How To Be Assertive (Not Aggressive) When Chasing New Business

When I was a senior in college, I wasn’t satisfied with my career options at home in Arizona. So I took pretty much all the money I had (it wasn’t much) and set up job interviews all across the country. I showed up unannounced at Time Inc.’s headquarters in New York City to ask for a meeting. And shockingly, it worked: I landed at the company right out of school. But as I’ve learned over the years, I was walking a very fine line. I may have verged on being tooaggressive. 

Of course, I didn’t realize this until I was often the one on the other side of the table, especially when I was being pitched for new business. The rise of “hustle” culture prioritizes going for it at all costs. But your can-do attitude can be working against you.

This is a sensitive subject, particularly for women. Studies have found that females are frequently penalized in the workplace for “dominant” behavior. (And when men do the same thing, no one bats an eye.) But knowing when to pounce and when to pull back might be the key to succeeding, say researchers from Stanford Business School. A recent study showed that women who are aggressive, assertive, and confident—but who can turn these traits on and off, depending on the social circumstances—get more promotions than either men or other women.

So, how can you make sure you’re being upfront and confident without taking it too far? Follow my three guidelines to strike the right balance. 

1. Demonstrate how you can be helpful. 

Way too many people make the mistake of taking a “spray-and-pray” approach, trying to reach as many prospective clients as possible and hoping that something sticks. There are two big problems with that strategy. First, you’re more likely to make mistakes during your pitch because you’re spreading yourself too thin. And because you didn’t have the time to do your homework, you’re more likely to come across as unhelpful. Nobody wants to get pitched by a company that’s not useful to them, and they definitely don’t want to bat away continual follow-ups. 

Congratulations: You’ve found a great way to be seen as too aggressive and out-of-touch. And it could leave lasting damage. Recent research from the Aimia Institute shows that millennials are the most likely to permanently cut off brands that spam them with too-general sales pitches. (Related: Fish Where The Fish Are: 4 Tips for Reaching Your Customers)

Don’t propose a partnership unless you’re able to clearly articulate how you can be helpful—not just to the company, but also to the individual you’re pitching. Look them up on LinkedIn and do some research into their job title and role. Avoid approaching people who aren’t the appropriate targets for a pitch, even if the company they work for is your dream client. You’ll save everyone time and energy: Studies have found that as many of half of your initial sales prospects can be eliminated because they aren’t a good fit.

2. Show that you respect their time. 

When you’re the one making the ask, it’s your job to ensure that you’re being mindful of the fact that you’re taking up another person’s time. No matter how much you believe in your product or service and how it can benefit the people you’re pitching, keep it short and sweet. It’s easy to show that respect. If you’re calling your target, the first thing you should ask is, “Do you have a few minutes to chat?” If they don’t, ask if sometime later would be better, and also offer to email them instead. 

This is key. A lot of people will tell you they don’t have time even if they technicallydo because a phone call can be disruptive to their work flow. In a digital world, even with smartphones practically glued to our hands, call volume has been on the decline for years. For many people, it’s just not intuitive to pick up when the phone rings. Suggesting that you email them instead isn’t an admission of defeat, but rather it’s a way to show that you respect their time and their process.

3. Prioritize clear communication and feedback. 

You will be way more effective in signing up new business if you are constantly evaluating and learning from your own performance. If a prospective partner or client tells you that they’re not interested, consider asking them, “If you have a moment, would you be able to tell me why it’s not a fit?” 

From this, you can figure out if what you’re pitching is out of the price range for that potential partner, if they’re already getting the same services from someone else, or if this person isn’t in a position to field pitches. (Related: Are You Listening to Your End Customer? Here Are 5 Reasons Why You Should Be) Take these learnings and use them to hone your pitch. You’ll ensure that you’re assertively chasing your goals without being aggressive to the point of ineffectiveness. By working that edge, you’re bound to be more successful.

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 Let’s Connect! Find me on Twitter (@KaraGoldin), and DM me your burning business questions and/or comments.

 Kara Goldin is the founder and CEO of San Francisco–based hint?, a healthy lifestyle brand that produces the leading unsweetened flavored water and a scented sunscreen spray that’s oxybenzone and paraben-free. Listen to her podcast,Unstoppable, where she interviews founders, entrepreneurs, and disruptors across various industries and keep up with her on Twitter, Facebook, and Instagram.