Most IT mistakes aren’t technical — they’re decision mistakes made under pressure, with incomplete information, and too much influence from sales teams.

I’ve spent my career on all sides of IT decisions: as an engineer, a consultant, a service provider, and a buyer. I’ve seen how good teams end up with the wrong vendors, the wrong contracts, or solutions that look fine on day one and hurt a year later.

Today, I help companies make IT decisions with less risk — from defining the right strategy, to choosing vendors, to reviewing contracts before they’re signed, to fixing environments that have grown messy or expensive over time.

I’m not a reseller and my role is simple: help you slow down just enough to make the right call, and avoid mistakes that are hard to undo.

If you’re making an IT decision and want a second set of experienced eyes before committing, that’s usually where I’m most useful.

Max Clark

Something I keep drilling into our younger team members:

The medium IS the message.

Email if you don't care whether they read or respond.
Text if you want them to see it but don't need anything back.
Call if you actually want to get something done.

I can't tell you how many times we're in a meeting reviewing next steps and someone says they're waiting on info. My first question is always the same:

"Have you called them?"

The answer is almost always no.

"Call them. Right now. I'm waiting."

It works every single time. I think "Have you called them?" is going to end up on my tombstone.

We back this up with clear internal expectations too:

Email: I'll respond that day
Slack: within 4 hours
Text: I need to know or a quick decision, emoji response is fine
Call: it's urgent, I'm picking up

And one rule everyone knows: no naked hello's. If you send "hey, are you there?" with zero context, it gets ignored. That's not rude, that's policy. Just include your actual question.

None of this is complicated. But nobody teaches it. So we do.

Independent IT Advisory - Buy Tech Without Regret

I hate this with the fury of 1,000 Suns

Docusign has decided to re-brand/change segment from eSignature to "AI-powered agreement management" that they're branding "Intelligent Agreement Management (IAM)"

Except (and this is the problem)...

IAM = IDENTITY AND ACCESS MANAGEMENT

Some genius has decided to brand around a term that already exists and is common, which will only cause more confusion in the market long term

Buyers hate vendors because of the games Sales and Marketing plays - and this is a perfect example

Making sure one IT decision doesn’t define your career.

AT&T is expected to move 10,000 people into its new HQ Campus

If you were AT&T IT what would your network build out look like?

Just finished planning 11 weeks of summer camps, activities, and travel for our kids

#AMA

The most expensive mistake in mid-market IT isn’t technical.

It’s structural - signing a three-year decision under someone else’s leverage.

Here’s the pattern:
- Renewal approaches.
- Urgency increases.
- The incumbent offers to “help” explore options.
- Procurement negotiates.

Everyone feels productive.

But the frame was already set.

You’re evaluating inside criteria the vendor helped define.
You’re negotiating inside timelines that protect their position.

So the conversation becomes price.
Not architecture.
Not flexibility.
Not long-term direction.

The real cost doesn’t show up in month one.

It shows up later:
- When switching feels prohibitive.
- When integrations are harder than planned.
- When the roadmap bends around a rushed decision.

This isn’t about bad IT leadership.

It’s about leverage.

And leverage disappears the moment urgency starts.

The teams that avoid this don’t negotiate harder.

They move earlier.

They create options before renewal pressure exists.

By the time renewal hits, the outcome is already shaped.

That’s not better negotiation.

That’s control.

Adobe probably made over a billion doing this, so totally worth it

A very real, and often overlooked risk with AI...

Is your confidential information being leaked out in chat sessions?

How do you know?

Forget the ‘em dash

Whenever I read “pressure-test” I 100% know it was written by AI

What are your favorite tells?

Buying tools without a clear data strategy is like hiring a team without defining the job.

We’re seeing a lot of companies invest first and ask questions later. That rarely ends well.

Full episode now live. 

👇 Link in comments

"The only constant in life is change."

-Heraclitus (c. 535 – 475 BCE)

Still true ~2500 years later.

We keep investing more into data… but I’m not convinced most companies actually know why. Collecting everything feels productive.

It’s usually just expensive. We get into this in tomorrow’s episode.

Episode live tomorrow. 

👇 Link in comments

Reminder the clocks changed in the US (UK & EU not till the end of the month)

There’s now 5 different timezones in the continental US and 11 timezones total

The dirty secret to SOC II compliance is you get to pick your controls.

Companies get boxed in when they pick controls around a specific vendor feature, only for that feature to be depreciated, or a new vendor brought in.

Use this information as you will.

Passionate about all things outdoors, technology and craft beer, I'm always looking to expand my knowledge and my network with like-minded individuals.

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The Battle

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