All In Technology

Jeff Hathcote has a simple way of making cybersecurity feel more real: look at your business the way an attacker would.

That sounds uncomfortable, but it is useful. Most security conversations start with tools, policies, and checklists. Attackers are usually looking for something much more basic: the easiest opening.

In our latest article, Jeff explains the thinking behind Think Like a Bad Guy® and why organizations need to pay attention to the everyday gaps that create risk: reused passwords, phishing attempts, exposed systems, vendor access, untested backups, and processes that depend too heavily on trust.

It is a practical read for business leaders and IT teams who want to make cybersecurity planning more grounded and less theoretical.

Read Jeff's thoughts here:
➡️ https://allintechnology.com/think-like-a-bad-guy-cybersecurity-risk/

We are also continuing this conversation live next week during our June PizzaCast, Cybersecurity in 2026: Think Like a Bad Guy®.

Join All In Technology and Jeff Hathcote on Thursday, June 18th at 11:30am MT / 12:30pm CT for a real discussion on attacker mindset, cybersecurity risk, and the questions leaders should be asking before there is a security incident.

Register for the event and a free 🍕 here:
👉 https://allintechnology.com/event-cybersecurity-2026-think-like-a-bad-guy/

Most Microsoft licensing issues do not start with one big mistake. They usually build over time.

A company grows, new users get added, tools get layered in, security needs change, and old licenses stay assigned longer than anyone realizes. On paper, everything can look manageable for quite a while. Then an audit or internal review forces a closer look, and suddenly there is a clearer picture of wasted spend, overlapping tools, inactive accounts, and compliance risk that had been sitting there all along.

That is why this latest article in our Microsoft series is worth paying attention to. A Microsoft licensing audit is not just about staying compliant. It is also one of the best ways to understand whether your environment still matches how your business actually operates.

Read the latest piece in our updated series here:
➡️ https://allintechnology.com/microsoft-licensing-audit-guide/

Cybersecurity is not just about tools, alerts, and checklists.

It is also about understanding how attackers actually think.

Join All In Technology on Thursday, June 18th for our June PizzaCast: Cybersecurity in 2026: Think Like a Bad Guy®.

This live virtual session will feature Jeff Hathcote, CISO and cybersecurity practitioner, for a practical discussion on attacker behavior, common business exposures, and the questions leaders should be asking as they plan for 2026.

We’ll talk through topics like phishing, credential theft, ransomware, vendor risk, identity and access, backups, user behavior, and how organizations can become harder targets.

Event Details:
📆 Thursday, June 18th
🕛 11:30am MT / 12:30pm CT
✅ Virtual session via Microsoft Teams

Qualified attendees who register by Tuesday, June 16th will receive complimentary pizza for the session 🍕

Register here to save your spot:
https://allintechnology.com/event-cybersecurity-2026-think-like-a-bad-guy/

At first glance, this looks like a pricing question. How much more does Microsoft 365 E5 cost than E3?

Fair enough. That is usually where the conversation starts. But it rarely ends there.

What looks like a licensing decision often turns into a bigger discussion around security, compliance, visibility, and whether the extra investment actually solves meaningful problems for the business.

If your team is weighing E3 against E5, the goal is not to chase the highest tier. It is to understand what changes, what matters, and where the extra cost is justified.

Read the latest piece in our Microsoft 365 series here:
https://allintechnology.com/microsoft-365-e5-vs-e3-cost-difference

Title: Microsoft 365 E3 Vs E5: Cost Analysis For Tech Enthusiasts Dive into the cost differences between Microsoft 365 E3 and E5. Explore whether the enhanced security and compliance features of the Microsoft license justify the investment for your organization. Get informed to make the best choice for your tech needs!

A useful AI conversation usually gets better the moment it leaves the product page and enters the workflow.

That was a big part of last week's PizzaCast with .

Instead of treating agentic AI like a category to admire from a distance, we focused on the practical side of customer communications. What improves when AI helps support conversations? Where does oversight still matter? What has to be true operationally before any of this creates real value?

If you missed the live session, the replay is now available:
▶️ https://youtu.be/gIgqXj1fBIQ

We also put together a companion blog that goes deeper into the same topic:
👉 https://allintechnology.com/agentic-ai-customer-communications-business

And if you want to keep up with future PizzaCasts and replays:
👉 https://allintechnology.com/events

A lot of Microsoft 365 decisions get framed too narrowly.

Which license is cheaper.
Which plan has more features.
Which one seems “good enough.”

That is usually the wrong conversation to be having.

The better question is whether your Microsoft 365 setup actually matches the way your business operates, secures users, manages risk, and supports growth.

That is why we structured this Microsoft 365 series the way we did.

We started with security, because Microsoft 365 plays a central role in communication, collaboration, and access across the business.

Now we are moving into licensing strategy with a breakdown of Microsoft 365 Business Premium vs. E3 vs. E5, and why those decisions deserve more thought than they often get.

Read the latest comparison piece here:
👉 https://allintechnology.com/microsoft-365-business-premium-e3-e5/

And if you missed it, start with the first post here:
👉https://allintechnology.com/how-to-secure-microsoft-365-checklist/

Agentic AI conversations sound polished right up until someone has to decide whether the tool actually fits the business.

That is usually where the real questions start.

🔶 Who owns it?
🔶 Where does it fit in the workflow?
🔶 What needs human oversight?
🔶 What does real ROI actually look like once it hits day-to-day operations?

That is exactly where we’re taking the conversation in our upcoming PizzaCast with Dialpad.

Today is the last day to secure your free pizza 🍕if you want to join us live, but registration will remain open up until the event on Thursday, 5/21 at 11:30am MT / 12:30pm CT.

If agentic AI, customer communications, workflow impact, and trust and security questions are already on your radar, this should be a worthwhile session.

Register here: https://allintechnology.com/agentic-ai-may-2026-pizzacast/

One of the easiest ways to get AI wrong is to treat it like a software decision before treating it like an operations decision.

That usually leads teams straight into feature comparisons before they have answered the more important questions around workflow fit, ownership, oversight, and what success would actually look like in practice.

That is a big part of why agentic AI deserves a more careful look, especially in customer communications where the promise sounds great, but the real value only shows up if it improves how work actually gets done.

We put together a new piece on that tension and what business leaders should be evaluating right now.

🤖 Read the blog here:
👉 https://allintechnology.com/agentic-ai-customer-communications-business/

And if you want to continue the conversation and score a free pizza, join us for next week’s PizzaCast with Dialpad where we will dive even deeper into Agentic AI models:
👉https://allintechnology.com/agentic-ai-may-2026-pizzacast/