Most owners start by asking "which AI should we buy?" That is backwards, and it is why so many of them end up with a subscription nobody uses.
What is the first step?
Find out where the time goes. Not from a report, from the people. Ask every person on the team to name the hour of their week they would pay to get rid of. You will hear the same five things: re-typing, looking things up, chasing people for answers, formatting, and copying from one screen to another.
That list is your AI plan. Every item on it is something the current tools are good at, and every item on it is something your people will be glad to lose.
What should I automate first?
The thing that is boring, frequent, and low-risk. Boring so nobody misses it. Frequent so it pays back fast. Low-risk so when it messes up, which it will at first, nothing bad happens.
A customer service inbox is usually a good first one: the tool drafts the reply, pulls the order, a person reads it and sends it. Month-end bookkeeping is another: the tool keys the invoices, a person checks the batch. Lead research for sales is a third.
What you do not start with: anything a customer sees without a human in between, anything legal, anything with money moving automatically.
Do I need to buy new software?
Usually not for the first step. Most teams are already paying for tools with AI in them and have never turned it on. The first win is often just using what you have properly. The second win is a small automation that connects two things you already own. New software comes third, if at all.
How do I keep this from scaring my team?
Involve them from the first minute. The workshop exists because the fastest way to get a team on board is to put their own jobs on the wall and let them pick what gets fixed. The fastest way to lose them is a memo.
And say the sentence: nobody is losing their job over this. If it is true, say it early. If it is not true, you have a different project.
How long before I see anything?
A day to get the list. A couple of weeks for the first automation. A quarter to feel it in the schedule. If somebody promises you a transformation by Friday, see the question about consultants.
What does this cost to start?
A half day of AI 101 for the team is $1,500. The full day in the room is $3,500. Both of those end with you knowing the next step, and you can take it without me.
Answered by Jared Lukes, Minneapolis. Twenty-five years in brand, UX, and technology, currently holding fractional AI and technology seats at three companies. About Jared.