1. What problem are you trying to solve right now?

Start here.

Don’t ask, “Would you attend a workshop on AI?”

People are generous with hypothetical enthusiasm. They’ll tell you something sounds interesting, useful, or “definitely something I’d attend” right up until registration opens.

Instead, ask about the problem.

“What’s getting in the way of growth right now?”

“What part of hiring is hardest?”

“What are you struggling to figure out?”

“What’s taking too much of your time?”

If you’re considering a hiring program, for example, you may assume members need help finding applicants.

Their real problem may be keeping employees.

Or training supervisors.

Or competing with larger employers.

Or writing job descriptions.

The first question helps you make sure you’re solving the right problem before you start designing the solution.


2. What have you tried?

This question can save you from creating something members don’t need.

If a business owner says hiring is a problem, ask what they’ve already done about it. They may have attended three workshops, hired a recruiter, changed benefits, increased wages, used workforce programs, and still be struggling.

That tells you something very different than hearing from someone who doesn’t know those resources exist.

The answer also helps you see where the chamber might fit. Sometimes members don’t need another class.

They need an introduction.

Or a resource list.

Or a conversation with someone who solved the same problem.

Or help navigating an existing program.

You don’t always need to build the solution itself.

Sometimes you can just connect people to something that already exists.


3. What would make this worth your time?

This may be the most important question for programming. Chamber pros often think about value from the organization’s perspective:

• We have a great speaker.
• The topic is timely.
• The information is useful.

But members are making a different calculation.

Is this worth leaving my business?

Is it worth an hour of my day?

Will I learn something I can use?

Will I meet someone who matters to my business?

Will this solve a problem I have now?

Ask them directly.

“What would make a program on this worth attending?”

You may hear:

“I don’t want another panel.”

“I need someone to show me exactly how to do it.”

“I would attend if I could talk to businesses already doing this successfully.”

“I need this virtually.”

“I want a checklist I can take back to my team.”

“I would rather have a 30-minute session than a two-hour workshop.”

That’s useful intelligence.


4. Who needs to be in the room?

This question can completely change the program you create.

If members want help with workforce issues, perhaps they don’t need a speaker. They probably need local employers, schools, workforce partners, and training providers in one room.

If they’re struggling with development or permitting, they may want access to city staff.

If they want to grow sales, they likely want buyers rather than another sales presentation.

If they want to learn AI, perhaps the most useful format is meeting with other local business owners who can show them how they’re using it.

Ask members:

“Who would make this conversation useful for you?”

The answer may turn a generic program into something members cannot easily get elsewhere.


5. What would you do differently after this?

This question forces everyone to move beyond “interesting.”

Ask:

“If this program were successful, what would you be able to do afterward that you can’t do now?”

If nobody can identify an outcome, the program may still be informative, but you should know that going in. The stronger the answer, the easier the program becomes to design and market.

“Attend our cybersecurity luncheon” is an event description.

“Leave knowing the three vulnerabilities your business should check this week” gives someone a reason to sign up today.