Frequently Asked Questions
Common questions about IT consulting, fractional leadership, AI deployment, and working with Dragonfish Media.
Fractional IT Leadership
What is a fractional IT director?
A fractional IT director is a senior technology leader who works with your organization part-time — typically 2 to 16 hours per week. You get strategic IT leadership, roadmaps, vendor management, and board-level reporting without the cost of a full-time hire (often $150K–$200K+ in salary and benefits). Fractional IT directors are ideal for organizations with 10–150 employees that need expert guidance but can't justify a dedicated executive.
How is fractional IT leadership different from hiring an MSP?
A managed service provider (MSP) typically handles day-to-day technical support — fixing things when they break. A fractional IT director operates at the strategic level: aligning technology with your mission, planning budgets, managing vendors (including your MSP), leading modernization projects, and advising your executive team. Many of our clients use both — we provide the leadership layer, and an MSP handles the ticket queue.
How much does fractional IT leadership cost?
Every engagement is scoped to what you actually need — there's no one-size-fits-all price. Most organizations start with a focused number of hours per week and scale from there. Compared to hiring a full-time IT director ($150K–$200K+ in salary and benefits), fractional leadership is significantly more cost-effective while still providing senior-level expertise. We'll give you a clear, honest quote after a discovery call — no inflated proposals.
Microsoft 365 & Google Workspace
Should our school use Microsoft 365 or Google Workspace?
It depends on your priorities. Google Workspace for Education is popular with K–12 schools because of Chromebook integration, simple admin, and generous free licensing. Microsoft 365 Education offers stronger document collaboration (Word, Excel, PowerPoint), better compliance tools, and deeper integration with enterprise systems. Many schools use both. We help you evaluate based on your specific needs — device fleet, compliance requirements, budget, and staff comfort — and plan migrations when needed.
What is Microsoft 365 Copilot and should we deploy it?
Microsoft 365 Copilot is an AI assistant built into Word, Excel, PowerPoint, Outlook, and Teams. It can draft documents, summarize emails, create presentations, and analyze data using your organization's own content. Whether you should deploy it depends on your data readiness (Copilot surfaces whatever it can access — so your permissions and data governance need to be solid), budget (it's $30/user/month on top of existing licensing), and use cases. We help organizations assess readiness, clean up permissions, deploy in phases, and train staff on responsible use.
Can you migrate us from Google Workspace to Microsoft 365 (or vice versa)?
Yes. Cross-platform migrations are one of our core services. We handle email migration, file migration (Drive to SharePoint/OneDrive or vice versa), identity and access management, DNS changes, and user training. We plan migrations in phases to minimize disruption, typically over 2–4 weeks depending on organization size.
AI Governance & Deployment
What is AI governance and why does our organization need it?
AI governance is the framework of policies, controls, and oversight that ensures your organization uses AI tools responsibly, securely, and in compliance with regulations. It covers which AI tools are approved, who can use them, what data can be shared with AI systems, how outputs are reviewed, and how to handle incidents. Every organization using AI — even basic tools like Copilot or ChatGPT — needs governance. Without it, staff may inadvertently share sensitive data, make decisions based on AI hallucinations, or violate compliance requirements.
How do nonprofits deploy AI safely?
Start with governance, not technology. Define which AI tools are approved (we typically recommend starting with Microsoft Copilot, ChatGPT Business, or Claude Enterprise depending on your ecosystem). Create a usage policy that addresses data sensitivity — especially if you handle donor, student, or health data. Train staff on what they can and can't share with AI. Deploy in phases, starting with low-risk use cases (drafting emails, summarizing documents) before moving to anything that touches sensitive data. We guide organizations through this entire process.
What is the difference between ChatGPT Business, Microsoft Copilot, and Claude Enterprise?
All three are enterprise AI platforms with data privacy protections (your data isn't used for training). Microsoft Copilot integrates directly into Microsoft 365 apps — ideal if your organization lives in Outlook, Word, Excel, and Teams. ChatGPT Business (by OpenAI) offers a flexible chat interface and custom GPTs, good for general-purpose AI use across any workflow. Claude Enterprise (by Anthropic) excels at long document analysis, careful reasoning, and organizations that prioritize safety. We help you choose based on your tech stack, use cases, and compliance needs.
Security & Compliance
What compliance frameworks apply to schools and nonprofits?
Schools typically need FERPA (Family Educational Rights and Privacy Act) compliance for student data, and may need COPPA compliance for children under 13. Nonprofits handling health data need HIPAA compliance. Many organizations also need to meet cyber insurance requirements, which increasingly mandate MFA, endpoint protection, backup verification, and incident response plans. SOC 2 applies if you handle sensitive third-party data. We assess which frameworks apply to your specific situation and build governance that fits your size and risk profile.
How much does IT modernization cost for a small organization?
Costs vary significantly based on scope — the size of your organization, current state of your infrastructure, and compliance requirements all factor in. Rather than publish ranges that may not apply to your situation, we start every engagement with a free discovery call and honest assessment. You'll know exactly what you need, what it costs, and what can wait before committing to anything.
Working With Us
What industries do you serve?
We specialize in three sectors: independent schools (K–12), nonprofits and foundations, and small to mid-size businesses (typically 10–150 employees). Our deep experience in education and nonprofit environments means we understand FERPA, HIPAA, lean budgets, mission-driven culture, and the real constraints of small teams.
Where are you located?
We're based in the San Francisco Bay Area and work with organizations locally and remotely across the United States. Most of our work — strategy, governance, vendor management, cloud administration — is done remotely. For hands-on infrastructure projects, we work on-site in the Bay Area or coordinate with local partners.
How do engagements typically start?
Every engagement starts with a free 30-minute discovery call. No pitch, no pressure — just an honest conversation about your challenges and whether we can help. If there's a fit, we recommend one of our structured programs — each with a defined scope, timeline, and set of outcomes. Most organizations start with a Health Check or Security Audit, then progress to governance or implementation programs as needed.
Still have questions?
Book a free discovery call and we'll answer anything specific to your organization.
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