How to Get Your Boss to Say “Yes”

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Executive Buy-in.

— Marketing and Communications Director

Tim, what can I say to my boss to persuade him to buy your software?”

I wish I had a dollar for every time I’ve heard this question.

This post is for anyone looking to get a boss on board. Don’t hope for a miracle. Come prepared. Whether you’re approaching your boss for the first time or giving him yet another chance to change his mind, you’ll need some techniques up your sleeve. Here are a few of my favorites.

Go for the “No”

If you’re afraid of rejection, you will buckle at the first sign of negativity. Or worse, you’ll get defensive. Our brains look for a shortcut in stressful situations. For most of us, this means going on autopilot and repeating past mistakes. Which may lead to any number of disempowering scenarios—unless you have a Plan B.

My Plan B starts with the idea that objection is not rejection. Any reasonable, responsible buyer should raise objections. A typical path to a “Yes” takes you from one objection to the next, until the buyer feels that benefits outweigh the risks. The sooner I discover all of them, the sooner I can move past them or move on to the next buyer. If the buyer is your boss, you could follow the same path to reach common ground.

I like to think of objections as real, fictional, or imaginary. I use a different strategy, depending on what kind it is.

Explore the Reality

For example, a real objection to our intranet software might be that a competitor is offering a better deal. If you’re going to overcome a legitimate concern, you must dig deeper. What makes it a better deal for your boss? Is it just the money? Will the competing solution meet all of the company’s needs? Is it easy to maintain and grow? Can you back out safely if it doesn’t work out?

There’s a great example of overcoming a real objection in the movie “The Wolf of Wall Street.” After unveiling his new brokerage firm, Stratton Oakmont, Jordan Belfort is training his salespeople to close deals. It goes something like this:

“Your clients have a problem with you: they don’t trust you. And they are right. Why should they trust you? You’re all a bunch of jerks.”

He teaches them to establish trust by convincing the buyer that their interests are closely aligned with his—a lie in this case—and by appealing to his ego.

A lack of trust is a common obstacle in any negotiation, including those between you and your boss. If that’s your problem, you must address it—though I don’t recommend lying to your boss. Other than that, Jordan Belfort had the right idea.

Sidestep the Fiction

A fictional objection is a lie, like “it exceeds our budget,” when there’s no fixed budget in place. It could be a negotiating tactic, for example, if your boss wants something from you in exchange. (Does he? What could that be?) Fictional objections are typically used to hide a real one. Perhaps your boss is afraid to ask his boss, but he doesn’t want to look weak and indecisive, so he gives a different reason.

This is how a Verizon sales rep learned about fictional objections. He was going door-to-door looking to get Comcast customers to switch to Verizon. Part of the sales pitch was a stronger, more reliable Wi-Fi. At one house, a couple came to the door. The husband seemed interested, but the wife was skeptical. First, she didn’t like the price. When the rep lowered it, she said she didn’t want to deal with the installation. When the husband offered to meet the technician, she said she didn’t have enough time to make a decision. The rep offered to come back after he had visited all the other houses in the neighborhood. When he did, she asked a lot of technical questions. After two hours of negotiations, the husband signed a contract with Verizon. The next day, the wife called and canceled it. It turned out she was worried about the health hazards of EMF radiation but didn’t want to say so in front of her husband.

During his sales training, this rep had received a script to help him overcome various customer concerns with logic and packaged solutions. He was eager to apply the script during his house calls. What he didn’t know was the difference between real and fictional objections. While persuasion and logic work great on real objections, they’re a waste of time when dealing with fictional ones.

A fictional objection is a smoke screen. The trick is not to fall for it. If you believe it, you’re duped out of your goal. Calling your boss out on it may backfire, too, because it puts him on the defensive. Nor is it a good idea to suggest a solution. The Verizon sales rep learned the hard way that solving a fictional challenge will not change anyone’s mind. To do that, you must get to the truth first.

Calm the Imagination

An imaginary objection is something your boss believes even though it’s not true. For example, he might say, “Social intranet is too distracting. If everyone reads and comments, no one would get any work done.” To dispel an imaginary objection, you need facts. For example:

“Live meetings and email are more distracting than a social intranet, because…” Give a reason.

“A social intranet helps cut down on meetings and email, because…” Give a reason.

“We can turn off any social feature we don’t like, because…” Give a reason.

Notice the word because following each statement. This word is your friend. It will help your boss see your claim as an established fact rather than a figment of your imagination. Your explanation is important, but the word itself holds a certain sway over the human brain—strange, but true because psychological experiments have confirmed it. I’ve tried it too. It works.

An imaginary objection is the easiest to overcome. If your boss continues to defend it, it’s a sign that you’re up against another kind of objection: a fictional or a real one.

That sounds great, Tim, but how can I tell which one is which?

8 Surprising Employee Problems You Can Avoid with a Modern Intranet

Use Active Listening

Depending on what is going through your boss’ mind, any objection he raises can be real, fictional, or imaginary. You need him to tell you more, and my best technique for that is active listening.

I talk about active listening in Chapter 13 of Who the Hell Wants to Work for You? I also gave some examples in a previous post, What to Do When Your Customer Is Dead Wrong. The idea is to hold the space for your boss to show his thinking. It’s the same technique psychotherapists use to get clients to talk. It consists of mirroring and labeling their responses, and waiting for more details to come out.

Unlike logic, which aims to distract the opponent with new ideas, active listening forces him to focus on the contents of his mind by shutting out all distractions. If you’ve had it done to you, you might have noticed how hard it is to keep your thoughts to yourself. Unless your boss has a strong reason to hide his true motives, a few rounds of active listening should reveal them. It’s my go-to strategy whenever I hit a roadblock.

