Sales Managers, we all know the drill: your team is working hard, sending out messages, but are they cutting through the noise? Inboxes are overflowing, LinkedIn DMs are ignored, and generic pitches are dead on arrival.

The secret weapon? Hyper-personalization. ✨

It’s not about mentioning their company name. It’s about demonstrating genuine insight and empathy, making your first touch point feel less like a sales pitch and more like a relevant, insightful conversation starter.

As an Outreach Personalization Trainer, I consistently see teams transform their reply rates (and ultimately, their pipeline) by shifting from “What can I sell?” to “What can I understand or offer them?”

This post isn’t just about theory; it’s a practical toolkit. I’ve compiled a collection of 15-20 prompt templates your team can use with their AI tools (like ChatGPT, Claude, etc.) or as a mental framework to craft irresistible first messages. These prompts are designed to be relevant, non-pitchy, and conversation-starting.

The “Secret Sauce” for Personalized Outreach:

Before we dive into the prompts, remember these foundational principles:

1. Deep Research: The best prompts rely on solid research. Train your team to look for:
   • Recent company news (funding, product launch, new hires, earnings reports)
   • LinkedIn activity (posts, comments, articles)
   • Industry trends impacting their specific role/company
   • Mutual connections or shared experiences
   • Their company’s strategic priorities or challenges (often found on their website, investor calls, or news)
2. Focus on THEM: Always ask: “Why would they care about this message right now?”
3. No Immediate Ask: The goal of the first message is not to book a meeting. It’s to earn a reply, build rapport, and open a dialogue.

The Personalized Outreach Prompt Collection 🛠️

Here are prompt templates, categorized by the core approach they embody, with examples for LinkedIn, Email, and DMs. Encourage your team to choose the style that best fits the insight they’ve found.

Group 1: Value-Led & Insightful (Sharing a Relevant Observation/Resource)

These prompts leverage specific observations about their business or industry to offer a relevant thought, question, or resource without direct pitching.

1. Prompt: “Based on [recent company announcement/news], share an observation about a related challenge their peers face, and ask how they’re navigating it.”
   • LinkedIn Example: “Hi [Name], I saw the news about [Company]’s recent [expansion into X market]. Many leaders I speak with in that space are grappling with [specific challenge, e.g., integrating new tech stacks post-acquisition]. How are you finding that transition?”
   • Email Example: Subject: Thought on [Their Company] & [Market Trend] “Hi [Name], I was reading about [Company]’s focus on [new initiative, e.g., sustainability]. It reminded me of a recent article on [related topic] that highlighted [specific insight]. Given your role, how are you approaching [related challenge/opportunity]?”
   • DM Example: “Noticed [Company] announced
     . That’s exciting! I’m curious if you’re seeing [related industry shift] impact that area as expected?”
2. Prompt: “Acknowledge a specific point they made in a public post/comment and add a supporting or curious thought.”
   • LinkedIn Example: “Hi [Name], really appreciated your recent post about [specific topic] – your point on [their specific argument] particularly resonated. We’ve seen similar trends with [briefly mention another company/situation]. What prompted you to share that perspective?”
   • Email Example: Subject: Re: Your Post on [Topic] “Hi [Name], I came across your LinkedIn post on [topic] and found your take on [specific aspect] incredibly insightful. I’m curious, have you considered how [related factor] might influence that in the long term?”
   • DM Example: “Loved your recent comment on [article/post] about [topic]. Your perspective on [specific point] was spot-on. What’s your biggest takeaway from that discussion?”
3. Prompt: “Reference a relevant industry report or trend and ask for their perspective on its impact on their role/company.”
   • LinkedIn Example: “Hi [Name], I just read the [Name of Report] report on [Industry/Topic], which highlighted [key finding]. Given your work at [Company], how do you see that impacting [specific area, e.g., customer acquisition strategies] in the next 12 months?”
   • Email Example: Subject: Quick thought on [Industry Trend] “Hi [Name], I was reviewing some data on [industry trend] and it seems [specific implication] is becoming a major focus. As [their role], are you seeing similar pressures/opportunities at [Company]?”
   • DM Example: “Saw that new report on [trend]. Definitely makes you think about [area relevant to them]. Is that something you’re seeing play out at [Company]?”
4. Prompt: “Point out a specific common challenge for their role/industry and offer a thought-provoking question about its solution or impact.”
   • LinkedIn Example: “Hi [Name], I often hear from Heads of Sales like yourself about the struggle to [common challenge, e.g., accurately forecast pipeline in volatile markets]. How has [Company] been approaching that particular hurdle recently?”
   • Email Example: Subject: A thought on [Their Role’s Challenge] “Hi [Name], In your role as a [job title], one of the most persistent challenges I observe is [specific pain point, e.g., scaling personalization without overwhelming the team]. What’s one unexpected lesson you’ve learned while tackling this at [Company]?”
   • DM Example: “For [their role], [common challenge] is always tough. What’s one strategy that’s worked well for you at [Company]?”

