Learning the Art of the Ask

Everyday, we ask others for things — to do something for us, or to give us something. Some asks, however, are more difficult than others, such as asking for a sale, the money to fund a new business, or for a donation to fund a big cause. Here are some thoughts on learning and mastering the art of asking.

By Stephen Dupont, APR

How will you ever know, unless you ask?

For many people asking for something from another person is very difficult.

In fact, sometimes, it feels like the hardest thing to do in the world.

Asking for money…

For a date…

For a job…

For a referral…

For a raise…

For help.

There are no college classes in learning how to ask for the things we need or want. We’re supposed to figure it out on our own.

And because we’re so worried about what the answer might be, we avoid asking, even when asking would be the best thing to do.

My friend, an insurance broker, laments that a younger associate just lost a $3 million contract.

“He tried to do it all himself,” he said. “He didn’t let me and or anyone else know that he was working on it. If only he had asked for help, we could have gotten that business for him and us.”

Losing Our Ability to Ask

Learning why you need to learn how to ask is the only way you are going to move forward to bigger and better things.

In our tech-driven world — where we’ve grown accustomed to asking Google or Siri for help — part of the problem is that we as humans are losing the ability to ask others. Not our ability to ask a machine, but to ask a living, breathing human being.

Instead of picking up the phone or meeting someone face to face, we hide behind emails and text.

Rich, who runs a real estate brokerage, shared his frustration with me in the hallway on our way out of the office one evening:

“I can’t get any of my people to pick up a phone and talk to a client, much less go meet our clients in person,” Rich said. “They spend all of their time on their phones and laptops emailing and texting their clients. I just don’t get it.”

And yet, our phones are with us all the time. Everywhere we go.

It’s in having those conversations that we can obtain the context that can lead to a mutually beneficially relationship.

Yes, we can ask people to share their pain points by email.

Yes, we can ask for information through online surveys.

But, if we really want to know — if we really want to understand and comprehend — we need to ask in a phone — or, better yet, face-to face — conversation.

Why You Should Ask

The act of asking is an exchange of value.

I ask you to buy my product, to give me your vote, to volunteer your time, or to donate to my cause.

I ask you for information that will help me make a decision for help to help me get somewhere I want or need to be, or to prevent something that may cause me harm.

I ask you to enjoy an experience together that will further our relationship, such as go to a movie or eat together at a restaurant.

Asking comes more easily when we know that our likelihood of being rejected by the person we’re asking will cause us little embarrassment, or shame.

That’s why it’s easier for us to ask those we trust and love.

The Secret Sauce of Asking: Trust

Where there’s a lack of familiarity and/or trust, asking is harder. In such a situation, there’s an uncertainty as to whether the “ask” will be mutually beneficial.

For example: You receive an email from a company of which you’re not aware, offering an incredible piece of software that will enhance your company’s operations. Why should you respond? You don’t know the company, much less, the actual person who sent the email. How do you know it isn’t some hacker out to scam you?

Or, what about those emails and calls you receive from a salesperson who sends an email that is obviously off message? Working for a creative firm, I love the emails from the companies that contact me to say they can help our firm create powerful content. Don’t they realize that we are in business to do just that? Why would we farm out that which defines us — the very thing we do better than anyone?

Building Trust

Sales consultant Bob Burg, author of Endless Referrals and Go-Givers, says “when all things are equal, people do business with those that they know, like and trust.”

Endless Referrals by Bob Burg

How do you build the trust to allow you to ask more effectively?

Like most things, you need to practice. Asking more. And asking for bigger and bigger things.

It’s through this process that we build trust.

We ask for a sale, and then we must deliver to the customer’s satisfaction, which earns us the opportunity to ask again. In that process of exchange, we learn to trust one another.

How do I know this? Well, for the majority of my career as a public relations professional, I’ve had to learn how to ask reporters to do stories about my clients. I have made tens of thousands of asks — from local bloggers to the most well-respected and influential news media in the world.

Through that process, I have persuaded thousands of reporters to write or produce stories about my clients.

