How to Ask for Something (in a Way That Leaves People Wanting to Say Yes)


Before we get to this week's post: Do you ever wish you could do more with your life, but held yourself back because you’re afraid of rejection? Check out The NO Game by my friend Jacob Sokol of Sensophy. The goal of the game is simple… collect 'no's by asking for things you’d like. Just imagine what’s possible if you weren’t afraid of getting a 'no.' You could expand your assumptions about what you think is possible in your life, develop the skill of asking for what you really really want, overcome your fears of rejection and develop more courage. There’s also a supportive FB group, so once you get a 'no,' you can celebrate with other participants. The challenge is completely free and runs until the end of January. You can join in anytime! Check it out here.I don’t always find it easy to know how to ask for something. As a staunch I’ll-do-this-myself-come-hell-or-high-water kind of person, the art of the ask has been a steep learning curve personally and professionally. As part of that learning curve, I've realised that part of living a whole-hearted and connected life means acknowledging interdependence with my fellow humans. This involves asking for things and making requests of people.Over the last few years (and especially running this website), I’ve had to ask for a lot. Doing this has helped me move from agonising over each individual ask, to experimenting and feeling a lot more comfortable making requests. I’ve also been on the receiving end of plenty of asks. Seeing the both sides of this process has taught me a lot about how (and how not to) go about it.Here are a few things I’ve learned along the way about how to ask for something in a way that not only leaves us feeling good about the request, but also leaves other people wanting to say yes:

1. Ask with empathy

Empathy is about considering the person’s position before making the ask and the kind of relationship we already have with them. Are they busy? Acknowledge that. Have they offered to help or already helped us in some way? Acknowledge that too.It's also about thinking over our ask and considering how it might feel to be the other person receiving it. When we feel self-conscious about making an ask, it’s easy to slip into focusing on our needs alone and make it all about us. The best asks are win-win asks. While it’s important to ask with humility (more on that below), it’s helpful to show the other person we’ve thought about them and how we could reciprocate too.

2. Ask from a place of enough-ness

This is a tricky piece, but it’s so important. What often makes asks feel hard is the idea that we need the other person to say “yes." Whether we’re talking “Do you want to go out on a date next Friday?” or “I'd like to ask for a raise,” desperation is a real turnoff.Asks are best made from a place of enthusiasm and openness to whatever unfolds. No matter how high-stakes the ask might feel to us, it’s important to remember that we don’t need the person to say yes. There will always be another way to move forward. In his book Getting to Yes, William Ury talks about creating a BATNA, which stands for “best alternative to negotiated agreement.”This is something I make a regular practice of using now, especially when I feel nervous about making an ask. For collaborative work projects, I usually ask more people than I need because I assume some people will say no (for The Entrepreneur’s Inner World, I approached over 50 people to take part, and interviewed the 24 people who said yes). For personal asks, I think in advance about what my plan B will be if the person declines.This isn’t the same as assuming the worst. In fact, I'm more optimistic going into the ask because I know if I get a “no,” everything will be just fine.

3. Ask with humility

Another way asking from a place of scarcity can manifest is in a lack of humility. A request is not a demand. Asking someone for something from a place of entitlement or superiority is not a good start and can hinder our chances of getting the yes we might have otherwise received.

4. Be reciprocal…

This isn’t applicable to all asks, but it harks back to point no. 1 about empathy.If we’re asking for someone’s time and energy, what can we give them in return? This doesn’t have to involve payment. It could be an offer to help them move house next Thursday or to take them out to dinner to say thank you. It could be a shout-out on social media, spreading the word about their work, or leaving a glowing review or testimonial. Sometimes, it's simply taking the time to say "thank you." The level of reciprocity will depend on the size and the context of the ask, but it’s always useful to think about what we can offer the other person.

5. … And then follow through

As great as it feels to be on the receiving end of a reciprocal ask, that great feeling doesn’t last long if the other person doesn’t follow through. Offering reciprocity then not holding up your end of the exchange is bad juju. Not only does it damage the relationship (and likely to lead to “no”s in the future), it also undermines your relationship with yourself, your self-trust and sense of integrity.

4. Remember a “no” is rarely personal

When you ask for something you’re meeting your needs. When someone says no, they’re meeting theirs.It’s rarely personal. More often than not, it’s just about needs. Remembering this takes the emotion out of hearing no and makes it easier to make requests that will meet our needs in the future.Do you have any suggestions for how to ask for something in way that leaves other people wanting to say yes? Leave a comment and share your thoughts.Further reading: navigating the minefield of advice & boundaries & how to ask for what you want without feeling awkward