Make the Ask

lead with people Jan 30, 2023




I’ll never forget how nervous I was. You’d think I wouldn't be nervous because of all the preparation I put into the presentation. But, you see, I was making the biggest ask of my life and I wanted to be ready.

My nerves were out of control. Even if I thought about making the ask, my nerves would send nerve bombs all over my body. Have you ever experienced a nerve bomb? These are moments when you get so nervous it feels like your body is under an actual physical attack. That’s what I was going through when I thought about what was going to happen when I made the ask.

I had started a non profit organization and getting it off the ground was daunting. At the time though, I thought it was the biggest and craziest thing I was ever going to do. There were a string of very important asks I would have to make. As I look back now, I chuckle at how nervous I was about it.

When I say “asks”, I’m referring to massively important conversations that I was going to have with some very key people over the course of three weeks. You see, every nonprofit organization has a board of directors that help oversee the organization and I had to ask people to be part of my board. Then I had to ask a large group of people to give financially to this brand new startup organization. Finally, I had to ask other individuals if they would donate funds, equipment, and other key pieces we desperately needed.

I had three weeks to make around 140 different asks. Luckily going in, I already knew a large percentage of the answers were going to be no or not now. A leader had prepared me that many of my asks would result in a no and that it was ok. They explained that every no would help lead to the right yes’s.

That was helpful to know, but, honestly, I still wasn’t ready. As much as I prepared, studied, and practiced my asks on others, I still wasn’t ready. What I really needed was going to happen soon enough. What I needed more than anything else was the experience of officially making my own asks and then waiting for the response.

Making an "ask" can be a daunting task. Whether you’re experienced or just starting out, it still can be nerve wracking. But, with the right approach and strategic plan, you will be ready. When I finally started attacking those 140 asks, in hindsight, I wasn’t as prepared as I thought I was. I did the best I could, and the experience was so beneficial to my growth and my leadership development.

If you’re in any type of leadership, you’re going to have to learn how to make an ask. What’s your approach to making asks? How do you go about getting ready to make your asks? Is it something that you prepare for or do you wing it? Let’s talk about each part of the journey to make solid asks and do the best we can to ask and present them with confidence and conviction.

Let’s start with misconceptions about making the ask.




There are three primary misconceptions about making the ask. These misconceptions stop many leaders in their tracks before they even get going because they keep the leader from ever making their first ask.

Misconception # 1: You will bother the person you’re asking. This doesn’t seem all that big, but it’s amazing how this first one will absolutely stunt many leaders from ever making the ask. We try to talk ourselves out of making the ask by having a noble reason: I don’t want to bother the person I thought about asking. The reality is, you will only bother them if you are unprepared and passionless about your project. Don’t shy away from presenting people with the potential of a great opportunity.

Misconception # 2: You’re being irresponsible with your relationship to that person. We feel like we are exploiting our relationships, trying to think of the other person and let them off the hook. But, in reality, many people are actually honored you thought of them. People are looking for ways to use their gifts, influence, or their wealth. They need options. Perhaps your ask will help give them purpose.

Misconception # 3: You’re the only one that will benefit from the ask. Sometimes we let this misconception stop us from asking because we think we’re the only part of the equation that will get something out of the ask. But, that’s not the case. The person being asked, obviously depending on what type of ask, will have numerous opportunities come their way from the ask. This could be a huge blessing for that person and it could be just what they have been searching for and needed.

There is a reason you have the idea. If you didn’t have the idea and the passion behind it, then you have no reason to ask. But, since you do, harness it and make the best ask you possibly can. You won’t accomplish anything unless you take the steps to make it happen. Whether the purpose is to get a raise, investment, donation or sale - whatever the reason is - you should make the ask and be as prepared as possible.

This process will grow you as a leader and communicator. It has the potential to catapult your growth and prepare you for opportunities so much bigger and even more complex. So, don’t let the misconceptions stop you and move forward with your asks.




Now that we’re over the misconceptions, let’s talk about the anatomy of an ask. If you embrace and employ these elements, you will be ready.

Element # 1: Research and Preparation. There is nothing more helpful than being fully researched and prepared. Research the person you are asking and tailor your request to their interests and needs. Spend as much time as you can studying, writing, and preparing your ask. Making these elements an important part of the process will pay huge dividends. To make an ask in a healthy way, it's important to be prepared.

Element # 2: Think Big. It's important to think big when making an ask. Don't be afraid to ask for something that you think may be impossible to achieve. While it may seem risky, thinking big can lead to big rewards. Also, really "wow" the person you are asking, consider going above and beyond. Offer to help them with something or provide them with a valuable resource. Show that you are committed to the request and that you are willing to go the extra mile.

Element # 3: Be humbly confident. Yes, a little play on words, but think about that for a minute. You don’t want to come across too humble or too confident. So, be humbly confident. Be respectful, convincing, and straight-forward. Be mindful of the other person's time and priorities while making sure to express your appreciation for their consideration. Be prepared to answer any questions they may have and be ready to provide evidence or data to support your request. Lastly, be clear and concise about what you are asking for and why. Avoid beating around the bush or using too much jargon.

These elements, when combined together, will help give you a great equation for success. Making an ask can be daunting, but by thinking big, being prepared, respectful, straight-forward, and going above and beyond, you can increase your chances of success.

When I worked through that list of 140 asks, of course it was daunting! But it was also exhilarating! The entire process of making an ask is completely beneficial for not just the possibility of receiving what you’re asking. But the growth that came because of this process was absolutely amazing! Don’t shy away. Get over the misconceptions and whatever is holding you back. Do your research, write your presentation, schedule the ask and make it the absolute most memorable, clear, powerful and potentially life changing ask anyone has ever heard.


By Jason Raitz - Founder of Speak with People