Rhonda Scharf, Certified Speaking Professional, trainer, and author, explains why we need to keep asking “why?”
Why is the sky blue?
Why do birds fly south in the winter?
Why do I have to grow up?
If you’ve ever spent time with a toddler, you’ve heard the question “Why?” a hundred times a day. I remember when my boys were young, they would bombard me with “why” questions non-stop. And now it is my grandchildren. The years have zipped past, but this question remains. It is still exhausting but also endearing. Their constant curiosity means they are learning, exploring, and trying to make sense of the world.
Then, something strange happens as we grow up.
We stop asking “why.”
It could be because we’re afraid of sounding like we don’t know the answer. We may not want to challenge authority or rock the boat. Or perhaps we become so busy doing that we forget to be curious. Regardless of the reason, letting go of “why” is a missed opportunity.
Why “Why” Matters
In my Strategic Partner workshops, I emphasize the importance of asking questions – especially the question “why.” When done with curiosity rather than criticism, asking “why” shows initiative, thoughtfulness, and a genuine desire to understand how your organization functions.
Asking why doesn’t mean you’re challenging decisions; it means you’re trying to learn. And when you understand the reasoning behind a task, a report, or a request, you can improve it, streamline it, or make it more valuable. You can save time, gain clarity, improve communication, position yourself as a strategic partner, and, most importantly, add value to what you do each day.
It’s not as simple as the “why” our toddlers ask, though.
Ask, Offer, Suggest
Take a three-pronged approach when asking “why” at work. Think about questions to ask, offers to make, and possible solutions to suggest.
Scenario 1: The Monthly Report
Imagine you’re responsible for creating a monthly report that tracks employee vacation and sick time. Every month, like clockwork, you pull the numbers, enter them into the spreadsheet, and send them off.
But has anyone ever told you what your executive does with that report?
What not to do:
- Keep doing the report without knowing its purpose.
- Assume the report is useful just because it’s always been done.
- Think, “It’s not my place to question it.”
What to do:
Ask: “I want to make sure this report is as helpful as possible. Can I ask what decisions it supports or what you’re looking for in the data?”
Offer: “Would a quarterly report meet your needs, or is monthly essential?”
Suggest: “Would it help if I also tracked the trends or compared departments?”
By asking why, you’re not pushing back; you’re trying to make sure your work is meaningful and effective. And who knows? You might uncover a better way of doing it.
Scenario 2: A Last-Minute Meeting Request
Your executive suddenly asks you to organize a team meeting for tomorrow morning, with no agenda provided. You scramble to reserve a boardroom, check schedules, and notify attendees.
What not to do:
- Assume it must be more important than all your other work just because it’s short notice.
- Chase down logistics without understanding the meeting’s objective.
- Let stress take over without asking for clarity.
What to do:
Ask: “Can I confirm the goal of the meeting so I can help guide the discussion or prepare the team?”
Offer: “Would you like me to draft an agenda based on the topic, or is it an open conversation?”
Suggest: “Would a quick stand-up meeting be more efficient for this update?”
Understanding why the meeting is being called helps you support your executive more effectively and lead others with greater confidence.
Scenario 3: Multiple Approval Layers
You’re submitting a vendor invoice for payment. It has already gone through three approval steps, but your company policy requires that it be sent to finance for a fourth approval. It delays payment every time.
What not to do:
- Grumble silently about the inefficiency.
- Assume there’s a good reason and keep following the outdated process.
- Add your own layer of approval “just in case.”
What to do:
Ask: “Is this fourth approval still required, or can we streamline the process now that roles have changed?”
Offer: “I’ve noticed that this invoice routing delays payments. Can we look at why all these steps exist?”
Suggest: “What if we create a threshold so that only invoices above $5,000 go through all four steps?”
Not only does this save time and money, but it also shows leadership and strategic thinking.
Scenario 4: Planning the Annual Retreat
You’re asked to coordinate the logistics for the company’s annual staff retreat. You’ve done it before: book a venue, organize the travel, order the meals, arrange the agenda.
What not to do:
- Treat it like a checklist task.
- Recycle last year’s format because “that’s what we always do.”
- Focus only on logistics and not on the bigger picture.
What to do:
Ask: “What’s the goal for this year’s retreat? Is it team building, strategic planning, or celebration?”
Offer: “If I understand the why, I can better tailor the activities and structure to meet your goals.”
Suggest: “Should we include a speaker to deliver a breakout session on strategic thinking?”
When you understand the why behind events, documents, and requests, you elevate your work from helpful to essential.
Timing Is Everything
But there are times when “why?” isn’t the right question to ask. If we ask why in front of others (for example, during a team meeting), it may create tension or look like you are challenging them. You also need to ensure that your tone doesn’t sound accusatory (or like a toddler) and that you don’t ask why when you’re trying to get out of the task.
Asking “why” works best when paired with emotional intelligence and good timing. If your tone and timing reflect curiosity and professionalism, the question is almost always welcome.
As administrative professionals, we often sit at the crossroads of operations, strategy, and leadership. We’re the information filters, connectors, and problem-solvers. But we can only operate at that level when we truly understand the “why” behind the work.
So, my challenge to you is, before you hit “send” on that next email or “save” on that next report, pause and ask yourself why you are doing it, why it matters, and why now.
If you don’t know the answer, find it.
Ask respectfully. Ask intelligently. Ask with curiosity.
You are not “just” an admin. You are the center of communication, the operational compass, and the strategic partner your team depends on. The more you understand the why, the more impact you have. You might just uncover a better way to do it or even discover that it no longer needs to be done at all.
So go ahead – ask why.
It just might be the most important question you ever ask.
