I've done this in the past. I find the best way is to do it in person. I made a habit of walking on my downtown street between lunch and asking the local business owners about their challenges of their business. I don't know if there's a number...I think idea extraction should become a part of your daily routine. Here are some questions you can ask:

So your business does X?

What is your role in the business?

What does a typical day look like for you?

Can you walk me through the first couple hours of your day? What are the first few things you do each morning?

How many customers are you working with a month right now? What’s been your best month? What’s been your worst?

What are a couple activities you have in your day that you just don’t enjoy?

Getting Deeper

Thinking about the last couple days at work, what has been the most challenging part?

What do you use excel for in your business?**

What is the most expensive problem in your business?

What’s a problem that you’ve tried to solve in the past but didn’t work for you?

What would you like to do with you mobile phone, but can’t?

Your approach to building a business - first find a PROBLEM and then build a SOLUTION - is a wise one.

Keep in mind that I'm answering as a Business Owner who also works with Business Owners (as a coach) so my insights aren't speculation... This is real world stuff:

If you are dead-set on cold calling then here are some suggestions.

1. Have a reason for your call that focuses on the "what's in it for me" from the perspective of the owner. Consider that your call is really a first contact in your marketing to them... So use your understanding of your chosen niche.

2. Be prepared to encounter the Gate Keeper
Have a plan on how to get to the owner.
This article has some good ideas: http://www.leadjen.com/stickied/7-must-dos-to-get-past-the-gatekeeper/

3. If you get through to the owner be respectful of their time. If possible - ask only ONE question. Talk as little as possible. And take lots of notes.

Regarding a specific approach (aka your Strategy) and specific questions - I would need to know more about your goals.

And if you are open to other approaches (approaches other than cold calling) let's set up a quick call and I'll share some ideas with you.

Best of luck to you!
Cheers,
David

If I got a cold call from someone who asked me what my pain point is, I would hang up on him. That's because I am too busy to take time out from my day to sit and think about all the things that bug me, slow me down, cost me money, or hamper my ability to make money. There are probably a dozen things I can thing of, and if I thought about it probably 100 things. But I am not going to waste my time thinking about all this just so you can take my ideas, start a company and make a ton of money by reselling my own ideas back to me and not offer me a dime in compensation.

And that's probably how a lot of business owners would think. So the problem with your approach is that you are missing the one critical element for success in any field -- you must have good relationships first before you call anyone up.

Let me say that another way: Success in business is almost entirely based on personal relationships! If you don't have personal relationships with people you want to do business, you simply will not get anywhere.

So before you do this, you should either develop personal relationships within the niche you are contemplating, or decide your niche will be within the personal relationships you already have. Which is easier? Obviously, the latter.

So start with the business people you currently know. It could be the person who cuts your own and owns his own hair salon. It could be the immigrants who run the dry cleaner that you always take your clothes to each week. It could be your neighbor who is a lawyer. You catch the drift.

Once you have a relationship, they are much more willing to help you out, and you can continue the conversation over time. They likely won't be able to think of anything immediately, so just encourage them to write down anything that comes to their mind as they go about doing their job.

It will also help if you take them out for coffee, and be sure to pick up the costs. they are going YOU a favor, so you should at least return the favor.

I will suggest you keep 10 business owners on your checklist this will really help you in comparing whose idea is the best and you can adopt that idea. I have done idea extraction as well and these are what I have experienced. Steps before making a cold call –
1. At least a day or two, send email to cold call group. Usually, I have tried emailing a group before I start calling. I do this, because if the gatekeeper asks why I am calling, I can say it is about an email I sent on such and such day. Before, I had a 1 in 10 chance of getting past the gatekeeper, now, I rarely get stopped by the gatekeeper.
2. Go to person in my call list - make sure I know First name, and last name.
3. Pull up company website - check the quality, know loosely where the company is from, and GUESS rough income based on the website. You can usually tell this within 1-2 minutes, at least well enough to know the basic facts.
4. Take a few deep breaths - say to yourself, OK - what is the worst thing that is going to happen here? They are going to say no. They are going to be annoyed. You will live, and it will not be the first time.
5. Get my Call Record option ready to go in case the call gets good. Grab a calculator and have it ready in case I need to do some price anchoring on the fly –
6. Make call - have script ready and already memorized.
7. Gatekeeper - Hi, may I help you?
You - “Yes, John Smith please, it’s George Wardman (I use the more formal version of my name, it sounds more business-like - Make it sound serious - not friendly - just deep voice, serious, no messing around. When I used to try and chit chat with the gatekeeper I almost always got shut down. Get by this person as fast as you can - IF they ask why - say again - "Tell him it’s about an email I sent to him two days ago” - be vague, 90% of the time, you’ll get put through.
8. Once the person you want answers - and you start talking do NOT stop for any reason. You must say what it is that you want, as fast and as short as you can to get them talking - Forget being friendly in this first part - it’s all about getting them to answer that first question. Have some sort of script ready in your head.
Good questions that you can ask are as follows:
1. Tell me a little about your business?
2. What is the most critical job in your business?
3. Could you walk me through your day?
4. What is the first [second, third, etc] thing you do in the morning?
5. How you create value for your customers?
6. What is your most challenging aspect of generating revenue or creating value?
7. What would help you generate more revenue or create value for your customers?
8. What is the most frustrating part of your business?
9. What software do you wish existed, but you cannot seem to find it?
10. “If you had unlimited resources, what would you develop to make your day more productive?
If you want to know more, you can ask the following questions as well:
1. Think about the last couple of days at work, what have been your biggest struggles lately?
2. What manual tasks in your daily routine would you like to automate?
3. Do you have any ideas on what would make your job easier?
4. Are there any features missing in your current software that you wish existed?
5. What is the most expensive problem in your business? Do you think this could be automated?
6. Are there any areas in your business where duplicate data entry exists?
7. What is something you know your customers want from you, but you have trouble providing?
8. Is there anything you want to do with your mobile phone that you cannot right now?
9. What is a problem you have tried to solve in the past, but it did not work out?
10. How much time do you spend emailing on a given day?
Besides if you do have any questions give me a call: https://clarity.fm/joy-brotonath