Why your team is afraid of AI
Telling your team to use AI misses the point - they're scared of it, and they're looking to your leadership to feel safe enough to give it a try
For as long as humans have been creating technology - from the first mortar and pestle all the way through to today’s AI tsunami - we’ve embedded the things we care about into the technology we build. The essence of our values is always reflected in our technology.
Way back in the day we cared about food for survival, so we made stone tools that helped us kill and skin animals and grind plants into consumable forms. Today, the AI technology we build and how we build it reflects our values.
With AI advancing at unprecedented speed, there has been been a time in human history when technology has so rapidly shaped our collective future.
As a CEO pivoting my own company towards this AI future, and as a founder coach working with other founders on their own AI transformations, I think a lot about what values we want to imbue into the technology we create and how we run our businesses.
One of the unique circumstances about this wave of technology shift is the degree of fear that it’s been met with. So many founders I speak with talk about how incredibly impactful AI has been on the areas of their business that have chosen to learn how to work with it - most often the software teams - and yet how reluctant the other areas have been to even give it a try.
There is so much fear. That fear is felt amongst engineers, who are rapidly seeing the unique role they used to play within companies be replaced overnight. That fear is felt amongst managers who don’t know if they can promise jobs to their teams in the future, or if their own role is even safe. That fear is felt amongst the individual contributors across sales, customer support, operations, finance, and every other function, who see AI rapidly moving in on areas of their expertise that they developed many years accumulating.
That fear is valid.
As founders, we must meet fear with leadership.
Leadership here isn’t about “power over” - telling someone what to do or how to do it. (”Just learn how to use this new AI tool and your job will be so much easier! You’ll have more time to do… MORE WORK!”)
Leadership here is about listening. About hearing all the fears. About compassionately responding.
Leadership here is about leading with vision and values. What will our company look like in five years? What role will AI play in our future? What will that mean for the people who are employed by us today? What are the values we have as a company that will guide those decisions?
What are your values?
How will you steer your ship into the future with those values?
How will you transparently and honestly communicate those values to your team? (Assuming transparency and honesty are part of your values.)
I’ve already seen so many different approaches to answering these questions. None of them are right or wrong, better or worse.
I’ve seen some founders say to their teams: “the job you had doesn’t exist anymore here. You are still employed, but it’s for a new job. And that job includes AI as part of every workflow and every system. Those are the new expectations for your job. If that doesn’t work for you, this isn’t the right job for you.”
I’ve seen other founders say: “this AI thing is scary. It scares me too. It’s also a tremendous opportunity for our business. I am deeply committed to the people who work here and I plan to build AI around the people who already work here. I promise that if AI “takes your job” and we lay people off due to AI, that will be my last day of employment here as well.”
And I’ve seen other founders say: “we don’t totally know what to do with this AI thing yet in our company, but we want to play and explore together. So every few weeks, we’ll do a company-wide hackathon, where anyone can work on any project they want to - company-related or not - and then we’ll ‘show and tell’ those. And we just think that if we let everyone play, we’ll find good ways to incorporate AI into our business over time.”
Each of these approaches has merit. Each of them has values embedded within it. The first is a capitalist-leaning approach that’s aligns with the fiduciary duty founders have when they raise money from VCs. It’s a capitalist winning mindset.
The second approach is a people-first approach, with deep loyalty to the team. Even if the business could survive longer or “make it through” a crunch period with layoffs, these founders are committed to the people who followed them on the journey. There’s a beauty in that.
The last approach is fun and playful. It accepts that we don’t know the future or how AI will impact things, and doesn’t declare anything about the safety or lack of safety of the jobs of the team. It focuses on the present moment and what we can learn as we play. It mimics the way children learn - through play.
Again, there is no single right approach, and anything you choose as a founder will be a reflection of your own values. And it can shift over time.
In my own experience as a founder, I’ve shifted between these. I leaned heavily - at times too heavily - in the direction of “people-first” #2, until I realized that leaning too heavily in that direction might mean I wouldn’t be able to serve the community we built the product and the company for. My AI-approach incorporates more of #1 than I have in the past. I’m rebuilding my team after stepping in as a boomerang CEO, and every job description is now different, including my own.
But the one that resonates the most with me is #3 - play. At the most challenging times in my company’s journey - the wandering-in-the-dark phase in the beginning, the throwing-everything-out-because-it-was-a-pandemic-and-what-we-first-built-became-irrelevant-overnight phase in the middle, and the current-moment-in-time-as-I-reimagine-everything-yet-again phase*,* play has always been the light through the darkness.
Once again, play seems to be the word of the moment. Perhaps this resonates because my company is a social app founded on play. Or, perhaps, it’s because in the face of fear, the best antidote is play.
If you’re a founder reflecting on how to transform your business through this AI era, here are a few questions to reflect on:
What are your own values? What of those values do you already see reflected in your company?
What values do you want to embrace more of in your life? What values do you want to bring into your company?
What vision do you have for your company in 5 years, 10 years?
What role do you imagine having within your company on those timeframes?
How do you imagine AI will be part of your business in 2 years, 5 years, 10 years?
What commitment can you make today to the people who are currently working with you? What can you share about how AI will impact the company and their roles? What do you not feel ready to share?
How do you want to compassionately hear and be with the hesitations and fears of your team around AI?
How do you want to commit to helping people gain the skills they’ll need to continue to be part of your team over the next 5-10 years?
Want to chat about this?
As a founder coach, I work with series A and later companies who are answering the above questions. I offer twice monthly coaching sessions and leadership offsites that guide your team through AI transformation for systems, culture, product, & operations. Right now, I’m offering complimentary AI strategy calls to up to 3 post-PMF YC founders who reach out by 9/21/25. Reach out: lunarayemail@gmail.com.