Interview scorecard template

Offensive Security Simulation Specialist interview scorecard

Evaluate Offensive Security Simulation Specialist candidates across 4 weighted areas: technical depth, real incidents and findings, risk judgement, and getting things fixed. Technical depth leads at 35%, so probe hands-on command of adversary emulation: Cobalt Strike or Mythic C2 profiles, AD abuse paths (Kerberoasting, ADCS ESC1-8), EDR evasion, and custom loader development. Use the rubric to compare role-specific evidence consistently.

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security complianceadversary emulationc2 infrastructuremitre attackred teaming
TL;DR
For technical depth, look for evidence the candidate names specific tooling and tradecraft, explains payload development and OPSEC-safe C2 configuration without reciting generic pentest checklists. For real incidents and findings, look for evidence the candidate walks through named engagements end to end, from phishing pretext to objective, including detections triggered and blue team response observed. Apply the written 1–5 anchors to every answer, record the evidence behind each rating, and use the factor weights to reach a consistent overall assessment.
Complete evaluation framework

What to assess and how to score it

Review the evidence signals before interviewing. Then use the anchored descriptions—not instinct alone—to choose the score that best matches each answer.

01
Evaluation factor

Technical depth

35% weight

Probe hands-on command of adversary emulation: Cobalt Strike or Mythic C2 profiles, AD abuse paths (Kerberoasting, ADCS ESC1-8), EDR evasion, and custom loader development.

Evidence to listen for

  • Command of the specific attack surface, tooling, and controls the role covers
  • Understands how the underlying system works, not just how the tool reports on it
  • Can explain an attack or control chain end to end
  • Distinguishes what they found themselves from what a scanner flagged

Five-point scoring guide

1
Poor

Tool operator only; no understanding of the systems underneath.

2
Needs Improvement

Runs tooling but cannot explain findings or how the attack works.

3
Satisfactory

Solid working knowledge; depth thins outside familiar tooling.

4
Very Good

Strong command of the domain; explains attack and control chains clearly.

5
Excellent

Names specific tooling and tradecraft, explains payload development and OPSEC-safe C2 configuration without reciting generic pentest checklists.

02
Evaluation factor

Real incidents and findings

30% weight

Ask for real engagements: full-scope red team ops, purple team exercises, TIBER-EU or CBEST assessments, initial access achieved, and objectives such as domain admin or crown jewel access.

Evidence to listen for

  • Brings specific incidents, findings, or audits they personally worked
  • States their own role rather than the team's
  • Describes what was actually at risk and what changed afterwards
  • Can talk about a finding that turned out to be wrong

Five-point scoring guide

1
Poor

No hands-on work; knowledge is entirely certification or coursework.

2
Needs Improvement

Limited exposure; cannot describe their contribution to an incident.

3
Satisfactory

Real casework with adequate detail; ownership sometimes vague.

4
Very Good

Specific incidents with clear personal scope and what changed after.

5
Excellent

Walks through named engagements end to end, from phishing pretext to objective, including detections triggered and blue team response observed.

03
Evaluation factor

Risk judgement

20% weight

Test how they scope risk on live production targets: rules of engagement, deconfliction with the SOC, avoiding data destruction, and prioritising findings by exploitability versus theoretical severity.

Evidence to listen for

  • Prioritises by actual exploitability and business impact, not raw severity scores
  • Can argue for accepting a risk as well as fixing it
  • Knows the difference between a finding and a problem
  • Does not cry wolf or wave things through

Five-point scoring guide

1
Poor

Treats every finding as critical, or waves real risk through.

2
Needs Improvement

Follows severity scores mechanically; no business context.

3
Satisfactory

Reasonable prioritisation; less confident arguing for risk acceptance.

4
Very Good

Prioritises by exploitability and impact; can justify accepting a risk.

5
Excellent

Sets clear rules of engagement, halts when scope is ambiguous, and ranks findings by realistic attack chains rather than raw CVSS.

04
Evaluation factor

Getting things fixed

15% weight

Check how findings become fixes: attack narrative reports, MITRE ATT&CK mapping, detection engineering handoff to blue team, and retesting closed gaps after remediation.

Evidence to listen for

  • Writes findings engineers can act on rather than a wall of output
  • Has persuaded a team to fix something they did not want to fix
  • Explains risk to executives in business terms
  • Works with the org rather than policing it

Five-point scoring guide

1
Poor

Adversarial with engineering; findings never get fixed.

2
Needs Improvement

Reports are unactionable; no influence beyond raising tickets.

3
Satisfactory

Adequate reporting; relies on mandate rather than persuasion.

4
Very Good

Actionable findings and a real record of getting fixes shipped.

5
Excellent

Produces reports engineers act on, maps techniques to ATT&CK, and can evidence detections or controls built as a direct result.

Evidence-led prompts

Interview questions for a Offensive Security Simulation Specialist

Use these prompts to surface evidence for the weighted factors above and compare candidates against the same role-specific criteria.

  1. 01

    Can you explain a situation where you identified and exploited a vulnerability during an authorised assessment?

  2. 02

    What experience do you have with red team operations, and how do they differ from penetration testing?

  3. 03

    What experience do you have with social engineering within authorised engagements?

  4. 04

    Can you describe your experience with scripting in a security context?

  5. 05

    What is your experience with penetration testing frameworks and tooling?

See the complete Offensive Security Simulation Specialist question set
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