What lessons have you learned from implementing major projects that revamp the entire business process?

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Director of IT in Software, 1,001 - 5,000 employees
I think there are two major themes in every implementation that I've driven. One is that stakeholders are at the core of your success and without enabling the stakeholders, your tool and all of your investment is worthless. You can put together the best in class implementation team and have a perfectly configured system but then, day one, you turn that on and they're like, “What is this? This is not what we wanted.”  If you don't show them how to use it properly, they're never going to adopt it and you just add to your tech debt.
Head of Business Technology in Software, 201 - 500 employees
I get a pulse from the stakeholder. Are they really feeling the pain? If they're just talking the talk but they're not willing to walk the walk, then there is no meaning in doing this. If they're really crying out loud and without this initiative taking place, there is no way the company can grow and succeed, then we have a real business case to go after. It goes back to stakeholder engagement. They must have put the resources in place and then continue to give the requirements to drive that.  But what I felt the most important thing is that, in things like the implementation of Salesforce or any HR system, the work is really done by the end users. You have to establish your change management from day one, informing the people on the floor about what is coming their way and how that would change their role. If they are not engaged from day one it could quickly turn the project into shelfware.  You’ll find yourself talking to 500 people to convince them that this is all you need to do, but there might be a gap between what their manager is thinking and what they are thinking. That's a big part of the puzzle. The second important piece was the data, because when you are doing these huge transformation initiatives across the organization, the systems, processes, technology, and policies built today are not going to be the same in the future, so there is data change. New policies are implemented. New processes are implemented. Now all of a sudden it sounds like their work will increase by X factor. So my focus is engaging the stakeholders so that not only do they agree, but they're also ready to put the money and resources towards that.  Underlying all that is a technology team to look at the data we are going after, and figuring out if data can even fit in the new world or if I need to enhance the data? Those are the things I normally look at. It has given me an edge when I implemented bigger initiatives.
Sr Director Bus Ops & SW Transformation in Software, 5,001 - 10,000 employees
I start with: what are your tenets or what are your guiding principles? What are you really looking to solve? I think this goes a long way in terms of 1) having those key stakeholder discussions; 2) once you're actually done with the implementation, how does that translate into metrics and reporting out what has been achieved by that project or by that implementation? For me, establishing the foundational principles or the guiding principles right up front is super important. The second piece of this is... I fully subscribe to the 80/20 rule where a lot of us go into projects or programs looking to solve world hunger, which is not going to happen. We need to understand that whatever we're trying to do, let's focus on 80% of the use cases, and not more. In my experience, we spend 80% of our energy trying to solve 20% of the use cases, not the opposite.  So let's focus on the big wins and solve for that through the project. The last thing is feedback. I’ve benefited from not only stakeholders’ perspectives but actually involving my sales reps, channel partners, whoever I’m doing the program for, throughout each stage of the program. NOT waiting until you're ready to go live, because that actually might be too late. It's better to start right at the beginning in terms of getting feedback. What's working, what's not working? What do you want to see change? And then as you’re designing and building, have that iterative agile process where you have identified 5 or 6 champions that you bring to the table at regular intervals, get feedback, and then you use those 5 or 6 champions to actually do the job for you in terms of change management.  That helps deliver the message.

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Chief Technology Officer in Software, 51 - 200 employees
My personal experience. 

I usually get the feedback and go back with data driven analysis providing details to cross leaders to understand the context and make decision basis data and and not gut feeling. 
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CTO in Software, 201 - 500 employees
Without a doubt - Technical Debt! It's a ball and chain that creates an ever increasing drag on any organization, stifles innovation, and prevents transformation.
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