7. The Assessment

Before you start, understand that you MUST have explicit consent from the business owner, for on that day, you will be looking at their network, devices, and potentially sensitive information. This is not a penetration test or vulnerability assessment. This is a light IT assessment to identify easy wins for improving their IT reliability, security, and backups. But still, you need written permission. Never conduct network scans without written permission. A verbal “go ahead” is not sufficient.

Preparation

Before the assessment, prepare yourself with the right documentation, tools, and materials. This section aligns with the in-scope activities defined in your consent email.

Documentation to Bring

Required

• Printed copy of the signed consent email (with client’s authorization)
• Client information sheet (business name, contact info, scheduled time)
• Assessment checklist (see below)
• Blank report template for documenting findings
• Business cards (2-3 to leave behind)
• Your company flyer or service brochure

Optional

• Printed copies of your service pricing sheet
• Follow-up email template on your device

Assessment Checklist

This checklist aligns with your in-scope activities from the consent email:

Network Equipment

• Visual inspection of routers, switches, and access points
• Document equipment age, make, and model
• Note any outdated or end-of-life devices
• Check equipment physical condition and placement

Wi-Fi Security

• Review Wi-Fi encryption type (WPA2/WPA3 vs outdated WEP/WPA)
• Check for guest network separation
• Evaluate signal strength and coverage

Device Assessment

• Count and document workstations, laptops, tablets
• Note device age and condition
• Identify any obviously outdated hardware

Backup Strategy

• Ask about current backup processes
• Identify what is being backed up (and what isn’t)
• Determine backup frequency and location
• Check if backups are tested/verified

Security Posture

• Discuss password policies and practices
• Review access control procedures
• Check SSL certificate status on website (if applicable)
• Identify any obvious security gaps

Business Context

• Understand current IT pain points
• Document who currently maintains IT
• Identify critical systems and uptime requirements
• Note any compliance or regulatory requirements

Deliverables

• Provide 3-5 immediate, actionable recommendations
• Answer any questions they have
• Leave business card and service materials
• Schedule follow-up discussion (if interested)

Tools and Equipment

Essentials

• Laptop or tablet with note-taking app
• Smartphone (for photos of network setup if needed)
• Pen and notebook (backup for notes)
• Wi-Fi analyzer app (optional, for signal strength checking)
• Timer/watch (to respect the agreed time window)

Ventoy USB

Ventoy USB with Useful ISOs (Optional but Recommended). Take the time to create a Ventoy USB drive, consider including these ISOs for network diagnostics and assessment:

• System Rescue - Linux-based rescue system with comprehensive network tools (nmap, tcpdump, iperf, etc.)
• GParted Live - For checking disk health and partition information
• Clonezilla Live - Useful for discussing backup/imaging solutions
• Memtest86+ - For diagnosing potential memory issues on problematic systems
• Ultimate Boot CD (UBCD) - Collection of diagnostic and repair tools
• Hiren’s BootCD PE - Windows PE-based environment with many diagnostic tools

Network-Specific Tools

Wi-Fi Analysis

• Windows/Portable: WiFiInfoView by NirSoft - Shows all Wi-Fi networks with detailed info (encryption, signal strength, channels)
• Android: WiFi Analyzer - Free, open source, shows channel congestion and signal strength
• iOS: AirPort Utility (enable Wi-Fi Scanner in settings) or Network Analyzer

Network Scanning

• Advanced IP Scanner (Windows, free) - Fast, reliable, shows device names and manufacturers. This is what you want for quick network discovery.
• Angry IP Scanner (Cross-platform, open source) - Good alternative if you need Linux/Mac support

SSL Certificate Checking

• SSL Labs SSL Test - The gold standard for comprehensive SSL/TLS analysis. Shows expiration, vulnerabilities, and configuration issues.
• Why No Padlock? - Great for finding mixed content issues
• Quick Browser Check: Just visit their website and click the padlock icon in the address bar

Speed Testing

For validating their internet connection vs internal network performance:

• Speedtest by Ookla (Website + Apps) - Industry standard, test from their devices to check ISP speeds
• Fast.com by Netflix - Super simple, no ads, great for quick checks
• LibreSpeed - Open source, self-hostable, no tracking
• Ethernet vs Wi-Fi: Run tests on both to show the performance difference and justify Wi-Fi upgrades or network improvements

