The contact list of today's effective business leader; photo illustration Marc Sullivan The contact list of today's effective business leader; photo illustration Marc Sullivan

At summer camp or your first swimming lesson, Rule 1 is always made clear: never swim alone. Without a "buddy" nearby, a quick dip can turn life-threatening.

Business is much like swimming: whether you dive in, wade in or fall in, it's easy to get in over your head. When market pressures, financial shortfalls or technical glitches threaten to sink your business, you need a buddy close by to offer advice, extend a hand or toss you a life preserver.

In business, there are few solo acts. If you want your company to prosper and grow, you need to surround yourself with people who understand the challenges and risks you face every day. But you don't have to hire them. Whether you're just starting out in business or still remember the day the GST kicked in, you should develop robust relationships with external experts who can bail you out or offer hard-won wisdom when the headwinds get too strong.

At a minimum, here are seven experts, advisors and mentors whom every entrepreneur should have in their Rolodex.

  • An industry old-timer: Maybe you met this person in your first job or at a trade show last month. He or she has been in your industry for years, knows everyone and remembers when the president of your biggest competitor started in the mailroom. These battle-scarred veterans tend to be cynical about change, but if you find any who retain great passion for your industry, keep them close. They know who you can call when suppliers turn surly, or when customers ask for a product or service that hasn't been seen in 20 years. Best of all, when you're freaking out about ominous industry trends or regulatory changes, they'll soothe your nerves by reminding you this has all happened before.
  • A butt-kicking IT expert: What do you do when the server crashes or your technology vendor recommends your organization upgrade to a buggy new operating system? You get a second opinion from a tech-savvy friend who eats business software for breakfast. You meet people like this at business events all the time—you probably excuse yourself hurriedly so you won't spend an hour talking Android apps. Next time, grab their business card, invite them to lunch and ask if you can call once in a while to get a trusted perspective on technology issues.
  • A management mentor. Most leaders recognize the importance of having a mentor they can turn to for advice on executive decisions, such as how to hire a sales manager, evaluate an employee's performance or determine whether your blue suit is still wearable. But most entrepreneurs don't know where to find a mentor. My advice: simply ask. Think of people you know who have had a corner office longer than you and have built successful businesses—in any industry. Let them know why you admire them and want their help. Respect their time; promise to pick their brain only a few times a year. Smart people know that mentoring benefits both parties, and they'll be happy to learn from you, too.
  • A good lawyer. Not to be too mercenary about it, but you can save a lot of money, as well as headaches, by staying close to a corporate lawyer who understands the legal issues you face from time to time. I know one entrepreneur who saved a bundle on legal fees by asking her lawyer to join her company's advisory board; suddenly, she was getting for free the same advice she used to pay for. Don't abuse the relationship—keep your inquiries simple, and throw your legal associate some business now and again. And always recommend him or her to people you meet. Relationships must be two-way.
  • A well-connected business broker. What's the market for businesses today? Who's selling, and what multiple did they get? What's your business likely to be worth? A great entrepreneur always has one eye on a successful exit, so make friends with a business broker and stay in regular touch. They love talking about their market. Your banker, accountant or lawyer should be able to recommend a broker to become your best financial friend (BFF).
  • A marketing guru. Whether you have someone on staff who produces your marketing materials or you buy time from a consultant, marketing is crucial to your business's future. So, keep a veteran marketing buddy in your pocket, someone with whom you can discuss strategy, social media and your next creative campaign. Many marketing pros avoid accountability and defend their turf jealously, so you need a source of sober second thought who can arm you with new perspectives and insights.
  • An antagonist. Many people around a CEO are chosen because of their loyalty and similar thought patterns. But what leaders need most are independent-minded supporters who will challenge their thinking by asking pointed questions and proposing alternative ideas. If you suppress your instinct to crush these people, you'll soon realize how important it is to resist "groupthink" and expose your plans to constructive scrutiny. Seek out friends or colleagues with the experience, courage and stubbornness to play devil's advocate. If you're really lucky, you may find people like this in your own organization. Treat them with great respect; you probably behaved the same way once. And one of them may become your next CEO.

Rick Spence is the Toronto-based author of the Canadian Entrepreneur blog and a consultant on marketing, strategy and business growth. You can reach him at rick@rickspence.ca.

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