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Can AI Make Career Services More Human? A Conversation with Matthew Wohl
A LinkedIn connection approached Matthew Wohl about an outplacement contract worth more than $10 million.
There was an opportunity to bid, but he and his potential partner didn’t have the capacity to deliver the support required. He considered taking it on and figuring it out along the way, but recognized that doing so could hurt the people relying on that support.
That experience raised a question around what would be needed to deliver on a contract like this when the next opportunity came.
In this episode of Career Transition Perspectives, Matthew and I discuss how that experience led to Outplacer, how it evolved with early user feedback, and how he believes AI can create more time for the human side of career services.
We also explore the role of relationships in a job search and how we can help people better understand the needs behind a hiring decision to improve their job search results.
Building a Platform for Career Services Work
Matthew already had the idea for Outplacer. The missed opportunity helped clarify the tools and capabilities he needed to take on that type of work.
He couldn’t find a solution that did what he needed, so he initially built Outplacer for his own use. As other career services professionals began testing it, their feedback helped shape the platform. Invoicing and scheduling were two examples of functions added along the way.
Part of his goal was to bring work into one place, reducing the need for multiple tools, subscriptions, and tabs.
As a resume writer, I can relate. Between job listings, Word documents, PDFs, and browser tabs, there’s a lot of bouncing around during the process.
How AI Can Create More Time for Human Support
Career professionals often work within a set number of hours or a defined service package. Manual and administrative work takes up a good chunk of that time. Matthew sees an opportunity for technology to help create an initial foundation for things like resumes, cover letters, or interview prep, leaving more time for conversations about a person’s experience, goals, and job search.
“If we can take some of the manual work away from the hours we allot to helping people, we can go back in and be more human.”
He described using AI for an initial draft, with a professional still involved in asking questions, understanding the person’s experience, and finalizing the work.
And that human input is critical. In consultations with multiple clients, I’ve asked about details on their resumes and learned that AI had written something that didn’t accurately reflect their experience.
This is a good point to remind you that everything on your resume is fair game to discuss during your interview. Better I catch those mistakes than an interviewer!
For those of us supporting career transitions, technology can take on some of the manual work, giving us more time and enabling us to better support the people we work with.
Building Relationships & Trust on LinkedIn
We also discussed what Matthew describes as a shift from an application economy toward a trust economy.
A resume, cover letter, LinkedIn profile, and job search plan provide what he calls a foundation. From there, he encourages job seekers to “make more connections, leave more comments, engage in more conversation that shows the way that you think.”
Matthew said that if he were job searching today, he would leave 20 comments a day on relevant posts from companies and people involved in hiring where he wanted to work.
He also encourages connecting with peers. They can introduce us to other companies, share knowledge, move into hiring positions, or start businesses of their own.
Relationships often don’t lead to an immediate opportunity. They develop over time. And when someone needs, or knows someone who needs what you offer, you might be who they think of. That’s why it’s important to start building and maintaining connections before you need them.
Matthew’s own story is an example. The opportunity that brought Outplacer into focus came through a LinkedIn connection. You never know where a relationship can lead.
Understanding the Problem Behind a Job Opening
Matthew’s advice on networking bridged our conversation to the psychology behind hiring.
He encourages job seekers to think about the problem an employer needs someone to solve.
- What work does the hiring manager need taken off their plate?
- What business or departmental challenges have gone unresolved?
- How does your experience show you can help?
The answers to those questions shape how you present yourself on your resume and prepare for an interview.
For career services professionals, they give us direction on what to ask our clients to help them articulate their experience in a way that addresses the needs of the organization they’re targeting.
Outplacement & How Employees Remember an Organization
Looking ahead, Matthew hopes to see organizations with the means to provide outplacement take greater responsibility for the cost of supporting people through a layoff.
He also sees that support as part of how an organization will be remembered.
Former employees continue to talk about their experiences. How they were treated during their departure influences what they say about the organization after they’re gone.
For leaders navigating workforce changes, consider what support you want people to leave with, and what you want them to remember about how you handled their transition. Watch or listen to the full episode of Career Transition Perspectives for more of Matthew’s perspective on building Outplacer, using AI in career services, and helping people build relationships during a job search.

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