Behind The Scenes: 1:1 Strategic Coaching Breakdown

⚡️ Today’s level up ⚡️

Today’s edition deconstructs an actual 1:1 coaching session with an enterprise AE who aspires to close a large transformation deal with a Fortune 500 company, move into a strategic account role, and ultimately define the way he wants to operate around his life…not just work.

Let’s go!

‍Read time: <7 minutes (+ a 33 minute highlights video of the session)

‍If you missed last week, read it here.

Playing infinite games

“You want to play infinite games to keep playing, not to win one round and then stop. That’s how you build truly significant, long-term value.” –Reid Hoffman

When I left the corporate world over two years ago, I knew I was taking a leap of faith.

But I was confident taking that leap because, for several years, I had been building for that freedom. A while back, I had decided that running on the hedonic treadmill was the equivalent of playing one-off games—ones designed to flex status, not create a continual source of abundance.

See, one-off status games are designed to teach you to compete and grind and that there can only be one winner (and you better hope it’s you). These silly games train you to think in terms of scarcity.

You see (and feel) this in the sales world constantly.

One quarter, you’re the hero. The next, you’re the villain when you’re back at $0. It’s an exhausting up-and-down cycle.

When I retired from corporate selling, I knew I wanted to do things differently. I had banked some decent dollars from my high earnings as a strategic seller so I could enter this next phase with a bit more flexibility, curiosity, patience, and creativity.

Granted, I still had to be disciplined to run a profitable business, but that business was always going to be one designed on my terms—not based on the pressure of chasing paper.

A dream I had was to use my writing to attract people I’d genuinely like to work with and eventually invite them to a special club where I could teach them everything I know.

And with the best of the best of that club, instead of charging them a ton of money upfront to go deeper (which would keep me playing silly one-off games), I choose to work with them for free. There is only an exchange of dollars when they put (significant) dollars in their own bank account first (freeing both sides to play infinite games).

I call it my "Diamond Program."

So far, based on my capacity, I purposefully have just three diamonds - Himanshu, Bobby, and Michael. My intent with the program was always to select people of the highest integrity (we use no contracts) and then be open to sharing what we create together with a broader audience so that closing mega deals, building a financially independent future, and making the right moves to shave off 10, 15, or 20 years off your corporate career becomes common knowledge. All while avoiding burnout and enjoying yourself more in the process!

Today’s edition is dedicated to doing just that.

Below, I break down a recent session I had with one of my Diamond Program members so hopefully you can walk away with valuable insights or get inspired to be more purposeful with your own performance.

Let’s go behind the scenes
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Overview‍‍

• ‍Category: Enterprise
• ‍Quota: Annual (currently at 34%)‍
• Solution: AI-assisted co-pilot for digital app adoption

Goals

1. Position 7+ figure transformation deals (vs typical 6-figure ones)
2. ‍Build a strong reputation inside the organization
3. ‍Enjoy the work and avoid “activity” burnout
4. ‍Graduate to a strategic account role
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Challenges

1. Behind pace on quota
2. ‍Calendar is full, but not actionable
3. ‍Heavy activity focus from org (vs strategic impact)
4. ‍Big visions are being discussed, but not written down

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Here’s our two-part plan for wild success
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We are using two specific design principles to level up Michael’s craft.

1. “Write it out first”

The $850K win he got in June has a multi-million dollar expansion path. This one opportunity can help him 4x his annual quota and put him into some serious accelerator territory ($$$).

He’s engaged with a key executive acting as a true Mobilizer and they’re aligned on the broad vision for the transformation.

BUT…That vision has only been communicated in meetings and calls.I encouraged Michael to get the vision written into a narrative format so his Mobilizer can review, co-draft with him, and then circulate it internally to allow the document to do the selling when Michael’s not in the room.

We chose the PR/FAQ (Press Release + Frequently Asked Questions) document as the best format for bringing the vision to life.

Here’s the structure of the PR/FAQ:

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‍Press Release (to forge an Emotional connection):

• ‍‍1-page- Includes a future date
• Bold headline at the top- Sub-headline to pull reader in
• The body is a crisp narrative that emotionally illustrates the transformation

💎 Bonus tip: Be sure to include actual quotes from their own leaders or employees for additional impact.

‍FAQs (to answer the Logical questions):

• ‍‍1 - 2 pages of proactively addressing their questions
• Use these to clearly explain how the transformation can come to life
• Optional: Any supporting (simple and clean) visuals that help your case

💎 Bonus tip: Have your Mobilizer review, scrutinize, and edit these before they get circulated around the client’s org.

Over time, this document will be turned into a business case (once more data is collected). Then, the business case will turn into a proposal.

From there, the business case becomes the contract. Finally, once signed, it turns into a project plan.

This is why “writing it out first” is a key design principle to accelerate every strategic sales deal win.

Here is an example of a PR/FAQ used with a sales lens. From there, using the MINTS framework, you can transform the PR/FAQ into a narrative business case (courtesy of Fluint and Nate Nasralla), and then finally a narrative proposal so you can land the transformation deal in less than a year.

2. “Turn your calendar into a game console”

When Michael showed me his calendar, I saw that it had two areas for improvement.

1. Every event was the same color (the default blue)
2. There were spaces unaccounted for required work
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We took a page out of one of my other Diamond Program member’s playbook (Himanshu), and I suggested he make two small tweaks.

The first one was to create a logical color scheme that works for him.

For instance, I suggested he do as my other client does, which is to start the week by filling up all of the HVAs (high-value activities) he has to do, like:

• Account research
• Team prep and planning
• Account debriefs and follow-up

Next, I advised him to block off time on his calendar on Fridays to schedule these HVAs on his calendar for the following week.

This ensures his time and attention are being directed on the most valuable actions (leaving little room for the trivial stuff).

Lastly, to make it feel like a fun game, I suggest he starts the week with one color (say purple) and after he completes it, turn it a different color (like green - for $$$).

Not only is this a more motivating way to work through the hard stuff, he can now take full advantage of “Time Insights” available in his Google Calendar.

He’ll now have a stronger baseline for what actions are making a true impact (instantly upgrading his 1:1s with his manager).

He can also review this monthly and more intelligently map to his true capacity, allowing him to step off the activity hamster wheel his company (and most companies) use to measure results, and instead take more ownership of how he manages his business, directing time, energy, and attention to the things that make the biggest impact (and puts a big smile on his face each quarter).

Watch the session

I cut down our 60-minute session in half, and obviously stripped out any sensitive data. You can watch it below.

YOU MAY ALSO ENJOY READING: Strategic Selling Teardown (Actual Company)

That’s a wrap!

Here’s how I can help you right now (changes coming soon - get these while you can):

‍

1 |Unlock the 7 Figure Seller OSLearn how to use design and systems thinking to become a 7 figure seller. There are 3 options to allow you to customize your learning journey.

‍2 | Download The 7 Figure Open LetterGet the creative strategic selling strategy that landed a $5.9M deal with a top 4 major global airline. Bonus inside!

‍3 |Book a 1:1 coaching session right nowYou can book a 60-minute coaching session with me (although the Pro above option provides access to 1:1 coaching with me at a 70% discount.