There's a reason why so many technology projects at firms end in failure or disappointment. And it's usually not the technology itself.
It's that nobody asked the right questions before starting.
The vendor showed an impressive demo. Everything seemed simple, fast, almost magical. The contract was signed with enthusiasm. And six months later, the system is half-implemented, the team uses it reluctantly, and nobody is clear whether it was worth it.
This article isn't meant to sell you anything. It's meant to help you not make a mistake when someone tries to sell you something. The questions you should ask before signing anything, and that many providers prefer you don't ask.
Questions about the real problem
Before talking to any provider, the most important conversation is with yourself.
What specific problem am I trying to solve?
"I want to automate" isn't a problem. It's a solution looking for a problem. The real problem is specific: "My team wastes 10 hours a week chasing documents that clients don't send" or "Deadlines slip through because we depend on an Excel spreadsheet that nobody updates on time."
If you can't describe the problem in one concrete sentence, you're not ready to look for solutions.
What does success look like?
Imagine six months have passed and the implementation was a total success. What exactly has changed? What is your team doing differently? What did they stop doing? What can they do now that they couldn't before?
If you don't have clarity about the after, it's very hard to evaluate whether a solution gets you there.
Do I really need technology for this?
Sometimes the problem isn't lack of tools. It's lack of process. I've seen firms that wanted a sophisticated document management system when what they needed was to agree on how to name files and where to save them.
Technology amplifies what already exists. If the process is a mess, automating it just gives you a faster mess.
Questions about implementation
This is where pretty demos crash into reality.
How long does it really take to implement this?
Not the time that appears in the brochure. The real time, with a firm like mine, considering that my team has other things to do besides learning a new system.
Distrust anyone who gives you an overly precise answer without knowing your situation. And distrust even more answers that are too optimistic. If they tell you "it'll be running in two weeks," ask how many of their clients actually achieved it in two weeks.
What do I need to contribute?
No implementation works by itself. Someone on your team will have to dedicate time to configure, test, give feedback, train the rest. How much time? What type of person? Can you afford it right now?
If the provider tells you that you don't need to do anything, they're lying or the system is so generic that it probably won't adapt to how you work.
What happens with my current data?
You have years of information in spreadsheets, folders, emails, previous systems. How does that get migrated? Does the provider do it or do you? Is there additional cost? How long does it take?
Data migration is where many projects get stuck. And it's what gets discussed the least in sales meetings.
Does it integrate with what I already use?
Your firm already has tools: email, calendar, billing software, cloud storage. Does the new solution talk to them or is it going to be another island in your archipelago of systems that don't connect?
Specific questions: Does it integrate with Gmail/Outlook? With my billing system? With my storage in Drive/Dropbox? If the answer is "we're working on that," consider that today it doesn't exist.
Questions about the day after
The sale ends when you sign. Reality starts after.
What happens when something fails?
Because something will fail. Is there support? What hours? In what language? Through what channel: email, phone, chat? How long do they take to respond?
Ask for concrete data. "We have excellent support" means nothing. "We respond in less than 4 hours by email Monday through Friday" means something.
Who keeps this running?
Once implemented, does the system run by itself or does it need regular attention? If adjustments need to be made, can I do them myself or do I depend on the provider? Is there additional cost for changes?
Some systems require a technical profile for any modification. Others give you autonomy. Knowing this beforehand saves you surprises.
What happens if I want to leave?
Nobody asks this question and everyone should. If in a year you decide it doesn't work for you, can you get your data out? In what format? Is there an exit cost?
Getting trapped with a provider because migrating is too complicated is more common than it seems.
Questions about real costs
The price they give you is only part of what you're going to pay.
What does and doesn't this price include?
Implementation, training, support, updates, integrations. What's included in the price you're giving me and what's charged separately?
Ask them to put it in writing. Surprises on invoices are one of the main sources of frustration with technology providers.
How much of my team's time is this going to cost?
Your team's time has value. If implementing requires your best person to dedicate 20 hours over a month, that's a cost. If the learning curve is long, that's a cost. If the system creates friction and people take longer to do things during the first months, that's a cost.
Ask the provider how much time their clients typically dedicate to implementation and training. If they don't have data, ask yourself why they don't.
What's the total cost of the first year?
License, implementation, training, integrations, your team's hours. Add it all up. That's the real number. Compare it with the benefit you expect to get. Does it make sense?
The most important question
Before talking to any provider, ask yourself this question:
Am I looking for a tool that solves a problem I'm clear about, or am I looking for someone to convince me that I need something?
If it's the latter, wait. Spend time understanding your processes, identifying where you lose time, where you make mistakes, where your clients experience friction. When you have that clear, finding the right solution is much easier.
And when you talk to providers, remember: their job is to sell. Your job is to decide well. They're not the same thing.
Want help identifying which problems at your firm really justify an investment in automation? We can help you make that diagnosis before you talk to any provider.