4 Questions to Ask Yourself About Your Business's AI Implementation Readiness

4 Questions to Ask Yourself About Your Business's AI Implementation Readiness

4 Questions to Ask Yourself About Your Business's AI Implementation Readiness

May 14, 2025

4 Questions to Ask Yourself about AI Implementation Readiness

Though it might feel like a one-time cost to hire an agency or a freelancer to build out AI workflows, automations, and AI agents, maintaining software is actually a long-term commitment, like a new plant or a pet. Here are some questions you should ask before starting a project, and ways to make the commitment feel easier:

  1. Are you sure that you’re automating the right workflow?

This is harder to determine than you think. 

In the software industry, we’ve created an entire profession who communicates between operators and software engineers, translating business needs into viable, minimal technology build-outs (product managers, like me in my former corporate career). 

You need to have a back-and-forth with the team you engage on why this particular workflow is troublesome, especially in the context of business goals. 

A smart, savvy team will help you redesign your workflows so that they’re simpler, while meeting your goals – which seems to be at odds with any hourly-priced work.

  1. Who on your internal team will be doing the monitoring, making sure that the automations are still working correctly?

This sounds like a simple “is it working or not” question, but imagine a scenario when an automated workflow aggregates data across a few different sources, and then does AI analysis on the aggregations. 

One of the underlying report structures changes. 

The data either shows up blank, skewing your AI analysis, or shows different data points than you intended.
On the surface, it looks like the analysis is still working as intended, so you’re not actively troubleshooting, and you’re making business decisions on bad data now. 

(This happens all of the time with unmonitored software.)

  1. Is there a budget to rework the flows when you change your business processes? 

If there is: expect to budget a similar amount of money to rework the flows.

If there isn’t, here’s what happens:

You outgrow this automation, but do process acrobatics to make this work.

You get to the point where working around this automated process is more painful than doing it manually again, so you abandon the automation.

  1. What happens when the flow inevitably breaks?

Maintain a backup plan, like a manual SOP, and make sure that your team is both up-to-date on training and ready to pick up the process when the flow breaks. 

And, of course, add some budget to pay to fix it.

How to sustainably implement AI and automation in your business

Hourly-based freelancer work is not the solution. Instead, here are two ways you can strategically implement AI in your business.

Look for a hosted SaaS solution. 

We offer “service as a software” at Crafty Crow – featuring a unique, value-based monthly pricing model, customization to your needs, and extremely good customer service (yes, we’re on Slack!). We partner together to automate your workflows so that they fit into your business processes, monitor and maintain your flows, and even update them as your business changes, for no additional cost. 

Upskill team members with an interest in AI and automation.

You can also bring basic capabilities in-house (no, you won’t be able to “vibe code” self-driving car software or financial automations without working with a software professional). Expect to allocate 20% of their time to learning these skills.

If you don’t know where to start, our founder hosts a live, cohort-based course on Maven that teaches operators to create automation and AI flows to save 20+ hours a week, no coding experience needed. It features hands-on learning and generous amounts of office hours and async instructor feedback to work on your real work problems. Sign up here to join a future cohort.

4 Questions to Ask Yourself about AI Implementation Readiness

Though it might feel like a one-time cost to hire an agency or a freelancer to build out AI workflows, automations, and AI agents, maintaining software is actually a long-term commitment, like a new plant or a pet. Here are some questions you should ask before starting a project, and ways to make the commitment feel easier:

  1. Are you sure that you’re automating the right workflow?

This is harder to determine than you think. 

In the software industry, we’ve created an entire profession who communicates between operators and software engineers, translating business needs into viable, minimal technology build-outs (product managers, like me in my former corporate career). 

You need to have a back-and-forth with the team you engage on why this particular workflow is troublesome, especially in the context of business goals. 

A smart, savvy team will help you redesign your workflows so that they’re simpler, while meeting your goals – which seems to be at odds with any hourly-priced work.

  1. Who on your internal team will be doing the monitoring, making sure that the automations are still working correctly?

This sounds like a simple “is it working or not” question, but imagine a scenario when an automated workflow aggregates data across a few different sources, and then does AI analysis on the aggregations. 

One of the underlying report structures changes. 

The data either shows up blank, skewing your AI analysis, or shows different data points than you intended.
On the surface, it looks like the analysis is still working as intended, so you’re not actively troubleshooting, and you’re making business decisions on bad data now. 

(This happens all of the time with unmonitored software.)

  1. Is there a budget to rework the flows when you change your business processes? 

If there is: expect to budget a similar amount of money to rework the flows.

