Let’s Build Your 2026 Leadership Playbook
Help me design the roadmap that solves your biggest headaches next year.
The Bottom Line
We are approaching the end of 2025. This is the time when budgets are finalized, and strategies are set. I am currently building the editorial calendar for 2026 and want to ensure every post delivers high-leverage value to you.
I do not want to guess what you need. I want to build this roadmap directly around your reality.
Please take two minutes to complete the short survey below. Your feedback will dictate exactly what we cover in the coming year.
Why This Matters
Leading technology and cybersecurity in an SMB is a unique challenge. You do not have the unlimited resources of an enterprise CISO, and you rarely have a large team to delegate to. You are often the strategist and the engineer simultaneously.
My goal is to make this publication a force multiplier for you. To do that effectively, I need to know three things:
Where are you trying to go?
What technical hurdles are standing in your way?
How are you balancing the technical demands with business leadership?
The 2026 Reader Survey
Please review the questions below. You can reply directly to this email or click the button below to submit your answers anonymously.
Part 1: Your Strategic Focus
Q1: When you look at your professional growth plan for 2026, what is the one “big rock” you must move to be successful?
Scaling the team and capabilities without increasing headcount
Securing budget approval for critical security initiatives
Improving executive presence and board-level communication
Transitioning from a “hands-on” technical role to a strategic leadership role
Other
Part 2: The Knowledge Gap
Q2: Which technical or security domains do you feel you need to understand better to protect and grow your business?
AI Governance: Practical use cases and safety rails for internal use
Zero Trust: Moving beyond buzzwords to actual implementation
Compliance: Navigating new regulations without a dedicated legal team
Incident Response: Mastering the “First Hour” of a breach
Vendor Management: How to vet and manage third-party risk effectively
Part 3: The Leadership Balance
Q3: As an SMB leader, how would you describe your current mental split between “keeping the lights on” and “understanding business strategy”?
100% Tech: I am fully consumed by tickets, fires, and stack management.
70/30: I try to focus on business outcomes, but operations usually pull me back in.
50/50: I have a healthy balance between technical oversight and business alignment.
Business First: I spend most of my time on strategy and rely on my team/MSPs for the tech.
Part 4: The Engagement Factors
Q4: The Magic Wand. If you could wave a magic wand and instantly solve one recurring headache that drains your energy every week, what would it be?
Q5: Delivery Preference How do you prefer to consume complex leadership or technical concepts?
Deep Dives: Comprehensive guides I can save and reference later.
Quick Hits: Short, actionable checklists I can implement in 15 minutes.
Case Studies: Real-world teardowns of what other SMBs are doing.
Q&A Style: Direct answers to reader-submitted questions.
What Comes Next
I will collate the responses and publish a breakdown of the results next week. We will look specifically at the “Tech vs. Business” divide, as I suspect many of us are struggling with the same operational gravity.
Thank you for helping me make this community better.