November 14, 2026 | Read online
Thursday afternoon, my email stopped working. Nothing coming in, nothing going out, and it stayed that way until Friday morning.
Microsoft 365 went down across multiple regions. Outlook, Teams calendars, SharePoint, and Copilot all choked at the same time. Downdetector logged around 130,000 Outlook reports at the peak, and Microsoft spent the night rebuilding servers and rolling back a network change trying to figure out what broke.
I'm not going to lie, I lost most of that afternoon. Or at least it felt like I did.
Then I started scrolling LinkedIn and noticed two very different reactions to the same problem.
One group basically shut it down. Without email or Copilot, they called it a day and went home.
The other group picked up the phone, got scrappy, and kept the day moving.
I wrote about it on LinkedIn here, and the comments made it clear a lot of you saw the same split.
That's when I realized how many of us have handed our entire workflow to one piece of technology. When it stops, we stop.
Agility is one of the biggest competitive advantages you can have right now, and I saw it show up three different ways this week.
THE WEEKEND THAT KEPT CHANGING
This weekend I'm at Bryant University for NISC, the Northeast Intercollegiate Sales Competition that my friend Dr. Stefanie Boyer runs. Last year 43 universities competed. I'm helping out with role plays and judging, and doing a short presentation for the students.
Thursday night Stefanie and I were on the phone walking through everything piling up against the event. The weather wasn't cooperating, flight schedules were getting shuffled, and then Microsoft went down on top of all of it.
Pulling off a two-day event for students, judges, and sponsors from dozens of schools while the ground keeps moving under you is no small thing.
Somewhere in that call we realized this IS sales.
Every student competing this weekend is going to walk into a role play where the buyer throws them something they didn't prep for. The ones who do well will adjust in the moment and stay with the buyer. The ones who force the script they memorized are going to struggle.
So we talked about bringing this week's chaos into the conversation with the students as a positive. Learning how to adjust when the plan falls apart is some of the best prep you can get for a career in sales.
TEST IT, DOUBLE DOWN, OR KILL IT
The same thing is playing out in my own outbound right now.
Things are evolving so fast that what worked six months ago is not working anymore, and if you're still running the same messaging you were running in the spring, you're probably feeling it.
A few months ago I had to set up a new sending domain and warm it up before I could send anything at real volume. If you've never done it, warming a domain is slow and boring. You send small amounts, build your reputation with the inbox providers, and wait. There's no shortcut, and if you try to skip it you end up in spam.
While that was warming up, I ran my messaging through ChatGPT and it rewrote a good chunk of it. Instead of arguing with myself about which version is better, I'm testing them against each other.
This is where Apollo (#sponsor) has changed how I work.
Apollo has an MCP connector that plugs directly into Claude and ChatGPT, so I don't have to log in and click through dashboards to find out what's happening. I ask in plain English. Which sequence is getting replies? Which step is falling flat? Is this a messaging problem or a deliverability problem?
It pulls the opens, clicks, and replies, lets me drill into the exact messages that drove results, and I can update the copy on the spot.
That's the whole game right now. Test something, look at the data, double down on what works, and kill what doesn't. The faster you can run that loop, the faster you find what your buyers respond to.
If you already use Apollo and haven't tried the connector yet, start there. If you don't, you can check it out here.
WHY I STOPPED TEACHING SCRIPTS
All of this connects to the biggest change I've made in my own training.
For most of my career I taught specific techniques. Here's the email template, here's the opening line for the cold call, here's how you respond to that objection. For a long time that worked because the playbook didn't change much from one year to the next.
That's not the world we live in anymore. A technique I teach in January can be stale by June.
So I moved my training to an agile framework. Everyone learns the same sales fundamentals and speaks the same language, so a team can talk about messaging, cold calling, or objection handling the same way. Then they use that framework to test different approaches, figure out what works for their buyers and their reps specifically, and keep adjusting as things change.
AI is a force multiplier inside that framework. It makes the testing faster and the data easier to read. The judgment on what to test and what to kill still comes from you.
This is also the heart of the keynote I'm doing most going into next year, The Age of the Agile Sales Org. I give the team the framework, then we work through three areas they pick (sales-ready messaging, cold calling, cold email, negotiation, or objection handling) so they walk out with something they can test the following week.
If you're planning a kickoff for the new year and want your team thinking this way, you can check it out here.
Microsoft will put out a post-incident report soon explaining what broke on their end. The more useful one is your own.
When your main tool went down this week, what did you do?
If you're one of the ones who shut down and didn't know what to do, you might want to rethink your approach and how to be more agile.
#MakeItHappen
Got value from this? Here’s how to say thanks.
I put a lot into this every week, and I’ll keep it free. If it’s helped you, here’s how you can help me keep growing it. Pick one.
- Forward this to one sales leader who’d get value from it. If someone forwarded this to you, subscribe here so you get it every week.
- Give back. Donate $10-$500 to the Future Founder Project and help a young entrepreneur get started.
- Refer me. SKO season is coming. If your team needs a kickoff speaker or training, reply to this email and let’s talk.
Thank you. It means more than you know.
|
| How did I do with this edition? |
|
|
|
|