The Difference Between Between Pushy and Tenacious – How to Make The Ask

Social Media Week

I am doing a series of posts based on the 7×7 Mentoring Salon I did for SMW 2014.  I gathered seven up-and-coming professionals / entrepreneurs to pose a question to seven experienced entrepreneurs and leaders. Over the next few weeks I will share the seven questions asked and the mentors answers. Today’s question focuses on how to get better at promoting yourself and your business without being “pushy”.

Question #3 Putting Yourself Forward

Amy Schoenberger specializes in CSR, cause marketing and social impact. She‘s passionate about the intersection between emerging communication technology and socially conscious brands. As she is increasingly involved in building new business and growing a company, she finds herself pondering the question of hustle.


Her question is, “What advice would you give to help guide people on getting out there and obtaining new leads selling your company or your services and promoting yourself and your own expertise without seeming too pushy?”  She is curious what the mentors have experienced in terms of gender discrepancy and how the different genders sell themselves in their company differently and how we can learn from each other.

A1.  Do be excited. Don’t be desperate. The key is to be interesting. 

Every month at New York Tech Meet Up we get pitched by companies who want to demo at the monthly meetup. More often than not, when a woman applies and I tell her “no,” she disappears and I never hear from her again. When guys apply  and I tell them, “no,” they don’t go away. One guy emailed me every day for 28 days straight with a different reason every day for why his company should get to demo.

I never let him demo because the company wasn’t a good fit for us, but when I see him around now, I still remember his dedication to pushing his company. It never became annoying because he put effort into coming up with a different reason every single day. If you just email me everyday going, “Can I demo yet? Can I demo yet? Can I demo yet?” I probably would have been annoyed. It’s the difference between seeming excited vs. seeming desperate. I could tell that he was really excited about his product and it came out in the way that he was explaining it. I think women tend to think they’re being pushy way before they actually are. A woman might think that sending two emails is being pushy and for a guy sending 28 emails is just starting to get pushy for him. – Jessica Lawrence, Executive Director of NY Tech Meetup


A2. Tenacity is the word….keep trying and add value to your follow-up.

Three years ago, I received an invitation to be a Vital Voices’ global ambassador and go to Tunisia. Then something called the “Arab Spring” happened and it got cancelled. I wrote back and I said, “I’d really like to do another one to another part of the world.” Never heard back. Six months went by and I wrote again. Four months went by. A year and a half later, like many women, I took it personally. I wondered, “Did I do something wrong?” But I kept writing every few months. It turns out my contact had left the organization and the good news is that this past May, I went to Singapore as the Vital Voices’ global ambassador. So tenacity is the word as opposed to pushy and assertiveness. There’s a way to continue as long as you’re adding value when you are making these follow-ups. – Susan McPherson, founder and CEO, McPherson Strategies


A3. Take the emotion out of it

What you’re talking about is really a version of networking. There’s a lot of research networking and it’s pretty clear that there’s a gender distinction between who men and women approach it. Not all the time, but guys tend to be more transactional and women are more relational. If I ask someone to do something I really need and they say no, I wouldn’t think, “Oh no, she doesn’t like me”. I would just call again the next day. That happens all the time.

When you are more transactional you don’t inject emotion into the “no” context. When you view it as a relational issue…you get concerned about the way that the other side is reacting. If you want to promote yourself, promote your company, get new business, you have to persuade people to do things that they might have not otherwise wanted to do or thought about doing….you have to be pushy. And you will get no’s all the time. So you have to accept that you need to be pushy to achieve the result you want and not be too worried about the relational impact of it. Most of the time, long as you do it in a thoughtful way, you can actually build something from it that’s positive. – Adam Quinton, Chief Financial Officer at Nopsec


A4. Don’t apologize for the ask

It’s interesting being in a room with a guy while he is having a conversation about raising money. Having observed how a guy asks and handles a no, I saw it was definitely transactional. He did not beat around the bush. It was “you either have $35,000 to give or you don’t.” It was clear that he was still going to like the people if they said “no.” It made me realize that I was more apologetic about asking for something. I focused on protecting the relationship. I would apologize for having to ask, for taking their time. Then I got over it really quickly because I was saw his method is a lot easier…and it takes a lot less time because you get to the point quickly. — Jessica Lawrence, Executive Director of NY Tech Meetup


If you are interested in reading more:

Question 1: What lessons have you learned on pitching?

Question 2A: What leadership qualities should I focus on in my 20s? – Part 1

Question 2B: What leadership qualities should I focus on in my 20s? – Part 2 

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