The Secret Strategy for Getting What You Want; Ask

“I was wondering if I might be able to get a Venti for the price of a Grande?” I asked.

“Ummmm, no.” was the attitude-ladened response that came back from the judgy-sounding Starbucks barista.

Awkward, yes. But I made it through the exercise – unscathed. Only nine more times to go. 

This was a challenge I accepted from Noah Kagan, Chief Sumo at Sumo Group (the people behind And I invite you to take the same challenge…if you dare.

What’s the point, you ask?

It’s a challenge that is logistically easy, yet surprisingly difficult – or at least it was for me.

This challenge illustrates that regardless of how clumsy and embarrassed we feel when it comes to asking for things, nothing bad actually happens. And surprise, surprise…one coffee shop employee offered me a caramel scone to go with my beverage for free. (Sure, it was the end of the day and I’m positive the scone was destined for the bin anyway) but that’s not the point.

The point is…there was zero downside to the exercise and only upside. It broke me of my fear of being uncomfortable – or at least it was a good start.

People hate asking for things. We are afraid of rejection. We are afraid of looking stupid. We don’t like feeling uncomfortable, and worse, we fear making the other person feel uncomfortable. We’ll endure just about any hardship so long as we don’t have to put ourselves out there and ask. Just confer with any man, driving aimlessly on the sidestreets, prior to the days of GPSs, and he’ll tell you that asking sucks.

I promise you though, getting comfortable being uncomfortable, can be the biggest game-changer not only in your travel business but in your life.


Asking for the Sale

I’ve done a lot of telephone sales coaching over the years, and it is not uncommon for travel agents to struggle with asking for the sale. I’ve heard some of the most knowledgeable agents consult for long periods of time – going over details of the cabin configuration, the meal plan, the flight options – the minute differences between one cruise ship vs. another. And then at the end of it all, they’ll say…Well, okay then. Talk to you later.

I wish I was exaggerating. 

Afterwards, when we are replaying the phone call, I’ll question…” Why didn’t you ask for the sale?” The response is usually some variation of…” well, I didn’t want to come off sounding pushy. I’m sure they’ll call me back when they are ready to book.”


Helping agents understand they should always ask for the sale with every consultation has had huge pay-offs. And at the very least, even if they don’t get the credit card as a result of asking, at least it opens the door to the follow-up question, which is why not? What will it take to make it a yes? That’s golden information.

Asking for a raise; ask for a promotion

If you are currently working for a travel company, not quite out on your own yet. (And let’s just say we are not in the middle of a pandemic) Don’t be afraid to ask for what you want. I’ve done my share of eavesdropping in the lunchroom. I’ve overheard conversations where staff members are lamenting over their salaries or their positions in the company.

“My boss doesn’t appreciate me. I do so much. I don’t know why I’m always passed over when positions come up? Why can’t she see how friggin’ awesome I am?”

If only I could have shaken them and said…Go ask!

(but then I’d have to admit to eavesdropping in the first place, so I stay quiet)

There have been many times that I’ve wanted to promote someone for a position but couldn’t. I once had a boss who warned me to never offer a position to someone who didn’t have the chutzpah to ask for it. He said, “Diane, if they don’t believe in themselves enough to put their hand up for the role, then how can they represent our company in the field.” That always stuck with me and to date…I have never offered a promotion to someone who didn’t ask for it.

Asking for an upgrade

Surprisingly…asking for a Venti in lieu of a Grande at Starbucks = HARD.

Yet asking for an upgrade from a standard room to a premier suite = less hard. Go figure. 

In the travel industry, it is amazing what you can get if you just ask. I dunno..maybe it’s because we are an industry filled with only kick-ass people, to begin with, but I have had major success with just asking. My coffee challenge experience – I had a 10% success rate. In the travel industry, my success rate is probably between 70 to 80% and…those odds are damn good.

Asking for help

We all mess up from time to time. Taking responsibility for that is the first step, of course. But once you have that done and dusted, the next step is to ask for help to fix things. Having worked behind the scenes for two of the largest travel wholesalers in the business, I can tell you that wholesalers will bend over backwards to help you out of a mess. So will hotels and suppliers in destination. You just gotta ask. 

And I’m amazed by how many agents seem to think…well, sucks to be me and move on. 

Asking for what you want

I’m about to have a woo-woo moment and for that, you may judge me but I don’t care. I’m doing it anyway because I believe it to my bones. 

You have to ask for what you want in life. You have to put it out there in the ether. The most successful people in this world know this to be true. They have a very clear vision about what they want and know that the first step in acquiring it is to ask for it.

It is the craziest thing, but I wouldn’t share this if I didn’t see evidence of it in my own life over and over again. 


7 Strategies to get the most out of your ask

Because I can appreciate how uncomfortable it is to ask – from personal experience, I wanted to impart some strategies that will improve your odds of getting more “yeses.”