But by the same token, I’ve been turned down thousands of times as well.

In fact, I’ve probably been turned down at least three or four times for every ask I’ve made.

That sounds like failure.

I learned early on that asking a person, such as a reporter, repeatedly to write a story about one of my clients without a really good reason not only was inefficient, but it often ruined my reputation and harmed my ability to work with that same reporter in the future.

Although I employ technology to assist me in my efforts, frankly, even today, many years after I entered the profession, the most effective asks still boil down to a personalized request to a single individual based on a fair amount of homework.

Before I ask, I try to learn everything I can to make that ask more relevant. This has helped me increase the percentage of yes responses.

It’s often the same for other professionals. Whether you’re seeking a major order from a large corporation or you’re the founder of a start-up, there you are, sitting across the table from another person, asking for the sale.

Overcoming No

While it’s common for sales professionals to take courses in how to sell more effectively, for the rest of us, learning how to ask more effectively isn’t something we’ve been taught.

And yet, if you look closely at your life, you’ve been practicing asking since you were a little child.

You asked a parent for a candy bar while standing in the check-out lane.

You asked Santa for a very special Christmas gift.

You asked a friend for a ride home after school.

I remember one of the most important asks in my life. I was 15 and a ninth grader. My father had a small janitorial business — his side hustle — in addition to his full-time day job as a barber. One Sunday afternoon, after helping him clean an office building, we were on our way home and we drove into the parking lot of the grocery store located in our small town on the outskirts of the Twin Cities.

Sitting on the passenger side of the front seat, he parked, turned off the car, and said, “I’ll wait here while you go in and ask for a job application.”

“What?” I said, “Okay, who should I ask?”

“You go in and ask one of the cashiers.”

So, I did. In my ripped-up football jersey and worn out blue jeans, I went up to Doris the cashier and asked for an application. Doris called for a manager, who led me to the store office in the back of the store where I met one of the assistant managers.

I was ready for a “no” right there on the spot. But, I asked, and was handed an application and told what time to come back the next day to meet with Tom, the store manager.

The next day, I biked backed to the store. This time I wore better clothes. I turned in my application, where I received a short interview from Tom, the store manager.

Again, I was ready for him to say “No, I can’t hire you.”

I have no clue what I said, or how I presented myself. But he hired me, and I started working that spring, just before the summer months as a bag boy.

Break It Down

To prepare ourselves for the big asks in life, we need to practice with obtaining small “yes’s.”

Start with small yes’s.

For example, you can’t attend a college without first completing and sending an application.

Same for most jobs — before you can actually ask for a job, you need to fill in a job application.

Want to see your art considered for a big show with other artists? Complete the online application.

Want to read a story about your organization in a local business magazine? First, go online and download a media kit. Or, request a media kit through a contact form.

Successful sales professionals follow this rule: Instead of going for one big ask, seek a number of small “yes’s” instead. They create a “yes ladder.”

We do this for many things. For example, when I proposed marriage to my wife Rebekah, we both had obtained smaller yes responses from each other. Yes to a first date. Yes to a second date. Yes to our first trip together. Yes to visiting each other’s families. Yes to moving in together. While proposing marriage felt like a huge deal, in reality, we had both said “yes” to each other before the big ask, which made that decision much easier for both of us.

The same process often applies to winning a big contract, or obtaining a large donation for a fundraising campaign. Way before we get to the big ask, we build a series of smaller asks. The process allows the two parties to build trust in each other until, they decide to fully partner on a big project or initiative.

Be Your Own Matchmaker

Over the course of my career, I’ve been asked many times, to what do I attribute my success at media relations or publicity?

To me, it’s always boiled down to this: do your homework (see: 15 Tips on Asking More Powerful and Relevant Questions)

Before I pick up the phone or send an email to a reporter, I carefully study what that person has reported upon in the past. I study other stories that a publication or program has published or aired. I get a media kit to better understand the ideal person that a media organization is trying to reach, and to whom it has tailored its content.

