This past December, my wife and I decided to get an Amazon Echo for a family Christmas present. Unfortunately we didn’t make that decision early enough to beat the holiday shopping rush– Amazon sold out of the Echo before we got around to ordering one. To top it off, that shortage quickly spread to all the local retail outlets that normally carry the Echo. An internet search revealed that there were no Echos within a 250-mile radius of my home. A notice on the Amazon site said that the Echo would not be in stock until the end of January. So we put our plans on hold.

We recently received our Amazon Echo and are really enjoying learning all the things that it can do.

While this article isn’t about the Echo, I bring it up because while I was waiting for my unit to arrive, I was reading everything I could find about it on the Web. As I did, my interest in digital assistants was reinvigorated and I delved back into investigating Cortana on my Windows 10 system. I had played around with it a couple of times in the past, but since I have an iPhone, I use Siri for directions, weather, reminders, music, and impromptu internet searches. I never really found it compelling to use Cortana for those types of things while sitting at my desk.

However, I decided to give Cortana a second chance and found that she does a nice job of providing me with the same types of features that I’ve grown accustomed to with Siri on my iPhone. Now, I haven’t yet attempted to add Cortana to my iPhone, but I just might do that sometime.

While I exploring Cortana’s functionality, I began focusing on the things she could do that would help me automate some of the file management tasks I normally perform on my desktop system, such as opening folders, launching applications, and finding files. I was a bit frustrated at first, but I soon discovered a few neat tricks I could use to get Cortana to expand her horizons. Let’s take a closer look.

SEE: Microsoft Cortana: The smart person’s guide

Activating “Hey Cortana”

To make this this endeavor work, you must enable the “Hey Cortana” feature. If you haven’t already done so, you’ll need to follow these steps. To begin, click the Search box to the right of the Start button. When the search panel appears, click Settings, as shown in Figure A.

Figure A

Click Settings in the search panel.

When the Settings window appears, turn on the Hey Cortana option, as shown in Figure B.

Figure B

Turn on the Hey Cortana setting.

Throughout the rest of this article, I’ll assume you know that all of the verbal commands I describe begin with my saying, “Hey Cortana.”

SEE: Amazon Alexa: The smart person’s guide

Launching applications

I found that for the most part, Cortana is quite adept at launching applications. For example, to run Microsoft Word, you say, “Hey Cortana” and then say one of the following:

“Open Microsoft Word”


“Launch Microsoft Word”

Immediately, Cortana will respond audibly while providing a visual, like the one shown in Figure C.

Figure C

Cortana will let you know audibly and visually that she is launching the requested application.

Sometimes when you ask Cortana to launch an application, she has trouble interpreting your request. For example, when I asked her to “Open Notepad,” she prompted me identify which one I wanted, as shown in Figure D. So I’d have to click one, which sort of defeats the purpose.

Figure D

Cortana never could figure out which Notepad I wanted.

This became frustrating as after so many times, I had hoped that she would learn that regular Notepad was my preferred choice, but that never happened. And when I asked specifically for Notepad++, she would launch Microsoft Edge and initiate a Bing search for Notepad++. I’ll keep working on this one and let you know if I find a solution.

SEE: How to control your Windows 10 PC using VoiceAttack

Searching for documents

Cortana is really good at searching for files on my Windows 10 system. I suppose that’s not all that surprising since she lives in the search area. To have Cortana search for files, you can use either the “Find” or “Show me” command. For example, I discovered the following commands useful in tracking down files on my Windows 10 system:

“Show me recent documents”

“Find the {document name} document”

“Find the {document name} PowerPoint”

“Find the {document name} PDF”

“Find the {document name} text file”

“Find documents named {any word in a document name}”

“Find PDF files”

“Find Excel files”

“Find PowerPoint files”

“Find text files”

However, no matter how I tried to phrase it, I could not get Cortana to find any image files, such as JPG, PNG, GIF, or BMP. I’ll keep working on this one and let you know if I find a solution.

SEE: Microsoft wants to make conversing with your computer the new normal

Opening folders

Opening folders is a pretty standard file management task. But no matter what I tried, I couldn’t get Cortana to open specific folders. Of course, I could easily have Cortana launch File Explorer with the command:

“Launch File Explorer”

I just couldn’t get Cortana to understand that I wanted to open a certain folder. Heck, I couldn’t even get Cortana to open standard folders, such as Documents or Pictures.

However, after doing a ton of research on the internet and performing a number of experiments, I discovered that I could get Cortana to run shortcuts if they were placed in the following folder:

C:\ProgramData\Microsoft\Windows\Start Menu\Programs

Once I found out that fact, it was easy figure out that if I created a shortcut to a folder, configured it just right, and then moved it into the Programs folder; I could get Cortana to open any folder I wanted. And indeed that turned out to be the case. But in between, there was a lot of trial and error in choosing a shortcut name that both made sense to me and that Cortana could recognize. This is definitely a situation where persistence pays off.

I created shortcuts to several folders and renamed the shortcuts with simple names and then tried to get Cortana to open them. Even when I did choose a perfect shortcut name, it took several attempts before Cortana learned what I was asking her to do. If after three or four attempts, Cortana still wasn’t opening the folder, I renamed the shortcut and then tried again.

With that in mind, let’s take a look at the procedure you’ll need to follow to create the shortcut.

Creating the folder shortcut

To begin, locate the folder you want to be able to access via Cortana. Right-click the folder and select the Send To > Desktop (Create Shortcut) command from the context menu, as shown in Figure E.

Figure E

Create a shortcut to your folder.

Next, rename the shortcut and move it into the C:\ProgramData\Microsoft\Windows\Start Menu\Programs folder, as shown in Figure F. Keep in mind that to locate this folder path, you’ll need to enable the Show Hidden Files, Folders, Or Drives setting in Folder Options. In this particular instance, I ended up renaming the shortcut CurrentWork, which worked for both Cortana and me.

Figure F

Move the shortcut from the desktop into the Programs folder.

When you drop the shortcut into the Programs folder, you’ll be prompted to provide administrator permission, as shown in Figure G, since the Programs folder is a hidden system folder. Just click Continue.

Figure G

You’ll be prompted to provide administrator permission.

Now, you’ll need to access the shortcut’s Properties dialog and fill in the Start In text box by typing the path to the Programs folder, as shown in Figure H.

Figure H

Type the path to the Programs folder in the Start In text box.

Be sure to enclose the path in double quotes:

“C:\ProgramData\Microsoft\Windows\Start Menu\Programs”

Since the Programs folder is a hidden system folder, when you click OK, you’ll again be prompted for administrator permission, as shown in Figure I. Just click Continue.

Figure I

You’ll be prompted to provide administrator permission.

At this point, ask Cortana to launch the shortcut using the “Open” command. For example, I used the command:

“Open CurrentWork”

The real benefit

Having Cortana at my beck and call to perform some standard file management tasks really does have its benefits. For instance, now when I walk into my office, I start giving Cortana commands even before I sit down at my desk. For instance, I’ll say:

“Open CurrentWork”

followed by

“Launch Microsoft Word”

Then when I sit down, everything is ready for me to get to work. I know it may sound kind of goofy, but hey, isn’t technology great?

Also see…

What’s your take?

Are you using Cortana? Have you had her perform file management tasks? Share your experiences with fellow TechRepublic members.