Independent Technology Consulting
I'm an independent technology consultant for solo attorneys, small firms, and owner-operated businesses. Whether you're already on Microsoft 365, considering the move, or just trying to figure out what's right — I help you make decisions with the rigor your work deserves.
Cole Flanders
Founder, Cole Christopher Solutions
Practitioner depth
Five years inside Microsoft 365, AI governance, and the compliance frameworks small firms and regulated businesses answer to.
Independent, owner-operated
No platform partnerships, no license resale, no upsell incentives.
Built for small firms
Right-sized scope, transparent flat fees, no enterprise bloat.
The Problem
Three things most owners I talk to cannot answer with confidence.
You don't actually know which AI features are already running in your tools — or what data they can read. Microsoft has been quietly enabling Copilot Chat, Teams meeting summaries, Outlook drafting, and AI search across the suite. Google and the consumer chatbots have done the same on their side. Many owners find out the first time an employee mentions a summary that auto-generated after a sensitive call.
Engagements end. Access doesn't. Old project folders. Guest accounts from a vendor three years ago. Sharing links that don't expire. Most businesses have years of accumulated external access nobody has reviewed since the work was finished — and for law firms, that's matter files and co-counsel logins specifically.
If your insurance carrier, regulator, or biggest client asked tomorrow to demonstrate reasonable security of their data, could you? Most owners can't answer with confidence — not because they failed, but because the ground has shifted faster than anyone could keep up.
What I Do
Most engagements start with one and grow into the next.
“Before you spend anything new, get a clear read on what you have.”
I review your Microsoft 365 environment — security baseline, sharing exposure, retention setup, AI surface area, license fit — and translate the findings into plain English you can act on. For law firms in particular, each setting is mapped to the duties you owe under the Kentucky Rules of Professional Conduct and KBA Ethics Opinion E-457.
“Build the right foundation once, on a flat fee.”
Move onto Microsoft 365 properly — or fix what was set up hastily — and bring AI in deliberately, not by accident. Email, files, calendars, shared documents, collaboration — configured for how a small business actually works. Includes data migration, security baseline, sensitivity labels for confidential and privileged content, and team training.
“The work that holds everything together after the project is done.”
A trusted advisor on retainer for AI Authorized Use Policy drafting, sharing and retention reviews, cyber-insurance compliance walkthroughs, and the planning sessions before any major change. Someone to call when you're not sure whether the tool the vendor is pitching does what they say.
How It Works
Hiring a consultant should not feel like a leap of faith. Here's the path most engagements follow.
We talk about your business, your current setup, and where you'd like to be. No pitch, no pressure. If we're not a fit, I'll tell you and point you somewhere better.
Within a week of our call, I send you a clear plan: scope, timeline, deliverables, and a flat fee. No hourly billing surprises, no scope creep.
I do the work, coordinated with your team's schedule. You stay informed without having to manage me. Status updates are short and in plain English.
When we wrap, you get documentation, training for your team, and the option to keep me on retainer for ongoing advisory.
About
I've built my career around helping organizations get real value out of their cloud productivity tools — first inside larger companies, then increasingly with the small businesses and small firms that get overlooked by the enterprise consulting world.
I started Cole Christopher Solutions for a specific reason. Too many small businesses get sold enterprise-grade complexity they don't need, by vendors and partners whose compensation is tied to license volume. I wanted to do this work the right way: independently, transparently, and at a scope that fits an owner-operated practice.
I'm not a Microsoft Partner and I don't resell licenses. I'm an independent advisor who happens to be deep on the Microsoft cloud platform. Much of my work today is with law firms — translating their professional duties into Microsoft 365 settings they can actually point to. That same rigor shows up everywhere else: HIPAA-adjacent practices, cyber-insurance compliance, AI governance, and the small businesses that just want to know their setup isn't quietly working against them.
Based in Louisville, Kentucky. Working with small firms and owner-operated businesses across the country.
Principles
A new practice with no clients yet has to be transparent about something else — how it intends to operate. These are the four rules I built the business around.
Independence is meaningless if it doesn't sometimes mean talking you out of a project. A real share of my discovery calls end with “you don't need to hire me — here's what to do instead.” That's not a sales technique. It's the work.
If a project takes longer than I scoped, that's on me. Owners have a hard enough time budgeting; the last thing you need is hourly-billing anxiety or surprise change orders mid-engagement.
You don't need to understand how the cloud works. You need to understand what you're deciding. Every conversation is in plain English, and every recommendation comes with the trade-offs spelled out.
When an engagement ends, your firm should be able to maintain what we built without me. Every configuration change, every workflow, every administrator setting — written down, handed off, owned by you.
Questions
The objections that come up most often in discovery calls, answered directly.
Still have questions?
Book a discovery callReady?
A 30-minute discovery call. No pitch, no pressure. We figure out together whether this is a good fit.
What you'll get from the call
Or email cole@colecsolutions.com