Then I try to match what the publication or program is trying to achieve with what my client wants.

It’s all about alignment and relevance.

The more relevant your story is to a media outlet’s readers, viewers or listeners, the more likely you will score a placement. In other words — the more likely the reporter will say yes to your ask and invest the time and effort to write a story, produce a segment, or conduct an interview.

There are two factors involved in this process. First, by lowering the risk for the reporter, the more likely are my chances to persuade a reporter to do a story about one of my clients. Second, you’re appealing to emotion — you genuinely want to see the person whom you’re asking feel excited about the prospect of writing or producing a story.

The same dynamic applies to other situations, such as asking an angel investor to put up money to fund a new venture, asking people to contribute to a crowdfunding campaign, or inviting someone to vote for you.

For example, I recently spoke to a venture capitalist about what he looks for in a new opportunity. It boils down to this: acquisition cost. If a business knows exactly how much it will cost to obtain a new client and has a goal in place to lower those costs, the venture capitalist told me he’d consider a deal. If a start-up owner is unsure of those costs, the venture capitalist won’t touch it.

That was the first threshold to be met by the venture capitalist.

The second is the upside potential. Is the business in an up and coming industry? Does the business have a game-changing new approach? Does the business have the potential to grow 10x, 20x or 50x?

It’s not just about anticipating what someone may want, it’s understanding who they are and what they need to make their lives better.

In working for a large manufacturer of HVAC equipment, I came to realize, it’s not about cooling a building. It’s about precisely controlling the indoor environment to help people feel more comfortable. People who are more comfortable are more productive workers. If they’re in a hospital, they heal faster. If they’re in a classroom, they’ll learn better.

Imagine the asks:

“Hey Building Owner, would you like to lower your heating and cooling costs by 20 percent?”

Answer: Yes

“Would you like more control over the indoor environment of your building so you can precisely change it to meet the needs of the users — and avoid hearing complaints that your building is too hot or too cold?”

Answer: Yes

“Would you like to have your building be more environmentally sound and sustainable?”

Answer: Yes

“Would you like to see how another building, which is about the same size as your building, is benefitting from our HVAC system? Talk to the owner of that building about their experience?”

Answer: Yes

What makes these asks even more effective is understanding if the Building Owner really does want to reduce their costs or if he or she really is concerned about the impact that their building is having on the environment, or if they really do want to make their building provide a more comfortable environment for the people using it.

That’s where doing your homework comes in.

First Question to Ask

That’s why that first question you should ask is NOT “Will you buy my product?”

Rather, the first question to ask is “What challenge are you facing?”

This question might be framed in different ways, depending upon the industry and the situation, such as:

An insurance underwriter might ask a tech company: “What risk are you trying to lower?”

A start-up might ask a venture capitalist: “Are you seeking an investment that can generate a 50 percent return in five years?”

The key here is to understand if a person is not only to understand exactly what another person needs, but to gauge the motivation of another person. Are they ready to make a change? Are they open to making an exchange?

Anticipate the Answer to Deliver a Solution

Of course, the secret is that you have a sense of what the answer may be to the question you’re asking.

If you’ve done your homework, you already know what an investor is seeking in a start-up investment.

You already know what a reporter is seeking in a story. You already know what a potential employee is seeking in terms of compensation.

If you’re asking someone to buy a product or service, you have a sense of whether they’re ready to buy or not.

After all — this is how you add value to the equation. If you’re not prepared with a solution, then why ask in the first place.

I’ve learned this process through trial and error, asking thousands upon thousands of times. What I have also learned is that asking can feel truly exhilarating when what you are asking is in complete alignment with meeting the needs of the person being asked.

When you master the lesson of alignment, you will master the art of asking.

Stephen Dupont, APR, is VP of Public Relations and Branded Content for Pocket Hercules (www.pockethercules.com), a brand marketing firm based in Minneapolis. Contact Stephen Dupont at stephen.dupont@pockethercules.com or www.linkedIn.com/in/stephendupont.

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