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The myth of “It doesn’t hurt to ask”

Posted in the following categories: Decision Making, Problem Solving

“It doesn’t hurt to ask.”

We’ve all heard this adage, often shared with the best of intentions, encouraging us to take that leap and reach out to someone to ask something.

The premise? The most you risk is silence or a simple “no.”

But that premise is wrong.

An ill-conceived question can inflict more damage than a “no.” It can hurt relationships, reputations, and opportunities.

Here’s an example.

My inbox is often flooded with emails from aspiring authors. One frequently asked question is: “I saw that your last book became a big bestseller. Could you share some book publishing advice? What’s the magic recipe?”

This question, at first glance, appears to be a simple appeal for guidance, a hope to learn from someone who’s walked the path.

Here’s the challenge: It’s impossible to answer that question succinctly. My book publishing experience can’t be boiled down to a one-size-fits-all formula. It’s a combination of trials, errors, and insights that can’t be condensed into a single email.

Someone who sends an email of that sort is highly unlikely to get a response from me—now or in the future.

But rephrase that question, add a pinch of consideration for the other person’s time, sprinkle in some evidence of your own due diligence, and voilà! You transformed a burdensome ask into a thoughtful conversation starter.

Consider this alternative: “I’ve already implemented Strategies A, B, and C for marketing my book. After extensive research, I’m on the fence about adding Strategy X or Y. I’ve listed my thoughts for each. Could you provide some insights on whether X or Y might be more effective?”

Now, that’s a question I’m far more willing to answer. It shows effort, preparation, and consideration for my time.

The danger in blindly adopting the “it doesn’t hurt to ask” mantra isn’t just the risk of a cold shoulder.

It’s the potential bridge-burning. By posing a question that reflects a lack of preparation or consideration, you risk not only failing to get your answer, but also alienating a potential ally, mentor, or friend.

The takeaway?

Ask, but ask wisely.

Pose questions that make it clear you value the other person’s time as much as your own.

Show that you’ve done your homework.

Ensure your questions are precise and well-considered, not just broad sweeps hoping to catch any morsel of advice.

In a world flooded with requests, stand out by asking better questions, not just more of them.

P.S. My friend Khe Hy is hosting a free 2-day event on September 26th and 27th called Minimum Viable Productivity. During the free event, he’ll teach you how to design a system to achieve your goals (while working way less). You’ll learn how to stay focused, think bigger, and stop putting things off. You can learn more and register at this link.

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