Working with a client's Windows-only tools.

Resist the urge to say yes and figure it out later. A few questions at the start save a great deal of trouble. Which programs exactly, and which versions? Do they hold the licence, or do I need my own? Will I connect to their network, and if so, how? Where may their files be stored?

Often the real need is smaller than the first email suggests. You might need one reporting tool and a spreadsheet, not the whole stack. Knowing that opens up lighter options.

Clients tend to offer one of these, and it helps to recognise them.

• They give you a laptop. Simple for them, awkward for you: another device, another set of updates, and a machine to return.
• They give you remote access to a machine on their side. Clean for them, but you depend on their setup and their support.
• You bring your own solution. Most flexible, but you need to show it is secure enough for their data.

From a client's point of view, the risk in an outside contractor is data landing on a personal device. If the program and its files live on a Windows machine that is not your laptop, much of that worry goes away. The picture reaches you, but the files stay where they are.

That makes the conversation easier. You are not asking to copy their data to your laptop. You are asking to use a tool in a way that keeps data off it, which is usually what their security person wanted anyway.

Settle early who holds the licence for their software. If it is theirs, they may need to add you as a user or approve remote use. If it is yours, check that its terms allow the way you plan to run it. Put the answer in your statement of work so nobody is surprised at invoice time.

Do not forget Windows itself, which your remote machine needs a valid licence for. A service that provides the machine handles that for you.

Before you start, write down the answers to these and share them with the client.

• The programs and versions you will use.
• Who holds each licence.
• How you will connect, and whether a VPN is required.
• Where client files will live, and where they will not.
• How access ends when the engagement does.

When the work finishes, close the loop. Remove your access, confirm no client files remain on any device you own, and tell the client in writing. It is a small courtesy that makes clients remember you well and call you again.