Ask Better. Get More.

Ask for What You Want: The Skill That Changes Everything

Many of the biggest opportunities in my life — and even some of the material things I’ve earned — came down to one simple action: I asked.

Growing up, my dad used to say:

If you don’t ask, you don’t get.

It’s a principle that’s guided me for years. I’m convinced that if I hadn’t made a habit of asking, I wouldn’t be where I am today.

But here’s the truth: a lot of people are afraid to ask. They’re worried about being seen as pushy or entitled. They fear rejection or awkwardness. So they stay quiet. And they stay stuck.

Let’s break that pattern. In this post, I’ll share insights, strategies, and real-life examples to help you confidently ask for what you want — and actually get it.

The Fear of Asking

Most of us have been there: nervous about making a request, overthinking how it might come across. But that discomfort? It’s temporary.

Ask yourself: would you rather feel a little awkward for 60 seconds… or stay stuck in the same place for 6 months?

In today’s world, you can’t assume people know what you want — even if you’ve been doing great work. Promotions, projects, raises — they often go to the people who advocate for themselves.

And advocating for yourself isn’t selfish — it’s strategic.

You’re Not Being Pushy — You’re Being Intentional

Great managers want people on their teams who speak up, who take ownership of their careers, and who are intentional about growth.

You might worry that asking makes you seem ungrateful — but here’s the reality:

Wanting more and being grateful can exist at the same time.

Think of it this way:

Advocating for myself helps my team see what I’m capable of.

When you grow, your team grows. That’s leadership.

Start Small: Practice the Ask

You don’t have to start with a huge ask. Build the muscle with smaller ones:

• Ask to shadow a meeting
• Ask for feedback after a presentation
• Ask to lead a small task or project
• Ask for clarification in a meeting
• Ask a peer for input

It’s like going to the gym — you don’t start by lifting the heaviest weight. You build strength gradually. The same applies to asking. Make it a weekly habit: set small goals, track what you asked for, and reflect on what worked (and what didn’t). Then, adjust and keep going.

Know What You Want

Vague asks get vague responses. The clearer you are, the easier it is for others to help you.

Instead of saying:

❌ I feel like I’ve been doing a lot…

Try:

✅ I’d like to move into a lead role next quarter. What would need to happen to make that possible?

And instead of:

❌ Is there anything else I could be doing?

Try:

✅ I’d like to build ownership skills. Could I lead the next sprint planning to start building toward that?

Be specific. Be intentional. Don’t make others do the work of defining your path for you — take the lead.

📖 Storytime

Right now, I’m at a crossroads in my career.

I’ve been a software engineer for the past 8 years. I love the technical challenges and building solutions from scratch. But lately, I’ve been thinking about management — about helping others grow and building strong, motivated teams.

So here’s how I plan to approach it with my manager:

I enjoy helping others grow, and I still love the technical side of my work. I’d like to start building managerial skills. Could we structure some of my work over the next few months to help me grow in that direction?

This approach opens a door, starts a real conversation, and invites collaboration. That’s what asking is really about.

Make It a Conversation

You’re not delivering a closing argument in court — you’re starting a dialogue.

Instead of:

❌ Am I getting promoted soon?

Try:

✅ I’d love to talk about growth opportunities for me here. Can we schedule some time to chat about that?

Instead of:

❌ I need a raise because my rent went up.

Try:

✅ Over the past six months, I’ve taken on new responsibilities and consistently delivered strong results. I’d love to talk about updating my compensation to reflect that growth.

It’s not you vs. them — it’s a collaboration.

Use Momentum

Timing matters.

If you just wrapped up a big win or received great feedback — use that momentum. That’s the time to make your ask.

Set a calendar invite. Be clear on what you want to talk about. Try:

After our last project wrap-up, I’d love to set up 15 minutes to talk about my growth path while it’s still top of mind.

Handling Rejection

Even when you do everything right, you might still hear “no.” That’s okay.

Rejection isn’t failure — it’s information.

No doesn’t mean never. It might just mean not yet.

Here’s how to follow up:

What would need to happen in the future for this to be a yes?

Or:

Can we revisit this in a few months? I’d love to know what I should focus on between now and then.

This kind of response sets you apart. It shows maturity, growth, and resilience — all traits of someone worth investing in.

You’ve Got This

The ability to ask — clearly, confidently, and intentionally — is one of the most powerful skills you can build in your career and life.

It doesn’t always feel easy. But like anything, it gets easier with practice. The more you ask, the better you get. And the better you get, the more doors you’ll open.

So next time you feel stuck, ask yourself this:

What’s one small ask I can make today that moves me forward?

Then go ask it.

You’ve got this.

Want to see this topic come to life? Check out my latest YouTube video where I dive into this in detail — complete with examples, scenarios, and a few stories from my own career.