Have a tough or important question to ask someone?

Nearly all of us do at some point. Maybe you want a potential client to sign a hefty contract with your company. Maybe you need more investors for the new business you plan to launch. Maybe you would like to ask your boss for a bigger bonus.

If you really want to get a yes answer, there are three rules to follow: Be prepared, be personal, and be present. In the process of following these rules, your emotional intelligence will be put to the test as you calm your anxieties about the ask while also recognizing the needs of the person you are asking.

Let’s take a look at each of these rules and how they can serve you.

BE PREPARED

When we talk about preparation, there are a series of questions you need to ask yourself, and they are all about knowing the person you are about to ask:

• How well do I really know the person I’m about to ask?
• Do I know what they are interested in right now?
• What can I ask them that may motivate them to help me reach my goal?
• What’s in it for them?
• Will they help me because they want to or because they have to?
• How do I do this without jeopardizing any prior relationship I had with this person?

If you don’t know the person you are asking, find out as many details about them as you can so that the focus of your ask is about them, not you.

This often comes up if you need to increase your customer or client base, or launch a new business where you don’t know the people you need to ask. The “cold call” you need to make is just that—cold—because you haven’t found a connection to them before you reach out.

Anyone can do some research online on the people they wish to contact, which does provide great background information. But it is those personal and connective tidbits—those jewels, if you will—that will improve your chances that the person will be willing to at least hear more about what you want.

The next time someone refers a person to you, or suggests that you contact someone, ask if they are willing to share more information about the person. How does that person like to be communicated with? Phone call, email? What interests do they have? How do they like to be addressed? Are there topics to avoid?

You never know what item of information might prove helpful.

BE PERSONAL

The more personal and sincere you are when making your ask, the better your chances. A couple of factors can come into play here: the environment in which you make the ask and your tone when making it.

Let’s first address where and how the conversation will happen. There are many choices: in person, on the telephone, in a text, over a live video, or in a proposal or letter.

Each has advantages and disadvantages. If you want your ask to be stable and predictable, you need a stable and predictable environment. For example, when you are in person you can look into their eyes and observe their body language. A downside is there can be outside distractions: waiters at a restaurant, interruptions at their office or yours, telephone calls at their home.

Maybe you’re more comfortable with one of the potential environments than the others. That doesn’t matter. The most important factor in selecting where and how you make your ask is to select the one that makes the person you are asking the most comfortable.

Then there is the matter of your tone during the conversation. Think of interactions you have had with other people when their tone annoyed or angered you. Maybe they were flippant or condescending. Maybe they tried to sound confident but came off as arrogant.

You don’t want that to happen to you.

I learned this lesson after listening to an audio link for a session I did with a women’s networking group. What I heard left me mortified. In answering questions, I must have used the word absolutely a thousand times. If that wasn’t bad enough, the way I said it must have turned everyone off. I came off cocky, like a know-it-all. It was an eye-opener.

To test your tone in advance of a meeting, script a short conversation and record it. Then play it back over and over. Do you like the tone you are using? Are you speaking too loudly? Too harshly? Too softly? Are you speaking with too much or too little energy? Are you too stiff, or are you too laid back? Remember: Your tone is as important as your words.

BE PRESENT

Finally, you simply cannot begin to even think of asking for anything and expect great results unless you have practiced the art of active listening.

Let me confess that in the past I’ve had my own listening problem. When I worked for the attorney general’s office in Philadelphia, I had to fill in for an attorney who became ill right before the start of a First Amendment case in which we were defending state officers. I had to prepare quickly and, on top of that pressure, my supervisor decided to sit in and observe the case. At the noon break he came up to me and said, “Did you hear it?”

Hear what? I thought. Here’s what I had missed: A witness claimed he had seen the actions of state police during a demonstration involving picketers. But later, that same witness said he was standing with his back to the police, which meant he couldn’t have seen what they did as he claimed on the witness stand. We won that case, and from that moment on I won many more cases on cross-examination because I learned to listen—really listen.

Mind you, though, listening takes constant practice. If you aren’t careful, even after you improve you can fall into old habits where you fail to really hear what the other person is telling you.

To listen with presence means there is nothing else in the world going on but the person in front of you. When you ask for something, you need to listen to the person’s every word with laser focus. Be present and show you are present.

Whatever the tough or important question is that you plan to ask, you may only get one shot. Follow these three rules and you will have a much better chance of getting that yes.