Email Teardown: Chris Winfield uses context to captivate my attention

Today we’re following up yesterday’s “context first” principle with a teardown of an email that illustrates this idea beautifully.

And while I’m at it, let’s go ahead and give this exercise a name:

Email Teardown Thursday: Chris Winfield uses context to captivate my attention with a gripping story.

Now keep in mind, I chose this email because it achieved its goal for me, even though it’s most likely not applicable to someone not in my situation.

So at some point during this teardown you might be thinking:

“CTO’s at ACME Corp. would never respond to an email like this.”

And that’s kinda the point.

Remember: it’s the context we’re interested in, and how in this particular instance the email is a perfect match for this specific context. Yours will be different.

(*Disclaimer: Teardown Thursday could continue, change into Teardown Tuesday, or simply cease to exist. I’d like to retain all of the advantages of a catchy name while remaining as non-committal on its continuation as possible. Thank you.)

On with the teardown…


I first came across Chris’ work a few years back because he had some unique commentary to offer on a few things I was particularly interested in at the time:

  • Productivity (and not just “hacks” but really thinking strategically about the value of your time)
  • Networking (I’ve always been sub-par at this)
  • Balancing business and family (this was the big one)

But, until a few weeks ago, I hadn’t been on his email list and decided to subscribe and see what he was up to.

When I did, in came 5 emails over the course of 7 days uniquely tuned to the constant churn of thoughts I have rolling around in my head related to the mix of work, productivity, and family.

Context Win #1: He met me right where my current awareness is.

I’m constantly thinking about how I can best balance my time.

How I can move my business forward without burning out.

How I can maintain an “active participant” role in my family as my two young daughters rapidly grow into true walkin’ talkin’ kiddos full of boundless energy and personality.

email teardown chris winfield

This series of emails also wins on another context front:

Context Win #2: The objective is clear. They’re built to onboard me into his thought process.

Each one is long-form, personal, and built around bringing me along with him on a mindset shift from how I prioritize my time at work now vs. how I would prioritize my time if I recognized certain strategic errors.

He’s cognizant of the fact that I’m aware there’s “something” wrong with my priorities, but not fully aware of what the solution might be yet.

There are some education and “aha” moments to be had.

And Email 5 is where the magic happened.

email teardown chris winfield full email
Click the image above to see the full email and follow along.

Right off the bat, he lures my attention with a curiosity-inducing subject line, followed right on its heels with a traditional “once upon a time” style story.

It would be cliche’ to do this in most cases, but I can tell that he knows this already… and has instead framed the discussion of something important around a creative narrative-based logic puzzle.

Okay crap. Now I HAVE to know where this is going…

email teardown chris winfield hook

A few lines down he completes the analogy:

“We all have a deal with this bank. It’s called the daily TIME ‘bank’.

Each morning, it gives us 86,400 seconds.”

Ahhh I get it. Nice.

“If you fail to use the day’s deposits, the loss is yours. There is no going back. There is no drawing against ‘tomorrow.’

So what are you going to do with today’s 86,400?”

So true.


I need to do better.

Then he does another pattern interrupt and jumps into story #2:

“I was 36 years old when I was finally ready to stop living for the future and letting my days slip by. I remember the exact day…

My world was melting down in front of me.

The business I had co-founded two & a half years earlier had imploded. The business that so much of my blood, sweat and tears had gone into.”


And as a business owner that fear is palpable.

It’s that nausea-inducing, sweaty-palm feeling you get when you slip up and daydream your way into what might happen if this “thing” fails and pulls you down with the ship.

But that’s all just teeing up the slam dunk…

email teardown chris winfield daughter story

These three lines hammer it home:

“Right then I realized that I was missing out on life.

My little girl didn’t feel like she could count on me.

I pressed END on my call and just sat down. I knew my life needed to change.”


That hits me right in the “dad” heart-strings.

Right there is the final big context win:

Context Win #3: He’s pulling the over-worked, yearning to be successful, yet still committed to my responsibilities as a dad lever BIG TIME.

I can immediately feel it… thinking about what it would be like to realize that I hadn’t “been there” enough for my kids.

Fear. Shame. Disappointment.

And that’s immediately followed by the thought of:

Wow, this dude has really been through it… and come out the other end. I need to pay some SERIOUS attention to what he’s talking about.

Then he closes it out with nothing other than…

email teardown chris winfield picture close

A cute picture with his daughter on what looks like a gorgeous NYC day!!

Damnit, Chris!

Inside I’m thinking.

Okay, what do I need to do to get “this?” Just tell me, please.

Chris has officially cemented himself in my mind as the “right guy” for the job of shining a light on how to navigate the business/family balancing act…

He’s “been there and done that” and clearly discovered something critically important along the way.

And now I’m all in on hearing what that is.

That’s the power of context.


P.S. This is a very personal, pointed example unique to a specific type of coaching. But that doesn’t mean the same idea isn’t directly applicable to your more “boring” niche. A story is a story… and applied in the right context, I’m confident you can create some “magic” too.

Questions about how this could work for your audience?

Email me at and let me know.

Happy to discuss.

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