When to Bring in Outside Expertise for Strategic Conversations

A professional business setting where a cybersecurity expert is having a conversation with a Chief Information Security Officer (CISO)

Estimated reading time: 3 minutes

Key Takeaways:

  • External expertise is crucial when companies face new technology challenges or uncertainties.
  • SideChannel’s value lies in offering both experience and context to help businesses navigate complex security and cloud adoption issues.
  • Having a strategic partner ensures informed decision-making during critical technology transitions.

It was a hot summer day in Manhattan. I had just finished a meeting with a Chief Information Security Officer (CISO) from a global financial services company. As we walked to lunch, I asked him how often he brought in outside experts for strategic conversations. His answer shaped the way I think about working with clients.

The meeting itself had been general—covering topics like cloud security, AI, and systemic risk. I expected a deeper, more specific conversation, which led me to wonder how often companies rely on outside expertise for critical decisions.

The CISO responded to my question with a question of his own: “How many CIOs and CISOs have you worked with?” After thinking about it, I realized I had worked with well over 100. He then explained that a couple of times a year, he encounters “unknown unknowns.” These are moments when he’s not sure where to go next because the company is heading into uncharted territory, whether due to new technology or an internal signal that something might be changing.

That’s when he calls in external experts. The goal isn’t just to get answers, but to gain context—insight into how other teams have handled similar challenges. This context helps him navigate through uncertainty and make informed decisions.

Why Experience and Context Matter

Whether you’re a startup or a large enterprise, there will come a time when you’re facing new challenges that your team hasn’t encountered before. This is where experience and context become critical. SideChannel offers that by bringing in seasoned experts who have dealt with these issues before.

From cloud migrations to security challenges, having a partner who can provide both a broad perspective and detailed solutions is invaluable. Companies don’t just need answers—they need someone who has been there before and can help guide them through unfamiliar situations.

Final Thoughts

As technology continues to evolve, so do the challenges businesses face. The next time your company is entering uncharted territory, consider bringing in external expertise. It might provide the context and experience you need to make the right decisions. At SideChannel, we’ve likely encountered the same issues you’re facing, and we’re here to help.

Empower Your Cybersecurity Leadership with SideChannel

Ready to tackle your company’s cloud security challenges with the support of experienced experts? Let SideChannel help guide you through the complexities of cloud adoption and cybersecurity. With our team’s extensive experience, we provide the context and solutions you need to navigate uncharted territory. Reach out today to learn how our Virtual CISO services can provide the strategic direction your organization needs to move forward confidently. Contact us now to get started!