Master the Art of Asking: 4 Proven Strategies to Get a ‘Yes’ Every Time
I remember being young and wanting to do something that I knew would push my parents outside their comfort zone—like a sleepover at a new friend’s house, a trip to the mall without a chaperone, or getting a cell phone for the first time. I’d think long and hard about how to get my mom (or dad) to say “Yes” before I even approached her. Chances are, you can probably time travel back to a similar memory of your own.
Preparation was everything. If I knew I wanted something big, I’d give myself as much time as possible to strategize. I’d observe her demeanor on any given day—was she busy? Stressed? Lighthearted and chatty? What was the vibe at the dinner table—tense or upbeat? Picking the right moment to ask made all the difference.
While I waited for the perfect opportunity, I’d think about how saying “Yes” would benefit her and anticipate her follow-up questions. If my older brother was having a sleepover at our house that night, my mom might not mind me being out of the house. Or if we’d recently had a pickup snafu at school, where she couldn’t find me after practice, maybe a cell phone would make both of our lives easier.
Then, on the right day, at the right time, I’d make my request—framing it in a way that I thought would give me the highest chance of success.
“Mom, I know Greg is having a sleepover here tomorrow, but my friend is also having one at her house, and I was wondering if it would be okay for me to go?”
Now, let me be clear—it wasn’t always an instant “Yes.” Sometimes I’d hear, “Let me think about it,” or “I need to talk with your dad,” or “Will the parents be there? I need to talk to them.”
If I had done my preparation well, I’d already have responses ready. “I talked to Dad, and he said it would be fine as long as you’re okay with it.” And, “Here’s the phone number for so-and-so’s mom if you want to call.”
We’d go back and forth on any other objections or details, and then we’d end up in one of two places: either a “Yes” (cue me skipping into the sunset) or “I need to think about it more.” If it was the latter, my next move was always, “When do you think you’ll be able to let me know by?”
Looking back, it’s pretty clear that I was destined for a career in sales.
In the last few articles, I covered The Top Five Things Holding You Back from Asking for What You Want and How to Stop Waiting and Start Asking. If those left you wondering, “But how do I actually ask?” you’re in the right place. We don’t have to look much further than the story I just shared.
There are four key elements critical to making your Ask:
Focus on what’s in it for the other person.
Be crystal clear about what you want.
Anticipate objections and have responses ready.
Pick the right time to ask.
Let’s break these down.
What’s In It for Them
What most people get wrong when formulating their Ask is focusing on what they want instead of what the other person wants. By centering your Ask around the other person’s needs or pain points, you make it easier for them to say “Yes.”
Scenario 1: “Mom, I want a cell phone to call my friends.”
Scenario 2: “Mom, I know a few times this month when you came to pick me up, we couldn’t find each other right away, and you seemed stressed and frustrated, in one case it caused us to be late dropping my little brother off for Soccer practice. If I had a cell phone, we could avoid that from now on.”
In both scenarios, the benefit to Mom is the same—avoiding stress and saving time. But in Scenario 1, she has to figure that out on her own. In Scenario 2, I do the heavy lifting for her.
Action: Think about an Ask you want to make. What’s in it for the other person if they say “Yes”? Bonus points if you can identify a pain point they’re already experiencing (e.g. stress, frustration, running late in the case of my mom).
Crystal Clear Request
Another common mistake is being vague or overly complex. If the listener has to decode what you’re asking for, you’ve already lost them. You might think softening the request makes it easier to say “Yes,” but it just makes it harder to understand.
Scenario 1: “Mom, I was kind of hoping that maybe, if you think it would be okay, I could possibly go to so-and-so’s house for a sleepover tomorrow... but only if it’s no trouble.”
Scenario 2: “Mom, I know Greg is having a bunch of friends over tomorrow night. I was thinking it might take a load off your plate if I went to so-and-so’s house for a sleepover instead. You could drop me off as early as 5 PM. Would that work?”
In Scenario 1, you’re uncertain and overly cautious, which plants doubt. In Scenario 2, you make a clear, confident ask that’s easy to respond to.
Action: Practice stating your Ask out loud. Make it concise and specific—no room for confusion.
Anticipate Objections
One of the biggest mistakes people make is not preparing for the other person’s follow-up questions. You know what makes sense to you, but the other person may have different concerns. If you’re caught off guard, you risk losing credibility or seeming unprepared.
Scenario 1: You ask for a cell phone without thinking about questions like, “Who will pay for it?” or “What rules will you follow?”
Scenario 2: You come prepared with a plan: who will pay, what boundaries you’re willing to agree to, and how you’ll use the phone responsibly.
Anticipating objections shows you’ve thought through your request from their perspective, making it harder to dismiss outright.
Action: Write down three potential objections and come up with clear, respectful responses to each one.
Timing is Everything
Timing matters—a lot. The best Ask in the world will fall flat if the person is stressed, distracted, or overwhelmed. Pay attention to their mood and your environment before making your request.
Scenario 1: You ask for a sleepover right after you bring home bad grades and your mom just finished yelling at your brothers.
Scenario 2: You wait until bedtime when your mom is relaxed and in a good mood before bringing up the idea of a sleepover that weekend.
Choosing the right moment shows respect for their state of mind and increases your odds of success.
Action: Be mindful of the other person’s mood and pick a calm, positive moment to make your Ask.
Conclusion
If a kiddo like me could naturally do all of this to get a “Yes,” then you can too. The art of asking is about preparation, clarity, empathy, and timing. By putting yourself in the other person’s shoes and crafting a clear, thoughtful Ask, you give yourself the best chance of getting what you want.
Practice makes perfect—don’t get discouraged if your first few attempts don’t go as planned. Keep refining your approach and learning from each experience. Eventually, you’ll master the art of the Ask—and getting the “Yes” you’re after.
Now it’s your turn. Think about something you’ve been hesitant to ask for. Use these strategies to map out your approach, and go make your Ask with confidence!
