How to Strike Up a Sales Conversation With Someone You Know

As entrepreneurs, we all know people who could benefit from our professional assistance. Here is how to begin the conversation without sounding too 'salesy.'

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By Dorie Clark • Sep 15, 2014

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As entrepreneurs, we all know people friends or acquaintances who could benefit from our professional assistance. But unless they specifically ask for help, beginning the conversation can be awkward. You don't want to jeopardize the relationship by sounding overly aggressive or "salesy." You also have to be careful not to insult their past choices. (One graphic designer asked me recently, "Is there a nice way to tell someone their logo sucks and that I could do a much better job?") Here are three ways you can steer the conversation to make it more likely they'll clue in to the skills you have to offer.

Ask how they found their current provider. People don't like to feel sales pressure, but they're often willing to answer general questions. You could say something like, "As an entrepreneur, I'm always interested in how people find out about the businesses they use. How did you first get connected to the firm that did your logo?" That implies curiosity – a desire to glean best practices – rather than a scheme to get someone to hire you. But it opens up the conversation, and if they're unhappy with their logo (or accounting software or landscaper), you'll probably hear about it and can move the dialogue along.

Related: 3 Ways to Make an Offer Your Prospects Can't Refuse

Send them relevant articles. Let's say you've identified someone as a worthy target, who can both afford and benefit from your product or services. Odds are, you won't be able to convert them to a client right away: this is about the long game. Create a schedule and get in touch with them regularly, but not with a stalker-like frequency – perhaps every 90 days. A great way to keep the relationship going and also demonstrate your expertise is to send them relevant articles, preferably written by you. For the example of the graphic designer, you might share a blog post you wrote about "The 10 Elements of a Great Logo," along with a note saying something like, "Jane, I hope you're well! I just wrote this piece about the elements of a great logo and thought it might be of interest to the small business owners I know. In case you or any colleagues of yours might enjoy it, I wanted to pass it along. How are things going with [name of Jane's business]?"

The goal is to write a friendly note that explains why you're sending the article (she's a small business owner so it may be relevant) but without any recrimination (mentioning that her logo is lacking). You also don't want to hint too hard – sending her quarterly articles you've written about graphic design is fine; sending four articles in a row about how to get a better logo is likely to offend.

Related: 25 Books on Persuasion, Influence and Understanding Human Behavior

Ask for referrals. A great way to make sure your friends know about your credentials and the services you provide – while feeling zero pressure - is to ask them for connections to others. You could reach out with a quick email saying, "Tim, I have a quick favor to ask. I've been expanding my logo design business recently and in the past year, I've designed more than 100 logos for local and national businesses such as X, Y, and Z. I know you're constantly talking with other business owners. If you happen to run across folks who are starting a business and need a new logo, or would like to update or redesign their current logo, I'd really appreciate it if you'd be willing to connect us." That way, Tim is aware of your focus and your experience, but you're not putting him on the hot seat. He may send you some referrals, and if he's begun thinking about his own logo redesign, it's now top of mind that you're the person to call.

Friends and acquaintances are a great source of new business, but getting there can be tricky. Trying these three strategies can help make that initial sales conversation smoother and more effective.

Related: The 4 Elements of a Stellar Sales Piece

Dorie Clark

Speaker, Marketing Strategist, Professor

Dorie Clark is a marketing strategist and speaker who teaches at Duke University’s Fuqua School of Business. She is the author of Reinventing You. 

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