Before joining TriplePoint I worked briefly for a growth stage fund at a venture capital firm, specializing in mobile, ecommerce, adtech, and cloud technologies. It’s not hard to imagine that my favorite part of the job was sitting in on the pitches entrepreneurs made to attract funding for their companies. When I moved over to the public relations side of the tech scene, I experienced a complete role reversal. Now I am the one presenting pitches, in the form of a tailored email or occasional call to a journalist. From this process, I’ve learned a bit about what makes an effective — and cringe-worthy — pitch. While I’m still always learning new ways to pitch, I’ve developed a few tips for pitching someone, whether you’re looking for investment support or media coverage:

1.) Keep it short but sweet

This one is pretty standard, but it’s true for a reason. Having a VC show up to your pitch expecting an hourlong meeting when you have a multi-hour deck planned does nobody any favors. Likewise, sending a reporter a novella and hoping they have the time to read through it to get to the heart of your idea could lead straight to the trash folder instead. Both journalists and venture capitalists are busy, and by keeping your pitch concise you are doing them, and in turn yourself, a favor. More importantly, keeping a pitch short forces you to really hone in on the message you are trying to get across. If you can’t state what your company does and why it is important in one paragraph, with all the fluff and buzzwords removed, you might need to take a closer look at your business model.

2.) “Knowing somebody” is not a guarantee

Like in all areas of life, there are certain benefits to knowing the right people, and getting your foot in the door. Maybe a business acquaintance or a former roommate helped you get some facetime (or screentime) with a VC, or an editor at a prominent news outlet. You’re halfway there! However, you still have the other half to go, and without a polished pitch, you may find yourself no closer to that funding/above the fold article than you were when you started. Which brings me to….

3.) Know what you are trying to get out of your pitch

Maybe that VC you are meeting with or the reporter you’ve been emailing just aren’t the right fit for your company or news. Pitching them is not a waste of time, but remember to take into account what you can reasonably expect out of your conversation, and adjust your strategy accordingly. Maybe you’re aiming for an intro to another investor or writer, or just to get some advice from somebody with deep industry understanding. Knowing what your ask is should be the primary driver of the information you share, and the way in which you present it.

4.) Answer questions preemptively

You may only get one shot to interest a specific investor or reporter in your story, so it’s important to make the most of it. Try to anticipate what information you think your target audience would like to know, and tell it to them as early as possible. Don’t wait to answer any questions that could come up, but instead proactively seek to eliminate the need for questions. As you think through your company’s core messages, it’s helpful to imagine questions that could logically arise about your business. Try to find a way to work the answers to those questions into your messaging, and into your pitch.

5.) Avoid being a robot

At the end of the day, there is another real person at the receiving end of your pitch, and they will appreciate being treated as such. If you are able to effectively communicate your own personality while getting your story across, it makes your message that much stronger. Likewise, know your audience, and show them that you have spent the time to find out what they write about/what types of companies they invest in/that according to their Twitter handle they are really into fly fishing.