I’ve always believed that a strong professional network is one of the most valuable assets you can have in your career. But let’s be honest: networking can be daunting. Crafting the perfect connection request, preparing for an important conversation, or just finding the right way to stay in touch often feels awkward. What do you say? How do you stand out without being pushy?
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This is where I’ve started using my AI assistant as a personal networking coach. By using carefully crafted, targeted prompts, I can leverage tools like ChatGPT to generate personalized messages, prepare insightful questions, and nurture my professional relationships with confidence. It handles the heavy lifting of drafting, leaving me to focus on the genuine human connection.
In this playbook, I’ll share some of the most effective prompts I’ve developed. These are practical examples you can adapt to build your own professional circle, whether you’re reaching out to a stranger on LinkedIn, preparing for an interview, or reconnecting with a former colleague.
🔗 Prompt 1: The Personalized Connection Request
The days of sending generic ‘I’d like to connect’ requests on LinkedIn are over. To make a real impression, you need to show you’ve done your research. I use my AI assistant to create a concise and genuine request that highlights a specific reason for connecting. This dramatically increases my acceptance rate.
Here is the prompt I use: ‘Draft a personalized LinkedIn connection request for [Name] at [Company]. I’m a [Your Profession] with a background in [Your Expertise], and I’d like to connect because [Specific Reason, e.g., ‘I admire their work on the recent X campaign’ or ‘I saw their post about Y and found it insightful’]. Keep the message concise and professional.’
The AI takes these details and produces a polished draft that I can quickly adapt. It shows the other person that I value their work and have a legitimate reason for wanting to be in their network. This simple step transforms a cold outreach into a warm introduction. This kind of specialized instruction is similar to how we’ll interact with future technologies, like the Halo AI Glasses, which respond to natural language.
🎙️ Prompt 2: Preparing for an Informational Interview
An informational interview is a golden opportunity to learn from someone in your field, but asking generic questions won’t get you very far. I use AI to help me generate thoughtful questions that demonstrate my interest and make the conversation more memorable. This preparation shows respect for the other person’s time.
Here is the prompt for this scenario: ‘I have an informational interview with [Name], a [Job Title] at [Company]. Their background includes [Key Details, e.g., ‘launching a new software product’]. Generate 5 thoughtful and specific questions I can ask to learn more about their career path, the industry, and their company.’
The AI often returns questions I wouldn’t have thought of on my own, such as asking about the biggest challenges they faced on a specific project or what skills they believe are most critical for success in their role. These types of questions lead to much richer conversations and provide me with genuinely valuable insights. This is a great example of using AI to augment your own intelligence, a theme I also explore in my deep dive on OpenAI’s GPT-5.
👋 Prompt 3: The Long-Term Reconnection
Building a network isn’t a one-time activity; it’s about nurturing relationships over time. Reaching out to a former colleague you haven’t spoken to in a year can feel awkward. I use AI to draft a friendly, low-pressure message that focuses on genuine reconnection rather than sounding like I’m just looking for a job.
This is the prompt I’ve had success with: ‘Write a friendly message to [Name], a former colleague I haven’t spoken to in about a year. I want to reconnect and give them a brief update on my career. The message should be warm and not feel like I’m asking for a favor.’
The AI helps me strike the right tone, often suggesting phrases like, ‘It’s been a while, and I was just thinking about our time working on…’ before I share my update. The message usually ends with a casual invitation to catch up over coffee or a quick call. This approach has been incredibly effective for reviving dormant connections and keeping my professional circle strong and active.
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