The Ace Freelancer’s Guide to Asking Questions: Helper Questions

Alright freelancers! Let’s kick some butt and take some names, shall we? The Ace Freelancer’s Guide to Asking Questions continues with questions that can help you win friends and influence people.

Up until now we’ve mostly been talking about questions that freelancers can ask to take charge; this week’s question is a bit different.

This week we’re going to talk about Helper Questions: questions which can help you make your case.

Ace Freelancers Guide to Asking Questions

By marc falardeau via

Freelancers are more likely to be asked Helper Questions than pose them. The reason I want to talk about these questions is because they can be sneaky buggers. It’s important to be able to recognize Helper Questions and use them to your advantage.

Don’t worry, we’ll also talk about when and how you can deploy Helper Questions to so you can enlist others to make your arguments for you.

What is a Helper Question?
A Helper Question is what would happen if a Babysitting Question and a leading question made out and had a baby.

But instead of trying to steer the person being asked the question toward the Right Path, Helper Questions are designed to persuade everyone listening to the answer.

You know these questions; they’re the questions that Nina Totenberg reads on NPR from the Supreme Court transcripts. “But certainly, counselor, the Founding Fathers, with the exception of maybe Franklin, would never have anticipated Facebook stalking?”

Helper Questions highlight either
(a) the weakest part of the opposing argument and give the answerer extra time to bash it; or
(b) the most likely objection to the answerer’s point of view, which allows the answerer to address the objection before it’s made.

Since you know about anchoring (see also here and here), you know that getting to establish how everyone else in the room perceives an argument is incredibly powerful.

“But Katie,” you’re saying, “I’m a freelancer, not Former Solicitor General Ted Olson! When am I ever going to hear a Helper Question and what does it matter?”

Ace Freelancer's Guide to Asking Questions

By Roadsidepictures via

If you ever find yourself on a conference call or a pitch meeting or an approval email chain, it is very likely you’ll encounter a Helper Question. And if you can’t recognize it when it happens you will miss out on a great opportunity to persuade the room with minimal effort.

When do Helper Questions Happen?
By virtue of what they’re trying to do, Helper Questions need an audience. Helper Questions are communication devices directed at the people listening to the answer, so they are most common in meetings of a group of people. (Interpret “meeting” broadly: it includes stuffy conference room, static-y conference call, and Happy Hour at the corner bar.)

What do Helper Questions Sound Like?
Helper Questions sound like a mix of confrontational, curious and leading questions. They invite the answerer to provide a lot of information, but answering them can feel almost like a trap. It’s not uncommon for Helper Questions to involve hypothetical situations.

“So Lucy, this approach you’re recommending, it doesn’t sound very conventional. Why should we consider it?”

“How could we use this work in future campaigns? What will it help us do after this project is over?”

“Why would we hire you over a large firm or agency?”


But look at those questions a bit closer: each is asking you, begging you, to describe why your recommendation or work is perfect for this client.

How do you answer Helper Questions?
First, you’ll have to shake off that defensive reaction you just got.

Even if the person intended to get your hackles up, treat it as an opportunity for you to show them why you are the best freelancer for the job. Don’t waste your time arguing with their words, make your very best case for why you and your work are right for what they need.

“So Lucy, this approach you’re recommending, it doesn’t sound very conventional. Why should we consider it?”

“No, Jan, it isn’t very conventional, but you don’t need conventional. You told me you needed to be able to quickly and effectively react to your clients’ needs; this approach lets you do that by…”

The Ace Freelancer's Guide to Asking Questions

By MTSOfan via

“How could we use this work in future campaigns? What will it help us do after this project is over?”

“That’s the great thing, you can use this image through out the campaigns you have scheduled for the remainder of the year, which is an excellent piece of branding. The copyright transfers to your company once the final payment is made so you can use it for literally anything.”

“Why would we hire you over a large firm or agency?”

“That’s a great question, Noah; I’ve had many clients ask the same thing. I’ve been able to provide work for all of them that just wouldn’t be possible from a large firm or agency. For instance, last month I…”

  1. Let them know you heard the question.
  2. Quickly transition to why your argument/pitch/point of view aligns with their interests.
  3. Provide examples of how they might use what you’re offering or how your work has been successful in the past.

Helper Questions are opportunities to advertise how great you are. So do that thing.

When should I ask Helper Questions?
Ask Helper Questions when you’re on a team and someone from your team is struggling to make a point. Give them the relief of a friendly face and a question that allows them to highlight their best stuff.

That team member, by the way, might be your client. You might be in a pitch session with your client and their stakeholders. If you can see your client struggling to make their point, especially if it’s a point that benefits both of you, consider offering up a Helper Question to get them back on track.

Ace Freelancer's Guide to Asking Questions

By andjohan via

The next time you get a question that feels like it is challenging you or your point of view, I want you to think, “Helper Question.” This isn’t time to show your defensive chops, it’s an opportunity to shine. Get to it.

Help write the next installment of The Ace Freelancer’s Guide to Asking Questions: what types of questions are you curious about? What kinds of questions do you want to know how to master? Add your suggestions to the comments below!

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2 responses to “The Ace Freelancer’s Guide to Asking Questions: Helper Questions”

  1. An Eyeopener says:

    as somone who feels the need to shine on my freelance skills this entry is the most empowering intro i could ever have to your work. I know i’ll be a regular around here. Thanks for sharing the power!

  2. Brent White says:

    Great article, this is what Social Media is all about, giving away some info up front so people can see you’re the go-to person when they have a need for your services.
    Brent White
    Freelance Gigs for Digital Marketing

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