Meet AskSherri AI: Aha Moments Anytime™

Are you a high potential professional,  parent, or student with learning, attention, or executive function challenges?

Whether you’re a new, existing, or returning client…

Welcome to an exciting digital solution that makes a version of my expert solutions-focused coaching, exclusively trained on my content, style, and approach, available anytime.

Here’s How It Works:

  • Affordable Pricing: Access AskSherri AI coaching for an entire year, for less than what you’d pay for two hours of live 1-to-1 coaching. Start with a No-Risk, Free 30-Day Trial, then just $29 a month/$299 a year. And…when you’re a full-service live coaching client, AskSherri is included free in your agreement.
  • Always Available: No need to schedule a time, 24/7/365, whenever you need guidance, AskSherri is there.
  • Personalized: AskSherri adapts to what works best for you, remembers each conversation, learns about you, and customizes future sessions just like a human coach would.
  • Secure and Private: Conversations are securely stored, remain 100% confidential, and will never be used as AI training data.

See what the experience is like! Here are real client conversations with the platform:

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AskSherri supports you with:

Barrier Thought Navigation:

  • Identifying and overcoming limiting patterns
  • Strategies for overcoming obstacles
  • Positive psychology-based interventions for resilience

“Thank you for creating a space for me to reliably and flexibly return to to make progress on my goals and receive help when I’m stuck, anytime.”
~JL, Investment Banker

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Personalized Strategies:

  • Custom approaches for learning, work, and personal challenges
  • Tools for managing attention and executive function
  • Sustainable habit-formation techniques

“I am a life-long learner and believe that everyone can have greater capacity to learn. What I liked about the platform is that it reminded me that every step, even one that I think is backwards, teaches me something about myself. And then when I make a choice to step forward or not, I do it much more consciously.”
~MC, Business Services

Practical Implementation Support:

  • Context-specific solutions and progress tracking
  • Just-in-time guidance for immediate needs

“AskSherri is very snappy and fast, so you can work through stuff quickly. It does a great job of asking questions to prompt you to work through whatever you ask it about. I asked for advice about a work from home challenge and got actionable suggestions that felt personalized to our conversation.”
~CD, Solopreneur, Podcaster

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Summaries of Key Points and Action Steps:

  • Remembers your session content to drive your success
  • Flexibly adapts to your present needs

“I love that I don’t have to feel embarrassed about what I’m saying to AskSherri. She helped me see my doubt and overwhelm and kept me from getting lost in my (too many!) details. AskSherri suggested trying 2 focal points instead of multiple ones. I especially liked when she could summarize what I was saying and suggest new insights.”
~DB, Health Care

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AskSherri: Coaching for the Digital Age

The AskSherri platform redefines how and when my expert learning support can be delivered. It’s available to all live coaching clients as well as stand-alone (following a Discovery Call).

AskSherri offers:

  1. Comprehensive Support – Going beyond productivity tools to address learning, working, and personal development challenges.
  2. Evidence-Based Techniques – Rooted in my proven coaching methods and principles from The Effort Myth.
  3. Sustainable Solutions – Equipping clients with lasting strategies they can apply independently across all areas of life.

Many clients need help at unexpected times—during a late-night study session, before a big presentation at work, in the heat of a parenting struggle. AI coaching ensures support is there when it’s needed most, meeting you exactly where you are.

FAQ

What is AI coaching and how does it work?

AskSherri is a digital version of me. It captures my professional experience, perspective, and personality, allowing it to conduct full 1-on-1 coaching sessions with you on my behalf. It is not just a “question and answer” bot, but a full coaching experience.

How is this different from ChatGPT?

ChatGPT is a conversational chatbot, and it helps answer questions using general knowledge. I’ve tried using ChatGPT for this purpose, and while it can answer my questions, it does not do a good job coaching me. AskSherri is built specifically to conduct full coaching sessions, and I’ve trained it with my expertise on how to be a good coach for my clients. It also remembers every session you’ve had, and continuously learns about you over time to offer personalized guidance.

How is AskSherri trained to replicate me?

I’ve trained AskSherri like I would an apprentice. After having it read up on all of the materials and content that informs my coaching sessions, including my own books and articles, I then taught it how to apply all these materials. From there, I’ve had many back and forth conversations to provide feedback and teach it my preferred session structure, communication style, and how I would approach various scenarios.

How does the AI coach ensure personalized coaching?

AskSherri continuously learns from each conversation with you, gathering and updating information on goals, challenges, and progress to tailor coaching sessions to your evolving needs.

How do I talk to AskSherri?

Today you can talk with AskSherri by speaking or typing into a chat. In the near future, you will be able to have voice-to-voice calls (it will also have my voice!).

Is AskSherri available at all times?

Yes, AskSherri is accessible 24/7, allowing you to get coaching whenever it’s convenient for you.

Is this for organizations, too?

Yes, AskSherri offers AI coaching for individuals in organizations, too. Schedule a Discovery Call Here

How secure is the data shared with the AI coach?

Strict privacy protocols are followed to ensure that sensitive information is protected. Sessions are confidential within the limits of the law. If I think you are at risk of hurting yourself or someone else, I will need to report it.

Does this AskSherri replace you?

No worries–I still offer live coaching. However, you can rely solely on AskSherri for consistent support, or mix things up by combining it with live sessions with me. AskSherri acts as a coaching force multiplier, and doing both will allow us to focus our live session time on high-value areas where my decades of experience and creativity are irreplaceable.

Can AskSherri be updated or re-trained?

Yes, AskSherri is continually updated and re-trained as needed. I frequently teach it new materials and research-based insights to refine its understanding. I also ensure it stays aligned with evolving coaching strategies over time. Remember that AI is a relatively new technology and there may be some bugs here and there. If you run into one of these or have any other feedback, please let me know!

Looking Ahead

Whether through one-on-one or group coaching, books, blog/casts, workshops, or AI solutions, my professional mission remains the same: to empower individuals by fostering motivation, perseverance, and performance through understanding and tailored support so people can:

  • Uncover and leverage their unique strengths
  • Break free from limiting beliefs
  • Achieve success on their own terms with personalized approaches.

As a leader in this space, I’ve trained AskSherri’s groundbreaking AI approach so it integrates my professional expertise with the scalability of technology. I’m committed to demonstrating how technology can maintain quality and personalization while reaching broader audiences. Privacy Note: Your information stays on the platform and will never be shared or sold.

Let’s connect!