How to ask questions the right way to get the results you want

Summary:  Why it’s critical to learn to ask questions the right way plus 6 tips to get you what you want. Also includes free printable checklist. May contain affiliate links. Get info here.

“Can you please locate and recheck my medical records to see if polyps were found in my last colonoscopy?”  I was on the phone with Felicia, the nurse for a doctor I’d only seen once – over seven years ago.

If Felicia said “Yes,” she could save me up to $6,000 in unplanned medical expenses.

Plus a day of green jello, bouillon and staying close to a bathroom while prepping for the procedure.

Why the right question mattered

My new doctor had scheduled a preventative colonoscopy.

Now my insurance company was refusing to pay for it.  The representative insisted my medical records showed that polyps were found in that long-ago screening.

I didn’t remember being diagnosed with polyps. But again, it was seven years ago.

How to ask questions - medical bills

How to ask questions the right way

The right questions are a powerful tool to get us what we need or want, sometimes more easily than we thought possible.

Men seem to know how to handle this tool instinctively.  Women don’t appear to be as skillful.

That’s why I’ve always revered females who ask questions the right way – boldly in a straightforward, non-confrontational manner.

And aspired to become one of them.

How we ask is critical

Unfortunately, many of us think we’re asking questions while the other person hears whining or complaining. Or worse, pleading, especially when we preface questions with an apology.

That’s why it’s important to know how to ask questions the right way, so we don’t sabotage ourselves from the get-go.

Six ways to ask questions the right way for results

1. Never start a question with “Why.”

“Why did you do that?”Did you feel the hairs on the back of your neck tingle? 

Most of us react to that query as a barely-disguised dig or as the opening punch in a verbal battle.  Psychologically people feel compelled to harden their position.

Sales trainers taught us never to ask “why” a client was using another vendor.  Therapists warned against it too.”Why” ignites a whole ammo box of unconscious emotional triggers.

 Use the next tip instead.

2. Replace “Why?” with “Is there a reason?

Alyssa Mastromonaco was President Obama’s Deputy Chief of Staff for operations. She told a story about her time in the White House in her book Who Thought This was a Good Idea?

Women’s restrooms in the West Wing didn’t have tampon machines.T o cope, Mastromonaco and the other women shared the location of their hidden stash with each other. 

Even with all this pre-planning, Mastromonaco got caught short one day.

So she asked the person in charge of facilities, “Is there a reason we don’t have a tampon machine in the bathrooms?”

Mastromonaco got this response: “Probably because no one asked. Do you need one?

”Within two weeks, the bathrooms had tampon dispensers. Mastromanoco joked these dispensers might be her lasting contribution to the government and to the women that follow her.

Because “why” seems like a veiled challenge, people to can over-analyze a request. “Is there any reason?” doesn’t require deep thinking.

Which leads to next embarrassingly obvious tip

The power of good questions

3. Don’t assume there is a good reason – ask

It was so ludicrous that the West Wing bathrooms didn’t have tampon dispensers, Mastromonaco and her female colleagues concluded there had to be a reason for this situation.

Maybe a Homeland Security thing.

Like many of us, the White House women hesitated to ask because deep down we think the reason is obvious to everyone else.

Get bold and ask. What’s the worst that can happen? Maybe we did miss a glaring reason. Know what to say then?

“I missed that. Thanks.” And for heaven’s sake, don’t say, “sorry,” another word that undermines us.

Related: How to stop saying sorry too much…and what to say instead

4. Do assume the right to ask questions boldly

Doctors don’t hesitate to ask the probing questions they need to know to help diagnose illness. “Is intercourse painful for you?” “Are your nipples sore?” “Do you have a lot of flatulence?”

Because they are matter-of-fact in their delivery, we respond to these questions as relevant.

When I was new in media sales, I’d haltingly probe, “Do you mind if I ask your budget?” My hesitancy immediately put clients on guard. They’d wonder if maybe he/she should mind.

My job share partner and close friend Debbie would never cushion that question.

