Katrina Widener Coaching

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Selling Yourself in Instagram DMs


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When it comes to making an impact on Instagram, it's time to add DMs to your strategy. Listen in while business and strategy coach Jamar Diggs shares how to make valuable connections and raise your bottom line through Instagram DMs.

Jamar Diggs is a business + marketing coach for coaches looking to attract high-paying clients. Together you’ll uncover missed revenue opportunities, create signature offers, and make you into a client magnet!

Website // Instagram // YouTube


The episode:

Katrina Widener: [00:00:00] Hi everyone. This is Katrina. Today I have Jamar Diggs here. He's a business and marketing coach for coaches who are looking to attract high end paying clients. Jamar was one of the guest experts for group coaching just in December. So thank you so much, Jamar, for being on the podcast. I'm so excited to have you here. 

Jamar Diggs: [00:00:22] Thank you so much for having me. I'm excited to be here. 

Katrina Widener: [00:00:24] So today we're going to be talking a little bit about social media and how to really optimize your social media so you can be selling in the DMS or attracting your dream clients and all of thatkind of stuff. But first I wanted to start out by just letting you tell us a little bit more about who you are and how you got started doing what you do. 

Jamar Diggs: [00:00:42] Yeah.  Coaching has been something that has been consistent in my path. So I first started in like just social media and in social media managing, I am a corporate escapee, a corporate dropout, however way you want to say it. But throughout that time, I've done my business on the side. And I first started as a social media manager where I was like teaching all people from all over the US like basically just getting them clients, giving them leads all through social media.

And then in 2017, I got burnt out. I was like, no, I can't do that. Social media management is not for me. In 2017, I finally decided to do coaching because I love teaching them the reasons behind why I have them do certain things. I love teaching and I loved it when my clients would have these light bulb moments. And March of 2020 leaving my full-time job and doing my business full time. I do coaching where I help coaches do the exact same thing. 

Katrina Widener: [00:01:47] That's really awesome. And it's something that I think that people very often times have somewhat a similar story where they're like, I tried this thing and it didn't work. And then I tried this thing and it didn't work. I know that for me, myself yeah, I'm also a corporate escapee. So it totally makes sense to be like, this is something that you tried. And you're like, maybe this isn't 100% aligned with me that this thing is, and that doing social media management helped you get there, which is really cool. And also, again, congratulations on leaving your corporate job in March. That was awesome. 

Jamar Diggs: [00:02:17] Thank you. I'm just so excited about that. I. It's so crazy every month that goes by, I'm like, Oh my gosh, I'm really doing this. This is amazing. People are willing to work with me oh, thank God. This keeps on getting better and better.

Katrina Widener: [00:02:35] So if we're talking about. I know that you're saying that you help a lot of other coaches. So if we're talking about something like selling in the DMS, what are things that you recommend that someone utilize or maybe they don't utilize? What are like your top tips? Yeah. 

Jamar Diggs: [00:02:52] So when it comes to selling in the DMS, I think that people like to think it as being this, like the sexy thing, that's just so cool and everyone is doing it but no one seem to know exactly how the money is being made. And it really comes down to selling in the DMS, like your DM selling is an accessory to your overall social media strategy.  Because you're doing a lot of selling in the DMS, you don't have to really post every single day on Instagram or on social media, you just really have to be present and be saying the right things.

And so I think people forget that you still have to be the authority in that space. You still have to give tips, give advice, give polarizing content that calls out people's pain points. You still have to talk about those things because when you make this connection with someone, they're going to go to your Instagram and they're going to make this judgment call on if you are exactly who you are or if you're just full of crap. That's the filter that everyone runs by. And so that's one thing that I think we all forget about whenever we're thinking about selling in the DMS.

We think that it's just strictly, just DM, like blowing people up. And that's not it. When you are posting content that is relating to your ideal client, that is really hitting those those pain points so hard that they come to you in a sort of way. So the conversation becomes a lot less sales pitchy and more building connection, building relationships, like learning more about them.

Katrina Widener: [00:04:22] That's really something that I think is super important. Also, I love the fact that you mentioned, you have to be consistent in your posts and in your DMS, or also on your stories or in your DMS. I don't know if you see this often, but I often see like with my clients, especially I work with a lot of wedding professionals in the wedding industry.

There's this idea that you have to be like "Oh, the first page of the next chapter of your life, or like all of this romantic flowery language. And I always tell people, if you don't talk that way, don't talk that way on social media. Don't talk that way in website copywriting, whatever it is, because then when someone comes and meets you in person, they're going to be like, who are you?

Jamar Diggs: [00:05:03] Yes. So here's the thing that I hate. I hate that we like to romanticize what we do for people. We like to say, I help you live the best life that you can through empowerment. And I don't know, mystical things. Whatever. No one knows what that means. Help me make this make sense.

No one knows that. And so look at a bio and the bio is some fluffy thing and then, Oh, by the way, you have a dog and you're a mom, that's great. But how is this helping the ideal client, right? How does this, how are they going to run this filter of if you're the real deal or if they should just move along.

