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How To Negotiate A Windows 10 Or Office 365 Migration Deal With Your System Integrator

On January 14th, 2020, the extended support for Windows 7 ends, which means that enterprises have about 26 months to fully roll out Windows 10. Similarly, Microsoft expects that at least two-thirds of its Office business customers will move to Office 365 by fiscal year 2019. Since a migration project of that size will take, on average, more than 124 man weeks to complete, it is about high time to get serious about upgrading!

According to our own research, only 44% of organizations are set on managing this IT Transformation internally; 28% are about to issue a Request-for-Proposal, 14% have not decided yet, and 14% have already engaged with a service integrator to outsource this massive project.

So whether you have already engaged with a service integrator for another managed service, or you have realized that you don’t have the required resources or skills in-house, you will need to negotiate a deal with them. Done right, a project delivered by a service integrator can bring skills, experience, methodology and lower risk. Below, we outline the six most important factors in driving a successful negotiation for your Windows 10 or Office 365 project.

How To Negotiate A Windows 10 Or Office 365 Migration Deal With Your System Integrator

1) Don’t Engage A System Integrator Before You Know What You Are Engaging Them For

While it seems tempting at first to send out a bunch of requests-for-proposal, select a vendor and let them deal with scoping the exact proportions of the project, it is beneficial to have both sides involved knowing what they are signing up for.

Before even considering an RFP, you need to create what I call a "Plan for the Plan". This should include the following components:

  • Engineering
  • Application packaging
  • Project management
  • Infrastructure
  • Deployment logistics
  • End-user communications & training

Of course, it is prudent to start thinking about what budget, in-house skills and resources you have to work with as you decide which of these areas you want to keep in-house and which ones you would consider outsourcing. Also, you need to know what kind of timeline you require this project to be completed by.

You will want to answer some difficult questions before engaging with an SI. For example:

  • How many devices and applications are in scope for the project?
  • What are your device refresh criteria, and based on that how many PCs will need to be replaced as part of this migration project?
  • How many applications will require additional testing and re-packaging?
  • How much of your application estate is already rationalized and compatible?
  • What does your application rationalization and packaging as well as your deployment strategy look like?
  • Are there any big rules that you need in place for directing the project?

To get answers to these questions, you will need an IT Transformation management tool like Juriba Dashworks that can be hooked up to all your internal desktop management systems, feeds and other data sources to give you an accurate picture of your current estate within hours.

Dashworks 5.1 screenshot #1.png

You could even give your final vendors access to the dashboards to level the playing field and ensure an open line of communication. Sometimes the service integrator will offer something like an assessment service to harvest and present this information back to you. We highly recommend this approach as it will give you a common set of data from which to start negotiations.

2) Know What Role You Want The Service Integrator To Play

Now that you understand the scope of your project, you will need to decide what role you would like the service integrator to play. Are you bringing them in purely in an advisory role to help you plan, do you need additional resources to get the job done under your guidance, or do you want them to handle either pieces of, or the entire migration themselves?

If you are planning to engage a new service integrator, understanding the intended role is the key to a successful RFP process. Every service integrator has slightly different strengths and weaknesses that they bring to the table, and knowing the request scope will help you narrow down the list of outsourcing vendors you might like to receive a proposal from. Ask yourself this: would I feel more comfortable with one of the big players or more of a niche player? Whom have we dealt with before that would be up to the task?

If you are already working with an integrator for managed services, you might have built this update project into your contract. However, we still advise you look at how the roles split out between what you need to do to ensure success, and what they do.

3) Ask Them About Their Detailed End To End Methodology & Tooling

As you go through the RFP process, you will hear a lot of sales pitches and flashy presentations. Service Integrators will typically bring their 'A' team to the pitch and solution proposal. To ensure you are setting your project up for success, we advise drilling deeper into the actual methodology and approaches used.

To get better insights into what your potential working relationship might look like, ask them:

  • How are you planning on gathering inventory?
  • What does your 30/60/90 day plan look like?
  • What is the methodology framework you use?
  • How do you structure your project management office?
  • Where in the migration process do you recommend using automation and how?
  • What is your best practice around tooling? Have you used this particular tool set in past engagements? Is this part of your routine process? Does the tooling stay for the next change project, or does it expire?
  • How are you planning to phase the deployment in terms of roll-out? (e.g., How can you determine the lowest hanging fruit, and how do you constrain capacity?)
  • Is there an option for self-service to enable my employees to take an active role in the project and how do you recommend end user engagement throughout the project lifecycle?
  • Whom do you work with in terms of hardware vendors if you are planning to do a larger hardware refresh?
  • How do they recommend that you will work together? Steering committees, PM face-off?
  • How will they report on every aspect of the project? How transparent do they intend to be?  Is there any real-time reporting?