If there isn’t, here’s what happens:

You outgrow this automation, but do process acrobatics to make this work.

You get to the point where working around this automated process is more painful than doing it manually again, so you abandon the automation.

  1. What happens when the flow inevitably breaks?

Maintain a backup plan, like a manual SOP, and make sure that your team is both up-to-date on training and ready to pick up the process when the flow breaks. 

And, of course, add some budget to pay to fix it.

How to sustainably implement AI and automation in your business

Hourly-based freelancer work is not the solution. Instead, here are two ways you can strategically implement AI in your business.

Look for a hosted SaaS solution. 

We offer “service as a software” at Crafty Crow – featuring a unique, value-based monthly pricing model, customization to your needs, and extremely good customer service (yes, we’re on Slack!). We partner together to automate your workflows so that they fit into your business processes, monitor and maintain your flows, and even update them as your business changes, for no additional cost. 

Upskill team members with an interest in AI and automation.

You can also bring basic capabilities in-house (no, you won’t be able to “vibe code” self-driving car software or financial automations without working with a software professional). Expect to allocate 20% of their time to learning these skills.

If you don’t know where to start, our founder hosts a live, cohort-based course on Maven that teaches operators to create automation and AI flows to save 20+ hours a week, no coding experience needed. It features hands-on learning and generous amounts of office hours and async instructor feedback to work on your real work problems. Sign up here to join a future cohort.

4 Questions to Ask Yourself about AI Implementation Readiness

Though it might feel like a one-time cost to hire an agency or a freelancer to build out AI workflows, automations, and AI agents, maintaining software is actually a long-term commitment, like a new plant or a pet. Here are some questions you should ask before starting a project, and ways to make the commitment feel easier:

  1. Are you sure that you’re automating the right workflow?

This is harder to determine than you think. 

In the software industry, we’ve created an entire profession who communicates between operators and software engineers, translating business needs into viable, minimal technology build-outs (product managers, like me in my former corporate career). 

You need to have a back-and-forth with the team you engage on why this particular workflow is troublesome, especially in the context of business goals. 

A smart, savvy team will help you redesign your workflows so that they’re simpler, while meeting your goals – which seems to be at odds with any hourly-priced work.

  1. Who on your internal team will be doing the monitoring, making sure that the automations are still working correctly?

This sounds like a simple “is it working or not” question, but imagine a scenario when an automated workflow aggregates data across a few different sources, and then does AI analysis on the aggregations. 

One of the underlying report structures changes. 

The data either shows up blank, skewing your AI analysis, or shows different data points than you intended.
On the surface, it looks like the analysis is still working as intended, so you’re not actively troubleshooting, and you’re making business decisions on bad data now. 

(This happens all of the time with unmonitored software.)

  1. Is there a budget to rework the flows when you change your business processes? 

If there is: expect to budget a similar amount of money to rework the flows.

If there isn’t, here’s what happens:

You outgrow this automation, but do process acrobatics to make this work.

You get to the point where working around this automated process is more painful than doing it manually again, so you abandon the automation.

  1. What happens when the flow inevitably breaks?

Maintain a backup plan, like a manual SOP, and make sure that your team is both up-to-date on training and ready to pick up the process when the flow breaks. 

And, of course, add some budget to pay to fix it.

How to sustainably implement AI and automation in your business

Hourly-based freelancer work is not the solution. Instead, here are two ways you can strategically implement AI in your business.

Look for a hosted SaaS solution. 

We offer “service as a software” at Crafty Crow – featuring a unique, value-based monthly pricing model, customization to your needs, and extremely good customer service (yes, we’re on Slack!). We partner together to automate your workflows so that they fit into your business processes, monitor and maintain your flows, and even update them as your business changes, for no additional cost. 

Upskill team members with an interest in AI and automation.

You can also bring basic capabilities in-house (no, you won’t be able to “vibe code” self-driving car software or financial automations without working with a software professional). Expect to allocate 20% of their time to learning these skills.

If you don’t know where to start, our founder hosts a live, cohort-based course on Maven that teaches operators to create automation and AI flows to save 20+ hours a week, no coding experience needed. It features hands-on learning and generous amounts of office hours and async instructor feedback to work on your real work problems. Sign up here to join a future cohort.

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Crafty Crow

AI agents and workflow automation SaaS for Operations teams

Crafty Crow

AI agents and workflow automation SaaS for Operations teams

Crafty Crow

AI agents and workflow automation SaaS for Operations teams