Hmmm. I would take that video with a massive pinch of salt. YouTube is opinion, rarely is it fact.

You never own software, you buy a license to use it.

So much of this resonates with me. I didn’t get in to design to do business

Speak their language and start with common themes;

• Hierarchy
• Pace
• Space
• Ratios
• Grid
• Typography
• Colour
• Legibility / accessibility

Highlight what's different

• Fluid canvas (no fixed size, people scroll)
• Layout needs to accommodates various devices (responsiveness)
• Interactions
• Think journeys rather than pages
• Being modular

Learn from others

• Observe design choices
• Get them to think about their own online experiences
• Study design guides and how they're applied

Just do

• Apply what they already know
• Experiment with the bland and the bold
• Think beyond a flashy landing page, think about long-form content
• Get them to open flat designs in a browser to see designs in-situ (much like printing a page to see if it visually works and the right choices have been made)
• Use the tools you want
• Start to learn the new tools

Whilst not specific, it's a pretty good list of topics to cover in my opinion.

That’s some debut comment!

I’m sure that in this cartoon the designer tried a couple of different routes all of which where considered and not just wild stabs in the dark.

We’ll never know for sure though.

Funny how you’ve just upvoted and posted Toptal content and nothing else.

That word again… “should”. Gets my back up and because of this title I’m going to right align and centre align from now on just to spite you (kidding).

Like everything, it depends.

Be interesting to see how you would handle left aligning the NYT and WSJ logos. Because of their wide and short ratio, scaling down will have legibility issues.

To this day I still have to design long-form content within Illustrator because Sketch can’t handle multiple text styles within a text box.

Feeling you on this.

Apple has form with professional products, I say that in a less than positive light.