Local Network Performance

• iPerf3 - Command-line tool to test actual throughput between devices on their network (requires running on two machines)
• File Transfer Test: Sometimes the simplest test is copying a large file between two PCs to demonstrate network speed issues

Personal Items

• Portable charger for your devices
• Water bottle and breath mints
• Professional but practical attire
• GPS/map app for finding location
• Parking information or cash for parking

Visual Tools for Client Demonstration

Part of selling your expertise is showing, not just telling. These tools have visual outputs that you can show clients in real-time to demonstrate problems:

Highly Recommended Visual Tools

1. Wi-Fi Analyzer (Phone/Tablet) - Shows channel congestion, signal strength, and encryption visually

   • Pull it up and show them: “See these 6 networks all on channel 6? That’s why your Wi-Fi is slow.”
   • Walk around with them showing signal drops: “Watch the signal go from -45 to -75 in the back office.”

2. Speed Test (Browser/App) - Big numbers and graphs are compelling

   • Run side-by-side tests: “Ethernet is 450 Mbps, but Wi-Fi is only 120 Mbps - that’s your bottleneck.”
   • Compare to their ISP plan: “You’re paying for 500, getting 450 - that’s actually pretty good!”

3. Advanced IP Scanner - Visual network map showing all devices

   • Shows device names and manufacturers: “Here’s your network - I see 23 devices. Do you recognize all of these?”
   • Can reveal unauthorized devices or shadow IT

4. SSL Labs (Browser) - Shows letter grade (A, B, C, F) for their website security

   • People understand grades: “Your website gets a ‘B’ for security. We should get that to an ‘A’.”
   • Shows exact expiration dates visually

5. CrystalDiskInfo (Windows) - Visual health status for hard drives

   • Color-coded: Green = Good, Yellow = Warning, Red = Failing
   • “This drive is showing yellow warnings - it’s dying. We need to replace it before it fails.”

6. Windows Update History - Shows failed or missing updates visually

   • “These 15 security updates failed to install - your system is vulnerable.”

How to Record Assessment Information

This is crucial - you need accurate notes, but you also need to maintain trust and professionalism.

❌ Don’t Do This:

• Audio recording - Too creepy, feels invasive, rarely worth the legal/trust issues
  • Even with consent, clients will be less candid
  • You don’t want to be the person who “records everything”
  • Transcription takes time you don’t have

Best Approach: Digital Form on a Tablet

Using a tablet (iPad or Surface) with a form or checklist app provides the optimal balance of professionalism and practicality:

Advantages

• Professional, modern appearance
• Faster data entry than handwriting
• Direct photo attachment capability
• Streamlined conversion to final report format
• Transparent documentation process visible to client (builds trust)

Recommended Form Solutions

1. Microsoft Forms + OneDrive (Works on any tablet)

   • Create a custom assessment form
   • Fill it out on tablet during visit
   • Automatically syncs to cloud
   • Export to Excel/PDF later

2. Google Forms (Android/iOS/Web)

   • Free, simple, works everywhere
   • Can add photos from phone camera
   • Results go to Google Sheets

3. Notion (Cross-platform)

   • Create a template assessment database
   • Looks very professional when showing client
   • Easy to export to PDF for report

4. Your CRM’s Mobile App (If available)

   • EspoCRM and HubSpot both have mobile apps
   • Document directly in client record
   • No duplicate data entry later

Alternative: Legal Pad and Pen

For technicians less comfortable with digital note-taking:

Advantages

• Simple, reliable (no technology failure points)
• Some clients perceive handwritten notes as more personal

Disadvantages

• Slower documentation process
• Less modern appearance
• Difficult to organize and convert to reports
• Requires neat, legible handwriting to maintain professional credibility

Laptop vs Tablet: Device Selection

Tablets (Recommended)

iPad or Surface tablets offer several advantages:

• Professional appearance without being imposing
• Easy to hold while walking through facilities
• Natural screen sharing with clients
• No physical barrier between technician and client
• Full-day battery life
• Lighter and more portable

Business-Class Laptops:

ThinkPad, Dell Latitude, or HP EliteBook models are appropriate alternatives:

• Professional, familiar in business environments
• Can run full desktop diagnostic tools
• Shows established business practices
• Avoid consumer or gaming laptops with RGB lighting

Operating System Considerations:

Windows: Most widely recognized and expected in small business environments. Clients immediately understand that a Windows technician can support their Windows infrastructure.

macOS: Acceptable and increasingly common in professional services. MacBooks project quality and modern technical competency. Keep the device clean and professional-looking.

