Tips for Tricking Your Boss into Being a Better Manager

    By Christina Tynan-Wood | Small Business

    A great boss can make the workplace your favorite place to be. A bad one can transform the daily grind into one of the circles of Hell. Or make you dream about which of those circles you’d like to see your boss suffer in … for eternity. Unfortunately, a good boss is about as rare as a return ticket at the River Tantalus. But, here’s a secret: Good bosses are made, not born. Your crummy boss might have an inspiring leader in there somewhere…hiding under some fears and bad habits. Rather than suffer and complain, look upon him as your next project. With a little cunning and some elbow grease you might be able to transform him into someone worthy of that “Best Boss Ever” mug he brings to every meeting. And even if he’s hopeless, you aren’t. Managing up is essential in every job. So while you are sharpening his bossing techniques you will also be honing your own workplace skills. So stop complaining and get to work. Here are six tips for tricking your boss into being a better manager.


    Tip 1: Be the a Puppy Trainer

    Maybe your boss isn’t inherently crappy at being a manager so much as brand new to it. This is an opportunity! “Some bosses aren’t comfortable yet in a leadership role,” says Sara Sutton Fell, CEO of Any time he makes an attempt – however feeble -- to manage, reward him. Did he offer some honest feedback on how a project went or accidentally give good advice? Time for a treat! Tell him you appreciate the advice, that it’s helpful to get feedback, or that what he thinks matters to you. “It might not be so long ago that your boss was in your position,” says Fell. “He may still be trying to figure out this ‘boss’ thing.” The best part of this trick is that by helping him develop his leadership skills, you are creating a boss that’s a custom fit for your work style.


    Tip 2: Ask and you’ll Receive

    Complaining over lunch to coworkers about a boss who doesn’t give direction, isn’t clear about what she wants, or complains no matter what you do will not make working for her any easier. Getting in the driver’s seat might, though. “Ask for advice,” suggests Samantha Ettus, CEO, entrepreneur, and the first expert mentioned in Sheryl Sandberg’s Lean In. “When you ask people for advice, it brings out the best in them. People shine when they are helping.” And making your boss feel wise and like someone you admire, will put her in a receptive mood when it comes to what you need. When asking for that advice, suggests Courtney Newman, Vice President of Learning & Development at Allison+Partners “Ask your boss, ‘How would you have handled this project?’ instead of ‘How did I do?’ It’s much easier for someone to talk about their own approach than to criticize yours.”

    Tip 3: Mirror, Mirror….

    Sales people, con artists, and magicians all use body language to create the reaction they want in their marks. This can work with your boss, too, as long as you aren’t too obvious about it. “Mirror your boss's body language and tone to encourage him to see you as one of his own,” says Samar Birwadker Co-founder and CEO Good.Co, an app that helps you find workplace happiness. “This will make him more amenable to your suggestions. If you overdo, it, though it could backfire. “Mirroring is usually an unconscious behavior,” says Birwadker. “Obviously fake mirroring can have the opposite effect.”


    Tip 4: Be Indispensable

    Your boss is flawed. Everyone is. But if you’ve taken the time to complain over drinks about your boss, you probably know all too well what his flaws are. And that’s exactly the information you need to make yourself indispensable. “Rather than waste your time complaining about those shortcomings, compensate for them,” suggests Mary Ellen Slayter a career expert for “Does he show up for meetings unprepared? Take on the prep work for him. Does she procrastinate? Help her meet deadlines. Does he deliver deadly presentations? Spiff his up with a bit of your own wit and charm. You won’t have to suffer in silence. He’ll be better at his job. And you’ll both be part of a successful team.


    Tip 5: Taming a Micromanager

    She spends more time telling you how to do your job than it takes you to do it. He criticizes every move you make. It’s maddening and unproductive. But so is sitting there helplessly fuming. Your boss is – mostly likely -- micromanaging out of fear. “What's your boss’s biggest fear?” asks Monster’s Slayter. Is she worried about blowing deadlines? “If so, assuage her fear by agreeing on check-in points for project milestones and hit them like clockwork.” Or is she simply afraid because she’s in the dark? “Be proactive about giving her frequent status updates before she has a chance to come to you,” suggests Allison+Partners’ Newman. “Notify her early if you think a project is starting to go south.” This way, at least, you manage the interruptions to your work caused by her constant meddling. But hopefully she will also learn to trust you, feel less afraid that everything is about to go wrong, and believe you can do your job.


    Tip 6: Toddler Tricks

    Parents – and hostage exchange mediators -- know that the best way to get a recalcitrant toddler – or hostage taker -- to do what they want is to give them simple choices. Instead of saying no or asking for something specific, offer a choice instead, preferably one where you like both options. For example, suggests, Elizabeth Lombardo, Ph.D., author of the upcoming book Better Than Perfect: 7 Steps to Crush your Inner Critic and Create a Life You Love “Make an offer something like, ‘I can stay late tonight and come to work late tomorrow or I could bring this project home to finish it up.’” These sort of easy choices work as well in the workplace as they do in the nursery.


    Christina Tynan-Wood is a freelance writer living in California. She writes the Family Tech column in Family Circle and blogs at

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