The 4 Advisors Who Could Save You From Yourself

The cheerleader, the detail freak, and other essential additions to your advisory board

Written by Phoebe Fung

It’s lonely business, being at the top.

As an entrepreneur, the buck stops with you. Every day, you make countless decisions about your company; some will be about trivial items, while others will have far-reaching implications.

It’s a lot of responsibility. We’re only human, and sometimes we get it wrong. Think of it this way: how often do you make a decision you go on to regret, or at least second-guess? I’d bet the answer is higher than you’re willing to admit.

As you grow your company, your risks become bigger and your mistakes more costly. How long will it be before these errors in judgement become a liability to your business?

Related: How do your decision-making skills stack up?

That’s why it’s so important to check your decisions by running them by a trusted panel of advisors. I’m not talking about management-by-committee here; the process need not be laborious, nor even much of a bottleneck. In my experience, you only need four filters to help you ensure you’re making the right call. Here are the people who can provide it.

1. The Devil’s Advocate

The successful entrepreneur knows how to create boundaries between decisions that require team discussion and those are best made alone. There’s a sweet spot between leading by committee and leading by dictatorship, and in it sits the devil’s advocate—someone on the management team who will challenge your assumptions.

This person isn’t afraid to take a differing opinion from you, whether they agree or not with your opinion. She forces you to think about issues that wasn’t in your line of sight. Often, we fall so in love with our own ideas that we’re blinded to the unintended consequences of decisions. A divergent perspective is so important, because it allows the right dialogue to occur.

But engaging someone who has the smarts to give an honest appraisal—and the chutzpah to challenge you with it—is easier said than done. At Vin Room, we create devil’s advocates by encouraging people to take a critical eye to everything we do. How? Here’s just one example: after we’ve finished an event or project, we’ll post-appraise it to find out what went well, what could be improved and what must be changed—all without applying blame to any individuals. This encourages people to provide constructive criticism and to start to really question the way we do things. And just like that, I’ve got a pool of devil’s advocates to turn to at decision time.

As a leader, it’s on you to create the right environment for this. That means checking your ego. Often, we can be quick to dismiss devil’s advocates as naysayers. That thinking has to go. In reality, the questioners among us play a crucial role in helping us to make the right decisions.  Always recognize your devil’s advocate for the constructive dialogue they bring to the table.

2. The Detail Freak

There are three good reasons a good strategy fails:  execution, execution and execution

In a recent survey of senior executives conducted by management consultancy Marakon Associates and the Economist Intelligence Unit, respondents said their firms achieved only 63% of the expected results of their strategic plans.  Hardly an “A”, is it? The message is clear: bad execution can totally destroy a great idea.

So, how do you prevent failure? When deciding whether to run with an idea, take a minute to run it by a detail freak in your inner circle. You know the type: he’s the guy who sweats the small stuff and encourages you to consider the details of execution—no matter how minute. His questions may seem annoying, but his granular take will help you determine how your decision will effect all aspects of the business—and, ultimately, whether it will be a positive change.

3. The Lawyer

All decisions have unintended consequences. Too often, these are legal—and this can be scary stuff for any business-owner. That’s why it’s best to keep your legal counsel on speed-dial. Good lawyers are trained to assume the worst-case scenario and can help you navigate through alternatives before they even occur.

Legal advice is all the more useful when the person giving it is familiar with your strategy and operations. A great business lawyer will keep in mind the growth of your business, provide the most cost-effective way to address legal complexities, help negotiate the best deals and help you structure your business plan effectively. In a world filled with contracts, developing a relationship with a trusted lawyer who will vet your decisions is one of the smartest moves you can make.

4. The Cheerleader

The devil’s advocate, the detail freak and the lawyer all exist to take the winds out of your sails. And while that’s essential, I find it’s also helpful to run decisions by someone with a more positive view. The cheerleader is an optimist at heart who will always look to the beneficial offshoots of your decision. His is an important seat at the table, as his enthusiasm provides a counterpoint to the negative and/or skeptical vibes the other three providers tend to give off.

As a bonus, the cheerleader tends to be really good at engaging frontline workers and building momentum for the execution of your strategy. After all, you can’t successfully execute the plan if people aren’t excited about it.

Related: The 5 advisors who cripple companies

Phoebe Fung is proprietor of Vin Room, a Calgary-based wine bar with two locations and that ranked No. 25 on the 2011 PROFIT HOT 50 list of Canada’s Top New Growth Companies, proprietor of VR Wine, a boutique wine store, and a former financial executive with a multinational energy company.

More columns by Phoebe Fung

Originally appeared on PROFITguide.com