Every startup is different, and so what constitutes good advice for each company is idiosyncratic. As are the exact roles of various advisers--lawyers and accountants, board members, a guy sharing a beer with his stressed out founder friend. With so much variation in both the content and delivery of counsel, is it possible to offer any meaningful advice to advisers themselves?

Veteran startup lawyer Ted Wang thinks so. While it's impossible to say what good advice looks like for each specific situation, you can offer some general wisdom about how to deliver your insights to best ensure your advisee understands and takes heed of your suggestions. On Medium, he recently offered three such principles.

1. Know your audience

"Some people prefer to work through an issue from first principles, rigorously stepping through the logic chain that leads to the ultimate advice. Others are heavily influenced by the way that industry luminaries have approached the same problem. Good advisers understand this dynamic and tailor their advice appropriately," he explains.

You should not only take note of your advisees' preferred method of reasoning, but also consider the pace at which they're comfortable making decisions. If one is a fly-by-the-seat-of-the-pants type, go with that. If you need to give an advisee time to ruminate, do.

2. Use analogies

You might think that complex matters demand long, in-depth explanations. Nope, says Wang. Helping your advisee understand something unfamiliar or complicated calls for examples and analogies not long, detailed monologues.

Wang uses his own work as an illustration in entertaining style (which, impressively, really makes you want to talk legal issues with the guy): "I advise about venture capital financings and mergers and acquisitions, topics with which even the most sophisticated entrepreneurs have little experience. I rely on a series of trusted analogies--involving speed traps, pre-nuptial agreements, thunder and lightning, dog racing, and the sexual proclivities of high school boys--to bring these arcane subjects to life. These analogies translate issues into familiar concepts and give the listener an understandable framework to which they can relate back as the issue develops."

3. Obtain context

Actively listening and keeping an eye out for nonverbal clues to your advisee's true concerns is essential, but it's not sufficient. You need to make sure that you get enough detailed information to say something truly useful. That generally means asking plenty of smart questions.

"I am sometimes asked to give advice on a very narrow topic without being given any context. That's like asking a doctor to diagnose a patient without doing an examination," Wang insists. "To get an accurate diagnosis, further investigation is required. Is this the first time this issue has arisen? What is the next best alternative? What have the conversations with the other party been like to date? Without understanding these types of parameters, it is difficult to give sage counsel."

Published on: Oct 6, 2014