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The Art of Persuasion

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Seven winning ways to approach your boss with a problem.

By John Langenfeld, Illustration by Sarah Quatrano

There are good butterflies to have in your stomach, and there are bad butterflies to have in your stomach. The good kind are a bit goofy and swirling from too much hibiscus nectar. We feel those when we’re in the same room with a pretty woman or a handsome man we have a crush on. The bad butterflies, though, seem hungover, sour and choppy in their flight. These are the ones we experience when we have to inform our supervisors of a problem, and we’re dreading it.

I don’t know anybody who looks forward to lumbering into their boss’ office and announcing, “Hey, there’s a big mess you need to know about. Brace yourself, because…” But sometimes we have to address uncomfortable issues with the men and women upon whom we’re dependent for employment. It’s not a fun position to be in, but there are techniques that are helpful for doing so. Here are seven suggestions for broaching distressing conversations with your supervisor and potentially even impressing with your tact and finesse.

Time it right. Who’s happy to be back in the office on a Monday? Not many people. Plus, it’s frantic. Better to wait at least a day to introduce a conflict. And if you bring it to your boss’ attention on a Friday, even if all goes well, there’s too good of a chance he or she will forget it over the weekend, which means either nothing will get done, or you’ll have to approach the subject again later. It’s better to bring up the problem on a Tuesday, Wednesday or Thursday.

Lead with a solution. A friend of mine who is a self-made millionaire business owner gave me an invaluable piece of advice years ago: “Never go to a supervisor with a problem unless you have a viable solution to it.” It makes perfect sense. He urged, “Knock on her door and when she lets you in just tell her, Ms. So-and-So, I have a solution to a problem I’d like to discuss with you. She’ll appreciate hearing about it when posed that way.” The years have proven my friend right.

Anticipate objections. Most people prefer maintaining the status quo to making changes, because changes can turn out to be good or bad. That’s a risky proposition for the one having to make the final decision. Your best bet is to foresee potential objections to your solutions. Once you’ve identified them, work out your spiel for each and practice your pitches. Practice them in the mirror, and practice them relentlessly. When you’re sitting in front of your supervisor assuaging his or her concerns, you should have your responses internalized so they flow naturally. Your supervisor will be reassured by your poise, foresight and acumen.

Propose win-win solutions. Rather than seeking solely to get your way, come up with solutions that benefit all involved. As Stephen Covey explains in his book The 7 Habits of Highly Effective People, “Winwin means that agreements or solutions are mutually beneficial, mutually satisfying. With a win-win solution, all parties feel good about the decision and feel committed to the action plan.” A solution to any problem is going to affect multiple people. Your proposal will breeze by if all parties are on board with it.

Weigh them down, then lighten their load. Robert Cialdini, best-selling author on the art of persuasion, cites baseball as an example of this strategy in his book, Yes!: 50 Scientifically Proven Ways to Be Persuasive. According to Cialdini, baseball players routinely warm up by swinging a bat with a weighted ring on it. This is because when they are at the plate, their bat is not only lighter without the added weight, it feels lighter than it would had they not practiced with its weight. In other words, 32 ounces feels lighter than 32 ounces. Use this phenomenon to score with your boss by proposing multiple solutions, starting with your least favorite, which should be the heftier burden for him or her. Then propose your favorite, which is a lighter load.

Show the bill. The only reason there’s ever a problem is because the situation is costing something, whether it be a loss in terms of money, morale or human resources. Oftentimes, people don’t equate a problem with a cost because they don’t see the indirect loss. If there is a problem with computers functioning slowly, then failing to invest in better equipment could mean less productivity, hurting profits. Show that the loss in profits outweighs the price of new equipment. If a coworker’s negative attitude is the problem, show how negativity diminishes overall morale, which adversely affects performance.

Lead along stepping stones of yes. If your supervisor does not immediately commit to one of your suggestions and a dialog ensues, follow the advice of Dale Carnegie. In his classic How to Win Friends and Influence People, Carnegie says, “Keep emphasizing, if possible, that you are both striving for the same end and that your only difference is one of method and not of purpose.” In so doing, according to Carnegie, ask questions that will elicit yes responses from your boss according to his or her self-interest. Accrue enough yeses, and it will be difficult for your boss to ultimately answer no.

Hopefully you won’t be knocking on your supervisor’s door any time soon with a dreaded problem. But when that time comes—and it will eventually—just follow the suggestions listed above, and you’ll be set for success. Have your plan mapped out and your presentation practiced until it flows naturally, then stride to your boss’ office with confidence. And say goodbye to those acerbic butterflies churning in your tummy. Consider them dispelled when you’re deft at the art of persuasion.


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