Tips for Navigating Outreach Conversations

A common outreach phrase to drop from your vocabulary (why it sucks and what to say instead): "I'd love to pick your brain". ❌ Why this sucks: As the recipient ↳ I'm not sure if you're prepared. ↳ I'm not sure what the agenda will be. ↳ I'm not sure it'll be a good use of my time. And if it's not a hell yes, it's usually a no. 💬 What to say instead: Get specific about what you want to learn from them. Share your core questions in the outreach. For example, "I'd love to learn more about X -- specifically your approach to Y and what you learned about Z while at Company." If you don't have specific questions, do your research. Ensure they're the best person to answer them (they will always be an expert on their own experience). ✅ Why this works: You're setting an agenda they can opt into or out of. They know you're prepared. You'll have a better, more informed conversation as a result. If they don't have the bandwidth to meet now -- you're more likely to get those questions answered async. You can begin a relationship that way. What other outreach phrases are a total turn off for you? P.S. Repost ♻️ to help job seekers have better conversations.

I keep hearing (seeing across my feed) about how... ❌ "Outbound is Broken" ❌ "Cold Calling is Dead" ❌ "SDRs don't work anymore" Our 3-8% meeting rate begs to differ. (And this is just through email. Our cold calls to meetings booked rate far exceeds this. 📈📈📈) As I look in my inbox, I know EXACTLY why there's a perception of outbound being broken. So-called sales leaders (VPs of Sales, Directors of Sales) spamming me with email templates that sound like: • "Would you be interested in?" • "Our company does [X]..." • "You're on my list of ideal customers to reach out to..." • "We work with [non relevant company]..." • "We have seen [Y] results from [another non-relevant company]..." • "Can we put some time on the calendar for...." So yes - If you're relying on email templates, automation, pre-written call scripts, and even AI to do your outreach for you - it is broken. - Here at LASSO, we follow 5 core principles for our outreach: 1️⃣ - Build relevance Why am I reaching out to you specifically? What drove me to seek to have a conversation with you? 2️⃣ - Be genuinely curious What am I trying to learn? About your business? About your processes? About your challenges? About your limitations? 3️⃣ - Seek to educate / inform What can we teach you? About your role? About what your peers are doing, or similar challenges that they've faced? About what's happening with the industry? About potential gaps that you may not know you have with your current processes? ("Everyone thought the horse was the fastest mode of transportation until the car was invented.") 4️⃣ - Make recommendations Similar to a doctor that has gained an understanding of your symptoms and come with an educated diagnosis of your illness, we seek to make recommendations (even if the answer isn't with us or our solution). 5️⃣ - Then, and ONLY then, ask for the meeting This should be the next logical step in the conversation. Only after we've accomplished 1-4 can we do this. 99% of the emails and calls I get skip to #5. If we are unable to book the meeting, that means we failed at one of the previous steps, and need to continue to strengthen those areas, before asking for the meeting again at a later date. - Had to get on my soapbox for a minute with all the posts about how outbound is broken. Outbound is alive and well. You just need to rise above the noise. - What step did I miss? What channel(s) have you successfully incorporated into your outreach? What results have you seen from it? ✌️ #outboundworks #outbound #sdr #salesdevelopment #coldcalling #makeoutboundgreatagain

Ask for advice, get a customer. Ask for a customer, get ghosted. Maybe that's overstating things a little bit (you should ask for the sale when a prospect is qualified), but it's my golden rule when it comes to outreach. You probably, like me, get 3-5 cold outreaches per day from people offering you leads, web design, SEO services, or similar services. I ignore all of them except for the persistent ones who get a one-word "no" from me. I have even trained my email system to mark them all as spam. Why? Because there's no trust. I don't know them. I know they're just trying to sell me something. The better way to approach people is to ask for their advice. "Hey John, I'm building an outreach agency for productized services. We've seen some success, but I don't feel like we've quite nailed the offering. Would you have 15 minutes to share your experience on a phone call?" I am more likely to say yes to that (though I probably won't because I'm busy). You'll find that once they've shared their experience, which helps you out, the law of reciprocity says that they'll then ask you about your experience and your offering. This gives you a chance to share and, if it's a fit, to talk about working together. Ask for advice, get a customer. Ask for a customer, get ghosted. Hope that helps.

