. You can develop the tools you need to sell well, whether you’re an introvert or extrovert. Whether you’re big vision or attention to detail.

Strategies vary by product or service and market. The skill set includes: relationship building, yes, but also the abilities to ask amazing questions and think like a consultant; the willingness to be contrarian; self-confidence; a system and the wherewithal to follow through on the system; and a complete disregard for what people will say to you/about you.

Take a moment to assess yourself in those areas. Where do you measure up? Where do you fall short?


I was just meeting with the CEO of a real estate firm here in NYC last week. He spoke about one of his agents, a 27 year old woman who was about to implode because of her extremely fast pace.

He marveled at her ability to bring in new business. I asked what her process was. He said, “She’s crazy. She does two hours of prospecting every day before she gets started with current listings and clients. She is the only person I’ve ever said needs to stop filling her pipeline.”

This girl has a system and she sticks to it NO MATTER WHAT. Even to the detriment of her health and her business.

That’s an extreme example but it shows what persistence can do for your pipeline. Create your system, then follow it!

Incidentally, she’s getting most of her new clients and listings from cold calls to property owners. I must say I field about one call a week at my apartment from agents wanting to list it (it’s not for sale).


Aside from sales strategy and sales skill set, you must be committed to the sales cycle in order to flourish.

If you haven’t been doing work with corporations for a while, you most likely don’t have a good idea of your average sales cycle. And even if you have been in business you probably experience the same thing I do: completely erratic sales cycles.

Three examples:

1.     I met a man at a bar in spring 2012. I added him to my ecosystem. When I moved to NYC I invited him out for drinks and to my parties at my home. About a year and some change after our first meeting, he invited me to his office to chat about how I could help him. It resulted in a nine month long engagement.

2.     I met a CEO at an event. He invited me to lunch to talk about business. At the end of the lunch he said, “Send me a proposal.” Within a week I had a first payment for a consulting contract and worked with that company for three years.

3.     Just a few weeks ago I received a linkedin message from a CEO who knew me via a startup in 2010. He and I played phone tag, finally spoke after a week or so. We will likely tee up some business this summer.

I hope you notice the dissimilarities in these cases, as well as the similarities.

As you can see, some of these took (are taking) years to mature into an actual contract. And that’s ok! I’m happy to interact with these guys, give them value in various forms, and otherwise invite them into my ecosystem/life.

They may be the people with whom I do business, but the could just as easily be their clients or best friends. Don’t count someone out of your network just because he doesn’t buy immediately.

Clearly some sales conversations happen so quickly that you have a check in hand in five business days (or fewer). Others require nurturing and development over a period of time. Still others require being top of mind at the exact time when a potential client needs exactly what you have, even if that’s years down the road.

If you can nail your sales conversations, systematize the nurturing of your ecosystem (i.e. pay attention to it even when you’re flush with business), and maintain visibility among your target market, then your sales cycles will be much more even and predicable.

To recap:

1.     Start to educate yourself on sales strategies.

2.     Nurture your ecosystem.

3.     Develop the sales skills you have and acquire new ones.

4.     Think of the long term when you are prospecting, not the immediate pay off.

Sales is your friend and the engine of your business. Learn to love it (if you don’t already) and think of it as one of the ultimate tools to self-mastery and personal development (as well as financial freedom).

Cheers and see you soon for Part Eight!