At one point or another, you surely received that LinkedIn message from someone asking you if you'd be interested in collaborating. You might check that person's profile to try and establish if they are legitimate and if there is clear synergy, after which you might respond back with a message along the lines of "Sure. What did you have in mind?"

At this point, more often than not, you'll quickly discover that engaging with this person was a waste of time and that they are using the word "collaboration" way too loosely.

Don't be that person. If you want to reach out to someone to discuss a collaboration, here are some important points to remember:

Don't reach out, get introduced.

This is a good general rule of thumb. Whether you are reaching out to investors or potential partners, a warm introduction from a mutual friend or colleague is always more effective than a cold email or message. Asking for that intro is, in and of itself, an art, but it is worth it and will increase your chances of getting a response considerably.

Do your research, and a lot of it.

Before you decide to reach out to someone asking about a potential partnership, it is worthwhile to spend significant time researching what exactly that person does. You might, for example, see from their LinkedIn that they write for some leading publications. But if you dig a tiny bit deeper, you might discover that they only contribute to those websites very rarely, and have no journalistic freedom to write what they want. This information might make your request totally irrelevant and help you avoid awkwardness. 

Truth be told, not only will this research help you avoid an irrelevant request, it might also save a relationship you would have otherwise damaged. I can tell you that when someone reaches out to me with a request that a little research would have revealed was irrelevant, I find it offensive. While I might not blacklist that person, it sure does make a bad first impression.

Maybe first learn the definition of "collaboration."

This point is the most important one for you to remember. A collaboration is a two-sided agreement. Both sides need to benefit from your suggestion. If what you are really after is for that person to promote your business or introduce you to investors, that is not a collaboration, that is a request for assistance. To be clear, asking for help is fine; there is nothing wrong with that. But calling it a collaboration, and thereby trying to hide your true intentions? There is most definitely something wrong with that.

Always err on the side of transparency.

Start with what's in it for them.

Once we've established that a collaboration means that both sides need to benefit, consider starting your message with the benefit for the person to whom you are speaking, and not your own. "Hey Hillel, I would love to talk to you about a marketing collaboration. We have budget to pay you and would like your help with building our go-to-market strategy."

Do not write a message like, "Hey Hillel, I would like to talk about a collaboration and figure out a way to get our message out to your audience." A message like that forces me to ask the awkward question, "How is that a collaboration?"

Come prepared with the granular details.

Once you've done your research and concluded that there is indeed mutually beneficial synergy, try to work out the details before reaching out. Nothing screams unprofessional more than your target responding, "Sure, happy to collaborate. Tell me more," and you having nothing prepared. 

If you play your cards right, be prepared for a positive response by being ready to hit the ground running.