Overcome the Fear of Asking for What You Want

by | 4 Feb 24

The ability to ask for what you want, even when you’re scared, is the ultimate quality of someone successful in their work.

Most people don’t ask for what they want; they just wish for it, drop a few hints, or make suggestions, hoping things will magically work out. But here’s the truth: in business, you only get what you ask for. If you don’t ask for it, you don’t get it.

It can be really scary to ask for something like:

  • “Could you outline the steps involved in your decision-making process?”
  • “Will you be renewing with us next year?”
  • “Can we book in the next meeting?”
  • “Can you help me understand what budget you’ve allocated for this?”

These are tough things to ask. But you must ask them.

And that’s where this blog comes in. I’m going to share with you some tips on how to overcome the fear of asking questions that help you succeed in your sales or customer success role.

Before I do, let me tell you a story.

Table of Contents

Use these links to jump straight to the part of the article that interests you most.

> A Real Life Example
> How To Get Over The Fear
> FAQs About This Challenge
> Now, Do This At Work

A Real Life Example

The power of asking is something, can only be truly understood when you experience it yourself. Thankfully I had that opportunity when I got my first-year student loan, back in the 1990’s. At that time, tuition fees were already covered for students (through a mix of loans and grants), so the student loan was used to cover living costs.

I have to admit, I didn’t really get the concept of budgeting money then. I saw my student loan as a significant sum that I could use for anything. People told me to plan for accommodation, and food expenses, and calculate a weekly budget. But for some reason, I didn’t pay much attention. I just kept thinking, “With this much money, there must be something exciting I can do!”

And then it hit me. There was a brilliant live music scene in South and West Yorkshire at that time, with loads of bars putting on local bands. I was in a band myself, and we all knew there was a common problem – we didn’t have enough money to buy our own PA systems and microphones, which were essential for gigs. And the pubs didn’t have their own either. We had the talent (we thought!), and we had an ample choice of places to play our songs, but the lack of equipment held us all back.

Idea Time!

But, I had an idea. I had my student loan.

I wasn’t great at budgeting – but I wasn’t completely carefree! I needed confirmation that people would pay me, to provide them with the equipment they needed, before I spent all my accommodation and food budget for the term on some nice new tech.

So, I decided to ask. I spoke with my friends in other bands and said, “If I can get you a PA system, mixing desk, and microphones for any gig you book, would you pay me £75, plus travel costs, for each gig?”

Loads of them said “yes”. They knew they could now play more gigs! The amount they were willing to pay was essentially what they earned from the gig. But, most bands played for the love of music, not for the money. They just wanted people to hear their songs! And honestly, my main focus wasn’t making a ton of cash either. I wanted to improve my sound engineering skills while covering my living costs as a student.

And if I could do that while having fun with my mates, that’s even better! By asking, I could achieve all three goals, which sounded loads more fun to me.

The Numbers Stacked Up

With five bands on board, each playing gigs every couple of weeks, I calculated that I could earn around £750 per month, totalling £9,000 per year. My student loan was around £2,500 per year. The numbers made sense, and it was clear people wanted this. But there was one more ask – I needed them to confirm. So I asked each band to book me for their next five gigs. By securing those bookings, I had £1,875 in orders. Albeit, I had no cash in hand from these bookings. But they were good friends. I trusted them. Plus, if they booked a gig – I knew they needed the equipment.

The only step now was to buy the equipment, which was easy! I just went to my local music shop and spent my student loan!

And there you have it – a simple, profitable small business created by asking a few questions.

There was one more thing I had to ask, regularly – “Mum/Dad, any chance you can pick me up and take me to Leeds tonight? I’ve got a gig!” 😀 But it wasn’t long until I had enough money to buy a car.

It was an amazing business venture for a student.

How To Get Over The Fear of Asking

That story I just shared was pretty long, and you might have skipped past it. No worries, though. The summarising point is that it was a profitable business formed from asking just a few questions.

