What are some challenges that get in the way of your automation projects or initiatives, and how do you overcome them?
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Agreed. When there’s so much change happening it can be frustrating and deflating for a lot of folks especially if the purpose for change hasn’t been communicated or if embracing change isn’t part of the culture. That said, even positive change time and energy over time.
On the technical side, the primary challenges are skills shortage, having/choosing the right tool. From a business/implementation side  is getting other teams/departments onboard, automation sometimes can be seen and making someone function redundant so it can be tricky to get a stakeholder(s) buy-in
We definitely see some of those aspects too. How have you seen success in getting stakeholder buy in?
The success depends on how well you position/present it. If you position IT/Automation as their helper and say that IT has a way to speed up the process so they can do more at the same time (it helps if you know a few other tasks that they struggle to do on time so you can put them as examples that this way they will have time to finish X, Y and Z on time) vs. hey, we can scrip it so it's done automatically (which is implying that, well we don't need you or you have no skills/additional value. I get the information from the employees that do the work i.e get the facts and what is their challenge but then talk to the department head on the topic of how can IT help you and your team. Once you have a buy-in from the department head, you identify champion in the department, someone that is usually exited for trying new things, energize that person and let him spread the word and awesomeness of the automation to the team<br>
The biggest challenge of an automation project is acceptance. The way automation is getting branded as a tool of eliminating people or reducing headcount is not right. This infuses insecurity in the mind of people about their job. Just imagine we are planning to sit with the process SMEs to understand their work, from them, with an idea of replacing them. To make RPA successful we should start with educating people about the advantages of RPA. The approach which I take is to explain to the user base that Automation is there to augment with them not to eliminate them. We need to conduct a lot of awareness workshop to build modernization advocates and promotors within the organization. This is a task of whole organization and not a KRA of certain set of people.

Having so many, it can be tough to keep buy-in when change fatigue starts to rear its head.