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Kanye West performs during the closing ceremony of the Pan Am Games Sunday, July 26, 2015, in Toronto.Julio Cortez/The Associated Press

This column is part of Globe Careers' Leadership Lab series, where executives and experts share their views and advice about leadership and management. Follow us at @Globe_Careers. Find all Leadership Lab stories at

Who couldn't use an extra billion dollars? I'm sure many people checking their bank balance after Christmas season could do with the extra cash flow. Apparently Kanye West had the same thought recently when he asked Facebook founder Mark Zuckerberg for that amount via Twitter.

While it seems unlikely that it will be a successful funding strategy for Kanye, this is a good opportunity to learn some valuable insights into how to approach business relationships online in the social age. This is particularly relevant if you want to sell something, whether it be products or services, or an investment opportunity.

Pick your moment

Any good relationship takes time. You wouldn't ask someone to marry you on a first date, so don't just jump in cold with a big ask in business without investing in learning more about your prospect. Social media has made this much easier by enabling you to keep track of the relevant decision makers within companies, take note of the articles and updates they share in a professional context, and look for opportunities to engage them with relevant content of your own. If Kanye had followed this advice, he may have avoided surprising Mr. Zuckerberg with that kind of ask on his birthday. Ouch.

Find the right people

Today, buying decisions by organizations involve an average of 5.4 decision makers. Even CEOs don't make decisions on their own. Each of these influencers may have different objectives and be influenced in different ways. Kanye would have benefited from doing more research before diving straight in with his pitch. This approach might take time, but building the right relationships within an organization improves your chances of success. Sales intelligence resources like LinkedIn's Sales Navigator can help you zero in on decision makers, research potential prospects, and get warm introductions through your network to more easily open conversations.

Context matters

Approaching Facebook's founder on Twitter, as opposed to on platform he created, may have been Kanye's downfall. By paying attention to where your prospects gather online, and where they find their information, you can more easily engage in conversation in a context where they're actively seeking relevant insights to help them make business decisions. Just as you wouldn't interrupt someone's family barbeque to tell them about your latest product or service, paying attention to the time and place in which you open conversations has a direct impact on your ability to convert a contact into a customer.

The digital age has transformed the way people buy and sell, especially in the world of business. Far from being a problem, this has made life easier for the world's salespeople. Social media has put an end to the dreaded cold call forever. Customers and prospects gather on social channels, so naturally this is where sales teams need to be as well. But to be a success, salespeople have to adapt their approach to suit this platform. Social selling – using social networks to develop useful and productive relationships with customers – is so easy that almost anyone can do it.

Even Kanye (with a little help).

Jonathan Lister is vice president of sales and country manager at LinkedIn Canada, Toronto.

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