Services Leadership Compliance Contact

Practical Checklist

The First-Time Security Assessment Checklist

A practical guide for business leaders hiring their first security firm

If you've never had a security assessment before, you're in good company. Most mid-market companies operate without dedicated security expertise for years before realizing they need help. This checklist will help you navigate the process - from evaluating vendors to understanding what a realistic engagement looks like.

10 minute read

10 Questions to Ask Before Hiring a Security Firm

These questions help you distinguish firms that will actually help from those just looking for a quick sale.

Question 01

"What experience do you have with companies at our stage?"

Look for: Experience with companies your size who haven't had security programs before. A firm used to enterprise clients may over-engineer solutions you can't maintain.

Question 02

"What will we be able to do ourselves after the engagement?"

Look for: Knowledge transfer as a core deliverable. Good consultants build your capabilities, not dependency.

Question 03

"Who will actually do the work?"

Look for: Named individuals with relevant credentials. Beware firms that sell senior partners but deliver junior staff.

Question 04

"What does a realistic timeline look like?"

Look for: Honest timelines with built-in buffer. Security assessments typically take 4-8 weeks depending on scope.

Question 05

"What happens after you deliver the report?"

Look for: Implementation support, remediation guidance, or ongoing advisory options. A report that sits on a shelf doesn't help.

Question 06

"Can you share a sample deliverable?"

Look for: Clear, actionable reports written in business language - not just technical jargon. You should be able to understand priorities without a translator.

Question 07

"Do you sell security products or tools?"

Look for: Independence. Firms that sell tools may recommend what they resell, not what you need. Advisory-only firms have fewer conflicts.

Question 08

"How do you prioritize findings?"

Look for: Risk-based prioritization tied to YOUR business context, not generic severity ratings. What matters for a healthcare company differs from manufacturing.

Question 09

"What does success look like in 90 days?"

Look for: Concrete, measurable outcomes. "Improved security posture" is vague. "Documented incident response plan tested with tabletop exercise" is specific.

Question 10

"What will this actually cost - including hidden fees?"

Look for: All-in pricing or clear scoping boundaries. Watch for "additional phases" that weren't in the original quote.

Red Flags in Vendor Proposals

Watch for these warning signs when reviewing security firm proposals:

One-size-fits-all scope: If the proposal looks templated with your company name dropped in, they haven't understood your situation.

Fear-based selling: Legitimate firms educate; they don't scare you into buying. Avoid "you'll definitely get breached without us."

Tool-first recommendations: If they recommend specific products before understanding your environment, they may be resellers first, advisors second.

Vague deliverables: "Comprehensive security assessment" means nothing. Look for specific outputs: asset inventory, risk register, remediation roadmap.

No mention of your team: Engagements that ignore your existing IT staff often create reports nobody can act on.

Pressure to sign quickly: "This price is only good until Friday" is a sales tactic. Legitimate firms don't create artificial urgency.

Credentials that don't match scope: A firm with only penetration testing experience may not be right for a compliance-focused engagement.

What to Expect in Your First Assessment

A well-run first security assessment typically includes these phases:

Phase 1

Discovery (Week 1-2)
  • Interviews with key stakeholders (IT, operations, leadership)
  • Documentation review (policies, network diagrams if they exist)
  • Technical inventory of systems, applications, and data flows
  • Understanding your business context and risk tolerance

Phase 2

Assessment (Week 2-4)
  • Gap analysis against relevant frameworks (NIST CSF, CIS Controls)
  • Technical vulnerability scanning (with your permission)
  • Review of access controls, configurations, and processes
  • Compliance mapping (if applicable: HIPAA, PCI, SOC 2)

Phase 3

Analysis and Reporting (Week 4-6)
  • Risk-prioritized findings with business context
  • Executive summary for leadership/board
  • Technical details for IT team
  • Remediation roadmap with quick wins identified

Phase 4

Handoff (Week 6-8)
  • Findings presentation to stakeholders
  • Q&A and clarification sessions
  • Implementation planning support
  • Knowledge transfer to your team

Realistic Budget Ranges

Security assessment pricing varies widely. Here's what to expect for companies with 50-500 employees:

Engagement Type Budget Range What You Get
Quick Assessment $10K - $25K High-level gap analysis, top 10 risks, executive summary. Good for "where do we even start?"
Comprehensive Assessment $30K - $75K Full security program assessment, detailed findings, remediation roadmap, compliance mapping
Penetration Testing $15K - $50K Active testing of your defenses. Often done after initial assessment to validate technical controls
Virtual CISO (Monthly) $5K - $20K/mo Ongoing security leadership. Strategic guidance, program management, board reporting, incident support
Compliance Program (SOC 2, HIPAA) $40K - $100K Full compliance readiness including policy development, control implementation, and audit prep

Note: Prices vary by region, firm reputation, and scope complexity. Get 2-3 quotes and compare scope, not just price.

Ready to Have a Conversation?

Trifident Security Advisory helps companies build their first security program - from zero to protected. No tool sales, no scare tactics. Just practical expertise from people who've done this before.

Schedule a Free 30-Minute Consultation

Let's discuss where you are, where you need to be, and whether we're the right fit to help.

Start the Conversation

Trifident Security Advisory
Kansas City • Tampa • Washington D.C.