Ask a CEO: How Can I Break In to Big Companies (When No One Answers the Phone)?

Breaking in to big companies. It’s the fastest, easiest way to increase your profits, make a difference in lots of people’s lives, and grow your business beyond just the solo-entrepreneur or independent consultant model.

So how do you do it? The obvious answer would seem to be: ask for the big opportunity.

As someone who’s spent more than 20 years working with executive leaders and their teams on structuring effective requests for more sales, I’ve noticed that women in particular have some issues with making big requests. Much more so than men.

We don’t want to be aggressive. If they don’t return our calls, doesn’t that mean they’re not interested? What if we don’t measure up to their expectations? Should we really be negotiating for more here - or just grateful for the opportunity?

If you don’t already have this well-honed practice of making effective requests of people who seem “way out of your league,” how do you get it?

I’ve been interviewing more than 100 CEOs and exploring the relationships between their success and effective requests. These women all own companies with revenues of 1MM and up.

My intention is that their answers will spark a fire in your belly. And next month you’ll be surprising yourself with your own requests.

This month’s question: How can I break in to big companies when no one answers the phone?

CEOs have fears of breaking in to big companies, just like the rest of us. Here’s how these successful women move through their fears by asking big things of big people.

4 Fears You May Have—and How These CEOs Overcame Them.

1. “I’ve heard cold calls and meetings get results, no one seems to answer the phone. I don’t want to be aggressive.”

Advice from a CEO:

“Sometimes a meeting will go well, and then I won’t hear back. There’s a way to show you’re “hungry” without coming across as desperate or aggressive. 

"I know that when people ask me for something, I want to see that the person really wants it! So sometimes I will follow up with a handwritten thank you note, or send an email just to check in. As long as you ask in a respectful and calm way, it can’t hurt to ask.

-Sarah Levy, Founder, Sarah’s Pastries & Candies

“Things are different today. If you call companies, they don’t even answer. There’s no personal connection. It’s painful. So how do you find clients and how do you get in? I just keep asking the universe and talking to everyone I know. ‘Whom do you know to get me into [major corporation]?’ We’re sending out an email to our list, asking them to refer us to people they know. That connection with people is the most important thing. You gotta ask. I ask people for things, but I don’t cross boundaries. I can’t just say, ‘Hey can you introduce me to Mark Zuckerberg?’ It will totally turn them off. It has to come from them—getting friendships and loyalty must come first. Once you find the companies that care about what you offer, you have to ask for the opportunity. ‘I’d like the opportunity to work with your company, to work on your bigger events.’ You have to keep asking. Rejection can be painful. But I just think, I’m closer to the next one. You just gotta get through this and make a win out of it.“

-Bobbie FakkemaCEO Events, Etc. 

2. “I want to ask for more money from a big corporate client, but I’m afraid to do it because I don’t want to damage the relationship.”

Advice from a CEO:

“When negotiating my first contract with a billion dollar company, their version of the contract was very one-sided. I realized I could ask for whatever I wanted changed and all they could do was say ‘no.’

"So, I asked and they said ‘yes’ to everything I wanted changed. At that moment, I realized two things. It’s business, not personal, and you never know until you ask. That’s been my mantra every since. Without being pushy, I will say something like, ‘I would like to see this item changed to this.’ Or, ‘If you change this item to this, we have a deal.’

-Jennifer Maier, CEOWomen’s Distribution Services,

3. “I want to get my foot in the door with a big corporate client in a new industry, but I’m afraid I won’t live up to their expectations.”

Advice from a CEO:

“My first Fortune 500 client was a result of a marketing cold call. I wasn’t clear on all the technology terms they were throwing at me and I had to give them a proposal for services, budget, and samples of the site look and feel within 72 hours, which happened to encompass a weekend. I knew I could make this happen, regardless of the time constraints and my lack of experience with this type of request. In that moment of courage, I assumed success was possible. The client is still part of my portfolio and their business needs have changed. We’ve grown together in meeting their event management needs and established a true partnership.

-Debra McDonald, President, Corporate Events & Occasions,

4. “I’m so afraid of hearing “no” or making people feel awkward that I never ask for the big opportunities.”

Advice from a CEO:

“Asking for a “break” into a new industry has typically yielded great results for me. What works? Pretty simple formula:
1. Here’s what I want/need/would like
2. Here’s why I want/need it
3. Here’s what I see “in it” for you
4. Here’s how I envision us moving forward

Before asking, I need to be very clear in my head, heart, and gut about the want/need, honest with myself about the “why?” and passionate about the purpose of and ultimate desired outcome of the request.”

—Linda Gold, CEO M3iworks

I always assume the answer will be yes. It never occurs to me otherwise. Obviously, I do get the occasional “no”, so then we negotiate and I never take it personally.

"But acting in the affirmative and always “assuming the sale” is both empowering and quite effective in most cases. What’s the worst that can happen? A No? Isn’t that what you get by not asking?”

-Deborah Millhouse CPC, CTS, CSP | President CEO Inc.

I’d like to hear from you in the comments.

1. How do you feel about asking for what you want?

2. What’s one thing you’re going to ask for in the next week as a result of reading this post?

Want more? Register to receive 5 scripts to make your next request easy, breezy, and absolutely doable.

(This is the first in a new monthly series in which we ask women CEOs a burning question, and they answer. Want to ask a CEO? Email your question to

She Takes On The World is an award-winning digital magazine for entrepreneurial women, aiming to inspire women to create their own careers and provide them with support in all facets of their lives. She Takes on the World has received accolades around the globe, including being recognized by Forbes as one of "Ten Best Entrepreneurial Sites for Women"

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