1. Ask as if it’s already been given or the answer will be, of course, yes.


“So, do you think you are ready to put down a deposit today…I mean…if it’s not too much trouble, and the moon is sitting in its ideal position in orbit, what do you think?”

Becomes this:

“We should tie down this booking today. We don’t want to risk losing the space or the rates we’ve secured. Do you want to pay with a credit card that gives you points for travel?”

2. Ask the person who has the authority to give it to you. This will just save you time.

When consulting with a couple, you may notice that there is always one that holds the authority. …maybe not in all things in the relationship but is the decision maker when it comes to travel. You want to be sure that you know which one that is and that you direct your questions to them. 

Or with upgrades or discounts, often the people on the front lines don’t have the authority. Be sure that you are asking the person who does.

3. Be specific.

When you are asking the universe for more money, be specific. Or the next thing you know…you’ll be walking along the sidewalk and trip over a penny. You asked for more money… And there it is!

Be specific with what you want. 

This also comes in handy when negotiating upgrades on behalf of your clients with suppliers. Asking…can I have an upgrade is very loosey-goosey. Instead, frame it like this:

“I was wondering if we could get these VIP clients of mine an upgrade to a junior suite if you have it. It’s their anniversary, birthday, honeymoon, babymoon,”…whatever. It’s so much easier to say yes to something like that.

4. Add a Call to Actions on all your correspondence – aka ASK

On every single touch point, you have with a client, there should be a call to action – which is an ask dressed up in a different colour. Whether it be in your ads or your social media posts, ask for what you want. Do you want your client to sign up for your newsletter, share your post, buy your travel package…ask them. Don’t leave them hanging.

5. Ask and then ask again. Are you sure the answer is no?

Don’t settle for your first, no. Sometimes…I swear, people just say, “no” as a matter of habit. Maybe they have kids. Haha. Step back and reframe your question. This will give them time to rethink things. Let’s say you asked for an upgrade to first class and got a “No.” Don’t just stop there. Go back in and ask for a spot in Premium economy. Exit row? Somewhere NOT by the bathrooms?

Or just re-ask, but this time, say…” I appreciate your position on that. What will you be able to offer me instead?” – You’ll be amazed by what this follow-up ask can get you.

6. 3rd time’s the charm.

Mostly, it’s just a numbers game. The more people you ask, the better your chances. You may be familiar with the story of Colonel Sanders. He asked 1009 times for someone to take on his secret recipe before he got a bite. 

And J. K. Rowling pitched 12 publishers before Bloomsbury took a gamble on her. I’m guessing those previous 12 publishers are feeling a bit sheepish these days.

Even if it means asking the same person again. You never know. Maybe they are in a better mood the next time you ask. Maybe you have more convincing material to support your ask. Maybe the moon is full – who knows why but how often have you heard someone say….” Well, deary…you have perfect timing…of course, I will”

The point is, if you ask often enough…you will get a yes…eventually.

7. Shut up

Final strategy…make your ask and then shut up. Let your request hang there. You will want to keep talking – especially when the air is thick with awkwardness, but don’t be deterred. Just keep your composure and say nothing. It’s like a game of chicken. Let your opponent make the first move.

What’s the worst thing that can happen

The worst thing is that we hear a “no.” That’s it! There is zero downside other than a small blemish on our precious egos. 

Before I walked into Starbucks on my first day of the challenge, I was prepared to pay an obscene amount of money for a grande latte. And other than the sneer I got from the barista who doesn’t know me, and who I’ll most likely never cross paths with again, there was no insurmountable fallout. Sure, I didn’t get the venti that time. But I also wouldn’t have got the venti had I not asked either. No harm, no foul.

Asking others to help allows them the opportunity to be generous


To be in true service to others is a phenomenal feeling. It’s why we are here. Denying people the opportunity to gain their divine purpose can be actually kind of selfish. We are all on this planet to help each other. So why not allow others their shot at generosity?

My final thought from one of the other all-time sports greats…


Maybe doing the coffee challenge is not for you. But you should consider that the more you resist something…the more likely it’s exactly what you need.  You will be amazed by how much is out there, left on the table, waiting for you…if you just ask.

And me…I’m going to make an ask. I’m asking that if you found this article helpful, or at least not painful, why don’t you share it with a friend?


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Rick Boettcher
Rick Boettcher
3 years ago

My dad used to ask for discounts from darn near everyone that wanted his money. (Including the counter workers at McDonald’s) As you alluded to in your blog, it embarrassed the rest of the family every time he did it. And like so many other things in life, he didn’t care a single whit about other people’s thoughts on the matter. All that being said, I now know why he had way more money in the bank at my age than I do. Sometimes father (and experienced Travel Marketing Blog Experts) know best.

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