I recently came back from a family vacation in Cancun. Between pool time, unlimited food, and trying to convince my kids that sunscreen is not optional, one thing stood out to me more than expected: how uncomfortable kids are asking for things. They didn’t want to ask another child where they got a lollipop from. They hesitated to ask the hotel staff for more water. Sometimes they even avoided asking simple questions because they felt embarrassed or shy. And honestly? Watching them made me realize that many of us adults never outgrow this (luckily my kids just got an intensive week of practice!).

The more I thought about it, the more convinced I became that asking is one of the highest ROI skills we can develop. I’m constantly surprised by two things: first, how rarely people ask for help, opportunities, discounts, introductions, or clarification; and second, how often people are actually willing to help when asked respectfully. Most big opportunities in life are hidden behind small moments of social discomfort.

Tip of the Week: Treat asking like a skill, should not be a personality trait. Start with tiny requests: ask a question, ask for clarification, ask for feedback, ask for help. Small asks train us for bigger opportunities later.

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The Theory Behind

We dramatically overestimate how often people will reject us. Research on “rejection miscalibration” shows that we consistently predict others are less willing to help than they actually are. In practice, most people like being helpful far more than we assume. This aligns with findings from social psychology showing that people tend to underestimate others’ willingness to cooperate, assist, or engage. This leads to many of us self-rejecting before anyone else even has the chance. We avoid asking for mentorship, opportunities, feedback, or support because we imagine rejection that often never comes. Ironically, the fear of asking usually hurts us more than the rejection itself.

Asking is a muscle built through exposure and repetition. Exposure Therapy, a widely used behavioral psychology technique, teaches that repeated exposure to uncomfortable situations reduces fear over time. Confidence doesn’t come before asking; confidence comes from asking repeatedly. I remember hearing about "the coffee challenge" from Noah Kagan (coach for entrepreneurs) encouraging people to intentionally ask for small discounts simply to train comfort with rejection and social discomfort. The point wasn’t saving money. The point was building emotional resilience. Tiny asks matter because they train us for larger asks later: networking, promotions, negotiations, mentorship, and leadership.

People help more when the ask is clear and specific. Research in communication and organizational psychology consistently shows that specificity reduces friction. Vague requests create cognitive overload, while concrete asks are easier to respond to. Compare “Can you help me sometime?” versus “Could you review this presentation for 10 minutes before Friday?” The second request is actionable *and relatively small). This becomes even more important with senior leaders and experienced professionals. Many highly experienced people genuinely enjoy solving problems and mentoring others, but they need clarity. A focused problem statement allows them to quickly engage their expertise and provide meaningful help instead of trying to untangle scattered context.

What I’ve Learned

The best asking relationships are reciprocal, not transactional. Robert Cialdini’s Reciprocity Principle explains that we naturally want to return favors and maintain balanced relationships. But in my opinion, reciprocity is can be more than just giving before asking. It can also be about closing the loop afterward. One of the biggest mistakes I see is people asking for help and then disappearing forever. Over the years, I’ve realized how meaningful it is when someone circles back after receiving advice. Sometimes a person reaches out asking for career guidance, presentation feedback, or help navigating a difficult situation. We talk, I share my thoughts, and then… silence. Months or years pass without hearing from that person again (or I may even not see them ever again!). On the other hand, when someone follows up a month later saying, “I applied your advice, and here’s what happened,” it honestly makes my day (sometimes my entire week). It makes me feel that my time was valued and appreciated. Ironically, this follow-up behavior also makes me more willing to help that person again in the future. A simple update builds trust, gratitude, and long-term relationships. In many ways, the follow-up is just as important as the ask itself.

Make It Happen

1. Start with micro-asks. Build comfort gradually. Ask for directions, recommendations, feedback, or a small discount next time you get coffee. Tiny reps build confidence for bigger asks later.

2. Be specific about what you need. Instead of “Can I pick your brain?”, try: “Could you help me think through these two options for 15 minutes?” Clear asks get clearer answers.

3. Ask early, not late. Don’t wait until you’re overwhelmed. Effective people raise their hand early enough for others to actually help.

4. Provide context, not a life story. Give enough information to make helping you easy, and explain why you thought of them specifically. People like knowing their expertise or experience is valued (and sometimes receive a little praise).

5. Respect the other person’s time. Put boundaries on the ask: “10 minutes,” “one question,” or “a quick review.” Small asks feel lighter and are easier to say yes to. Please don't schedule a one hour call with a person you've never met.

6. Normalize hearing “no.” Rejection is part of the process, not proof you shouldn’t ask. Treat every ask as practice, not as a judgment of your worth.

7. Follow up after receiving help. This is the big one. Let people know what happened. Tell them what worked, what you learned, or what changed because of their advice. Gratitude compounds relationships.

8. Become someone who also helps others. The best askers are usually generous people themselves. Support others consistently, and asking starts to feel like part of a healthy exchange rather than an uncomfortable favor.

Now excuse me while I go back to raising kids that feel fine asking for extra fries (starting small...).

Askingly yours,

Jorge Luis Pando

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Enjoying what you’re reading? Help a friend out… and you will win something for yourself too.