How to Ask Questions that Will Save You Time, Energy and Money — and Why We Don’t

Siobhán Gallagher
4 min readOct 30, 2020

One of the best pieces of advice I’ve ever received was from Heroic Public Speaking founder, Michael Port, and it was ‘Choose early and often’. As someone who historically has been a bad decision-maker, this advice has been something I always come back to. (Oh, the torture I’ve inflicted upon myself choosing between the burger and the seafood!)

Through my discourse analysis and personal leadership practices, I’ve come across this issue many times and I’ve noticed that at the root of indecision and lack of decisive action in others and myself, is, almost inevitably, delayed communication.

How often have you found something out and then said to yourself, “I wish I had known that sooner!”? Let’s face it — what we really mean is, “I wish I had asked about it sooner. I wish I had made the effort to inform myself sooner.” The information and answers have always existed. We just haven’t accessed them.

In these common cases, the reason we don’t get things done, we don’t get what we want, and we don’t progress, is because we put off telling people what we want, asking for help, and looking for solutions.

Instead, we allow ourselves to carry on, often uncomfortably, wondering, not knowing something, not receiving the help, not making life easier. We’ve assumed that we already know the answer, that we won’t get actually what we want, or that it won’t work, so there’s no point in asking.

There’s no time like the present — ask now

Two simple, personal examples: pre-Covid I put off inquiring if the local library had rooms available for classes. When I finally did, the answer was a surprising ‘No’. I wasted time confidently assuming that it did. That time could have been spent finding other suitable locations.

The first year I lived in Mexico, I delayed informing myself about residency, because I assumed it was too difficult or too expensive or not worth the hassle. It was none of those things. And all I had done was hold myself back.

Therefore, I’m adding to Michael Port’s advice: First, ask early and often. Then, choose early and often.

Considering these moments, the adage ‘Knowledge is power’ comes to mind. Even if, when you finally get an answer to that nagging question, it isn’t the answer you want, at least you know. At least you no longer have a question nagging at you. At least you are no longer using energy wondering about it, or struggling without the information. At least you can move on and forget about it, and turn your attention to something that does work for you. You now have the power to make a decision and take action one way or another.

We also commonly don’t ask questions because we’re afraid of bothering someone, although we don’t actually know that we will. I’ve had coaching clients holding themselves back in their dream projects because they’re afraid to ask for help. To get them out of this hole, I ask them, “How do you feel when someone asks you for help?”. Their response is usually positive. The reality is that people generally enjoy being asked to help. Many are flattered to have an interest taken in them and an opportunity to share their knowledge. And if they don’t or they can’t, very well. Thank you, and next!

Strike while the iron is hot — say it now

It’s natural that we hesitate about asking delicate questions or having difficult conversations. But ignoring them doesn’t make them go away. Waiting might make them worse. When we get an answer to an awkward question, then the awkward question no longer exists. Yes, what may exist in its place is an uncomfortable knowledge, but that truth always existed. We, however, have taken one step forward and now we have the power to decide what to do with it.

The secret to all difficult conversations is having them. Step-by-step, question-by-gently-asked-question is a route to relief for all concerned. A difficult conversation will have an ending — an unasked question or unaddressed issue lingers on and on for as long as you avoid doing anything about it.

Holding ourselves back from getting the information we want and need in life is like having an exam to prepare for, but just staring at an unopened book and expecting to pass. It’s like getting into a car to reach a destination, but never consulting a map, a sign post or asking for directions — and still expecting to get there on time. Ultimately it’s self-sabotage and poor personal leadership, as we allow our energy and progress to be paralysed by doubts, fears and limiting beliefs.

Our frequently misplaced hesitation, fear, discomfort, laziness and assumptions are time, money, energy and opportunity wasters. You might not get a second chance. We all know what it feels like when the moment has passed. Speak now or forever hold your peace.

They who hesitate are lost — inform yourself now

Knowledge is power that fuels our lives; it helps us make the right decisions and advance. The sooner and more frequently we gain that knowledge — What time to do you open? Can you help me? Do you agree? How do you feel about …? Is this possible? How much does it cost? — the sooner and more frequently we can reach our destinations, and most likely help a few passengers along the way.

Image by Dean Moriarty from Pixabay

Originally published at https://iguanatalkinternational.com.

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Siobhán Gallagher

Communication for Growth and Wellbeing. Coach, Educator + Editor/Writer for the Coaching, Wellness & Lifestyle Industries (http://siobhangallagher.co).