David Simpson knows all too well the tough battles that need to be fought to successfully transition a family business. He has worked with many of Canada's leading family businesses and he has worked in one himself, with his brother. He now teaches the next generation of entrepreneurs at the Richard Ivey School of Business MBA program in London, Ont.

He also knows the important role played by lawyers.

"When talking about transition success, your long-time lawyer may not let you in on a little secret," says the founder of the Ivey Business Families Centre. "The lawyer may not ask if you realize that the legal documentation of your transition or success strategy is the easiest part of the succession process."

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Is Mr. Simpson implying that family business lawyers have it easy? Not at all.

A family firm lawyer will know the law, but a good lawyer will also get to know the family very intimately and how the members interact. This close and frequently personal relationship brings its own set of challenges, often requiring a lawyer to step outside of the legal box. The lawyer is like a ring master, advising the owner on when to call in experts to deal with various non-legal family issues encountered when running a business and balancing the long-term succession planning.

"The toughest part of transition is asking three key questions, which have nothing to do with the law or the business itself, but they will challenge every family business," Mr. Simpson says.

His questions are as follows:

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Jacoline Loewen is a director at Crosbie, which focuses on succession advice for family businesses and closely held small to medium-sized enterprises. Crosbie develops customized strategies, particularly in relation to M&A, financing and corporate strategy matters. Ms. Loewen is also the author of Money Magnet: How to Attract Investors to Your Business. You can follow her on Twitter @jacolineloewen.