Katrina Widener: [00:05:39] Totally. It's one of those things like your elevator speech. I'm always like, cover who you are, what you do, who you help, and what the result is, because if you're just like, "Hi, I'm Katrina, I'm an entrepreneur coach they'll be like, cool. But if I'm like, "Hi, I'm Katrina. I help entrepreneurs feel really excited and lit up by their businesses." Someone's going to be like, "Oh, I want that." 

Jamar Diggs: [00:06:02] Yes, exactly. And that's, what's so important. Okay, I'm gonna get a little corny here. So think of  Instagram, your profile as the Zillow listing of social media. And if you want people to come to your open house, honey, you need to actually make it make sense, make your listing make sense. Totally. And the open house is the DMS and and the comments and stuff. 

Katrina Widener: [00:06:26] I love that. I've never thought about it that way, but it is one of those things where I'm like people I always tell people about the profile, this is where someone's going to land.

They're going to want to immediately get a vibe from who you are and whether or not they want to get in your realm. And so if you're not being true to yourself there, then it's not going to work out. Yeah when you get to the DMS, when you start actually having those conversations to try to sell to them. And I know that you and I are also really big on alignment. You're someone who's just as much of an alignment nerd as I am. 

Jamar Diggs: [00:06:58] Oh yes. Yes I am so for it. It has to all be aligned and I think I think one more thing, if you don't mind me adding this, is no one really knows exactly what to say or they don't know what they should be doing. Like when I say selling in the DMS, they actually think that I'm talking about services and offerings, right off the bat and that's not exactly what's happening. And who am I talking to? Like, Who are these people? How am I finding these people? 

And I want to offer this one piece of advice. One of many, I guess what's probably going to happen, but utilize the collections feature inside Instagram. I love using the collections feature to save posts. But you can also save your ideal client matches, people who fit the mode of who you want to work with.

So I keep I keep three main collections in my Instagram account. So I have my ideal client matches. I have my hero accounts, which are people who have the following that I want, so maybe they're not in the same field as me, but our ideal clients somehow match up together.

So this may be like a financial coach or something who works with other coaches. Maybe they're my hero account maybe we don't have the same industry, but we have the same clients. Then I may even put that financial coach into my ideal client collection as well.

And then the third collection that I use is my industry peers. So people who are just like me doing the same thing out in the streets making sure that I am connecting with them as well. So these are the three categories I put people in to make sure that I am continuously making connections building relationships  with these people every single day.

Katrina Widener: [00:08:43] That's something too that I know that you mentioned when you came and spoke for group coaching, which I think everybody was like, "Mind blown. I've never thought of using collections that way", because when you get really clear on who you want to serve, and you actually like. Yes. There are ideal client avatars.This is something that like I preach. I know a lot of people are like, Hey, know your client. And really it does make everything so much easier. But when you really actually are like, here's a whole collection of the exact person I'm speaking to, what they're talking about, what they look like, what they are interested in, all of that kind of stuff. It makes it so much easier for you to then cater your content and your conversations and all of that kind of stuff, which is really the whole trick to marketing. 

Jamar Diggs: [00:09:31] Yes. And it eliminates the BS that we tell ourselves that our ideal clients are not out there. I cannot tell you how many clients I've had and they were like, huh? I'm engaging, but I don't know what's happening. But what's happening is that their engagement is them commenting underneath cat memes or like these odd, these odd really things. Like I ask how much time are you spending on Instagram each day engaging? And they're like I'm on there doing things and they're talking to like their home girl. And yes, maybe they are talking to like people who they would love to work with, but their like industry peers, it's not gonna work the same way. And so these collections allow you to separate your people into these three categories. And now you cannot say that when you are spending your hour of engagement each day, that you don't know where to go. You don't have to be lost in the feed by a random cat meme or random Reel, like some TikTok dance, take your butt to your saved section and start engaging with these people every day. 

Katrina Widener: [00:10:36] That's something too that I think that when people think about engaging, which I know that like, when you were saying selling in the DMS, it's not like going and popping into 50 people's DMS with just a straight sales pitch. It's like actually having these conversations. And when you have identified the fact that you have actual ideal clients out there and you know exactly who they are, then it does make it easier to just go out and say "Hey, how are you doing?" Or what I always love to do is reply to stories. Because I can, I feel like people are like, "Oh my gosh, yes, me too." Or I know when people do that with me, I'll be like, "Ooh, who's this person who's commenting on my cat?" Or "Who's this person who's responding to me dancing in my kitchen?" and it does, it seems to build more of a genuine relationship than as opposed to being like, three clapping emojis in the comment. And I'm like, okay, bye. 

Jamar Diggs: [00:11:24] No, we have to learn to go beyond the three clapping emojis, three heart emojis, the yes girl, or the love that! Like those we've seen them all, right? Those are played out. We have to do better. And you're so right. So what happens is after we comment on these peoples' accounts, then I also say go into the stories. And you have to literally watch their story and give a thoughtful response back. And I just received this little update today that Instagram is testing out a new way for engaging with Instagram stories. So they're switching how reactions are done.

