Welcome to Ask a Girlboss! It's our advice column where real experts answer your burning career questions. Have a dilemma that needs solving? DM us on Instagram, and we'll get right on it.
The dilemma: “I am navigating a career pivot and don’t know where to begin. My friends say I should hire a coach, but if I need to save some money, can’t I just use AI to do the same things?”
The experts: Laura Sheehan, associate director of graduate coaching at Georgetown University’s Walsh School of Foreign Service (learn more about Pivot Coaching with Laura), and Jenny Blake, author of Pivot: The Only Move That Matters Is Your Next One and host of the podcast, Pivot with Jenny Blake.
The solution is not an either/or; rather, it is an inclusive yes, and…
The most effective job search strategies today incorporate AI-driven tools and human support systems. AI is not meant to replace coaching, though it is a powerful tool to augment it, especially when financially strapped.
Laura witnessed two significant events last year that brought this question to the forefront of her everyday work: the overhaul of the federal government and international development industries, parallel with the exponential growth of AI.
The former rendered tens of thousands of people unexpectedly unemployed. The latter provided a potential tool for all of those new job seekers to immediately leverage in their career pivots.
Alongside a lean team funded by the Rockefeller Foundation and run through Georgetown University, she was honored to help pull together resources for those impacted. The series, Pivot with Purpose, highlighted dozens of career-change experts and successful pivoters. One thing became clear—to successfully navigate a stormy job market, we needed to harness the power of people and embrace the many ways AI could help.
If you are mid-pivot or anxious about the changes we’re all facing, you are not alone. The U.S. Bureau of Labor Statistics reported the March 2026 rate of unemployment at 4.3% or 7.2 million people, all navigating what’s next. Here is a quick guide on when to use AI and when to rely on the tried-and-true support of a certified (live) coach.
We should also note that some are understandably opposed to using AI for ethical, environmental, and/or privacy reasons. If that's you, a coach is your best bet. You will appreciate Amelia Hruby’s recent Off the Grid podcast series, starting with “3 Reasons You Feel So Conflicted About AI.”
As the recent 2026 ICF Coaching Futures Report says, “Technology may support coaching, but its role is complementary. While AI and digital tools will increasingly shape coaching, they cannot fully replicate the relational, intuitive, and ethical foundation that defines coaching as a professional human practice."
Here’s where each tool can be most helpful:
5 Ways AI Shines When Navigating Career Pivots
Note: Before using AI in your job search, protect your privacy: don’t paste confidential employer information, sensitive personal details, or anything you wouldn’t want stored or reviewed. When in doubt, anonymize first.
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A shame-free starting space. Many feel embarrassed to admit to another person that they're lost, unhappy in their career, or that they have no idea what they want. If you need time to process before putting ideas into action, AI can serve as a low-stakes environment where honest answers can surface.
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Brainstorming, idea generation, and market research. If you’re feeling stuck, leverage Google Career Dreamer to start exploring what possibilities are available—the more information you feel comfortable sharing, the more accurate (and inspiring) the results. Job seekers tend to focus on a tiny fraction of well-known employers when the majority of opportunities are in smaller or lesser-known organizations. AI processes massive data sets instantly, immensely helpful in expanding matching roles and companies. Try this prompt: "Show me 100 open roles in (insert city, state) that match these strengths (insert list of strengths)." Further refine your results by sharing a scrubbed version of your resume, anonymized feedback, and future goals.
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Document drafting and reviews. Creating tailored application documents (resumes, cover letters, essay responses, etc.) can be one of the highest-friction tasks when looking for work. AI is helpful at getting a first draft started or editing an existing document so you can put it into your own voice.
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Mock interviews. Audio-based AI interview practice with voice chat is now surprisingly good, either as your chat tool interviewing you, or the other way around, so you can hear what potential polished answers sound like.
- Accessibility. If money is tight, AI can be a real lifeline. It is fast, thorough, tireless, and always available.
5 Signs It's Time to Hire a Live Coach
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Your AI chat momentum has stalled, or you are getting stuck in your own head. The tools can be useful, but if you've hit a wall, it may be time to work with someone more experienced. AI can sometimes make analysis paralysis worse by giving you infinite options, rabbit holes, and plans to refine. AI can also hallucinate with confidence. It might tell you a company is hiring when it isn't, cite a salary range that's outdated, or describe an industry trend that doesn't exist. For someone making a major life decision, bad data delivered confidently can be worse than no data at all.
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You're experiencing an emotional block like fear, grief, or a full-blown identity crisis that practical advice alone isn’t helping with. A coach can help spot these underlying patterns in what’s not being said, and help you navigate tough conversations with your inner circle.
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You are at a high-stakes pivot point: a big transition with financial risk and/or limited runway. Investing in a live coach may help you move through it more quickly, though even they can’t make any promises when it comes to specific outcomes and timing.
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You want a specialist with relevant experience and a proven network. Someone who knows your target industry or has personally navigated the same kind of transition, who can make warm introductions, curate relevant resources, share tools and templates, and advocate for opportunities on your behalf.
- You benefit from accountability. An appointment on the calendar with a live coach helps you show up for yourself; someone who will notice if you start ghosting, and encourage you as you keep showing up, like having a trainer meet you at the gym.
If one-on-one coaching isn’t in your budget, group coaching programs are another strong alternative. Jenny recommends Career Pathfinder (led by her first coach, Adrian Klaphaak), and Laura recommends Never Search Alone, a peer-support method for job seekers.
In many ways, AI is now better than bad—or even mediocre—coaches. But ultimately, a skilled coach has strong intuition and pattern recognition built on years of guiding people through transitions. They notice when your energy rises or dips, when you seem more animated talking about certain next steps than others, and they might blurt out a seemingly left-field suggestion that offers your next, surprisingly resonant clue.
Early in her career, Jenny described the power of career coaching as 1+1=100. With AI, it’s now 1+1+1 = 1,000. Coach and coachee both have an increasingly powerful resource at their fingertips to facilitate clarity and insight, especially between sessions.
But as the ICF report reminds us, “Machines can replicate conversations but not consciousness.” That’s where a coach comes in.
MORE ASK A GIRLBOSS
"I Need a Career Change but Have No Idea What to Do Next. Now What?"
"I'm Feeling Defeated After Job-Hunting For Six Months"
“I’m Burning Out. How Can I Recharge and Find My Next Career Move?”
