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Look Without Looking: The Seasoned Pro’s Guide to Stealthy Holiday Job-Seeking


Look Without Looking: The Seasoned Pro’s Guide to Stealthy Holiday Job-Seeking
Look Without Looking: The Seasoned Pro’s Guide to Stealthy Holiday Job-Seeking

Co-Authored by Christine Grimm with Michele Calderigi of Next Career


Are you looking to make a career move while keeping it under the radar?

Want to explore your options without making a big announcement?

Looking to test your network and see if any of those casual job offers or board seats are real?


It seems as if everyone is always thinking about their next move. In a post-Covid world, you could be one of the many people daydreaming of a new role, thinking about jumping to a new industry or feeling like your path forward should be different from the path you’ve been on. And if you are like many of our clients (and friends!), you dread the idea of formal job-seeking. You can’t imagine the endless interview processes, and maybe you haven’t updated your resume in years.


In this blog, we will discuss strategies and tips on how to lean into stealthy and discreet exploration without putting pressure on yourself or the people in your network. These are our top 10 tips for exploring with class — without making it awkward for anyone.


1. Schedule Time to Contemplate and Research

If you are curious about other industries or roles, you will need a compass point. Create a schedule for yourself and allocate time each day for research. Are there companies, industries, or ecosystems you have been admiring from afar? Browse LinkedIn and websites, press releases, and association news to see what companies and key people are up to. Review the profiles and biographies of people who are in roles/jobs you think are interesting. Make the goal to learn and gain inspiration.


2. Use the Holidays to (RE)Ignite Your Network Attend industry-specific holiday events, holiday parties, and any other social opportunities to meet new people or connect with acquaintances. Connect and reconnect with people you don’t talk to daily. Send handwritten thank-you cards or direct-to-individual (not group) emails wishing people a great year ahead. The holidays give you the perfect reason to reach out to anyone and everyone in your network. Don’t think of networking as a transaction, but rather nurturing your relationships.


3. Schedule One-on-One Time with Employees, Colleagues, and Customers

The holiday season is a great time to recognize and appreciate the people who are “in your corner.” Identify 10 people you want to thank for their support, friendship, or trusting long-term relationships. Schedule coffee or a meal with each and leverage the holiday “cheer” to reconnect or deepen the connection. You don’t need any other agenda but to say thank you and strengthen the bond.


4. Be the Master of Following Up

Close all the loops and reply to all the emails left in your inbox. Review and respond to direct messages (from people you know) in your LinkedIn and other social feeds. This demonstrates your professionalism and will make you stand out because most of us are too busy to respond or miss the “real “messages in the spam.


5. Learn Something New

Use your holiday break to enhance your skills and knowledge. If there is a new tech platform that is being utilized in specific industries you are interested in, learn about it. Read a book or listen to an audiobook. Take free online courses or attend an in-person class to learn how to increase your productivity on your devices at Apple or Best Buy. Choose a new podcast that is interesting to you. This will not only make you more interesting and smarter, but it will also make you a more attractive job candidate later.


6. Volunteer, Mentor, or Freelance

Consider using your time to serve others through volunteering and mentoring. Universities often need seasoned professionals to mentor and coach undergraduates preparing for their first job. You might also give time for free (or for a small fee) to non-profits, small businesses, or associations who might need you to take on freelance projects in your current or desired field. You probably have a long list of skills that, while you may take them for granted, a small business or non-profit desperately needs. This will allow you to give back, help others, gain experience, and expand your network and perspective.


7. Learn to Use LinkedIn Many executives, specifically those who have been employed by the same company for a long time, don’t utilize LinkedIn to its full extent as a tool. You may casually browse your LinkedIn feed, like other people’s posts, and occasionally, you may even post yourself. However, having a stable job and a busy life make it a low priority to learn to use the best and most useful functions of this platform (that is, until you need it — and by then, it may be too late).


If you are thinking about a job search, LinkedIn is the perfect place to do it passively. The algorithms running LinkedIn work based on activity. The more active you are on the platform, the higher your profile will show up in a search. For a passive, quiet job search, your profile must be searchable. Make it easy for people to find you.


These are the 4 areas in LinkedIn that you can’t ignore:

  • Head Shot. Make sure you have an up-to-date, professionally taken photo on your profile.

  • About Section. Use keywords that talk about who you are as a leader, what you do, and how you do it.

  • Experience Section. This should include your most recent title and company. Ideally, add 1-2 bullets with meaningful responsibilities.

  • Engage Actively. Interact with people and content by liking, commenting, and reposting if something resonates with you. Post original content. Follow companies you are interested in, and engage with their content by liking, commenting, and reposting.

8. Leverage Social Media

Use LinkedIn, Instagram/IG Threads, and X (formerly Twitter) to connect with professionals in your industry and follow companies you are interested in. Engage in discussions with people in and out of your network, share or repost relevant content that is interesting to you, and showcase your expertise to increase your visibility.


9. Polish your Online Presence

Take an audit of your full online presence. What do people see when they search your name? How does your LinkedIn look on a desktop vs. mobile? What types of photos and copy do you post on Instagram, Facebook, and other platforms? Employers often research candidates online, so make sure your online presence is professional and up-to-date. Update your LinkedIn profile, clean up your social media accounts, and delete any photos or posts that aren’t the “brand” you want to present to a potential employer.


10. Update your Resume

Reviewing and updating your resume is a great way to allow yourself to think about what you have accomplished and where you want to go without having to tell anyone else about your intentions. If you are applying for opportunities online, it is important to know that many companies use Applicant Tracking Systems to streamline their hiring processes. Make sure that your resume is ATS-friendly and has the keywords reflected in the job description. Take your time to identify and highlight relevant skills and experiences. This will increase your chances of standing out in a sea of people who may look the same “on paper.” Make sure your resume is telling the story you want it to tell. Don’t let it just chronicle your experience.


With the global job market in such flux, it might feel scary to take a leap into a new industry. There’s never been a better time to explore your options and research discreetly with a stealth search. Rather than waiting around for your dream career to appear on its own, make a space for yourself by creating an opportunity to gain some understanding of what lies beyond your current limits. Your path may not present itself to you easily, but with personal clarity and perseverance, you can make sure you end up with something that satisfies you professionally and personally.


If you’d like more help to kickstart this process, don’t hesitate to contact us at any time for support. Our team of experienced professionals is here to guide you through every step of the way. We are dedicated to helping our clients find meaning and have a life they love. And make sure to join me for Deep Work Fast LIVE on LinkedIn, Facebook, and Instagram, this Tuesday at 3:00pm PT.


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