Authentic AI Adoption and Cultural Impact: Dessalen Wood
Workplace Stories by RedThread Research
00:00
Flipping fear into excitement through hackathons
Dessalen recounts a CTO-led town hall and hackathon that turned AI fear into enthusiasm and produced practical bots.
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From overcoming initial anxieties through hackathons and playful experiments, to setting an ambitious organizational roadmap for AI, Dessalen Wood shares how Syntax is embedding artificial intelligence across departments, focusing on pragmatic progress rather than hype.
You’ll hear stories about driving excitement, learning by doing, and the all-important challenge of measuring real impact. More than just technology, this episode dives into the culture shifts, collaboration with IT, and leadership mindsets that are pushing companies out of their comfort zones and into the future, while keeping authenticity and humanity front and center.
You will want to hear this episode if you are interested in...
Overcoming AI Anxiety
Early stages of AI adoption in organizations are often marked by fear. Employees worry about being displaced, making mistakes, or failing to keep up. At Syntax, Dessalen Wood and her fellow leaders tackled these concerns by creating safe, engaging, and transparent opportunities to experiment.
One of the most effective strategies was an organization-wide AI hackathon. Everyone, regardless of their role, was invited to submit ideas for automation and improvement—ideas that the tech team then built. Not only did this demystify AI, but it also provided a healthy dose of competition and excitement. Dessalen describes that, “Instead of people fearing automation, it became a competition... People were saying, please, automate my tasks!” This shift from apprehension to enthusiasm helped break through adoption barriers and foster a culture of creative problem-solving.
Structuring Success: A Multi-Layered AI Roadmap
Syntax’s approach moves AI from a buzzword to a set of actionable strategies. The leadership distinguished between three core areas:
The creation of AI champions, employees trained as internal advocates and solution designers, helped ensure that innovative ideas didn’t just sit in a backlog. Instead, those not ready for large-scale investment could be adapted, piloted, and iterated by these champions, keeping the spirit of experimentation alive while prioritizing resources for the highest-value initiatives.
The Human Element: Authenticity, Experimentation, and Measurement
As AI tools become more prevalent, a new challenge emerges: maintaining authenticity in communication, development, and leadership. The team discussed the “hollowed-out leader” phenomenon—where over-reliance on AI could dilute critical thinking and personal investment. Dessalen explains why expertise, context, and human customization are more important than ever: If it doesn’t demonstrate expertise and isn’t highly curated, it just turns people off.
Measurement is also evolving. Early wins in AI productivity are being tracked, not just in terms of completion rates or tool adoption, but in demonstrable business outcomes and stretch goals. Syntax uses tools that help employees articulate their productivity gains and set new impact targets, ensuring that activity translates into organizational value.
Resources & People Mentioned
Connect with Dessalen Wood
Connect With Red Thread Research
Subscribe to WORKPLACE STORIES
You’ll hear stories about driving excitement, learning by doing, and the all-important challenge of measuring real impact. More than just technology, this episode dives into the culture shifts, collaboration with IT, and leadership mindsets that are pushing companies out of their comfort zones and into the future, while keeping authenticity and humanity front and center.
You will want to hear this episode if you are interested in...
- 00:00 Overcoming AI fear through collaboration
- 03:30 Defining AI readiness today
- 09:55 AI's role in business transformation
- 15:46 AI anxiety in the workplace
- 22:05 Making AI adoption fun
- 28:11 AI expertise requires human touch
- 36:42 AI strategy: Three layers explained
- 41:31 True transformation vs. improvement
- 53:21 Rethinking work, technology, and AI
Overcoming AI Anxiety
Early stages of AI adoption in organizations are often marked by fear. Employees worry about being displaced, making mistakes, or failing to keep up. At Syntax, Dessalen Wood and her fellow leaders tackled these concerns by creating safe, engaging, and transparent opportunities to experiment.
One of the most effective strategies was an organization-wide AI hackathon. Everyone, regardless of their role, was invited to submit ideas for automation and improvement—ideas that the tech team then built. Not only did this demystify AI, but it also provided a healthy dose of competition and excitement. Dessalen describes that, “Instead of people fearing automation, it became a competition... People were saying, please, automate my tasks!” This shift from apprehension to enthusiasm helped break through adoption barriers and foster a culture of creative problem-solving.
Structuring Success: A Multi-Layered AI Roadmap
Syntax’s approach moves AI from a buzzword to a set of actionable strategies. The leadership distinguished between three core areas:
- Department Initiatives: Leveraging AI for productivity and process improvement within teams
- Customer Value: Enhancing solutions and services delivered to external clients
- Business Transformation: Reimagining core business models and operations for strategic advantage
The creation of AI champions, employees trained as internal advocates and solution designers, helped ensure that innovative ideas didn’t just sit in a backlog. Instead, those not ready for large-scale investment could be adapted, piloted, and iterated by these champions, keeping the spirit of experimentation alive while prioritizing resources for the highest-value initiatives.
The Human Element: Authenticity, Experimentation, and Measurement
As AI tools become more prevalent, a new challenge emerges: maintaining authenticity in communication, development, and leadership. The team discussed the “hollowed-out leader” phenomenon—where over-reliance on AI could dilute critical thinking and personal investment. Dessalen explains why expertise, context, and human customization are more important than ever: If it doesn’t demonstrate expertise and isn’t highly curated, it just turns people off.
Measurement is also evolving. Early wins in AI productivity are being tracked, not just in terms of completion rates or tool adoption, but in demonstrable business outcomes and stretch goals. Syntax uses tools that help employees articulate their productivity gains and set new impact targets, ensuring that activity translates into organizational value.
Resources & People Mentioned
Connect with Dessalen Wood
Connect With Red Thread Research
- Website: Red Thread Research
- On LinkedIn
- On Facebook
- On Twitter
Subscribe to WORKPLACE STORIES
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