People & Access
Employee count, roles, account ownership, administrative access, onboarding, offboarding, permissions, and support responsibilities.
BUSINESS IT ASSESSMENTS
Get a clear picture of your technology before deciding what to fix, replace, secure, or manage.
Stilwell Support reviews the people, computers, accounts, communication systems, protections, vendors, and support needs behind your business. The goal is a practical starting point for companies with 1–40 employees—not a confusing list of products.
Remote assessments nationwide
On-site throughout Southwest Florida
1–40Ideal employee range
60 minRemote assessment
90 minOn-site assessment
ClearPractical next steps
WHAT WE REVIEW
Your technology is more than a list of computers.
An effective review connects users, access, devices, security, communication, data, vendors, and daily workflow. The exact depth depends on the selected assessment, available information, and authorized access.
Computers & Devices
Device inventory, operating systems, age, condition, update practices, remote support, monitoring, warranties, and replacement needs.
Cybersecurity
Endpoint protection, account security, multi-factor authentication, patching, email protections, password practices, and known risks.
Email & Microsoft 365
Domains, mailboxes, licenses, shared accounts, aliases, recovery details, administration, security, storage, and employee changes.
Business Phone System
Numbers, carriers, extensions, auto attendants, call routing, voicemail, schedules, mobile apps, ownership, and support concerns.
Backup & Recovery
Important data, backup locations, retention, access, recovery expectations, restore testing, cloud dependencies, and business impact.
Network & Connectivity
Internet providers, firewalls, switches, Wi-Fi, remote access, guest networks, office layout, reliability, and physical equipment.
Vendors & Support Process
Current IT provider, contracts, software vendors, escalation paths, documentation, recurring problems, ticket handling, and ownership gaps.
A SIMPLE ASSESSMENT PROCESS
Focused enough to respect your time. Broad enough to expose the important gaps.
The assessment begins with business priorities rather than tools. We use the available time to understand what you have, what is creating risk or frustration, and which next actions deserve attention first.
- No obligation to replace every system or vendor.
- Plain-language discussion with technical detail when useful.
- Scope is matched to the selected remote or on-site appointment.
- Any deeper testing, remediation, documentation, or project work is scoped separately.
Prepare
Share your employee count, locations, main concerns, current providers, and the systems you want to discuss.
Discover
Walk through daily operations, recurring issues, risks, responsibilities, technology ownership, and planned changes.
Review
Examine available systems, settings, equipment, documentation, or screenshots appropriate to the appointment.
Prioritize
Identify the most important concerns, practical improvements, and whether managed service, a project, or no change is appropriate.
CHOOSE THE RIGHT FORMAT
Remote for focused discovery. On-site when the physical environment matters.
Both appointments review business priorities and current technology. The on-site assessment adds direct observation of the office, equipment, work areas, and network environment.
60 MINUTES · ONLINE
Remote IT Assessment
Best when you need a structured review of users, computers, Microsoft 365, phones, security, backups, support problems, vendors, and priorities without an on-site visit.
- Available nationwide
- Microsoft Teams meeting
- Useful for initial managed IT discovery
- Screens and documents can be reviewed with authorization
90 MINUTES · SOUTHWEST FLORIDA
On-Site IT Assessment
Best when physical computers, networking equipment, Wi-Fi, cabling, office workflow, equipment placement, or visible conditions need to be reviewed in person.
- Southwest Florida businesses
- Physical environment walkthrough
- Direct review of accessible equipment
- Business representative should be available
HOW TO PREPARE
A little preparation helps us spend more time on the decisions that matter.
You do not need perfect documentation. Bring what you have and identify who understands the business, the technology, and the problems employees experience.
People and locations
Approximate employees, contractors, offices, remote workers, and planned growth.
Providers and systems
Current IT provider, internet carrier, Microsoft 365, phone provider, backup service, and major applications.
Main concerns
Recurring problems, recent incidents, slow systems, security worries, employee complaints, or upcoming changes.
Decision timeline
Contract dates, office moves, new employees, replacements, projects, compliance needs, or other deadlines.
FROM ASSESSMENT TO ACTION
The next step should match the business—not a predetermined package.
An assessment may lead to ongoing managed IT, a focused cybersecurity improvement, email or phone work, computer monitoring, a one-time project, or a recommendation to leave a working system in place. Any proposal, remediation, deeper testing, or documentation is confirmed separately.
COMMON QUESTIONS
What to expect from your IT assessment.
Is the assessment a sales call?
The appointment is a discovery and review conversation. We will discuss services when they fit your needs, but the assessment is intended to identify priorities rather than force a predetermined solution.
Do you need administrator passwords?
Not necessarily. We begin with discussion and information you can safely provide. Any account or device access requires authorization and should be limited to what is appropriate for the agreed scope.
Is this a penetration test or formal compliance audit?
No. The standard assessment is not an invasive penetration test, certification, or formal compliance audit. Specialized testing or compliance work requires a separate written scope.
Who should attend?
The owner, manager, or decision-maker should attend. Include the person who understands daily technology problems, current vendors, and employee workflows when possible.
Will I receive a written report?
We will review key findings and recommended next steps. Any formal written report, inventory, remediation plan, proposal, or technical documentation will be confirmed as part of the agreed follow-up scope.
Can you assess a company outside Southwest Florida?
Yes. Remote assessments and nationwide remote services are available. On-site assessments are limited to the Southwest Florida service area.
READY FOR A CLEARER IT PLAN?
Choose the assessment that fits your location and current questions.
Schedule a remote or on-site review, or begin with a shorter Business IT Consultation when you are still deciding what kind of help you need.