Do you ask great questions in your business?

When I was in grad school studying to become a classroom teacher, I was trained in how to ask questions.

Questions that evoke response.

Questions that engage.

Questions that spark curiosity in a student’s mind.

Even though I am no longer a classroom teacher — and just paid off my debt for grad school in March – I use much of that training in teaching business owners how to write great marketing. Nothing is wasted.

A great question is an attention grabber.

On a practical level, a great question can be used as an email subject line. In the first line of an email. As a headline on a web page. As the start of a call to action, inviting your reader to do something.

Unfortunately, a lot of people have been trained to in a rather formulaic approach to question asking. They end up with boring, commonplace questions like:

Are you struggling with _____?

Are you overwhelmed by ___?

Do you wish ___?

Now, there’s nothing wrong with starting with templates. That’s actually how I teach my clients how to the see patterns and psychology underlying all marketing and sales writing.

But you can’t stop there.

Because if you do, your questions probably won’t be great. And they probably won’t contain the full juice of your personality, or your passion for your work.

In my working helping hundreds of business owners find the great questions for their business – and do it in a way that sounds fresh and genuinely interesting – I take a different approach. I’ll walk you through it in just a moment, but first, let’s talk about what it looks like.

Shayla is a spiritual teacher who took one of my production labs. She had lived in India for 20 years, and is gifted at helping her clients advance in their spiritual journey, where other practices had them feeling stalled.

She was working on copy to promote initial sessions to meet new clients.

Her original copy started like this:

“Do you find yourself longing for a new way to relate with the people in your life? Does it feel like something is missing in the way you are connecting, and in the way people are connecting with you? Our longing for deep connection, for intimacy, is an essential part of being human. We may try to hide it, or find other ways to fulfill this yearning, but it doesn’t go away. We need this intimacy with ourselves, with others and with the universe. We experience great joy and freedom when we can dissolve the obstacles that prevent us from being real, open and undefended with others. When we find out how to be ourselves, without hiding or holding back, a natural vitality and brilliance start to shine in us.”

Shayla told me that she wasn’t confident these questions would work. She said she felt like she was writing a lot of words, but wasn’t sure they were the right ones.

We talked about it. I asked her a few questions, because I wasn’t clear what she actually DID with her clients. Everything she’d written sounded soft and nice, but not like something I would take action on, if I were an ideal client.

Once Shayla told me that a lot of her ideal clients were spiritual seekers who were having relationship issues, I grinned. Bingo!

We came up with this great question instead:

“Is someone you love driving you nuts?

Or maybe your relationship is “okay”… but there is a juiciness… a depth… that is missing.

There may be a “deadness” there — a lack of real, deep contact.

And it really bothers you.”

She was thrilled. She loved the word “nuts” – it made her laugh. And she said she felt lighter – less weighed down – just reading this.

This is how you know in your body that you are onto something great.

Shayla turned around and tested this new approach on Facebook (she didn’t have a list, but didn’t let that stop her). After two days, she had 27 people signed up for initial sessions with her.

That, guys, is the power of a great question.

So, how do you start to come up with your own great question for your business? Here are some tips:

  • Talk out your ideas before you write them. This is where having a partner is really helpful. They can hear all the words you are saying, and notice what really shines. Often, we are too close to our own work to hear the gold in what we are attempting to communicate.
  • Ask yourself: What’s the thing that is driving them nuts in their daily lives? This usually gets you some sloppy, goopy pile of words. Or something that you don’t think is useable. Doesn’t matter. You can clean up the language later. For now, look for the problem. When you cut to the heart of the matter, what’s bugging them?
  • Use uncommon words. For Shayla, we used the phrase “driving you nuts” instead of saying something like “is your relationships making you crazy.” Often, an unexpected word like ‘nuts’ adds more personality and color, and helps you stand out. This takes some practice to get the hang of, but experiment. Play with saying things in your own way. Your audience will love it.

Asking questions is an art. Give yourself permission to get a little messy, as you try out what works best for you and your audience. Pay attention to what resonates, what people lean in for and respond to. And don’t beat yourself up if not every question you write triggers a huge response. This is a marathon, not a sprint.

Stella Orange is a copywriter who helps people put their work into words. For eight years, she wrote email campaigns that resulted in more than a million dollars in sales for her clients. In that time, Stella also taught popular marketing writing workshops to business owners on both sides of the Atlantic -- and a few in Australia and New Zealand. In 2017, Stella cofounded a creative and consulting shop offering a complete and slightly unorthodox line of business advising and marketing services. She continues to write copy and advise clients on customer delight, how to resonate with more sophisticated, discerning clientele in your marketing, and just who, exactly, your ideal clients are. Stella is the founder of Show Up And Write, a weekly writing group and writes a letter every two weeks or so (here’s the sign-up). She lives with the Philosopher and their two kiddos in Buffalo, New York, a fifteen-minute bike ride to the Canadian border.

2 Comments


  1. emmy

    Funny I am reading this now. I just read your email today – the one on the sh*tty first draft. It hit me between the eyeballs. You prompted me to write and rewrite who I really am and what I can do for you until it felt real.
    You are inspirational! And real!

  2. Stella

    Glad to hear it got you to drill down more, Emmy. That’s great!

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