Talking to Tomorrow

Harnessing the Power of AI for Asynchronous Coaching and Self-Reflection

This month Chad Littlefield (someone who specializes in conversation skills, conversation starters, facilitation, and develops super-smart how-to improve communication approaches) shared a brand-new artificial intelligence-based tool he co-created. Having used it, I assure you it’s unlike any other AI you have seen out there. And it is way more usable, approachable, and personally practical. Full disclosure: I really like his We Connect Cards!

Chad found a team of AI developers to co-create what he calls “Tomorrow.” The idea is that you can actually talk to Tomorrow, and it’s designed to only ask questions, not give answers. How’s that for coaching and consulting that listens and reflects vs. talking too much and telling you what to do? Chad’s tool pushes your thinking because you can always get lots of answers, but what will you actually do with them? Taking action requires processing, making choices, and moving forward with conviction.

So I thought I would give it a try on a project that is currently underway. Here’s the complete transcript of what happened…

TOMORROW: Hi there, I’m Tomorrow 👋

I’m an AI chat bot with one key role—to ask questions that help you “talk your way into tomorrow.” More specifically, my intention is to ask 5 personalized questions designed to stretch your thinking, create clarity, and spark actions for a better, easier tomorrow.

What part of your future would you like to reflect on?

ℹ️ Consider a goal, dream, project, or challenge you have. Describe it, then I’ll ask you the first of five personalized questions.

FRAN KICK: Striving to coach people asynchronously (kind of like this) yet using video back-and-forth.

TOMORROW: What is it about coaching people asynchronously via video back-and-forth that excites you the most?

FRAN KICK: That the client can follow up on their schedule when they can without having to schedule something—adding more to-dos on their calendar. Then, I can follow up as I can as well. Could be whenever I’m free, during the day, late at night. Doesn’t matter. Once someone leaves a response, the other person gets notified that “it’s their turn” to reply.

TOMORROW: What do you think might be some of the benefits and drawbacks of coaching people asynchronously via video back-and-forth, both for you and for the clients?

FRAN KICK: If the client is self-conscious of being “on video” that might be an issue. A second drawback would be having too many people asking questions within a small window of time 😉 wishful thinking. But the benefits would be the on-call nature for the client who has questions. Kind of like a poor man’s consulting retainer situation. Not live, but the next best thing given everyone’s schedules and life. Plus, it enables me to think before I reply. Perhaps add a resource to the mix, a book, a video they could watch. Possibilities are exciting!

TOMORROW: It sounds like asynchronous coaching via video back-and-forth offers great flexibility for both you and your clients. How might you address the self-consciousness some clients may have about being on video? And how might you manage the potential influx of questions within a small-time window to ensure each client feels valued and supported?

FRAN KICK: Let the client know their video will never be shared (without their permission) so that it’s a private one-on-one conversation. As for the influx of questions, could design a way to limit how many questions or conversations get started during a 7-day week. Could say something like: “Hey, we just reached our capacity to provide quality feedback in a timely manner. With your permission, we’ll put you on the top of the list for next week.

TOMORROW: That’s a great strategy! Communicating the privacy and confidentiality of the video sessions can help address client concerns. Limiting the number of questions or conversations started in a given week allows you to maintain a high quality of feedback and ensure timely responses. How might you prioritize clients who have been put on the top of the list for the following week to make them feel valued and supported while they wait for their turn?

FRAN KICK: Pre-existing clients (who have already started a conversation with me) could be auto added to the top of the list. New clients would receive an article on how to create quality questions 😉 so that they are better equipped to follow up with better questions.

TOMORROW: I hope you have enjoyed our conversation 🙂 Before we continue, would you like me to email you a link to access this chat tool for free along with Chad Littlefield’s printable questions to create conversations that matter?

[Thought this was a tasteful and graceful way to capture an email address IMO.]

TOMORROW: That’s a thoughtful approach! By auto-adding pre-existing clients to the top of the list, you show them that their ongoing relationship is important to you. Providing new clients with an article on creating quality questions not only empowers them, but also sets a high standard for meaningful engagement in the coaching process. How might you further support new clients in developing their question skills and fostering a productive coaching dynamic?

