About
Hi, I’m David Weeks.
CEO and Principal Trainer, DW Clarity Group · MCT · OBA
I’ve spent over 30 years in technology, much of it helping people understand it and apply it to their work and lives. Today I help organizations and business users get real value from Microsoft Copilot and agents, and I help Microsoft Certified Trainers build and sharpen their instructional skills.
My story
From the classroom to Microsoft and back again
My career started in the U.S. Army, repairing communications security equipment in Germany. That’s where I learned that the best technology in the world is useless if the person holding it doesn’t trust it or understand it.
I carried that lesson into technical training, first at The Information Management Group and then as a trainer and Training Manager at Executrain. Then came 20 years at Microsoft, where I spent the last 6 years as a Skilling Specialist, building custom skill plans for Fortune 100 and mid-market enterprises.
“The AI skills gap is a judgment gap, not a technical one.”
I retired from Microsoft in July 2026 and founded DW Clarity Group to focus on the work I care about most: helping people use AI with purpose, and helping trainers become great at their craft.
The path
Thirty years, one thread
- U.S. ArmyField General COMSEC Repairman31 Sierra, stationed in Germany
- Early careerTechnical Trainer, The Information Management GroupWhere teaching technology became the job
- Early careerTrainer and Training Manager, ExecutrainTeaching, then leading a team of trainers
- 2006 – 2026Microsoft20 years, including the last 6 as a Skilling Specialist building custom skill plans for Fortune 100 and mid-market enterprises
- 11+ yearsMicrosoft Certified Trainer and Onboarding AdvisorOne of only 42 OBAs worldwide certified to deliver the MCT Onboarding Experience
- July 2026Founded DW Clarity GroupIndependent AI and Microsoft 365 training, speaking, and consulting
How I work
What I believe about AI and learning
Stop random acts of AI.
Scattered experiments don’t add up to results. Purposeful, intentional use tied to real business outcomes does.
Judgment beats features.
Knowing which button to click is the easy part. Knowing when, why, and whether to trust the output is where people need help.
Clarity today, capability tomorrow.
Break it down simply, use real-world examples, and people build skills that last well past the class.
Beyond the classroom
A little more about me
Based in Bloomington, Illinois, and happy to travel to you.
DW Clarity Group is co-owned with my wife, Debbie.
Proud U.S. Army veteran.
“[I am] consistently impressed by David’s ability to bring clarity to ambiguity. He combines deep expertise with a genuine commitment to helping others succeed, making complicated topics approachable, practical, and actionable.”
Coworker and mentee
Let’s put this experience to work for your team.
Training, speaking, or a Skilling Blueprint for your organization.
I reply within 24 hours.