🤖 Are you turning to A.I. chat tools for career coaching and/or therapy?

Weigh in on our PivotList poll 🗳️

Hi Friends,

A.I. is still at the tip-top of my mind, as just yesterday I delivered a Pivot keynote for a conference—👋 welcome new CMA-SIMA readers!—where it was the hot topic, woven into nearly every discussion about where their industry is heading. I can’t discuss pivoting without asking some of the same big questions, as I did with your helpful input in the previous edition of PivotList: Is AI going to take our jobs?

Now I have a follow-up question and would be grateful for your input: is AI going to replace some or all of your work with (live) coaches and/or therapists?

There are many aspects of both that it’s surprisingly exceptional at — for myself included! — and yet, I still love working 1:1 with people as both coach and coachee.

This has been a hot topic in the news, too, as I’m sure you’ve noticed (sorry to pile on if you’re already maxed out on A.I. hype!). At its worst, A.I. can be a dangerous, sycophantic hallucinator replacing necessary human interaction; but at it’s best . . .

• Dr. Harvey Lieberman wrote, “I’m a Therapist. ChatGPT is Eerily Effective.”

• NYT reporter Cade Metz covered “Experts Exploring AI ChatBots for Therapy.”

• AI-industry insider Matt Shumer’s post (originally on X), “Something Big is Happening” went instantly viral, racking up over a million views in the first week.

If you’ve already been experimenting, I’m curious about where A.I. chat tools succeed and where they fall short. 🗳️ First, a poll (voting closes in one week on 2/25), and then please do elaborate in the comments!

💬 I would also love to hear from you in the comments . . .

No pressure to answer all of these—even just one is great:

• What experiments have you tried?

• Do you have any favorite prompts?

• What do you think the limitations are for therapy use-cases? For career coaching?

• When would you hire a live coach or therapist, and when would you turn to AI?

• Do you prefer one of the AI tools over the others for these conversations?

💻 Here are some of the career-related prompt ideas I shared in yesterday’s Pivot breakout:

• My friend Elisa Doucette created an advisory board with public figures (include anyone you admire, even throughout history). She provides a few notes about why she chose each one (i.e. what strengths and values they represent), shares the goals she’s working on, and runs tough questions by the committee — asking A.I. to simulate a conversation amongst themselves in response to her challenges.

• Upload personality assessment results (MBTI, Clifton Strengths, even numerology and astrology profiles, etc.) and ask for patterns and language to describe your strengths; research roles where you will shine.

• Rewrite your resume (and generate more compelling LinkedIn headline ideas) to emphasize your unique strengths; help make the case for why you are the perfect candidate for a stretch role.

• Interview prep and run-throughs (behavioral, technical, situational); if you’re not sure where to start, switch roles where you interview the A.I. first.

• Skill gap analysis: What parts of your role or industry are at risk regarding A.I.? How can you elevate your work to have even greater impact and reach?

• Negotiation strategy, company research, and anything else you can think of . . .

• What have you tried? Let us know in the comments 👇

Speaking of career coaching—I can’t resist plugging our very own Pivot coaches, who all offer a beautiful blend of experience, strategic thinking, warmth, and intuition:

👥 Work 1:1 with a Pivot Coach to Clarify Your Strengths

How it works: Check out their longer bios here, then fill out this interest form letting us know if you have a coach member preference. We’ll reply with the booking link for a complimentary 30-minute get-to-know-you call :) If you need help narrowing down the best fit, we’re happy to weigh in! Send us a note at hello@pivotmethod.com.

We’re all wishing you abundance, serendipity, curiosity, and ease during your 2026 pivots and beyond!

❤️  Warmly,