Linux: Best reserved for specific market segments. While demonstrating technical expertise to other IT professionals, it may confuse non-technical business owners who question whether a Linux user can properly support Windows environments. Exception: Tech-heavy markets (startups, software companies) where Linux proficiency may be viewed favorably.

Key Success Factors:

• Clean, well-maintained professional equipment
• Confident demonstration of technical knowledge
• Respectful of client time and workspace
• Clear, jargon-free communication
• Actionable, prioritized recommendations

A confident, professional technician with a clean ThinkPad running Ubuntu will consistently outperform an unprepared technician with premium hardware.

Professional Mindset

Part of what you are doing here is building trust and selling your expertise. Keep these tips in mind:

• Arrive 5 minutes early (but not more than 10)
• Be respectful of their time (stick to 20-30 minutes)
• Focus on listening and observing
• Don’t oversell or pressure
• Deliver at least one actionable insight
• Be ready to answer questions clearly
• Maintain confidentiality at all times

How Did We Get Here?

You have done your outreach, and the business owner has agreed to a free IT assessment. They understand that this is a low-pressure conversation where you will identify easy wins for improving their IT reliability, security, and backups. You need to get their written permission to conduct the assessment.

The Permission Email

Below is an example email template you can use to obtain written consent for the assessment:

Hi {{Name}},

Thanks for agreeing to the free IT assessment. Before I can proceed, I need your written permission to conduct this assessment at your business location.

Assessment Details:

• Business Name: {{Business Legal Name}}
• Business Location: {{Full Street Address, City, State, ZIP}}
• Date: {{Scheduled Date}}
• Time Window: {{Start Time}} to {{End Time}} (approximately 20-30 minutes)
• Technician: {{Your Full Name}}, {{Your Company Name}}

In-Scope Activities:

• Visual inspection of network equipment (routers, switches, access points)
• Review of Wi-Fi configuration and security settings
• Assessment of physical device conditions (age, model, condition)
• Discussion of current backup strategies and processes
• Review of SSL certificate status on your public-facing website (if applicable)
• Identification of outdated or end-of-life equipment
• General security posture evaluation (password policies, access controls)
• Documentation of current IT setup for recommendations

Out-of-Scope Activities:

• No penetration testing or vulnerability scanning
• No changes to network configurations or settings
• No installation or removal of software
• No access to sensitive business data or personal information
• No modification of existing systems or devices
• No remote access tools will be installed

Important Terms:

• This assessment is READ-ONLY and informational in nature
• No changes will be made to your systems without separate written authorization
• This assessment carries no risk to your business operations
• All observations will be kept confidential
• This consent is valid only for the date and time window specified above
• This consent expires automatically when I leave your premises or at {{End Time}}, whichever occurs first
• You may revoke this consent at any time during the assessment
• No warranty or guarantee is provided with this free assessment
• Any recommendations provided are advisory only

Data Retention and Right to Be Forgotten:

• Assessment findings, notes, and recommendations will be retained for up to 90 days to facilitate follow-up discussions
• If we do not enter into a business relationship within 90 days, all assessment data will be automatically deleted
• At any time, you may request immediate deletion of some or all information collected during this assessment by emailing {{Your Email Address}} with the subject line “Data Deletion Request - {{Business Name}}”
• Upon receiving a deletion request, all specified information will be permanently deleted within 5 business days
• You will receive written confirmation once the deletion is complete
• This right applies regardless of whether we enter into a business relationship

To Provide Consent:

Please reply to this email with the following statement:

“I, {{Name}}, as {{Title/Role}} of {{Business Legal Name}}, hereby authorize {{Your Full Name}} of {{Your Company Name}} to conduct a read-only IT assessment at {{Business Address}} on {{Date}} between {{Start Time}} and {{End Time}} as described above. I understand this consent expires when the technician leaves the premises or at {{End Time}}, whichever occurs first.”