Group 2: Curiosity-Led & Engagement-Focused (Asking a Thoughtful Question) 🧐

These prompts aim to open a dialogue by asking a genuine question based on their public profile, company direction, or shared interests.

5. Prompt: “Reference a specific career move or longevity at their current company and ask about their experience or key takeaway.”
   • LinkedIn Example: “Hi [Name], I noticed you’ve been at [Company] for [X years] and have seen them grow through [key phase]. What’s been the most impactful change or learning you’ve experienced during that time?”
   • Email Example: Subject: Your journey at [Company] “Hi [Name], Your career path from [Previous Role] to [Current Role] at [Company] is really impressive. I’m curious, what inspired that shift and what’s been your biggest surprise or challenge along the way?”
   • DM Example: “Saw you moved from [Old Company] to [Current Company] recently. What’s been the biggest change you’ve noticed in [relevant area, e.g., team culture, strategy]?”
6. Prompt: “Point out a specific goal or mission statement on their company website/LinkedIn and ask how they’re tackling it from their role’s perspective.”
   • LinkedIn Example: “Hi [Name], I was browsing [Company]’s website and saw your mission to [specific mission/goal]. From your seat as [their role], what’s the biggest internal hurdle you’re working to overcome to achieve that?”
   • Email Example: Subject: Question about [Company’s Mission] “Hi [Name], I’m interested in how companies translate their overarching missions into daily operations. [Company]’s goal to [mission statement] is compelling. In your role, how do you ensure [specific aspect of your work] contributes directly to that?”
   • DM Example: “[Company]’s mission to [mission] is awesome. How are you contributing to that from the [their role] side?”
7. Prompt: “Reference a shared connection and ask a low-pressure question about their interaction or the connection itself.”
   • LinkedIn Example: “Hi [Name], I noticed we’re both connected with [Shared Connection]. How do you know [Shared Connection]? They’re fantastic!”
   • Email Example: Subject: Mutual Connection: [Shared Connection’s Name] “Hi [Name], I hope you don’t mind the outreach. I saw that we’re both connected with [Shared Connection’s Name] on LinkedIn. They’ve always spoken highly of you. How did you two originally meet/work together?”
   • DM Example: “Hey, noticed we’re both connected to [Shared Connection]. Small world! How do you know them?”
8. Prompt: “Acknowledge a piece of content they created (article, video, podcast) and ask a follow-up question that shows you truly engaged with it.”
   • LinkedIn Example: “Hi [Name], just finished watching your [webinar/video] on [topic]. Your point about [specific detail] really stuck with me. What was the most challenging part of implementing that strategy?”
   • Email Example: Subject: Your [Content Type] on [Topic] “Hi [Name], I was impressed by your recent [article/podcast episode] on [topic]. I particularly enjoyed your take on [specific point]. What do you think is the biggest misconception people have about [that topic]?”
   • DM Example: “Loved your article on [topic]! Your insight into [specific detail] was great. What’s your next big focus in that area?”
9. Prompt: “Observe a unique aspect of their company culture (from their careers page, social media) and ask for their perspective.”
   • LinkedIn Example: “Hi [Name], I was looking at [Company]’s careers page and saw the emphasis on [specific cultural value, e.g., ‘radical transparency’]. As someone on the ground, how does that play out in day-to-day decision-making for your team?”
   • Email Example: Subject: Your Culture at [Company] “Hi [Name], Your company’s commitment to [unique cultural aspect, e.g., ‘continuous learning’] really stood out to me. I’m curious, how does that translate into tangible benefits for your team members?”
   • DM Example: “Hey, your company culture around [value] sounds awesome. What’s your favorite part about it?”

Group 3: Empathy-Led & Problem-Aware (Acknowledging Common Pains) 🤝

These prompts demonstrate an understanding of common challenges faced by their role or industry, inviting them to share their experiences.

