I’ve noticed something remarkable throughout my career working with entrepreneurs, athletes, and business leaders. Most people don’t ask for what they want. It’s such a simple concept, yet I’ve watched countless opportunities slip through people’s fingers because they couldn’t bring themselves to make a request.
The truth is painfully obvious: The people who get what they want ask for it. Nothing more complicated than that.
Recently, a young man approached me after one of my speaking engagements. With determination in his eyes, he said, “I need you to business coach me, but I can’t afford you.” Many would have stopped there, accepting defeat before even trying to find a solution. But this young man continued the conversation.
When I asked what he did for a living, he told me he trained dogs. Had he pushed just a bit further and asked if I owned a dog, he would have discovered a perfect opportunity. As it happens, I had just bought my eight-year-old a puppy for his birthday, and we were actively looking for a dog trainer.
The solution was right there: he could train my dog, and I could train him in business. A simple value exchange that would benefit us both. But he never asked the question that would have unlocked this possibility.
Why We Don’t Ask
What stops us from asking? In my experience coaching thousands of individuals, these barriers typically include:
- Fear of rejection or hearing “no
- Not wanting to appear needy or desperate
- Assuming the answer will be negative before even trying
- Feeling unworthy of receiving what we want
- Pride that prevents us from showing vulnerability
These mental blocks cost us dearly. Every time we fail to ask, we’re essentially saying “no” to ourselves before anyone else has the chance to say “yes.
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The Power of the Ask
I’ve built my career on asking. When I wanted to work with top athletes, I asked. When I needed mentorship from business leaders I admired, I asked. When I saw opportunities for partnerships that seemed out of reach, I asked.
Did I hear “no” sometimes? Of course. But I also heard “yes” far more often than most would expect. And those yeses have made all the difference.
The most successful people I know have mastered the art of the ask. They understand that:
- Every “no” brings you closer to a “yes
- People generally want to help if they can
- Creative solutions often emerge from simple requests
- Asking demonstrates confidence and clarity of purpose
That young dog trainer missed his opportunity that day, but I hope he learned a valuable lesson. The exchange we could have had would have benefited us both tremendously.
How to Ask Effectively
Asking isn’t just about blurting out requests. There’s an art to it:
- Be clear about what you want – Vague requests get vague responses
- Understand the value exchange – What can you offer in return?
- Ask questions that open doors – Like “Do you have a dog that needs training?”
- Don’t assume rejection – Enter conversations with positive expectations
- Follow-up – Sometimes timing is everything
When you master these principles, you’ll be amazed at what becomes possible. I’ve watched people transform their careers, build incredible networks, and create opportunities seemingly out of thin air—all because they were willing to ask.
Start Asking Today
What opportunities are you missing right now because you’re not asking? What doors remain closed simply because you haven’t knocked? What exchanges of value could benefit both you and others if only you’d initiate the conversation?
A simple question might bridge the gap between where you are and where you want to be. So take a lesson from that dog trainer’s missed opportunity: identify what you want, find someone who can help you get it, and ask.
Remember, the worst that can happen is hearing “no,” which leaves you exactly where you started. But the best that can happen? That’s where all the magic lies.
Frequently Asked Questions
Q: What if I’m afraid of rejection when asking for what I want?
Fear of rejection is natural, but consider this: rejection doesn’t change your current situation. You’re already not getting what you haven’t asked for. By asking, you create possibilities where none existed before. Start with smaller requests to build your confidence, and remember that even the most successful people hear “no” regularly.
Q: How can I make my requests more likely to receive a positive response?
Focus on creating win-win scenarios where both parties benefit. In my example with the dog trainer, we both had something valuable to offer each other. When making requests, clearly articulate the value exchange, be specific about what you’re asking for, and, when possible, time your requests appropriately.
Q: Are there situations where it’s inappropriate to ask for what I want?
While I encourage boldness, context matters. Be mindful of timing, relationships, and appropriateness. For instance, asking for a raise during company layoffs might not be ideal. However, most people err on the side of not asking enough rather than asking too much or at the wrong times.
Q: How do I know what to ask for if I’m not sure what I want?
Start by clarifying your goals and needs. If you’re uncertain, ask for guidance or information first. For example, instead of asking someone to be your mentor immediately, you might ask for a 15-minute conversation about their career path. Asking questions helps you gather information that clarifies what you ultimately want.
Q: What’s the difference between asking confidently and coming across as entitled?
Confidence comes with preparation and a genuine understanding of mutual benefit. Entitlement emerges when you expect others to give without considering their needs or the value exchange. Approach conversations with curiosity about how you might help the other person, express gratitude regardless of the outcome, and be willing to accept “no” gracefully.
