Whether red teaming is new to the conversation or returning with higher expectations, the decision rarely feels simple. The proposals look similar. The promises sound familiar. And it’s not always obvious which engagement will actually help answer the questions you’re being held accountable for.
What leaders are often trying to avoid isn’t technical failure. It’s uncertainty. The kind that shows up later, when you’re asked to explain why something wasn’t caught, why a control didn’t hold, or why a past investment didn’t deliver the confidence you expected.
But red teaming only delivers value when it’s done with intent. When it’s tied to real threats, real objectives, and real decisions that security leaders have to make. Without that grounding, even technically strong engagements can turn into activity without clarity.
From conversations with security leaders, a consistent theme comes up. The challenge isn’t whether or not to run a red team, but how to choose the right partner. Your vendor should understand your environment, respect your defenders, and can translate technical execution into insight you can actually use.
In our recent virtual session, we spent time unpacking what separates meaningful red team engagements from ones that miss the mark. Below are the key things Trevin Edgeworth, Red Team Practice Director, consistently recommends leaders look for when you’re evaluating red team vendors.
1. They Focus on Objectives, Not Checklists
A good red team engagement has a clear mission. Many leaders have seen the opposite play out: a time-boxed engagement, a long list of findings, and very little clarity about what actually matters when it’s time to make decisions.
Instead, you want a team that understands why you’re testing, not just what is being tested, and builds scenarios that reflect real attacker goals. That means:
- Define what “success” looks like up front.
- Map scenarios to your critical assets.
- Ask the questions your board will actually care about.
A report full of low-impact vulnerabilities doesn’t move the needle. A narrative that explains how an attacker might win does.
2. They Emulate Real-World Adversaries
Not all threat models are created equal. The best vendors tailor their approach to:
- The threat actors most relevant to your industry.
- The tools and techniques those adversaries actually use.
- The controls you depend on today (identity, cloud, SaaS, AI systems).
This isn’t about playing “hacker dress-up.” It’s about credibility. Red teams should challenge your environment the way real attackers would.
3. They Bring Clarity and Evidence to Decisions
Security decisions are expensive. Leaders need justification. A strong red team doesn’t just say “here are the gaps.” They show how an adversary moves, why a control failed, and what impact that has on the business. That kind of evidence helps security leaders prioritize investment and defend those choices to executives and boards.
If a vendor can’t clearly articulate business impact, they’re delivering output, not insight.
4. They Validate Your Defenders, Not Just Your Tech
You’re hiring a red team because you want confidence in your overall security posture, including people and processes. The most valuable engagements look beyond tools and assess how teams respond in real conditions, including:
- Detection and response workflows
- Your SOC or MSSP effectiveness under pressure
- Incident response readiness
Done well, this kind of testing doesn’t undermine defenders. It highlights where teams perform well and where better tooling, training, or playbooks would make a meaningful difference.
5. They Embrace Complexity in Modern Architectures
Today’s attack surfaces extend far beyond traditional networks and servers. Cloud platforms, SaaS ecosystems, third-party integrations, and automated workflows infused with AI now shape how organizations operate. Leaders often discover that the most meaningful gaps live at the seams between these systems.
A Red Team that only looks at traditional infrastructure might miss the real gaps where adversaries are already poking.
6. They Provide Actionable Reporting
By the time testing wraps up, reporting is what determines whether the effort actually pays off. And leaders need something they can use, not just something that proves work was done. The most effective red team reporting:
- Is scenario-based, not verbose prose.
- Distinguishes between quick fixes and long-term, strategic improvements.
- Ties findings back to business risk, not just CVE numbers.
When reporting is done well, it becomes an input to roadmaps and planning, not another PDF that sits on a shelf.
7. They Partner With You, Not Just Test You
The red team relationships leaders value most feel collaborative, not adversarial. The strongest partners:
- Communicate clearly before, during, and after testing
- Take time to align with your team’s maturity and goals
- Share insights that remain useful long after the engagement ends.
Red teaming should build confidence over time. The right partner is invested in helping you improve, not simply in proving what’s broken.
A Final Word
Choosing a Red Team vendor isn’t just a procurement task, but a strategic decision. The right partner provides clarity when decisions are hard, evidence when tradeoffs are unavoidable, and confidence when accountability matters most. When the focus stays on objectives, real-world emulation, and business impact, red teaming becomes more than a test. It becomes a way to continuously strengthen resilience.
In the end, the question isn’t who can run a red team. It’s who can help you make smarter, more defensible security decisions.
Want to dig deeper into red teaming and how it drives security outcomes? Check out our Red Team Readiness Assessment to evaluate your current readiness and create a strong foundation for success.
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