If you have any questions or concerns about the scope of this assessment, please let me know before providing consent.

Best regards,
{{Your Name}}
{{Your Company Name}}
{{Phone Number}}
{{Email Address}}

If they agree, they should reply with the consent statement. Save this email for your records and bring a printed copy with you to the assessment.

Conducting the Assessment

The day of the assessment has arrived. You have your documentation, tools, and mindset ready. Remember: you have 20-30 minutes to make a positive impression, gather useful information, and demonstrate your value. Stay organized, be professional, and focus on listening.

Part 1 - Initial Conversation (10 Minutes)

Start with a friendly, professional greeting and verify you’re speaking with the authorized person who gave consent. Briefly restate the purpose of the visit and the timeframe.

Opening

“Hi {{Name}}, thanks for having me today. As discussed, I’m here to do a quick IT assessment - should take about 20-30 minutes. I’ll ask a few questions, take a quick look at your setup, and then share some observations. Sound good?”

Discovery Questions

Ask open-ended questions and take notes. Let them talk - their answers will reveal priorities and pain points.

Environment Overview

• “How many devices do you have here? Desktops, laptops, tablets?”
• “Do you have any servers on-site, or are you mostly cloud-based?”
• “Are you using any cloud services like Microsoft 365, Google Workspace, Dropbox?”

Current IT Support

• “Who handles your IT maintenance now? In-house, outside person, or ad-hoc?”
• “When something breaks, what’s your process? Who do you call?”
• “How quickly can you usually get help when you need it?”

Backup Strategy

• “Tell me about your backup situation - what are you backing up?”
• “How often do backups run? Daily? Weekly?”
• “Where are backups stored? On-site, off-site, cloud?”
• “Have you ever tested a restore? Do you know the backups actually work?”

Network and Connectivity

• “How’s your internet speed? Does it meet your needs?”
• “Any issues with Wi-Fi coverage or reliability?”
• “Do you have a guest network separated from your business network?”
• “Ever experience slowdowns or outages?”

Pain Points and Security

• “What’s your biggest IT frustration right now?”
• “Have you had any security incidents? Phishing attempts? Malware?”
• “What keeps you up at night regarding your technology?”
• “Are there any compliance requirements for your industry? (HIPAA, PCI-DSS, etc.)”

Listen for Red Flags

• Outdated systems (“That server? Oh, we got that in 2012…”)
• No backups or untested backups
• No IT support or unreliable support
• Security incidents or close calls
• Compliance concerns
• Frustrated employees dealing with slow/broken systems

Part 2 - Visual and Technical Assessment (10 Minutes)

Now that you understand their environment, it’s time to see it with your own eyes. Ask for permission before touching anything or entering any restricted areas.

“Would you mind showing me your network equipment? Usually in a closet or back office?”

Network Closet/Equipment Room

What to look for

• Router/Firewall: Note the make, model, and age. Check for dust buildup or overheating.
• Switches: How many? What speed (10/100/1000/2.5G)? Managed or unmanaged?
• Patch Panel: Is cable management clean or a rat’s nest?
• Power: Are devices on UPS/battery backup? Or just plugged into a power strip?
• Wi-Fi Access Points: Where are they located? How old? What brand?
• Environmental: Is the equipment in a hot closet? Proper ventilation?

Document

• Take photos (with permission) for your notes
• Write down make/model numbers
• Note anything obviously outdated or problematic

Wi-Fi Analysis

Use your Wi-Fi analyzer tool

Use WiFiInfoView, WiFi Analyzer app:

• Check their Wi-Fi network encryption (WPA3, WPA2, or older WEP/WPA)
• Look for channel congestion (are they on a crowded channel?)
• Check signal strength in different areas
• See if they have a separate guest network

Ask to connect

“Mind if I quickly check your Wi-Fi settings?”

Open your analyzer and show them what you find:

• “Your network is using WPA2, which is good.”
• “I see you’re on channel 6 with 4 other networks - we could optimize that.”
• “Your signal strength drops significantly in the back offices.”

