While the use of AI tools have spread across the job search process, it pays to take the time to craft specific uses that will both accelerate your discovery of useful networking contacts and employment opportunities and highlight your qualifications. Lisa Rangel, CEO of Chameleon Resumes, offers three ways to make profitable use of generative AI on LinkedIn.
For CIOs and other technology executives seeking new opportunities, using generative AI-powered tools like ChatGPT, Perplexity and Claude is not simply about keeping up with the competition. It is about enhancing your effectiveness as you seek out the best fit for your next role.
Surfacing new opportunities, refining outreach, and deepening your understanding of your own professional value can happen using AI properly. When used thoughtfully and meaningfully, AI tools can fine tune how candidates position themselves and accelerate connection with the right executive opportunities. The thought and meaning matter. For example, C-suite leaders are three times more likely to be adding generative AI literacy skills to their LinkedIn profiles compared to two years ago , a 2025 LinkedIn study found. Adding skills is a good idea. But the use of these tools can also go too far. So many jobseekers on the network have embraced the tools that they have overwhelmed employers with AI-generated resumes, as The New York Times noted in June 2025.
Taking the time to use generative AI right has important benefits. Becoming fluent in using these tools not only increases the executives’ job-market relevance but also signals to boards, investors, and hiring panels that they understand cutting-edge tools that are now reshaping business priorities worldwide. And using AI tools to search for new positions can speed up the process. But users must invest time in crafting the right prompts, vetting the outputs of AI models, and then customizing the information for specific job-search and networking purposes.
Even if a prompt does not yield a career-changing insight, AI can serve as a brainstorming channel or mental sparring partner. Experimenting with generative AI propels personal growth. Executives can use AI to become better equipped to lead, evaluate, and discuss AI-driven projects within their organizations.
Below, find three concrete prompts you can use today to streamline and elevate your IT executive IT job search, along with practical guidance for each.
Prompt 1: Make Interview Conversations More Fluid (and Make Yourself Shine)
Goal: Use generative AI prompts to prepare for an upcoming interview.
How this works: This type of prompt taps the ability of AI large-language models to compare your experience with the interviewer’s as listed on LinkedIn. The resulting output provides context about their company and information to generate thoughtful, high-level questions. You gain conversation ice breakers that not only sound intelligent but also connect your story to theirs, helping foster rapport.
Sample prompt: “Using my LinkedIn profile (include your LinkedIn profile URL) and the LinkedIn profile of the interviewer (include interviewer’s LinkedIn URL), give me 10 ice-breaker questions for an interview for a (position title) role with (interviewer’s company name).”
Use example: Suppose you’re applying for CIO at Acme HealthTech, and your interviewer is the COO. Inputting both LinkedIn profiles, an AI-assisted prompt could yield personalized questions such as:
“Given our mutual experience leading digital transformation projects, how does Acme align its IT initiatives with clinical innovation?”
“I noticed your recent work incorporating AI in patient engagement; what technical leadership qualities helped you succeed in that rollout?”
Why this matters: This prompt will analyze both profiles under the context of the company information and could offer insights on what a fellow leader would want to see in a candidate for the job you seek does. And it will perform this task in a way that saves time over manual work.
Prompt 2: Nurture Your Network and Spark Replies
Goal: Ask generative AI models to identify valuable network connections and craft messages to create a constructive professional interaction and nurture relationships.
How this works: Generative AI scans your LinkedIn profile alongside that of your target contact to uncover mutual interests, relevant achievements, and strategic conversation starters. It then provides tailored outreach suggestions and message templates designed to build rapport, reference shared connections or timely topics, and spark authentic replies. This prompt can speed your efforts to discover meaningful, relevant conversations of mutual interest.
Sample prompt: “Using my LinkedIn profile (include your LinkedIn profile URL) and the LinkedIn profile of the target connection (include connection’s LinkedIn URL), give me 10 ways to reach out to this person, in the spirit of networking, which will increase the odds of them replying to me.”
Use example: If targeting the CTO of a cloud services firm, AI might suggest:
“Compliment them on this recent webinar they led related to digital infrastructure (with citation to the webinar).”
“Reference this shared alma mater or professional certification.”
“Ask for their perspective on a specific regulatory challenge facing the sector.”
These ideas help you move past generic requests and increase the odds of a meaningful exchange. Remember to filter and add your own style—AI suggestions offer inspiration, not a replacement for human nuance. Always default to what your judgment dictates you should do.
Why this matters: Expanding your executive network is critical to surfacing new career opportunities. AI can scan both profiles and suggest nuanced, context-rich connection messages that increase response rates by giving you suggested leverage to use in your outreach.
Prompt 3: Target Employers Who Truly Value Your Background
Goal: Use AI to pinpoint employers whose strategic needs directly match your unique achievements, elevating your executive job search by focusing on organizations most likely to value what you offer.
How this works: AI analyzes your achievements and unique value proposition, then sifts through available company data to identify firms where your capabilities align with current priorities. This helps narrow the playing field to companies where you have a realistic edge.
Sample prompt: “Using my LinkedIn profile (include your LinkedIn profile URL), give me a list of 20 companies with revenues at or under $XXX that will most likely want to talk to someone with my background to (insert your goal and/or your expertise) for their company.”
Use example: A CIO focused on SaaS scale-ups with revenue under $50M could see AI-recommended targets such as U.S. health industry technology startups, European supply chain platforms, or niche SaaS vendors—all actively seeking IT leadership to scale operations.
Customization, as always, is essential. The quality of suggestions hinges on how well your LinkedIn profile spells out your expertise and measurable impact. If your measurable outcomes are outlined clearly in your LinkedIn profile, a match could be made based on outcomes companies seek as explained in their public documents.
Why this matters: Executive time can be limited for executive job searching. Using research discovered using AI prompts to discover precisely sized companies and/or firms with shared values can shorten search timelines and help avoid poorly matched engagements earlier on in the search process.
Elevate Your Skills as You Practice Job Searches and Networking
Integrating generative AI into an executive IT job search is about more than efficiency—it’s about increasing your relevance, sharpening your strategy, and demonstrating leadership agility at a pivotal moment for the industry. These prompts not only streamline the mechanics of job searching but also support ongoing executive development as AI and digital transformation become inseparable from forward-thinking business leadership.
Give the above prompts a try, review AI output critically, and use the results to improve your positioning for your next move. This process will make your search more efficient and focused today.