“What’s your budget?” Debbie’s directness showed professionalism and commitment to solving problems efficiently.

I see that now that when I’m on the other side of this conversation.

A friend who is a car salesman suggests we ask this direct question when shopping for a new vehicle: “Is there a car on the lot that you’re getting a special incentive to sell?”

We could find out the dealership ordered too many of that model or that option package. The dealership needs to move those vehicles before month’s end to trim expenses.

Helping your salesman meet his/her goal may get you more car for your money. Both sides benefit. So ask.

5. Use “What would you do in my situation?” to battle bureaucracy

Gretchen Rubin of the Happier podcast revealed the question that rescued her family’s European vacation.  It worked because it helped a customs agent think outside the box.

Many countries require that your passport be good for at least six months after you enter their country. One of her daughter’s passports didn’t meet this criterion.

And the trip was only days away.

After hearing the agent’s rote answer about how you must allow six weeks to get a passport renewed, Gretchen asked her, “What would you do now in our situation?”

The agent told Gretchen about a place in NYC that could turn around a passport within a day.

Breaking out of the mold of being a faceless customer on the phone or in the line changed Gretchen’s relationship with the agent.

“What would you do in our situation?” puts the other person in your shoes, makes them the expert and taps into the power of asking a favor.

This next tip also makes the other person an expert.

6. Stop talking once you ask a reasonable question

This lesson also comes from Gretchen Rubin’s Happier podcast episode 169.

Often, we jump in to answer our questions. Or more frequently, we start to provide solutions to the person who should be the expert.

That’s my problem.

When we shut up, we hand ownership of the problem to the other person…and give them time to work on it. We might have a solution, but theirs is usually better.

Take a podcast listener’s situation. Her 15-year-old son wanted to take the direct train back from camp to New York City. But the train conductor wouldn’t let him on board because of a regulation against minors riding the train alone without additional paperwork.

The frantic son and the conductor called mom, who was hours away. The conductor said the regulation was for the safety of minors.

Then the mom used common sense, something often lacking when emotions run high. Instead of arguing the regulation, she asked a question that recognized the conductor as the expert,

Where would her son be safer – on the train with other people, headed to the city where his father was waiting to pick him up?
Or alone on the station platform for hours, waiting for someone to drive up and get him?

Then mom shut up.

The conductor ended up working with the family and put the boy on the train. Mom didn’t rush to offer to drive all the way up there. She let the expert come up with the solution.

And the expert came through. Just like Felicia came through for me.

Ask questions right and then keep quiet
 Resist the urge to talk

Asking a question the right way got the results I wanted

Remember Felicia, my old butt doctor’s nurse?

She went back seven years and combed through my medical history. And called me a few days later with an answer.  After reading the procedure notes to me, she said, “You never had polyps.”

No polyps meant no colonoscopy for another three years.

Waiting three years meant insurance would pay for it as a preventative procedure so no budget-busting unplanned expense.

And best of all, no polyps meant no green jello day.

Asking without apology to have my long-ago medical record rechecked, staying quiet and not offering another solution and waiting for the expert (Felicia) to come through got me the results I wanted.

Download your free printable: How to Ask Questions the Right Way

This checklist includes the techniques in this post. Use it to help get around roadblocks and learn how to ask questions effectively to get the results you need.

  • 1. Download the free checklist. Join my weekly-ish newsletter, and as a bonus, you’ll get the printable
  • 2. Print a few copies and/or save to your Dropbox on your phone. Keep the checklist handy. And use it to help script your questions in advance of getting on the phone or in front of someone.
  • 3. Practice getting comfortable with these tips in everyday situations. At the grocery store, in your book club, etc. Make these techniques second-nature.

Share what works for you

What frustrates you about asking questions? And what other suggestions do you have for the rest of us?

Please scroll down and leave a comment. We are all learning from each other!

Please help me out.  Typos get by me.  See one? Please let me know so I can fix it!  Thanks,   Linda