So now you don't get a DM whenever someone sends a reaction, which I love.  And the reason why I love it is because that was a cheap trick to get into someone's DMS. And it really didn't, it really didn't do anything. Instead we need to start trying. Social media is not easy. You have to try. And so instead of doing the little fire emoji on a story or the little heart eyes thing or the celebration thing, truly respond back to the story an actual reply that's a complete thought and then that's going to elicit a response that you're going to be happy to receive. That's how the connections are made. 

And I also want to just make sure that I hit this part. We talked about how do we collect these people, where we put them, and we talked about how we do it.  We are engaging in the comments and we're also responding really well inside the story. And so now we're like, okay, so where does the selling happen? What is happening in this wild West of this DM land?

 What you're going to see is you're going to see a lot of rando conversations. You're gonna see a lot of getting to know this person, maybe you're liking their dog. Maybe you also do CrossFit. Maybe you also have a crazy toddler at home that ya'll are like relating to.

But then you're also going to find these comments from the same person on your reels. On your other posts, that are giving expert content, and how they relate to you. And then what happens is when you are selling something or when you're launching something, they're going to ask you more information about it, right?

That's one way that happens, or after you make that extra piece of content, maybe they start saying, "Oh my gosh, Jamar, I actually need to talk to you about this actual piece". And then you can take that right over into the DM and learn more about what they're talking about and you can do a sales call inside the DMS. You like learn more about what they're talking about. I learn more about their issues, relate to their issues. Validate it. Say that, yeah, that sucks that's happening. And if you have something to offer, then offer it. They're there. Like you've already loved them up. They're like, yo girl, I have this issue. What is the solution like, this is where it's time for you to talk a little bit more about what you have to offer.

And and after that, bam, that's what it is. That's how it happens. You're still, it's like a little cycle where you are still engaging, but then when it's time for you to sell something or when they are there, they are ready. Or when you know a little bit more about this person, maybe you can invite them into an offer as well. But that won't happen unless you'd know more about that person. 

Katrina Widener: [00:14:47] 100%. And it's something too that I think oftentimes when people think about those kinds of conversations, they're a little intimidated or they aren't exactly sure how to bring that kind of stuff up. And I'm just like, what would you say to me? How would you have a genuine conversation with someone when you're not trying to just sell to them at the end? Because that's the actual trick is not to just be like I'm only talking to you because I want to sell it to you. But actually being like, I want to talk to you because I'm connecting with you on a human level, or I'm trying to actually understand things about you, actually understand what your pain points are.

And I think that goes hand in hand too with then being able to say, Oh, I can't help you, but I'm not going to drop you or stop talking to you completely. If you want to find your dream clients, you also have to be comfortable saying no to the people who are not your dream client.

Jamar Diggs: [00:15:37] Yeah. Oh my gosh. Yes. I've had to do that so many times where I will get a DM from someone who wants to, this is I and no offense if this person's listening, but I've had someone asked me, can I help them get their album out there or get more people to buy their album. And I'm like, ah, I am not in the business of that. I have a strict, like ideal client. I have a strict framework that I can help people through. And applying it to your music business is just not what it is. Or even artists, like I can help people sell their artwork. That's totally within my wheelhouse, but does it bring me joy? Does it align well with me? No, it does not. And so unfortunately I cannot take that person on. And what I do instead is if I know a coach that specializes in that, I totally send them that way. I still help. And we still Kiki in the DMS every now and again. But just being okay with saying no, and detaching yourself from the outcome is so important. 

Katrina Widener: [00:16:37] Unfortunately, we're out of time now, which is so sad cause I could just talk about all of this stuff forever and talk to you forever. But last question is just, is there any one big tip that you would give someone or what's the first step that you would recommend they take?

Jamar Diggs: [00:16:54] Lead with empathy. I think that's the really good first step. Take all of the things that we talked about today and when you are thinking about speaking, like what, like actually writing down what you're trying to say, lead with empathy. What would you like to hear from someone in the comments or in the DMs, right.

And just don't get tied to the outcome, detach yourself from the outcome and just have fun, make connections, meet new people. 

Katrina Widener: [00:17:22] That's I think one of the best pieces of advice too, because if you lead with empathy, then you can start that genuine connection off on the right foot. So thank you so much for coming on here. I love this conversation. So how can, Oh, go ahead.

Jamar Diggs: [00:17:40] I just want to say thank you so much for having me I'm so happy to be on this podcast, talking about selling into DMS. It's something that we all have to learn sometime.

Katrina Widener: [00:17:51] How can everyone find you afterwards? If they're like, Ooh, I really want to get into Jamar's world.

Jamar Diggs: [00:17:56] Oh my gosh. Follow me on Instagram. My Instagram stories are freaking lit. Okay, honey. And that's @jamardiggs. J-A-M-A-R D-I-G-G-S.


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