After 25+ years in this industry, here are two questions I would tell a good friend to ask if he was evaluating a custom development project.
"Can you show me something similar you've done before and tell me how much it cost?"
When you hire someone to build a house and know that all the similar houses on the street are $250,000, yet yours comes in at $700,000, you know something is wrong. Why? Because everyone knows how much houses cost, at least roughly. People generally don't know what CRM systems cost or what custom software costs.
If someone tells me they paid $50,000 and I could have done it for $5,000, I know they have been taken advantage of because they didn't know what it should cost before they started.
Generally, I see the expensive software coming from IT firms, likely because they think it is normal. Most “IT people” aren’t business people. They are thinking in terms of the latest and greatest of what's out there. Not what will work and is still affordable.
A $750,000 house probably has all kinds of fancy add-ons, but did the developer ask if you would have been just as happy with the $250,000 version?
Shop around, know what the project should cost. Then ask the developer to tell you about projects they have done at that cost.
"How would you do it if this was your company?"
I love when people ask me is how I would do it. It is easy for me to answer because almost everything I do for others is the same thing I do it for my own business. If we talk about email provider integration to
Even if you want to do something that has nothing to do with my business, asking this question still has value. I think it causes us all to take a step back and think, "Hmm, how would I do it? I know I'm telling you to spend a $25,000. Would I do that?"
This is the advice that I would give a good friend if he or she were trying to choose a software development partner. I am always happy to answer questions like this, openly and honestly.