Silicon Valley’s biggest companies pay Karen Wickre for her advice — but at the Help Desk, it’s free to you.
I’m a writer, editor, teacher, and researcher with three relevant degrees. I’ve written guides, proposals, and book chapters; taught math and science; and done freelance writing and editing. The problem is that these have all been temporary positions, often with big gaps between gigs. I’ve been trying this entire time to land a permanent position and further develop my skills. I’ve been applying for positions for which I know I can do a great job, but frequently I don’t even get an interview. For over a decade, the response I’ve gotten has inevitably been something along the lines of “You interview very well, and you were a strong candidate. But we’ve decided to hire someone with more (or more specific) experience.” Every. Time.So how do I get out of this Catch-22? If employers don’t want to hire me because I don’t have the right job title on my resume, how can I get the right stuff on my resume when I can’t land a job for lack of the right job on my resume? I’m getting angry and frustrated, which I know only makes things worse, but I’ve been hearing the same refrain for so long. I’m stuck, and want to know how to get unstuck. Can you help?

As a lifelong generalist, your problem really resonates with me. I used to jump at all kinds of projects simply in order to get known, and get more experience. At different times I’ve worked with ad copy, software reviews, book indexing, video scripts, presentations, study guides, and event production. All of these and more are in my checkered past. Having a passing familiarity with most helped me build credentials and connections, as well as rule out things I didn’t want to do. Over time, I wanted to characterize myself more specifically, and have an overarching theme about my offering. So I made up a category for myself — business communicator — and sure enough, all that random stuff fit into it.

There are quick things you can do to make a meaningful pivot. First, ask a few of those you’ve had good interview experiences with to give you a little more intel on the particulars. (Since some time has passed since you met, maybe they’ll be more willing.) Encourage their candor. The question you want to ask is not “Why didn’t I get the job,” but rather, “Knowing what you know about my experience, what do you suggest I do in order to be hired?” The answer might be some additional training, or it might be that they really did require X years of specialized experience for that one gig, or they might admit an internal candidate came in first. You might get clarity about what you do (or do not) want to pursue, or spark a conversation about future possibilities with that organization.

In addition, may I suggest a bit of revisionism? Review your resume. You might need to describe yourself differently, and to play down, compress, or expand some of your experience. LinkedIn is surprisingly elastic for this purpose, and I’d recommend making active use of it, since so many recruiters are there. Craft a broad summary of your interests and goals for future work at the top. Then summarize past work under broader categories—even if that means collapsing a bunch of projects. When I was actively freelancing years ago, I grouped all the world under the umbrella of a single consulting stint (encompassing the correct date range), which made for a respectably stable gig featuring a bunch of client work.

Next, you will want to work your personal contacts heavily so that you don’t have to rely only on the awful process of sending applications into a black hole. Make the rounds with coffee dates or video calls to gather information and ideas about jobs and places. The better you have an idea of what you’re looking for (the kind of place you’d like to work, the sorts of jobs you’re currently qualified for, what you’d like to gain on the job, people you’d like to meet), the easier it is for your interviewees to offer specifics. Another networking goal: whenever possible, get personal introductions to an organization, hiring manager, or other people who work there. These are the connections that can become referrals and help you get in the door.

At some point all this should lead to sending someone your resume or LinkedIn profile. You want to provide a very personalized cover letter, aimed at the hiring manager. The letter serves a purpose: to acknowledge the elephant in the room—your work history—and explain why your range of experience, applied learning in related areas, and newfound (industry-specific) knowledge make you the perfect candidate. Employers can be swayed by an applicant’s passion and commitment, especially if you back it up with strong thinking about you can tackle their challenges.

One more thing: Quite a few places these days, including large companies, engage some people first as contractors. It’s a bit of a test, for chemistry as much as anything, and gives the employer time to get a sense of how much you’re needed and how people like working with you.

Early on, I spent a long 15 months as a Google contractor, since there was no job precedent for anyone like me. During that time I made myself useful taking on every kind of project and building camaraderie across the team. Finally, after everyone thought of me as part of the furniture already, the team head proposed a new role for me. There’s nothing wrong with this approach. But get an understanding up front: this deal means your temp stint can lead to a permanent hire. There should be a timeline with check-ins along the way to make sure you’re on track. I hope these suggestions can help lift you out of your well-worn groove.

I am a 35-year-old software development manager working in a cloud solutions services startup. I have been on the technical side most of my professional life, but now I would like to be a sales professional in the tech industry. Can you advise me on how I can make this transition?

It’s great news that you already have solid technical skills, since they benefit you in any other kind of job in a tech business. Without knowing the size of your current company or if you’re interested in staying there, I’d suggest that you look into roles that are generally called “technical sales.” Though I don’t profess to know a ton about the field, I did a little searching and found a concise post on the questions to ask when moving from a technical to sales role. People holding these jobs are variously described as engineers, managers, support staff — but all of them have a solid technical understanding about their company’s products and the broader arena they fit in, whether it’s complex machinery, cloud solutions, or devices ranging from medical to consumer. In general, sales engineers are part of a sales team that helps customers buy in (initially) or buy up (over time).

If your company already has such a role, investigate what it might take to transition. If not (or if you want to make a move), work your personal contacts to see who you can meet with to learn more about such positions. If you need to get some training to be certified, it will be worth it. The team is likely to have sales goals, and your efforts should be recognized. (It’s a great way to demonstrate that you know how to bring in revenue.)

If you’re interested in sales roles in another realm (business development, partnerships, major accounts, et cetera) and you’ve already been a sales engineer for a while, you’ve already made the first leap. From there, most companies offer a variety of sales training and the chance to shadow more experienced people or work with others until you’re ready to do more on your own, in a dedicated sales role. Good luck!

Irritated by misguided company culture and hapless co-workers? Send your professional quandaries to advice@backchannel.com.