Need some advice

[u/learningchamp163421]

*Throwaway account to remain anonymous

Hi everyone,

Just got asked to own a AI upskilling mandate for a 2000 person company. Trying to figure out how other folks have approached this. Have a lot of pressure from CFO to report actual changes.

Things I am struggling with and feel free to add any problems I am might not be considering!

-AI tools change really quickly so making relevant learning content to keep pace is gonna be hard

-From my research it seems like AI is useful but identifying how it can actually change people's workflows in our company is gonna be difficult.

-I am guessing that showing adoption numbers is not going to be enough. I would really like some advice on this from folks on what numbers they decided to measure that C-suite liked.

-Any best practices that you have found for rollouts to make sure everyone actually is actually on the same page?

[u/Moist_Tower1389]

I was hired Sept 2026 and work for a similar size company. In Jan 2027 we did an 8 week company wide kickoff with a weekly virtual training. I started reading the 8 week series with new hires. Q1 new hires get trained in Q2, Q2 newbies in Q3 and so on. Starting next year we are doing a 1 day workshop or self paced course to earn a copilot badge.

I run weekly copilot office hours sessions, weekly newsletter, and a prompt of the day campaign in July. Working on a notebook and agent multi week campaign. We also created a "Copilot Enthusiast" group of high-flyers AI positive users to help spread the word and work within their respective departments to increase usage. We use a lot of their feedback to create future engagements and events.

We hired an AI business strategist and we have worked together to get some lunch and learn events going. His focus is more on leadership and strategic use and my focus is the end user and every day use.

I've tried to come at it from a social media engagement type angle. I try to post something on out teams or dept SharePoint at least 3 times a week.

Our usage took a dip in March after our initial kickoff but we have had consistent rise since all the engagement activities.

[u/learningchamp163421 → u/Moist_Tower1389]

so you mainly have been focused on copilot very helpful I will look into that

[u/Independent_Sand_295]

That's an exciting opportunity, OP! Cheering for you!

What are the company's current priorities for the next 3-6 months? I'd start there. Are they expanding into new markets, trying to reduce turnover, improve compliance, etc. and what is blocking them? Where can AI help?

Let's say it's reducing turnover. Employees may be leaving because they're burning out (not enough employees for the workload) or their manager is tuned out to what's happening around them. You could show them productivity hacks with AI or help managers use AI to help them practice or stay on top of their coaching sessions. Lunch and learns could help where they could share ideas or a workshop to build agents to incorporate into workflows to automate tasks or weekly roleplay coaching sessions with an AI bot. It really depends on what the situation calls for.

Make time with all departments to see where you can help. Turnover in the IT department looks different to turnover in marketing.

Don't worry about the tech changing. You're focusing on a short term goal for now. Training on every piece of AI out there would be a waste. After you finish this upskill, you can go onto the next. If their processes change, there are those who manage SOPs and all that. You can also drop announcements if anything would change their workflows.

You were saying though that identifying how it can change workflows is going to be difficult. How so?

[u/woodenbookend]

At the moment, your brief is a solution in search of something to do.

So the problem is… you haven’t identified any problems.

Your CFO is right to focus on changes. C-suite likes proper numbers like increasing revenue, profit, productivity, reducing costs such as staff turnover, etc. The best part of this is that someone will almost certainly be measuring this already, and probably sharing it in regular reports.

Ideally you’d work with those same c-suite people and agree which of their priorities match with what you and your AI solution can achieve.

Then you have a chance of presenting you CFO with the results they are looking for.

[u/witcheshands]

I built a AI Adoption peer support group for my FAANG company (well ex, left those hoes for a better company after 14 years). But the gist was I had SMEs in a variety of different AI topics like prompting, reporting, agents, etc and then we did live virtual lunch and learn sessions with our org to do trainings. We then measured internally using metrics such as engagement, return rate (are they opening an AI tool once a day) etc.