My favorite form of active listening is a technique I learned from Chris Voss, master negotiator and author of Never Split the Difference. I use it with friends, family, customers, and employees. It’s a good idea to use it as much as possible because it saves you time and aggravation, but also because it’s counterintuitive and it takes practice to replace your old ways.

When was the last time you had a circular conversation? Most likely within the last twenty-four hours. Maybe you were trying to get a child to clean his room or a boss to stop micromanaging you. You did your best to make your point, but the conversation went around and around… Why is this so common?

Voss says it’s because we’re emotional creatures, but we don’t like to admit it. We argue over facts, but the reason we can’t agree is an emotional one. As long as it remains hidden, we are powerless to resolve our differences. Voss calls it “playing in the weeds.”

To come out of the weeds, set your own arguments aside and focus on your boss’. Understand the emotion behind his attitude and label it. Use the words, “It seems/sounds/looks/feels like…” to get him to reflect on it:

It seems like you’ve got a lot of problems you’re trying to solve…” (Let him talk.)

It sounds like you have a good idea of what you’re looking for…” (Let him talk.)

It looks like you’re afraid of making a bad decision…” (Let him talk.)

Labeling moves our brain from fight-or-flight to rational thinking. It breaks the hold the emotion has on us. When your boss sees his emotions reflected back to him, his instinct is to explain why he feels that way. This is your path out of the weeds and into a wide-open space. All you have to do is be quiet and let him talk.

Don’t interrupt his speech, and, more importantly, don’t interrupt his thinking. A lot of it goes on when both of you stop talking. Don’t be the first to break an awkward silence. Let him do it. When he finishes, feed it back to him and, once again, wait for a response. If you stay with this process, one of two things will eventually happen: either he talks himself out of his position—or better yet—you get to the bottom of his feelings so you can address them.

If you get stuck, ask one of these questions:

“What is the biggest challenge you/we face?” (Let him talk)

“How will we know when we’re on track? How will we address things if we find we’re off track?” (Let him talk)

“What do you mean by that?” (Let him talk)

“How am I supposed to do that?” (Let him talk)

“How should we proceed from here?” (Let him talk)

“What can I do if I can’t do that?” (Let him talk)

If you sense his frustration, label it…

“I’m sensing some frustration here…” (Let him talk)

For an aggressive boss who doesn’t beat around the bush, a good label might be:

“It sounds like you’re trying to be honest.” (Let him talk)

When your boss takes the conversation into the weeds, arguing about irrelevant details, ask him these questions to stay in the clear:

How does this fit into your/our objective?” (Let him talk)

How can I help you get what you want if you don’t put me in a position to do so?” (Let him talk)

“It seems like it’s important to you to [paraphrase his thought]… “ (Let him talk)

If your boss disagrees with you on a key point, say:

“It seems like you have strong evidence to support that.” (Let him talk)

When your boss makes a claim he cannot defend, and you handle it this way, he will see the problem. If he refuses to resolve it logically, then the problem is emotional for him. He may feel as though he’s lost the argument and is desperate to save face. Help him out! Make him feel like he won or at least got something out of the conversation. Did he make a valid point? Even a simple recognition might put him at ease.

When we’re used to playing in the weeds, it’s hard to resist the urge to say the first thing that comes to mind. You might feel like you’re playing a role or a game. To start, use canned responses (quoted above.) As you get better at active listening, give yourself more freedom to experiment. Be patient with yourself. Soon, you will build your own arsenal, and the right words will come naturally.

Keep in mind that your demeanor matters more than your words. Our brain uses subtle clues to decide who’s a friend and who’s a foe. Tone, posture, facial expression, and projected sincerity are more powerful than the content of your message. Be likable. Show sensitivity. Smile. Laugh. Relax. Have fun.

Don’t try to win at all costs. If the conversation isn’t going your way, accept it for now and give yourself time to strengthen your case. Many negotiations take multiple rounds. If you’ve learned something new about your boss’s perspective, you’ve done well. Use your knowledge to improve your strategy for the next time.

Take it Personally

Sometimes it’s all about the messenger. Like most humans, your boss may require social proof, before he takes action. If he has said “No” to you, to whom is he likely to say “Yes?” The same idea that sounds dumb coming from you may be a stroke of genius coming from someone else. Enlist this person’s help to advance your agenda. You can take credit later. On the bright side, if yours is indeed a dumb idea, your boss will have someone else to blame.

Use Visual Aids

When you’re sure you’ve uncovered your boss’s real issue, it’s not a bad idea to put your thoughts on paper. Not only will it speak to his visual/auditory/tactile learning skills, but it will help you sort your arguments and fireproof your case.

Notice that this step is last. There’s no point in making color slides if your boss doesn’t care about the topic or doesn’t take you seriously. Eliminate those options first. Most bosses hate surprises. Don’t ambush him with your presentation. Tell him you’re working on the idea you had talked to him about and set up a time to make your pitch. Read this post one more time from the beginning. Now you’re ready. Good luck!


If you like to have your boss on your side, you might like my book, because it shows you how to get inside his mind.

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Written by

Tim Eisenhauer is a co-founder of Axero Solutions, a leading intranet software vendor. He's also a bestselling author of Who the Hell Wants to Work for You? Mastering Employee Engagement. Tim’s been featured in Fortune, Forbes, TIME, Inc Magazine, Entrepreneur, CNBC, Today, and other leading publications.


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