strategic IT planning - Free Resources From CTO Input

An image of a leader getting executive coaching on digital strategy legal

Executive Coaching on Digital Strategy Legal: A Quiet Power Tool for Justice Leaders

The work you lead is already heavy. Case backlogs. Emergency grants. New reporting rules every year. Now AI tools, cloud systems, and cyber risks sit on top of it all. For legal nonprofits, executive coaching on digital strategy legal is no longer a nice-to-have. It is focused support that helps legal executives, such as the […]

Executive Coaching on Digital Strategy Legal: A Quiet Power Tool for Justice Leaders Read More »

An image of team members from a justice organization creating a technology roadmap

Justice Organization Technology Roadmap: A Calm Path From Chaos To Clarity

Leadership Insights / Leave a Comment

If you run a justice-focused nonprofit, your tech probably feels like a pile of Jenga blocks. Old systems needing legacy system modernization. New tools. Manual work everywhere. A justice organization technology roadmap is a simple way to turn that pile into a plan through smart technology investment prioritization. It is a 1 to 3 year

Justice Organization Technology Roadmap: A Calm Path From Chaos To Clarity Read More »

3 Questions CEOs Must Ask About Security Investments To Protect Growth

Leadership Insights / Leave a Comment

If you feel unsure whether your security budget is too high, too low, or simply misdirected, you are not alone. Most growth-minded CEOs and founders feel the same tension. You sign off on six-figure renewals, sit through vendor pitches, then still worry about the next ransomware headline. Boards, lenders, and large customers now expect clear

3 Questions CEOs Must Ask About Security Investments To Protect Growth Read More »

An image of a team reducing spreadsheet overload in legal aid

From Spreadsheet Chaos to Clarity: Reducing Spreadsheet Overload in Legal Aid

Leadership Insights / 7 Comments

Legal teams did what they had to do. Intake logs in Excel. Clinic rosters in Google Sheets. Grant reports in a dozen different files, each with its own tabs, color codes, and macros that only one person understands. Over time, those quick fixes turn into a shadow system. Dozens of trackers live in different folders

From Spreadsheet Chaos to Clarity: Reducing Spreadsheet Overload in Legal Aid Read More »

An image of someone learning how to control cloud costs

Cloud Costs Are Out Of Control: How To Control Cloud Costs

Leadership Insights / Leave a Comment

You are a growth-focused CEO or founder. Your cloud spending has quietly doubled in the last 12 to 18 months, yet revenue has not. You see the invoices, but you do not see the story. Cloud was sold as flexible and a source of cost efficiency. Now it feels unpredictable, hard to budget, and even

Cloud Costs Are Out Of Control: How To Control Cloud Costs Read More »

$A CEO working with a fractional leader making their life better and their business soar$

Real-World Best Practices for Working With Fractional Leaders

Leadership Insights / Leave a Comment

You are a CEO or COO who keeps writing bigger checks for tech and security and getting weaker returns. Projects slip, cyber risk feels fuzzy, and the board is asking pointed questions you cannot answer in one slide. The tension is clear: rising spend, flat impact, and growing exposure. A fractional CTO or CISO gives

Real-World Best Practices for Working With Fractional Leaders Read More »

Aligning Technology Projects With Strategy For PayOff

Leadership Insights / Leave a Comment

You are a CEO, COO, or founder who is trying to leverage technology and getting less back. Projects slip. Systems do not connect. Vendors push shiny tools that do not align with your digital strategy or fix core problems. Your board keeps asking how IT spend supports the IT strategy, and you do not have

Aligning Technology Projects With Strategy For PayOff Read More »

An image of a team facing a project that is stalled in AI pilot purgatory and how they break out.

Why Your Project Is Stalled In AI Pilot Purgatory (And How To Break Out)

Leadership Insights / Leave a Comment

You are a growth-minded CEO or founder who has said yes to one, two, maybe three AI pilots. The demos looked sharp. The vendor decks were glossy. Your team was excited. Yet your EBITDA has not moved. The executive leadership is asking what your AI strategy is, and you do not have a clean answer.

Why Your Project Is Stalled In AI Pilot Purgatory (And How To Break Out) Read More »

A team that is modernizing legacy systems to find lower risk and greater business value from their technology investments.

Modernizing Legacy Systems Without The Risk

Leadership Insights / Leave a Comment

You are a CEO who is spending more on tech and getting less back due to mounting technical debt. Projects drag on, outages keep showing up in Monday reports, and the board is starting to ask sharper questions about risk and return. You know those fragile legacy systems are at the center of it, but

Modernizing Legacy Systems Without The Risk Read More »

An image of a board checklist for AI projects to manage risk and drive outcomes

Board checklist for AI projects that manages risk and drive business outcomes

Leadership Insights / Leave a Comment

You are a CEO, COO, or founder who is spending more on tech and getting less back. Your inbox is full of AI pitches, your team brings slide decks to every planning session, and your board asks, “What is our AI strategy?” while also warning you about risk. You feel the squeeze from every side.

Board checklist for AI projects that manages risk and drive business outcomes Read More »