Getting Your Foot in the Door

Looking for a new role is challenging under any conditions, but especially so if you’re in a category of people that often gets overlooked (e.g. experience doesn’t at first glance look relevant, there’s a gap on your resume, etc.). Here’s the advice I give to people in those situations:

  • Applying to jobs online may be a necessary part of the process, but don’t solely rely on that effort
  • The people reviewing applications online are frequently recruiters or junior level HR reps who have never built or led their own teams, been responsible for deliverables or results, or done the type of work you are looking to do
  • As a result, they often have trouble deeply understanding the job and holistically assessing candidates and just match keywords in a resume to a job description
  • This leads to an extraordinary number of amazing candidates getting overlooked whose resumes might be a little different but who might provide the most value long-term

Despite that, if a position you want is officially posted, it’s still important to apply online. There are usually hundreds of candidates for an open position that is posted online, and if you only directly email the hiring managers (and don’t apply online):

  • You may fall through the cracks since you are not in the candidate tracking system
  • It’s possible you may be viewed (by some) negatively for going around the process
  • There’s a good chance 50+ other candidates had the same idea, and the manager’s email is getting flooded with direct outreach. They are usually very busy if there is a vacancy in their department, so timing is not ideal
  • If you apply online but get no response, sending one follow up email a week or so later is acceptable, but make it thoughtful, not generic, and worth the time to read it

A large percentage of job openings are never advertised – department leaders frequently hire people they know, have worked with before, or who has been recommended by someone they know. Figure out who those people are in your target companies by:


  • Scouring LinkedIn
  • Conducting internet searches
  • Attending trade / industry / other events they might attend (but not events e.g. career fairs that are crawling with other candidates). If you go to events, research attendees in advance, in order to have meaningful conversations with your ideal targets

Ask people they know for introductions (look for shared connections on LinkedIn). Work to meet those people, and build really strong relationships:

  • Offer to buy them coffee sometime – and be sure to think of something that would make it a valuable use of their time
  • Ask for advice/guidance based on their expertise – people love to feel like their opinion is valued, so are frequently very open to requests like that
  • Keep in mind that their time is valuable, and send a thoughtful thank you note afterward
  • Follow up again by emailing an article or blog post that is relevant to them or to a conversation you had with them
  • If they have written a blog post or article, comment on that piece in a thoughtful and insightful way (through an email, commenting directly on the blog, or sharing it on social media)
  • Do a gut check first to determine if this appropriate, but in some cases, sending a book that is relevant to them or that you think might inspire them could go a long way
  • Send a piece of work you created that is relevant to the work you want to do, that they might find interesting or useful. This of course will simultaneously demonstrate the amazing work you are capable of and how you go above and beyond to provide value
  • Important: Show passion, an eagerness to learn and contribute, and do your homework (research + critical thinking) in advance

If you have trouble getting your ideal hiring manager’s attention, consider outreach to a more junior person in the organization.


  • It’s best if that person’s LinkedIn profile shows that the person may be respected and valued in the organization (e.g. stellar recommendations from people at varying levels of seniority and functions in their organization, a series of promotions, etc.)
  • That person may be able to introduce you to someone more senior with hiring authority, put in a good word / help you get your foot in the door, or they may know other people at great companies in the industry who are hiring
  • Once you meet them, stay top of mind with ongoing follow up (e.g. “Hi! I just came across this article and thought of you.”)
  • Don’t just use that person to get your foot in the door. Continue to treat them as the valuable person they are long-term and look for ways to be of service in the future

Be careful about taking a job that you don’t want, just to get your foot in the door.


  • The cost of a replacement hire is incredibly expensive. The company is likely investing a tremendous amount in hiring someone for this specific position, and onboarding them, and likely hasn’t budgeted to replace you 6-12 months later
  • If you don’t have a passion for what you’re doing, there’s a good chance that will come across to others, and you may not do your best work anyway
  • The exception to this, of course, is if you and your target company have specifically agreed in advance to you starting in position A and moving to position B in a specified timeframe (depending on performance)

This is certainly easier said than done at times, but here’s the most important piece of advice…


  • Being in the job market can be really tough. It’s easy to lose hope. And this can be very palpable to others
  • Take care of yourself so that you can show up with contagious enthusiasm / positivity, with a focus on being of service to others, and making a valuable contribution. Since we spend more time working than anything else during our waking hours, the people who get hired are usually those who the hiring managers/team would actually want to work with every day
  • Take a little time away from the job search to do something you love doing, get some rest, and find ways to help someone else (for a break in thinking from your own search)

Again, easier said than done at times, but work toward having freedom from attachment to outcome. Think about interactions you’ve had with salespeople in your past. Think of how you responded to those who were obviously attached to outcome (making the sale), versus those who were focused on you as a person, were passionate about what they were doing, and were interested in your actual needs. Which of those types were most successful in making the sale to you? Same deal with candidates.


  • Freedom from attachment to outcome will allow you to see / be available for opportunities you might not otherwise have seen that are much better than anything you imagined on your own
  • It will also help you to show up in a way that really makes people want to work with you
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