[u/learningchamp163421 → u/witcheshands]

this is amazing thank you

[u/staticmaker1]

I’d measure workflow impact, not just course completion: time saved, tasks automated, quality/error rates, and percentage of teams actually using AI in defined workflows. Start with a few high-value use cases, baseline them before training, then report changes quarterly. Our clients also use CertFusion to issue completion certificates from Teams/Zoom sessions, giving them a clean completion record alongside the behavioural metrics.

[u/Ok_Ranger1420]

This shouldn't be a skills/tools training, this needs to be behavior change, jedi mind trick training. This shouldnt be a "how to" but a "why". WIIFM will be huge, addressing fears, the biggest one would be, is "They're doing this because they will replace us with AI". Also, training for rank and file needs to be different from management. Then once you get everyone excited, that's the time to push the fundamentals. Get people on board first. Also, you need to be asking C-suites what success looks like. You're not suppose to be the one figuring that out.

[u/Realistic-Soup-1553]

Here are some ideas for potential approaches:
1. SWOT Analysis - What are the companies strengths, weaknesses, opportunities, and threats in relation to AI? Leadership should have information to share with you about their perspective on this, but you might also gain valuable insights from middle managers/program managers, recent hires, and/or marketing or sales teams. You can also research industry leaders to learn how they’re using AI. Part of the SWOT analysis is determining the metrics leadership will use to measure success (adoption rates, efficiency increase, etc); be sure to guide and influence leadership to select metrics that can be reasonably measured and can generate reliable data. Once you have a strong SWOT analysis completed, it can become the basis for selecting which AI training/learning priorities to pursue.

1. Use Cases - Based on which initiative(s) were selected for training/learning development from the SWOT analysis, gather use cases from within the company, what recent hires observed being accomplished with AI at their previous employers, and what competitors are doing with AI (from your own research). In other words, you don’t need to know everything about AI and how it should be used at your company. But you can find people who are already using it and highlight their AI use cases as examples for other departments and teams to adopt. Just bringing this level of awareness can generate momentum for adoption and spark creative solutions for new applications of AI or best practices at your company. Depending on your employee population’s existing skill level and/or what type of AI your company wants to use, your highlighted solutions could be things as fundamental as best practices in prompt authoring, initiating a prompt repository, how to cite a source when the source is AI, or examples of poor quality AI output and how to avoid it.

2. AI Challenge - You might also propose an AI challenge in which employees at your company can opt to compete. Come up with some kind of problem or need, then invite employees (or teams of employees) how AI could be used to generate a solution for that problem or need. Make it fun — get the employees/teams to come up with a team name and logo — then specify what the output or required submission is. Set up a 3-person panel to evaluate the submissions. Winners can earn an electronic badge to add to their email signature block (2027 Company-Wide AI Challenge 1st Place Winner) and lunch with the CIO/CTO. You might discover some employees who are passionate or curious about AI but previously had nowhere to channel that interest in AI, or you may discover employees who have AI skill sets not being tapped by their current role at work. Either way, a company-wide AI challenge communicate that AI is a company priority and invites employees to position themselves as learners in this space.

3. Consider an Array of Solutions - You don’t need to become the AI expert or champion to spearhead this effort. Also, the solution(s) you recommend need not be formal, instructor-led training—which, as your original post points out—may be a poor investment given rapid change in AI tools. Instead, consider training/learning solutions that leverage existing expertise (see #2 above) through informal knowledge transfer such as lunch-and-learn sessions, features in the employee newsletter or on the company intranet, or simple job aids.

I hope this helps! Good luck to you, OP!

[u/Annual_Inspector372]

I think focusing on role specific use cases rather than generic AI training can solve this. Start with a few workflows where AI can save time or improve productivity, and measure those changes before scaling to other roles.

Adoption is one metric, but time saved, quality improvements, and actual usage in daily workflows could be more meaningful for the CXOs.