10. Prompt: “Acknowledge a recent industry challenge or shift and ask how it’s impacting their specific team or strategy.”
    • LinkedIn Example: “Hi [Name], With the recent shifts in [specific industry trend, e.g., ‘remote work regulations’], I imagine sales leaders like yourself are rethinking [related strategy, e.g., ‘field sales effectiveness’]. How is [Company] adapting its approach?”
    • Email Example: Subject: A thought on [Industry Shift] “Hi [Name], The recent [economic downturn/supply chain issues] have put pressure on many businesses. In your role leading [their department], what’s one key area where you’re feeling that impact most directly?”
    • DM Example: “These [economic/industry changes] are tough. As a [their role], what’s the biggest challenge you’re seeing emerge for your team?”
11. Prompt: “Express understanding of a common difficulty for their role and open a door for them to share their experience.”
    • LinkedIn Example: “Hi [Name], I can only imagine the complexities of managing [specific challenge for their role, e.g., ‘multiple disconnected data sources’] in a growing company like [Company]. Is that something that often keeps you up at night?”
    • Email Example: Subject: Thinking about [Their Role]’s Challenges “Hi [Name], For many [their role/title] I speak with, balancing [common challenge 1] with [common challenge 2] is a constant juggle. How are you navigating that delicate balance at [Company]?”
    • DM Example: “Hey, I know [their role] often struggles with [specific challenge]. How are you tackling that at [Company]?”
12. Prompt: “Reference a publicly known challenge their company might be facing (e.g., rapid growth pains, competition) and ask about their specific approach.”
    • LinkedIn Example: “Hi [Name], [Company]’s growth has been incredible! With that rapid scaling often comes the challenge of [specific issue, e.g., ‘maintaining quality control at scale’]. How has your team been able to proactively address that?”
    • Email Example: Subject: Question about [Company Name] & [Challenge] “Hi [Name], I’ve been following [Company]’s journey, and your market position in [niche] is impressive. In a competitive landscape like yours, keeping [specific area, e.g., ‘customer churn low’] can be tough. What’s your strategy for fostering long-term loyalty?”
    • DM Example: “Congrats on the growth at [Company]! With that, I imagine [challenge, e.g., ‘onboarding new talent quickly’] can be tough. Any tips you’d share on that front?”
13. Prompt: “Acknowledge the difficulty of a specific task or responsibility often associated with their job title and ask about their strategy.”
    • LinkedIn Example: “Hi [Name], As a [job title], you’re likely responsible for [complex task, e.g., ‘driving alignment between sales and marketing teams’]. What’s been your most successful approach to ensuring that collaboration is seamless at [Company]?”
    • Email Example: Subject: A thought on [Their Job Responsibility] “Hi [Name], I understand your role as [job title] often involves navigating the complexities of [difficult responsibility, e.g., ‘optimizing sales tech stack ROI’]. How do you approach evaluating new tools and ensuring adoption across your team?”
    • DM Example: “Hey, for [their role], [complex task] can be a beast. How do you approach [that task] at [Company]?”
14. Prompt: “Reference a recent external event (economic, social, technological) and inquire about its specific impact on their sector/role.”
    • LinkedIn Example: “Hi [Name], Given the current economic climate, many leaders are re-evaluating their [departmental budget/strategy]. How has that broadly impacted your team’s priorities at [Company]?”
    • Email Example: Subject: Impact of [External Event] on [Their Industry] “Hi [Name], With the recent advancements in [specific technology, e.g., ‘AI in customer service’], I imagine its potential impact on [their industry/role] is a hot topic. What’s your perspective on how it will reshape [specific function]?”
    • DM Example: “That [recent tech breakthrough/policy change] is big. How do you think it’ll affect [their department/industry] at [Company]?”

How to Use These Prompts Effectively with Your Team:

1. Train on Research First: These prompts are only as good as the research behind them. Dedicate time to teaching your team where to look and what to look for.
2. Encourage Specificity: Replace [ ] with concrete details. The more specific, the more personal.
3. Focus on the “Why”: Why did you choose that prompt for that person? What insight are you trying to share or uncover?
4. Embrace Iteration: Not every prompt will land. Encourage your team to experiment, track reply rates by prompt type, and share their successes.
5. Quality Over Quantity: It’s better to send 5 truly personalized messages than 50 generic ones. This approach is about starting better conversations, not just more conversations.
6. Human Review: Even with AI, every message should be reviewed by a human for tone, accuracy, and genuine intent. Make sure it sounds like them.

By equipping your Sales Managers with this prompt collection and the mindset to use them, you’re not just improving outreach; you’re cultivating a team of insightful, empathetic communicators who build relationships before they ever try to sell.

Which of these prompts are you excited to try first with your team? Share your thoughts below! 👇