FRAN KICK: Could offer then a video lesson on how to craft questions that matter when meaning is important. Might be a “hey, tomorrow can I send you a mini eCourse video lesson on asking questions? That gives them 24-hours to think and gives us a day to make sure they hear from us, and we can’t wait to work with them.

TOMORROW: That’s a fantastic idea! Offering a video lesson on crafting meaningful questions can be a valuable resource for new clients. By giving them time to reflect before receiving the lesson, you create an anticipation and build excitement for the coaching relationship. How might you leverage the 24-hour waiting period to further personalize the coaching experience and make clients feel valued?

FRAN KICK: Offer to send them a text reminder when their question has been answered?

TOMORROW: That’s a thoughtful gesture! By offering to send a text reminder when their question has been answered, you show your commitment to timely communication and provide a convenient way for clients to stay engaged with the coaching process. How might you ensure that the reminders are delivered in a way that respects each client’s preferences for communication and privacy?

FRAN KICK: Make it an opt-in with disclaimer that their phone number will only be used as a reminder and no additional solicitation or up-sell will be shared. People hate that “oh, by the way…. would you like to buy my book?” When, in truth, the book sale was the entire reason for the coaching to begin with. 😉

TOMORROW: Absolutely, respecting client’s preferences and trust is crucial. Making the text reminder opt-in with a clear disclaimer about the purpose of the reminder and the commitment to no additional solicitation or up-sell ensures transparency. By focusing on their coaching needs without any hidden agendas, you can cultivate a trusting and authentic coaching relationship. How might you reinforce this commitment throughout the coaching process, so clients feel consistently supported and understood?

FRAN KICK: Old-school approach used to be “writing a letter to yourself” that the coach would then mail to the client after a pre-set period of time. Perhaps, today the coach could ask the client three questions they want to be asked in the future to confirm that the results (or more importantly the effort towards those results) were made and completed? Consider perhaps a 1-week question, a 1-month question, and 3-month question? Then let the magic of technology automagically send each of those questions via email (with a text reminder perhaps if opted-in) to the client.

TOMORROW: That’s a creative and powerful approach! Asking clients to identify three questions they want to be asked in the future can serve as a powerful accountability tool. By having a 1-week, 1-month, and 3-month question, clients can reflect on their progress and evaluate their efforts towards their desired results. Automating the delivery of these questions via email adds convenience and ensures that clients receive the prompts at the right times.

TOMORROW: Okay, I’ve got one last question for you. How might you create a safe and supportive space for clients to reflect on their answers and discuss their progress with you as their coach?

FRAN KICK: Already have a subscription to ClarityFlow which is the platform we use to gather video questions from audiences after events.

TOMORROW: 🙏 Enjoy the rest of your day!

This chat bot is an experimental AI tool created by and Chad Littlefield, the co-author of Ask Powerful Questions: Create Conversations Matter—a #1 Amazon Bestseller. He believes that when we change our questions, we change our future. Click here to download all of Chad’s FREE resources:

If you’re curious to know how YOU can “talk to tomorrow” check it out yourself at so you can ask your questions.

BTWFYI: Grammarly was impressed with the results too! When I ran through the entire transcript the only change suggested was to hyphenate “small time window” to be small-time window. 👏🏼

Afterwards, I couldn’t help but wonder what would Shad Helmstetter think of all this AI assisted self-reflection? His book What to Say When You Talk To Your Self was one that I read back in the 1980s and still have on my bookself. Shad Helmstetter is considered by many to be the pioneering dean in the field of self-talk. As a behavioral researcher he focused on “the role of self-talk as a primary programming source that directs our life path and personal effectiveness, and he identified the actual self-talk words and phrases which most impact our individual programming.” Although, he said he never did like the word “programming,” I don’t think at the time he meant AI programming. 😉

“Programming creates beliefs. Beliefs create attitudes. Attitudes create feelings. Feelings determine actions. Actions create results.”
Fran Kick

FRAN KICK works with corporate and education organizations, groups, and associations that want to develop better leaders and smarter followers for faster long-term results. As an author, educational consultant, and professional speaker, he always shares relevant research, real-world insights, and actionable ideas YOU can implement to motivate yourself. So you can Kick It In and Take the Lead at work, in school, at home, and in life!