The point here is to really understand whom you are going to be working with and how they operate. That’s an important step in those discussions. Too many projects are won on presentation and price alone. Get to the bottom of 'how' they are going to manage your project, and what innovation and best practices they are bringing to the table.

4) Look For Automation & Cost Saving Potentials

You will want to find the service integrator that has a strategic, well-thought out methodology that leverages automation and data insights wherever possible. For example, can they automate the heavy lifting, including scheduling and email communication with end users, will they automate deployment and what is their process to do this, or do they need to pay dozens of resources to do it for them? Do you need to provide an army's worth of desk space, or are they running the project efficiently with a small layer of staff?

Give bonus points to vendors who suggest using an IT Transformation Management tool, like Dashworks, as a central command & control platform. Normally, you will have to acquire the licenses for any tooling used, so be sure to ask for the cost involved, if they have pre-negotiated rates with the tooling manufacturer and whether or not you can leverage the solution after the initial migration to manage your Windows 10 Servicing and Office 365 Update cycles.

Unfortunately, some service integrators still pitch people and process, not people, technology and process, so be prepared for spreadsheet hell, and hand-cranked databases. Mark these ones down - they are dinosaurs! Don't accept that throwing people at this project is the right way to go.

5) Understand The Cost Involved & Decide What Pricing Structure Would Suit You

One of your biggest consideration points is probably pricing. Usually, the most common ways to determine the cost of this type of migration project are either a Travel & Expense type pricing model or a fixed dollar per desktop/user cost.

The compensation model you choose will greatly depend on the project scope. For example, if you are only planning to outsource the deployment element, then you will want to approach them differently from another company who is looking to use outside help for application packaging or outsource the whole lot.

It is worth noting that, typically, a fixed project price will offset most of the risk onto the service integrator. Since they are the ones hiring the resources and providing the service, they carry most of the responsibility and should carry the risks involved. This will protect you from having to sort out a budget mess should progress stall down the road.

When negotiating your price, keep in mind that the system integrator also needs to make a profit on this project, so be prepared to give a little here. They will slap a profit margin on whatever they think the actual costs of the migration will be, and consequently, it will always look more expensive than running it internally. But the value is in the people, technology and processes they will bring to the table, especially if you do not possess the skills in house, nor are prepared to take a punt on buying the skills in from the street and managing it yourself.

If you heed the advice earlier, you will have a clear understanding of the current and target state of your IT landscape which will enable the vendor to more accurately determine the baseline costs.

In a fixed price deal, as the integrator will carry the risk (and they may not know what they will see once they lift up the hood), they need to account for those potential snags somehow — and usually that will be in the price you pay. Also, be prepared to get what you pay for. If you are going for the cheapest option, you could end up paying much more down the road because the delivery may not be quite as good as those that charge a higher amount.

Still. avoid overpaying or having to bump up the project later on to keep on track.  If you can agree a sensible price that mitigates risk, brings the right solution framework and provides scope for a good profit margin for the integrator if run successfully, then you have a win-win situation.

6) Be Crystal Clear In Your Contracts

Once you have down-selected and chosen the individual outsourcer that you want to move forward with, you will have to go through the contracts.

From my experience, it is only in the best interest of both parties involved to be as concise and precise as possible — spelling out what you’re going to do and what they’re going to do. Otherwise, you’re going to end up in change control for the next two years while you argue whether it was or wasn’t in the scope of the project.

Be prepared for this phase to take two or three times longer than you had planned for. The lawyers are notoriously slow when it comes to the finer detail, so projects often find that they are months behind before they even start, simply because the end goal posts didn't move, but this process took longer than expected.


To summarize: do your homework, be prepared and know what you want. Knowing the scope of the project, how you would classify your devices for refresh, how you would phase your roll-out and so forth will help you anticipate a lot of the problems. The most successful projects are those where all parties can collaborate effectively within a transparent project framework.

While you won't be able to foresee every hurdle, it is well worth doing your due diligence ahead of negotiations as service providers, no matter how good they are, need to understand your specific IT environment and processes. They need to get some in-house knowledge into their teams, especially if they’re a brand new outsourcer. It's foolish to expect them to come in and just know everything about your business, so make sure you allocate plenty of time to bring them up to speed, just as you would a new employee.

Finally, look for automation and cost saving potential. Setting yourself up for a seamless update management after the initial rollout of Windows 10 and Office 365 is just as important as a swift and well-managed migration. You can do so by implementing the right tooling, such as Dashworks, and by creating an agile and repeatable project framework methodology.

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