Outreach + Conversations with Strangers

Let’s talk about outreach, cold outreach, and how to start conversations with strangers without being spammy, weird, or annoying.


If we haven’t met yet, my name is Ryann Dowdy and I am a sales coach. I help brand new entrepreneurs build six figure businesses by mastering your sales conversations and your mindset. And I am super excited about this conversation because it is one that I get a lot of questions about.


So, let’s talk about outreach, cold outreach, direct messaging, all the drama that comes up for you when we talk about it. I really want to actually first focus on the mindset piece of this. There are a lot of people out there that really believe that outreach and cold outreach is just the worst thing ever to do in business.


Don’t ever direct message a stranger and don’t ever, you know, DM ME. If I wanted something I would reach out to you, and that has caused you, as a brand new entrepreneur, to have a lot of fear and anxiety about the idea of sending a message to a stranger without having permission to do so.


I want to kind of level set on that because I think it’s really important for us to think about all of the outreach that we do as we’re growing a business is actually cold outreach in and of itself. Building a relationship with a stranger is cold outreach. If you go to a networking event to meet new people, it’s called outreach. If you meet a friend at a cocktail party who introduces you to somebody new it’s called outreach. We are all learning and meeting new people all of the time.


That means that these are technically cold leads people we did not know before and are starting conversations and relationships with them. So that is the first thing I want you to think about is if you’re like, Oh, I don’t want to do cold outreach.


Really guys, it’s all cold outreach when we’re networking and connecting and talking to strangers, it’s all about building relationships with new people, which is where the magic happens in sales. So how do we do any kind of outreach without being spammy, without being weird, without pissing people off?


What I have learned is most people that are really up in arms about cold outreach are actually not too upset about cold outreach in general, they’re upset about the cold pitch. It is about somebody trying to sell them something in their direct messages without ever building a relationship without ever qualifying them for the product and without ever in any way, shape or form asking, do you have a need or a want for my product or service?


That is the kind of cold outreach that people don’t like. That is what fires people up. And the reason I know that this is I’ve pulled a lot of people. I’ve asked a lot of questions about this, and I really want you guys to think about it. It is not about the idea of I don’t ever want to connect with a stranger. It’s the idea of, I don’t ever want to be sold something. I didn’t give someone permission to sell me.


That is one of my number one rules. We never sell to anyone unless we have permission to do so. And it’s so important for you to remember that we are not selling things to people who aren’t interested, who don’t want to have a conversation. We’re not forcing our products or services onto anyone. We are focusing on building relationships. And when someone does in some way, shape or form fit the criteria of a potential ideal client, we want to start building a relationship with them. We do that through outreach.


That is really what it looks like in sales. And that is what happens in the corporate world that I am slowly but surely working on bringing into entrepreneurship is this idea of building relationships with strangers is not a bad thing. So how do we do that in a way that doesn’t feel gross, where they don’t feel like they’re getting cold pitch, where they don’t feel like it’s being invasive?


So the first thing is I want to do when we start conversations with strangers is I always want to make it about them.
I always want to ask them a question about what themselves, what does that look like? So say for instance, you are a life coach and you connect with somebody in a Facebook community and it’s someone that just totally fits the criteria of an ideal client for you.


And you’re like, Oh my gosh, I just really love that woman. I think she’s fantastic. How do I, how do I get in touch with her? How do I reach out to her? How do I start building a relationship with her without being spammy or weird?


What I recommend doing is going and checking out whatever social profile you guys connected on. Maybe you connected on Facebook. Check out her Facebook, and then send her a direct message that says, Hey, Sarah, you and I are in a Facebook group together. And you’re always giving such a fantastic advice. So I checked out your profile and I noticed that you have two kids that appear to be same in age to my kiddos. How old are your kiddos? Thank you so much for providing so much value in that community!


It was all about her. You weren’t pitching her, anything you weren’t asking her, anything, you were starting a conversation with her about her. Will she responded? Who knows? The response rate is somewhere between 20 and 30%. I think that sometimes, we think that nobody responded. Well, if you send 10 messages and three people respond, you actually have a well above average response rate. So first things first – make it about them.


Second of all, I want you to always ask questions.
That is how we continue conversations. Anytime you’re stuck in a conversation, ask somebody a question about themselves. The fastest way to build a relationship to learn about them is to ask them a question. So notice I had that example of the life coach with Sarah and the woman we reached out to, and it’s like, Oh, you know, it looks like our kids are similar in age. How old are your kids?


