I’ve had the pleasure and privilege of working at WorkTogether since Nov of 2017- which means I’ve been “hopping on a quick call” with job seekers for almost 8 years! This Ten Year Anniversary month has been a really fun time for me to look back on what job seekers were asking about then, and compare that to now.
Remote is now the norm, rather than the draw
In 2018, the most popular role I worked on was a remote Program Manager for a national education non profit that supported teacher recruitment. At the time, every interview I led started with, “I’m so excited to work from home.” Now, in 2025 and post-COVID, the majority of our job seekers have remote work experience. In fact, we’ve actually started to hear job seekers- especially those who have been remote for the past 5 years or so- seek in person roles again, because they’ve learned it’s a better fit for their style.
Job seekers are much more benefits-literate, and value benefits far more than they used to.
Of course, COVID accelerated this change, but job seekers are asking about benefits packages earlier and earlier, oftentimes even before applying. And, even more than that, job seekers are doing their homework to assess the value of the benefits package, checking if their providers or medications are covered, and aligning on parental leave or fertility benefits well before an offer is made, much less accepted. In 2017-2018, I was rarely asked about an organization’s benefit package and truly believe most job seekers saw them for the first time when they got an offer! Now, we include as much benefits info in job postings themselves, and prefer to link directly to the organizations’ resources in our earliest outreach.
Flexibility Over Growth
This is a big generalization-so take it with a grain of salt- but one interesting trend I’ve noticed is how many job seekers state “flexibility” as a goal for their next role. My question back is, “what does that mean to you?” because flexibility can, and does, mean really different things. For many, it’s about their daily schedule, especially those with caretaking responsibilities. For others, it’s about flexibility in their work responsibilities and seeking exposure to diverse workstreams. Whereas I used to get asked about “growth trajectory” or “promotional pathways” in each call, I now get asked about flexibility. Do I think growth and opportunity for promotion still matters? Of course! But, I do think job seekers are thinking more holistically about their next move.
One thing that hasn’t changed about our search work here at WT is our commitment to serving both job seekers and employers. This isn’t a conflict; by serving both of our stakeholders well, we ensure a smoother and more successful process. Think crocodile and plover bird, they are symbiotic! With that in mind, I have a few tips.
For our job seekers: If you have a question to ask your recruiter, hiring manager, or interviewers, take the time to write out your ideal response. Asking the question isn’t the goal, getting clarity on the specific need you have is the goal. That’s not the same thing.
Job seeker question: “I see the organization has an unlimited PTO policy. What is typical or expected usage on the team?”
Job seeker ideal response: “I get 15 days of PTO at my current role that rolls over and gets paid out if I don’t use it, which this policy does not. So, I want to make sure the typical usage is at least 20 days to make a meaningful difference in my overall package.”
For our employers: Include as much technical information on your job posting as possible. Approach these postings not as descriptions but as a marketing opportunity to share the scope of work for the role, the most compelling parts of the organization’s Employee Value Proposition, and how interested candidates can learn more.
