When I joined the company formerly known as YouSendIt as CMO in 2012, we had a major marketing challenge in front of us: stay with a name that the company had already outgrown or re-name and cast aside nine years of brand equity. We chose the latter.

A year after we took the leap and became Hightail, it’s interesting to look back and see what lessons I can pass on to other businesses -- not only those thinking about a rebrand but startups looking for a good name.

Too often entrepreneurs -- especially in tech -- treat a name as an afterthought, absent-mindedly settling on either a descriptive mouthful, something whimsical or just using a product name rather than an actual brand name.

Related: Growing Your Business When You Can't Trademark Your Name

Having lived through the unavoidable pain of a rebrand, I know how important it is to get your name right. So, here are seven tips for naming (or, if necessary, re-naming) your business.

1. Start with your brand promise. It’s vital to know what your brand stands for before you pick your name. Your brand promise is not what your product or service does, it’s the deeper emotional connection it should have with your users. It’s the way your brand should make your customers feel.

Airbnb’s recent re-brand showed the company really understood their brand promise with their audience. The central concept of “belong” gets to the company’s true emotional appeal. Airbnb is not just about cheap accommodation but about staying in places that feel more like home with people who will become your friends. They didn’t change their name but their entire re-brand speaks to this idea, this brand promise.

2. Be evocative, not descriptive. Descriptive names like YouSendIt are fine, especially when you’re first starting out. While a descriptive name can help your product get discovered in search marketing, ultimately, such a name will probably limit your business. If you have taking-over-the world-sized ambitions, follow the Apple model. In a world of International Business Machines and Microsoft, Apple’s more abstract name allowed them to move from computers to music players and phones without consumers balking. It has brand extensibility. But Apple is not just a random name plucked from the dictionary. It evokes important symbols of human development. It’s the fruit of the tree of knowledge in the Bible and the object that fell on Isaac Newton’s head, inspiring the theory of gravity.  And it had personal significance for Steve Jobs from his days living on an apple orchard commune.

Related: 3 Routes to Register Your Business Name

3. Use a real word. It will be tempting, when faced with the difficulty of securing URLs and trademarks, to make your life easy by making up or misspelling a word. My advice is don’t do it. You’re just making things harder for your potential customers to pronounce it, spell it and remember it.

In general, people prefer the familiar. By taking familiar words and applying them in unconventional ways, a name will stand out.

4. Consider the context. Company names are like baby names. When it’s still in the womb, tell people a name you’re considering and they may have a visceral reaction based on their own experience: “I had a horrible boss named Jeremy.” But add context in the form of a tiny, adorable human being: “Oh, he really looks like a Jeremy.”

It’s the same with your company name. Even when you’re at the stage of presenting options to the other decision makers, don’t just show naked words.  Put the name in context. Design a logo (it doesn't have to be the one you actually use), mock it up on a web page or business letterhead. Seeing the name in action makes it easier to envision. Square is a great example. On its own, the word hardly suggests forward thinking. But in the context of a beautiful, square-shaped gadget that has changed how small businesses accept payment, it’s perfect.

Related: 3 Tips for Naming Your Business in the Modern, Mobile World

5. It’s not a democracy. Choosing a name is not a democratic process. With no hard rules for success, names will always be subjective. Getting a consensus will be difficult, so keep your creative and approval teams as small as possible. But once you’ve picked your name, get everyone on board.

We knew that changing our company name was controversial internally so we made sure employees were the first to find out. We had a grand unveiling at an all-company party with custom-made Hightail cocktails and gave away Hightail-branded free swag. This was partly another great way of putting the new name and logo into context but also a subtle reminder that this was a done deal.

6. Have a thick skin. People will hate the name you choose -- from the baffled board member to the sneering Internet troll. There will always be a loud minority of haters. You just have to accept their right to criticize. Plus, you can always be amused by the inevitable charge of obscenity.

It wasn’t long before people started comparing Airbnb’s new logo to body parts. People told us that Hightail sounded like a high-class escort agency or a service for “hookers on dope.” (I’m not making that up.) For me, this reaction is like a Rorschach personality test and says more about the accuser than your business.

7. Don’t rebrand unless you have to. If you’re choosing your first name, this is one last warning to get it right the first time. If you’re thinking of re-naming your business, think hard. Re-naming is a messy, expensive process. Some of your customers will hate it, which is understandable because name changes are for the company’s benefit, not the customer’s. Even if you’re just thinking about changing your logo, really challenge yourself to prove that it’s necessary.

Related: How to Name Your Startup