Three hacks I recommend to my executive coaching clients before they go into a challenging conversation: 1️⃣ Ground in your values before you go into the conversation. Write down three words to answer this question: "How do I want to be perceived by the person I'm talking with today?" This is a fast way to check that your planned behavior aligns with your values. 2️⃣ Get curious. Google the "Ted Lasso get curious scene" if you need inspiration. Many times, conflict happens because two people simply aren't seeing each other. They get so stuck in their own perspective, fears, and hurt that they aren't able to see the other person's viewpoint. Go into the conversation with the intention of asking questions to better understand the person across from you. 3️⃣ Reflect the other person's perspective. Even if you disagree with someone, you can always make them feel heard. You can listen to them and "reflect" back what you hear them saying. Say: "Here's what I hear you saying. {Summarize in your own words.} Am I getting that right?" Reflecting allows us to help another person feel heard, and then you can present your own alternative opinion on the topic. We're always going to bump with other people inside our work lives and personal lives. We're all different humans with different perspectives, values, ideas, motivations, fears, joys, and needs. When we're different, we will naturally bump into others. Our goal isn't to prevent friction. Our goal is to make friction a useful tool for productive conversation. As long as we can see each other, we can move forward together. We can turn conflict into a trust-breaker into a trust-maker. I want to know from you, LinkedIn friends: How do you prepare for a challenging conversation with someone?

Let's cut to the chase. Reaching out to someone for their opinion on where they work? It's not just about asking questions. It's about connecting on a human level. Why is this important? Stick with me here. When you're considering a new job or company, you're looking for the inside scoop — what's really happening behind those walls. Your outreach is the golden ticket to that insight. Now, here's the kicker. When you reach out to someone for their opinion on their workplace, don't just ask, "How's it like working there?" Go deeper. Here's your play: Meticulous research. 1. Read recent news articles, press releases, and industry reports. They're your windows into the company's world. 2. Listen to earnings calls or industry forums where leaders speak candidly. You'll be surprised at the nuggets of information you can learn. Hi [Name], I've been following {Company's} journey and am genuinely impressed with [specific achievement or quality]. I want to get your personal insight on how [Company] is dealing with [specific challenge] and its impact on your day to day. What does your schedule look like next week for a 15-min chat? Eager to hear your story. Best [Your Name] Why does this work? It shows you've done your homework and signals respect for the person's time and their contribution to the company. Remember, it's not about bombarding someone with questions. It's about starting a dialogue that could lead to valuable insights and, who knows, maybe even opportunities. So, when you reach out, be curious, be respectful, and be genuine. - - - - - - - - - Thanks to Dylan Parry (a future workforce leader) for inspiring this post.

Saying "this might hurt" is not the best way to soften the blow of a difficult conversation. 📌 The phrase "this might hurt" can be confusing and misleading. It can make the other person feel defensive or anxious, and it can make it difficult for them to hear what you have to say. Instead of saying, "This might hurt," it is better to be direct and honest about what you need to say. State the issue clearly and concisely, and explain how it is impacting you. For example, instead of saying, "This might hurt, but I need to talk to you about your work performance," you could say, "I'm concerned about your recent work performance. It's not meeting my expectations, and it is impacting our team." It is also essential to be open to the other person's perspective. Be willing to listen to their concerns and try to understand their point of view. This will help you to have a more productive conversation. Here are some ideas to help you deliver difficult feedback: Set aside time for the conversation. Don't try to have a difficult conversation when you are rushed, stressed, or hungry. Instead, schedule a time to talk when you can both be focused and present. Choose a private location. Have the conversation in a place where you will not be interrupted and where you feel comfortable speaking freely. Focus on the behavior, not the person. Avoid personal attacks or generalizations. Instead, focus on the specific behavior that is concerning you. Be specific and provide examples. Don't just say that the person is "doing something wrong." Instead, give specific examples of the behavior that is problematic, as you want to give them a chance to find a solution. Be open to feedback, even if you think your needs and expectations are precise. It is possible that your message was misinterpreted or that the other person has a different perspective. Be willing to concede their point of view and be open to hearing their feedback. They may have some valid points that you did not consider. If you realize that you made a mistake, apologize. Remember, difficult conversations aim not to hurt the other person. It is to communicate your needs and expectations in a way that will lead to an improved outcome. By being direct and honest and by being open to the other person's perspective, you can have more productive and effective difficult conversations. 🧙♂️ Imagine that you have a magic wand that can make one thing about difficult conversations easier. What would it be? #management #humanresources #personaldevelopment #partnerships

