How to ask questions boldly & get results

Ask questions that get resultsI’ve always admired women who can ask questions boldly in an easy, non-confrontational manner.  Direct questions are a powerful tool to get what you need or want, sometimes more easily than you thought possible.

Unfortunately, many of us think we’re questioning while the person we are talking to hears whining or complaining.  That’s why it’s important to know how to ask questions boldly so you don’t sabotage yourself from the get-go.

6 Ways to ask questions boldly & get results

1.Never start a question with “Why”

“Why did you do that?”  Did you just feel the hairs on the back of your neck tingle?   That’s because most of us react to that query as a barely-disguised put-down or as the opening punch in an argument.

Sales trainers taught us never to ask “why” a client was using another vendor.  Psychologically that made the client feel compelled to define their decision.  Therapist warn against it in trying to uncover disfunction in romantic and family relationships because of that same unconscious trigger.

Sometimes you just want to understand the reason something is done a certain way.  In that situation, can’t you just ask questions boldly starting with “why?”

Even in an upfront search for more information, “why” is a double-edged sword.  So why would you chance it?  Use the next tip instead

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

Alyssa Mastromonaco  was President Obama’s director of scheduling and advance, and eventually his deputy chief of staff for operations.  In her book, Who Thought This was a Good Idea? she told a story about her time in the White House and the challenge of finding tampons in an emergency.

Bathrooms in the West Wing didn’t have tampon machines.  To cope, Mastromonaco and the other women shared the location of their 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?”

Within two weeks, the bathrooms got tampons.  Mastromanoco joked that she wanted a brass plaque honoring her placed under a tampon dispenser.  She reasoned that machine may be her lasting contribution to the government and to the women that follow her.  Now that’s a brazen girl!

Because “why” seems to challenge, people to analyze a request.  “Is there any reason?” is powerful because if doesn’t require deep thinking.   Ask questions boldly in this manner and you can and often do get the ultimate good response – “Probably because no one asked.  Would you like us to put one in?”  Which leads to next embarrassingly obvious tip

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

Because no tampon dispenser in the bathrooms meant on-going problems for Mastromonaco and the other girls, they assumed it was that way for a reason.  Maybe some Homeland Security thing.

Like many of us, the White House women were afraid to ask because deep down we think the reason is obvious to everyone else.  How often we make life hard on ourselves by assuming there is logic in an illogical situation?

Get bold and ask.  What’s the worst that can happen?  Maybe you did miss a glaring reason.  Know what to say then?  “I missed that.  Thanks.”  No apologies, no self-administered putdowns.

4. Assume the right to ask questions boldly

Doctors don’t hesitate to ask the probing questions they need to know to help diagnosis an 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 manner and those questions seem obviously in both our best interest.

When I was in media sales, I’d shyly ask, “Do you mind if I ask your budget?” That immediately made my potential client pick up on my hesitancy and think 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 I’m sometimes on the other side of this conversation.

Here’s another example.  After years of assuming annuities were bad business, I’m rethinking that.  I’m also asking my financial folks, “How do you make money on this?” That is a very legitimate question in this decision.  And I get very direct answers that I need.

Or try asking a car salesmen, “Is there a car here  that  you’re getting a special incentive to sell?”  The answer could be something helpful.  Maybe you find out the dealership ordered too many of that model or that option package and need to move it before month’s end.  Helping your salesman meet his/her goal may get you more.  Both sides benefit.

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

Gretchen Rubin in her Happier podcast revealed how a question helped rescue her family’s European vacation because it helped a custom agent think outside the box.  After hearing the agent’s rote answer about how you had to allow six weeks to get your passport renewed, Gretchen asked the agent, “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!  Obviously, I wonder why the agent didn’t tell her that in the first place.  Maybe because until you break out of the mold of being just another faceless customer on the phone, you get a faceless answer.

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

6. Stop talking after you ask a reasonable question.

I also got this tip from Gretchen Rubin’s Happier podcast episode 169.  As bold women, sometimes we jump in to answer our own questions.  Or even more common, we start trying to provide solutions to the person who should be the expert.

When you stop talking, you hand ownership of the problem to the other person…and give them time to work on it.  You might have a solution but theirs could be so much better.

Gretchen gave an example from one of her listeners.  This woman’s 15-year-old son wanted to take the direct train back from camp to New York City.  Apparently, there was a regulation on a minor riding the train alone without some additional paperwork.  The conductor of the train wouldn’t let her son board.

The frantic son called the frantic mom, who was a few hours away.  The mom got on the phone to talk to the conductor.  The conductor explained that 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 this logical question.  Where would her son be safer?  On the train with other people and headed to the city where his father was waiting to pick him up?  Or on the station platform, alone for many hours while someone drove up to get him?

And then the mom shut up.  The conductor ended up working with the family and put the boy on the train.  She hadn’t rushed to offer to drive all the way up there.  She let the expert come up with the solution.  And the expert came through.

Use questions boldly

The ability to ask direct questions is a powerful tool that can get you what you need or want. Harness the power of effective questions to improve your life in all areas.

To summarize, substitute “Is there a reason” for “why” and don’t assume that there is a logical reason.  Do assume that you have a right to ask the question and ask it in a direct manner.  And let the other person be the expert by asking what they would do in a situation and then BE QUIET.

Practice, Practice and Practice some more

Asking questions this way gets more automatic the more you practice on everyone and everywhere.

Is there a reason you haven’t sent me a comment?  Would you send me a questioning technique that works for you?  You know I love to hear from you.

Ask questions boldly




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


  1. Julie says

    At home, my husband says, “chicken” whenever the kids start a conversation with “why”. Even before they finish the question.

    I always say, “get a job and move out” when the kids complain unreasonably (e.g., we’re sitting in the theater watching a movie and they state they’re bored).

    When leaving a baseball game one day my youngest said, “why…”. My other child predicting the course of the conversation said, “you know, when I grow up I’m going to have a baby and I’m going to name it Chicken.”. To which, my older son stated, “That’s right Chicken, get a job and mover out.”

    We all laughed out loud together; deep down we could all relate to wanting to know why. This is such a simple and great approach (and I love the Happier podcast too)!

    I can’t wait to try these strategies myself. I will secretly think about Alyssa asking for a tampon when I need courage =p

    • growboldernotolder says

      So glad you like Happier podcast. I get so many common sense tips. As far as “chicken” goes, when anyone in our family asks where something is and it is hiding in plain site, we hiss at the offender. As in “If it had been a snake…..” My family will probably all need therapy one day from being mothered by me!

  2. Mary says

    I think it would be quite useful to learn about these magic phrases…such as “Is there a reason…” which you say inspires a useful thoughtful response whereas “why” is taken as stupid or threatening. Maybe there are other magic phrases…I know of one: when I was checking references for job applicants, someone told me that at the very end of the conversation, after I’ve gone through all the standard questions, ask: is there anything else you would like to share with me about the candidate? my god…it was magic. All of a sudden they just told me all the real info. it was like open sesame…a magic phrase. Wouldn’t it be great to have an arsenal of these phrases?

    • growboldernotolder says

      Last week I learned another magic question. A friend told me that his finance people were giving him some reports and he asked: “What do you think is most meaningful or important about this report?” He got information that would have taken him hours to find, if ever. Thanks for commenting!

  3. Karen Russell says

    Excellent advice – it really hits home with me. Thanks for such thought provoking and useful info.

    • growboldernotolder says

      Thanks. I’m having to take my own advice as I try to ferret out how much a medical procedure will cost me. It should make an interesting post! Thanks for commenting. L