Asking Your Manager for Things Doesn’t Have to be Scary. Here’s Why.

Asking your manager for a raise, promotion or more resources isn’t easy. Follow these steps to overcome your fears and ask for what you want. 

Written by Laura Fredricks
Published on Aug. 22, 2023
Asking Your Manager for Things Doesn’t Have to be Scary. Here’s Why.
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Have a tough or important question to ask someone and just can’t bring yourself to ask it?

Nearly all of us have felt that way 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 tech business you plan to launch. Maybe you would like to ask your boss for a raise or a promotion

3 Rules of Asking

  1. Be prepared: Research the person you’ll be asking and think through responses to questions that may come up.
  2. Be personal: The more personal and sincere you are when making your ask, the more likely the person is to say yes.  
  3. Be present: Practice active listening and silence any potential distractions like phones or chat apps. 

Even though we know the only way forward is to just ask the question, it can be difficult to take the leap. What holds us back from just asking? 


6 Reasons Why It’s Difficult to Ask for Things

There are a number of thoughts that run through our mind that make it difficult to ask for things. Below are some of the most common reasons that prevent us from asking the big question:


1. Don’t Want to Hear “No” 

 We don’t want to hear ‘No’ for an answer. It feels awful to get a negative response.


2. Fear of Personal Rejection

When we do get a ‘No,’ it feels like a personal rejection. When we hear that rejection, we often internalize it to mean that we aren’t good enough for what we just asked for. 


3. Thinking They Will Give You What You Want WIthout Asking

We think that if we spend more time with the person we want to ask, they will know what we want and will give it to us without asking.


4. Overthinking

We overthink our ask. Another common barrier is to overthink the ask to the point that we convince ourselves we don’t really need it, or to wait a bit longer before making the ask.


5.  Past RejectionS

We asked before and didn’t get it. In some cases, we may have already been rejected once for your ask or watched someone else ask for the same thing and not get it. So, we may think, “Why bother asking?”


6. Fear of Not Being Able to Respond 

The number one reason we don’t ask is that we fear we will hear something that we will not be able to respond to. For example, let’s say someone suggested that you ask their contact to be a potential investor in your start up. In your head, you play out the scenario and you envision the person saying:

  • “Why me?”
  • “Why do you need it now?”
  • “What do I get in return?”
  • “Who else have you asked?”
  • “How did you come up with this valuation?”

The list goes on and on, so much so that it becomes overwhelming. Rather than getting one of these responses and looking unprepared because we don’t know what to say back, we never ask. 

More on Career Development10 Ways to Effectively Handle Negative Feedback


3 Rules of Asking

You can avoid asking paralysis by following these three rules of asking:

  1. Be Prepared
  2. Be Personal
  3. Be Present


1. Be Prepared

Preparation wins the day, it is just that simple. Preparation for any ask requires that you ask yourself these questions:

  • 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 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, your job is to find out as many details about them as you can so that the focus of your ask is about them, not you. Research provides great background information. It’s those personal and connective tidbits 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 for your ask.


2. 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.

There are many ways you can make your ask: in person, over the phone, in a text, over a live video or in a proposal or letter. Each has advantages and disadvantages, but I’m here to tell you that making the ask in person significantly increases the odds of getting a favorable outcome. 

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. But you also need to keep an eye out for outside distractions, such as waiters at a restaurant, office interruptions and phone calls. 

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. So, be sure to ask the person where they prefer to meet you

Then there is the matter of your tone during the conversation. Think of interactions you have had with other people where 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.

More on Career DevelopmentWhy Patience Is the Job Search Superpower You Need


3. Be Present

Finally, you can’t even begin to think of asking for anything and expect great results unless you have practiced the art of active listening

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. Push away the distractions like your cell phone, files and music. Especially if you are doing this via video conferencing, make sure your cell phone is off, your background is not distracting, your windows are closed and that you are dressed appropriately for your big ask.

It’s also important to listen to the person’s entire response. While it can be easy to dwell on the “no” and spiral, you might miss out on important details that can help you turn it into a yes. People often share their reasons for a no, and listening to those can help you address those concerns. Keeping your awareness puts you in the best possible position to receive that yes.

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.”

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