You’re sending the wrong messages. Let me show you. —— “Let’s jump on a call” vs. “Hey Josh! I’ve been following Dragos for a while and am a huge fan of the work your Intel team does (congrats on Pipedream!). I have solid experience in CTI and I’m interested in exploring ICS security. I’d love to learn if I could be a match in the future. Would you be open to a 15 minute intro call? If it’s too much to ask I understand.” “Can you review my resume?” vs. “Hey Josh! I imagine you’re plenty busy reviewing applications for [role]. I recently applied because I have direct experience with [x]. This seems like an ideal fit but I wanted to ask for your opinion. Do you see a match?” “Can you be my mentor?” vs. “Hey Josh. I hope you're doing well! I’ve been researching people who made the jump from healthcare into cyber. Your transition from [company] to [company] stood out to me. It's a big ask coming from a stranger but I’d love to learn more about your journey. Would you be willing to share one tip that helped you get where you are?” —— These examples show the type of effort you should put into your outreach. Always be yourself. Always be genuine. You’ll get ignored some but stay consistent and you’ll win. This stuff takes time.

Most SDRs, AEs, and CSMs are trying to get attention and break through the noise of emails, InMails, and cold calls. Unfortunately, many are resorting to some cheesy tactics -- bait and switch email subjects, gifs, etc. Sure, your email might get opened, and they might even chuckle occasionally -- but the reaction you’ll likely get most of the time will be an eye-roll followed by a delete or hang-up. It’s time to stop acting like a cheesy GTM professional and act like a modern GTM professional. Here are some tips: 1. Write as you speak. Be clear, not clever. 🗣 2. Avoid using filler words like "revolutionary", "best in class", "innovation", etc. in your emails. 🙅♂️ 3. Use simple language and usually, less formal is preferred. 🙌 4. Avoid buzzwords and instead use simple words. 🚫 5. Re-read your emails a few times out loud before sending them. 🤓 6. Mimic the communication style of your audience and be flexible with different personalities. 🔄 7. Observe how the executives in your company communicate and try to emulate that. 👀 8. Get to the point and keep it short. Busy professionals appreciate just jumping right in. ⏱ 9. Build rapport through natural engagement over LinkedIn, Cold calls, etc. 💬 10. The best way to build rapport is to provide value first without any ask in return. 🎁 11. Finally, earn the right before you ask for the time. ⌚️ I'm sure – you all know these basic tips. 🤷♂️ But I hope this helps as a gentle reminder. 😇⏰ #coldemail #coldoutreach #prospecting

Managing Difficult Conversations Original Content Creator: Harry Karydes (Give him a follow) --------------- Do you find yourself avoiding confrontation at all costs? Here's a better way: 🟢 Step 1: Setting the Stage ↳ Prepare Mindfully: Prioritize introspection to align your intentions and desired outcomes for the conversation. ↳ Cultivate Empathy: Step into the shoes of the other party to grasp their perspective and foster genuine understanding. 🟢 Step 2: Navigate Emotions ↳ Maintain Composure: Stay poised and composed, refraining from impulsive reactions triggered by emotions. ↳ Validate Feelings: Acknowledge and validate the emotions expressed by both people, creating an atmosphere conducive to constructive dialogue. 🟢 Step 3: Active Listening ↳ Listen Intently: Devote your full attention to comprehending the speaker's message without interruptions or distractions. ↳ Seek Clarification: Pose clarifying questions to ensure mutual understanding and prevent misunderstandings. 🟢 Step 4: Choose Your Words Wisely ↳ Use "I" Statements: Express your thoughts and feelings using first-person language to avoid accusatory tones. ↳ Present Solutions Positively: Frame suggestions in a constructive manner, fostering collaboration and mutual respect. 🟢 Step 5: Finding Common Ground ↳ Identify Shared Goals: Explore common objectives or values to establish a foundation for agreement. ↳ Highlight Mutual Benefits: Emphasize the advantages of resolving the issue for both parties involved. 🟢 Step 6: Manage Expectations ↳ Be Realistic: Set attainable expectations for the conversation's outcomes, considering all perspectives. ↳ Clarify Responsibilities: Clearly outline the next steps and responsibilities to uphold accountability and progress. 🟢 Step 7: Focus on Solutions ↳ Adopt a Problem-Solving Mindset: Shift the conversation's focus from assigning blame to identifying actionable solutions. ↳ Foster Collaborative Brainstorming: Encourage input from all parties to cultivate innovative approaches to problem-solving. 🟢 Step 8: Follow Up ↳ Reflect and Improve: Evaluate the conversation's effectiveness, identifying areas for refinement and growth. ↳ Schedule Follow-Up: Plan subsequent discussions to monitor progress, address any remaining issues, and ensure the implementation of agreed-upon solutions. 📌 PS...Remember, the ability to navigate difficult conversations is a skill that grows with practice and patience. ________________ Original Content Creator: Harry Karydes (Give him a follow)