So You Want to Have a Conversation With a Strategist in Advertising:
5 Tips For Sliding Into My LinkedIn DMs
Lately I’ve had a lot more up-and-coming strategists reach out to me on LinkedIn hoping to have an introductory chat — about my experience as a strategist, about my role at 72andSunny, or about my move to Amsterdam. Chalk it up to becoming more experienced in my career or the fact that I’m a loudmouth on LinkedIn, but there’s a noticeable increase in cold messages desiring to pick my brain. If I’m being honest, I’m horribly bad at this type of thing. Partially because I don’t have the time. And partially because I just don’t care enough to make the time. I don’t say this to make me sound like an ass (though maybe I am), but to be transparent about the uphill battle you have to be willing to scale in order to get through to me. Not just me, but a lot of my peers in advertising, too.
On the one hand I applaud people for sending a cold message. It’s not my style nor was it the approach I used to advance in my career. So I have a certain amount of respect for people who can take that leap. But if you’re going to take that leap, I implore you to put some effort into it and do it right. Because so many of the messages I get don’t feel like they’ve been considered enough to be worth my time. Telling me you want to live in Amsterdam or that you like 72’s work are autopilot messages. ChatGPT could write them. So they get my autopilot response: I move on without responding. You’re playing a game of quantity. Mass messaging anyone that will listen. When you should be playing a game of quality.
After ever so slightly ranting about this with a near and dear colleague, she had some thoughtful advice: “Why don’t you help people understand what it is that you’re looking for when they reach out to you for a chat. Because when you’re just starting in your career, no one tells you about these things. And certainly no one speaks about them so openly as you, Armando.” So I came up with some advice. It’s not the be-all-end-all of reaching out. Nor should you feel like you have to check ALL these boxes. Rather, I am providing you with a variety of ways to increase the chances of getting that coffee or call. And while other people might be looking for different specifics, I’m willing to bet a lot of this advice is universal for any role in advertising or the creative industry at large.
1. Tell me something about yourself that the other 20 people in my inbox can’t say about themselves.
I’m not sure generic introductions ever got anyone anywhere. But in 2023 where we’ve basically been taught to cultivate our personal brand since the time we could hold a phone, I expect more than “I’m interested, here’s where I’ve worked, wanna chat?” If I’m going to put in the effort to have a conversation with you, I want you to put in the effort to sell the hell out of yourself. Because if you can’t do it for yourself, how can I trust you to do it for the brands you work on? Maybe you’re obsessed with K-Pop. Or your experience as the middle child of 7 siblings has made you an expert on familial relationships. Or you’re a classically trained flamenco guitarist. I don’t need you to write an essay. Just give me a taste of you that leaves me wanting more. Pro-tip: Look at my LinkedIn bio. It’s clearly and unabashedly me. Make sure your message to me is unabashedly you, too.
2. Tell me a point-of-view
We have a lot of things to say in the advertising industry, but I don’t think we have enough points-of-views. It’s the same reason why we have a lot of copy lines in our presentations, but very few ideas. Because landing on an idea or a point-of-view is hard. It takes some craft and experience. And it requires risk. I appreciate that a lot of people that reach out to me are early in their career and haven’t had the opportunity to develop their points of view as easily as they might like. So here’s some tips:
- A point-of-view picks a side or a position.
- It’s backed by research and data.
- It doesn’t just tell the what. It tells the how and the why, too.
- It should make people FEEL something — surprise, outrage, inspiration, curiosity.
Your POV could be on advertising (I don’t actually give a shit about advertising, and here’s why). It could be on culture (I’m obsessed with anti-aesthetic and what it says about the values of Gen Z). It could be about me (I think you’re arrogant, Armando, but I think arrogance makes for great work for this reason). Whatever your POV, just make sure it’s something you’re genuinely passionate about, and that your excitement shows through.
3. Tell me what you can do for me. Or my agency. Or the work. Be specific.
Conversations are a two-way street. I understand that you’re reaching out to me to make a connection. To help yourself grow. Maybe to score a job. But I have too many people requesting a conversation to say yes to everyone out of the goodness of my heart. I’d like to think I’m a good person, but I don’t consider myself particularly altruistic. You’ll give yourself an edge if you can tell me why having a conversation with you would benefit me. It doesn’t necessarily have to be me personally (though I’m sure I wouldn’t mind). For instance, instead of telling me that you love 72’s work, consider getting me excited about what you might do to make the work even stronger. Hell, you could even tell me you hate the work, but have an idea to help that. I’m not looking for generalizations or cliche responses. I’m looking for specific reasons that make connecting with you an asset.
4. If someone you know knows me, get them to reach out for you.
Studies show that you make moves in your career not by your most well known connections but by your weak connections. The connections that lie one or two rungs out. So if you know Billy who I worked with at my last agency and Billy recommended you reach out to me for a conversation, get Billy to make that first move for you. Just because you know someone I know doesn’t necessarily grab my attention on its own. But if someone can put in a good word for you, nine times out of ten, I’ll take the introduction. Really, I’m looking for you to demonstrate why a conversation with you is worth my time. The connection alone doesn’t do that. The recommendation from that connection does.
5. Ask me a question that stops me in my tracks
I lowkey dread when people reach out to me saying they would like to hear about how I’ve risen in my career. Or that they’re looking to make a move from the US to Amsterdam and want to hear about my experience. Because I’m getting tired of having the same conversation over and over again. My story is pretty straightforward: I worked with a recruiter who liked my work on Taco Bell at Deutsch and thought I would be a good fit at 72andSunny Amsterdam. After a 2-year dance, 72 brought me over. But I have so many other stories to tell. So I’d be far more interested if someone reached out to me and took the initiative to steer the conversation in an unexpected way by asking me a question or two that a) shows me how you think thoughtfully or critically and b) gets me excited to have a conversation I don’t always have. If your question leaves me going “wow, no one has ever asked me that before” you’re on the right track. Bonus points if you also have an opinion on the question being asked.
One final note on all this. Since the original writing of this piece I’ve had people express that this article makes me too intimidating. Especially for young strategists trying to figure out the industry. I want to clarify that I don’t write this to be intimidating. I write this to get you to think more critically about yourself and your work. Which I understand can be intimidating. But it’s also a prerequisite for 72 and my team. So if that self- reflection and self-understanding is intimidating…maybe that’s the thing you want to discuss with me. I have plenty of ways to help you figure it out.