Workstation Spot Check

Ask to look at one or two workstations:

“Can I quickly check one of your computers?”

What to look for

• Operating System: Windows 10? 11? Still on Windows 7? (Red flag!)
• Updates: When was the last update installed?
• Antivirus: What are they using? Is it active and updated?
• Age: Check System Info (Win+Pause) - when was this PC manufactured?
• Performance: Does it feel sluggish? How long to open apps?
• Password Policy: Do they have to change passwords? Any complexity requirements?

Server Check (If Applicable)

If they have an on-site server:

• What’s it running? File server, email, specific applications?
• Windows Server version? (2012, 2016, 2019, 2022?)
• When was it last updated?
• Where’s it backing up to?
• Is it virtualized or physical?

SSL Certificate Check

Open their website in a browser:

• Click the padlock icon in the address bar
• Check certificate validity and expiration date
• Look for mixed content warnings
• Use SSL Labs for a quick grade

You can verbalize your findings:

“Your SSL certificate is good, expires in 6 months - you’re fine there.”

Or:

“I see your certificate expired 2 months ago - that’s hurting your Google rankings and customer trust.”

SEO Check

Open Google Chrome -> Developer Tools (F12) -> Lighthouse tab and run a desktop and a mobile audit on their homepage. That produces a visual score for things like performance, accessibility, best practices, SEO, and PWA. That’s a visual thing you can show them on the spot.

Speed Test

Run a quick speed test (with permission):

“Mind if I run a quick speed test from your network?”

• Test on both Ethernet (if available) and Wi-Fi
• Compare results to what they’re paying for from their ISP
• Note the difference between wired and wireless

You can share the results immediately:

“Your ISP plan is 500 Mbps down, but I’m seeing 450 on Ethernet and 120 on Wi-Fi. The wired connection is good, but your Wi-Fi could be better.”

Part 3 - Deliver Immediate Value (5-10 Minutes)

This is where you demonstrate expertise and build trust. You’ve gathered information, now synthesize it into actionable insights.

Summarize your findings clearly and concisely:

“Okay, here’s what I found in the last 20 minutes…”

Provide 3-5 Specific Recommendations

Pick the most impactful issues and explain them clearly. Focus on:

1. Quick wins (easy fixes that show immediate value)
2. Security risks (things that could cost them money/data)
3. Performance improvements (things that save time/frustration)
4. Compliance issues (things that could cause legal problems)

Example Recommendations

Below are some common findings and how to present them:

Outdated Equipment

“Your router is 9 years old - that’s well past its useful life. Older routers have known security vulnerabilities that can’t be patched, and they don’t support modern Wi-Fi standards. This is your biggest risk right now. A new router with proper firewall would be about $300-500 and would immediately improve your security and Wi-Fi performance.”

Backup Issues

“You mentioned you have backups running, but they’re only going to an external drive sitting next to your server. That’s a single point of failure - if there’s a fire, flood, or ransomware attack, you lose both your data and your backup. We need to get you a proper 3-2-1 backup strategy: 3 copies of your data, on 2 different types of media, with 1 copy off-site or in the cloud. I can help implement this for about $100/month.”

Wi-Fi Problems

“Your Wi-Fi is using WPA2 which is okay, but you’re on channel 6 with heavy congestion. Also, your signal barely reaches the back offices. You don’t have a guest network, so visitors are on the same network as your business data. A proper Wi-Fi upgrade with a modern access point would cost around $400-800 and solve all of these issues.”

Outdated Operating Systems

“I saw you have 3 computers still running Windows 7, which hasn’t been supported by Microsoft since 2020. These machines can’t receive security updates and are vulnerable to malware. We should either upgrade these to Windows 11 or replace them with new hardware. Each upgrade is about $150 in labor, or new PCs start around $800.”

No Password Policy

“Right now, your team doesn’t have to change passwords regularly, and I noticed a few sticky notes with passwords on monitors. We should implement a proper password manager like Bitwarden or 1Password ($4-8 per user/month) and set up multi-factor authentication on critical services like your email and banking.”

SSL Certificate Expiration

“Your website’s SSL certificate expires in 15 days. When it expires, browsers will show a scary warning that your site is ’not secure,’ which kills trust with potential customers. We need to renew this ASAP - I can handle it for you for about $100-150 including setup.”