I’ve asked a question. She doesn’t have to think, she doesn’t have to come up with anything. I have basically told her how to respond to me by asking her a question. So we always want to make sure when we’re having a conversation with someone new, that we are asking questions, not in a way to interrogate, but in a way to get to know them. So they don’t have to come up with what to say next.


Some people are really anxious and uncomfortable talking to new people. So, I never want them to have to come up with the burden of continuing the conversation. The way that I can do that is by always asking a question.


Number three is to be genuine.
If you are not at all interested in building a relationship with Sarah and learning about her kiddos, don’t ask that question.

People can smell BS from a mile away. Believe me. I know that can. As an online entrepreneur, I get a ton of messages all of the time, and people can smell BS a mile away. So make sure that you’re being really genuine in your outreach.


If you don’t have any interest in their kiddos, don’t ask them a question about their kiddos.  If you don’t have any interest in the work that they do, don’t ask a question in that way. Please make sure that you’re being genuine and that you were coming from a place of genuinely building relationships. Cause like I said, people will smell it a mile away and they won’t like it. You will instantly come off as spammy. So make sure that wherever you are, whatever energy that you were in, when you were doing this outreach, that you’re really mindful of who the other person is and being really genuine.


Ask yourself: if you received this message, would it feel genuine? Would you see connection in this? Would this be a conversation you would want to be a part of? That’s always a really good test of your outreach.


A fourth piece of advice on starting conversations with strangers is to do your research.
The internet gives us so many tools and it takes like 90 seconds to do some research on someone to learn a little bit about them, and check out their Facebook page, or check out their Instagram, or check out their LinkedIn. If you’re a business owner, check out their website.  It takes 90 seconds to do that research. And it will put you light years ahead of anybody else who’s cold pitching them spammy stuff because you actually took the time to learn something about them.


It goes back to my first point, which is always making it about them. But doing that research, finding some way to connect on a personal level will definitely get you a much higher response rates and also help you be more confident in that outreach because you have found that connection. It’s not just a shot in the dark. You’ve actually found a real place to connect with this person.


The final piece of this is to make sure that you’re personalizing!
Again, going back to being genuine, people can smell a copy and pasted message a mile away. They know when it is a copy and pasted message. So if you have any of you ever received the message from someone who actually had like the wrong name in it, when it was like, Hey Carol, and you’re like, my name’s not Carol….

It was because somebody copied and pasted a message. They sent it to 10 people and that never feels good. Even if your heart’s in the right place, that never feels good. So, make sure that there’s some level of personalization. This goes back to doing your research, and then personalizing that conversation specifically to that person.


You’re always saying kind of the same thing when you’re starting new relationships and connecting with new people, I’m not proposing that we totally reinvent the wheel here, but I am saying find some level of personalization. That way, the person knows that you’re interested in them. Remember – sales and getting clients is all about relationship building. It’s all about having that connection with someone and human to human connection. That’s how we get clients in our business. And that is how your outreach will stand out over and above any other kind of outreach that people are getting.


So quick review!
How to start conversations with strangers.

Number one is to always make it about them.
If your message has the word I in it too many times, rewrite it. It’s always about them.


Number two is to ask questions.
That’s how we continue conversations. You take on the burden of controlling the conversation by asking questions.


Number three is to be genuine.
Don’t connect with people that you don’t want to connect with. Go with your gut. You’re intuitive. You can decide whether or not to have a cup of coffee with this person, or to have a glass of wine with this person. And if the answer is no, then no, they’re not your people. Then don’t have that conversation that don’t start that conversation. People will sense it. So be genuine.


Number four, do your research.
Take 90 seconds. Yes. This takes time. Relationship building takes time. Building a business takes time. Ninety seconds to build a connection that could result in a client that is worth thousands of dollars is 110% worth it. So do your research.


Finally, Number five is to personalize your message.
Personalize your outreach, make that person feel like you genuinely care about getting to know them. Make them feel you have taken that time to do that research and that you are a real person on the other side of it, not a bot, really seeking to find that connection. So that is how we start conversations with strangers without being spammy, weird, and without being uncomfortable and without pitching our services without permission. That is never something I would encourage you to do.


If you are not yet a member of the Ambitious Women Entrepreneurs Mastering Sales Skills Facebook group, I would love for you to join us over there. We do a ton of free trading, all about networking, connecting, selling, and serving. We’d love to have you also, I have a fantastic free resource for you and it’s called the uncensored sales system. It is my proven five step system from lead generation to closing and onboarding. It’s a really great PDF. So you can feel free to download that. And then of course, if you’re not following us yet on Instagram, we’d love to hang out with you. It’s @UncensoredSales. I’ll see you soon!

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