The key to its success was the lack of fear when asking those questions. It didn’t matter if the answer was no. No one would’ve gotten hurt, no respect would’ve been lost, and no one would’ve been sad.

And here’s the main point: to be as successful as you can be, you’ve got to overcome the fear of asking questions and you have to become comfortable with rejection.

Now, here’s a great little tip I picked up a while back. I’ve shared it with many salespeople and customer success folks over the years. And once you do this, trust me, you’ll feel so much more at ease when asking for things, even when you get rejected.

So, let’s practice getting rejected! Let’s practice by asking for something that you’re guaranteed to get a “No” response to.

It’s really easy. The next time you’re at your favourite coffee shop, pub, or cafe and it’s time to pay, try this out:

  • “Any chance you could knock a pound off the bill, please?”

Now, 9 times out of 10, or even every single time, you’re going hear them say, “No, we can’t do that.”

And you know what? That’s absolutely fine. In fact, that’s exactly what I want them to say to you. I want you to get comfortable with asking and hearing someone say “no.”

If you keep doing this every time you make a purchase over the next couple of weeks, I guarantee you it’ll become so easy and rejection will feel so insignificant that you won’t even care anymore.

Just give it a shot for 2 weeks, and you’ll notice that your fear of asking for something disappears.

Oh, and here’s a great little tip to start: you can soften the ask with a smile. Make it a bit cheeky at first. That’ll help you ease into it. Eventually, though, you’ll feel completely fine and won’t need the cheeky smile anymore.

FAQs About This Challenge

Because you’re overcoming a fear of something, this task does come with a few questions. I usually introduce this to people face-to-face, so I can respond to those questions. But as this is a blog, I’ve written the two most frequently asked questions for you:

“Won’t this make the other person feel awful?”

Simple answer: Nope! You’re just asking if it’s possible based on their company’s policies. It’s not offensive at all, and they’ll probably just say “No, I don’t think we can do that.” You can respond with a quick “No problem!”

“Won’t they hate me for it?”

No, not at all! You’re just asking a question, being a bit cheeky maybe. But nobody hates someone who’s cheeky. Plus, when you respond with “worth a try” and a smile after their “no,” you’re likely to get a compliment!

If you have any more questions, feel free to message me on LinkedIn or send me an email at: tom@goaccelerate.org!

Now, Do This At Work

If you’re afraid of asking your customers for something and getting rejected, try the above task for 2 weeks. Trust me, it’ll make a huge difference.

So why is this task so powerful? Well, when you start asking for something in your role at work, you’re actually much more likely to get a positive response to your questions.

At work, the questions you ask actually help solve problems for you and your customers. Let’s take a look at some of the questions I mentioned earlier in this blog:

  • Could you outline the steps involved in your decision-making process?” – This makes your customers’ buying journey simpler and faster for them and you. It’s a win-win.
  • Will you be renewing with us next year?” – It’s a straightforward question that saves everyone’s time. They’ll appreciate your directness.
  • Can we book the next meeting?” – Again, it’s all about saving time. If they don’t need another meeting, they can say no, and you can stop chasing them through emails and phone calls.
  • Can you help me understand what budget you’ve allocated for this?” – I know it’s a tough question, but remember, you’re not asking them to pay out of their own pocket. It’s a business budget, and it’s as simple as that.

See, asking these work-related questions is much easier than the ones you asked during the coffee shop task. Why? Because there’s a higher chance of getting a positive response. Not every answer will be a flat “no”.

Oh, and here’s something to think about. If someone asked you those same questions, would you hate them? Would you think they’re horrible? Would it ruin your day? The answer to all those questions is “no”.

So go ahead and practice this task. In two weeks, start asking the tough questions at work. You’ll see shorter sales cycles, you’ll be helping your customers see the value in your products faster, and they’ll have more faith in your friendly assertiveness.

It’s a win-win for everyone!

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