No Redundancy

“You have a single internet connection and a single server. If either fails, your business stops. We should look at a backup internet connection (cellular failover) and consider moving some workloads to the cloud for redundancy. The backup internet is about $100-150/month.”

Exposed Credentials

“During my review, I noticed that some of your team members are using weak passwords like ‘password123’ and ‘welcome1’ and have those on Post-It notes on their monitors. This puts your business at risk of credential stuffing attacks. We should implement a password policy requiring strong, unique passwords and consider using multi-factor authentication for critical systems. This can significantly reduce the risk of unauthorized access. Also, we should look into a password manager to help your team manage their credentials securely.”

Frame Recommendations Properly

You don’t want to freak them out, but you do want to convey urgency where appropriate.

Use the “What, Why, How Much” framework

1. What: Clearly state the problem
2. Why: Explain the risk or impact (security, downtime, money loss)
3. How Much: Give a ballpark cost so they know what to expect

Don’t be alarmist, but be honest

• “This is urgent” vs “This can wait a bit, but don’t forget about it”
• “This is a security risk” vs “This is nice to have”
• “This will cost you more money if you wait” vs “This just improves convenience”

Answer Their Questions

Give them space to ask questions. Common ones:

• “How much would all this cost?”
• “What should I do first?”
• “How long would this take?”
• “Do I really need to do this?”

Be honest and straightforward. If they can do something themselves, tell them. If they need professional help, explain why.

Leave Materials Behind

• Hand them your business card
• Give them your service brochure
• Leave a one-page summary of your top 3 recommendations (if you prepared one)

Set Expectations for Next Steps

Let them know what to expect after you leave:

1. “I’ll send you a detailed report within 24-48 hours summarizing everything we discussed.”
2. “That report will include prioritized recommendations and cost estimates.”
3. “You take your time to review it - no pressure.”
4. “If you want to move forward with any of this, just reply to my email or give me a call.”
5. “If you decide to go another direction, no problem - this assessment was free and there’s no obligation.”

(Optional) Offer a time-limited incentive

“If you decide to move forward within the next 30 days, I can offer 10% off the first project we do together.”

Close Professionally

“Thanks for your time today. I know you’re busy, so I appreciate you letting me take a look around. I think there are some easy wins here that would make a big difference for you. I’ll get that report to you soon.”

Shake hands, smile, and leave on time. Don’t overstay your welcome.

After the Assessment

Within 24-48 Hours: Send the Follow-Up Report

Create a professional PDF report that includes:

1. Executive Summary (one paragraph of key findings)
2. What You Evaluated (scope of assessment)
3. What You Found (organized by category: Network, Security, Backups, etc.)
4. Prioritized Recommendations (High/Medium/Low priority)
5. Cost Estimates (ballpark pricing for each recommendation)
6. Next Steps (how to engage your services)

Keep it concise - 2-3 pages max. They’re busy.

Follow-Up Timeline

• Day 1-2: Send the report
• Day 5-7: Send a friendly check-in email: “Just wanted to make sure you received my report. Any questions?”
• Day 14: If no response, one more gentle follow-up: “Wanted to circle back - are any of these recommendations on your radar for this quarter?”
• Day 30: If still no response, move them to a “nurture” list for occasional check-ins (every 2-3 months)

Track in Your CRM

Document everything in your CRM:

• Date of assessment
• What you found
• What you recommended
• Follow-up dates
• Client’s level of interest (Hot/Warm/Cold)

This is valuable data for your business development efforts.

Key Takeaways

What Makes a Good Assessment:

✅ Professional - You showed up prepared, on time, and well-organized
✅ Educational - You taught them something they didn’t know
✅ Actionable - You gave specific, concrete recommendations
✅ Pressure-free - You didn’t hard-sell or push for an immediate decision
✅ Valuable - They walked away with useful information, regardless of whether they hire you

They should walk away thinking:

• “This person knows what they’re doing.”
• “This person cares about my business, not just making a sale.”
• “I learned something useful today.”
• “I can trust this person.”

If you accomplish those four things, you’ll win the business - if not immediately, then when they’re ready.