The best way to play a video in a Skype for Business meeting is to insert it in a PowerPoint slide, then upload the PowerPoint to the meeting.
Note: We recommend that video files be less than 50 MB. See Compress the media files in your presentation to solve the issue.
Insert the video in PowerPoint
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Open PowerPoint in Normal view.
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Click the slide that you want the video to be in.
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On the Insert tab, click the arrow under Video, and then click Video on My PC.
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In the Insert Video box, double click the video that you want to insert in the slide.
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Save your PowerPoint file.
Upload the PowerPoint in Skype for Business and play the video
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In your Skype for Business meeting, click the presentation (monitor) icon, and click Present PowerPoint Files.
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Find your presentation and double-click it to upload it to the meeting.
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Go to the slide that contains the video, then pause on (hover over) the video to unhide the video controls:
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Click Play to start the video and then Pause to stop.
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Click the speaker icon to change the volume or mute/un-mute the audio.
Important: The audio plays for participants who use computer audio, but not for people on the phone.
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Use the annotation tools on this slide, just like any other slides.
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You can also press F5 on your keyboard to go to full screen.
