Congratulations, you have done it!  You have finally convinced your executive team, and they agreed.  Maybe you have funded the upgrade of your accounting system.  Perhaps that web site, long in the tooth, will finally get refreshed with new features. That custom invoicing application will now get replaced or upgraded. Your troubles are coming to an end.  No more relying on that helpdesk guy, too busy to deal with your “user” issues.  No more missing records, double data entry, waiting for the overnight process to finish.  All you have to do is get some specialists in; contract a software developer, find a good Project Manager, or maybe find a Vendor who will just do it all for you. 

The story of an Accidental CTO typically begins when an employee of a small to a mid-size firm takes on a delivery of a technology project.  They are professional, usually a manager,  head of a department or a team leader who gets approval to spend money on a project and authority to do so.  While the Accidental CTO is not a technology professional, they like and are comfortable with technology.  They feel confident that their managerial and business skills, coupled with hard work,  and executive support will help them answer the call, and deliver their project.

Following will be a journey, which will take longer than anticipated, cost more than intended, and deliver worse results than promised.  Most of the issues experienced, will not be technical.  Vendor responsiveness, team cohesion, staff availability, the timing of the project and impact on operations will surprise by their disruptive nature.

Once the project launches: goal clarity, the ability of staff to voice their requirements, effective project management, technical availability will confound and challenge the Accidental CTO.  All of it, before a single line of code, or platform configuration has even been made.  When technology is ultimately delivered, the gap between requirements, outcomes, and the actual user wants, will make any coolheaded Accidental CTO question their sanity.

Finally when finished, when the actual technical work is done, end-user training, promoting adoption, governing access, documenting the work will feel like unnecessary steps; things that have to be done just for the sake of doing them.   Some tasks will be glossed over, some even skipped.

A statistic often repeated in Change Management circles claims that 70% of all projects fail.    The fact of the matter is that delivering on time, on a budget, and with promised functionality, is a daunting challenge.  IT and Software Industry has a structural problem which prevents organizations from beating the overwhelming odds, that something will be missed.  A Limits To Growth archetype, or some fundamental opposing force still waiting to be discovered.

While industry of experts, business consultants, and project managers continue to profess their answers for success, while technology moves forward and offers evermore exciting opportunities, the projects that place these opportunities in the business owners hands, continue to fail.  Year after year the same overwhelming failure statistic, like a foreboding omen, remains.

In the end, the Accidental CTOs will probably deliver.  They will be exhausted, and question their own competency.  If they managed to produce working software, their name will forever be attached to the platform they delivered.  They will serve as its owners, govern its use, respond to its issues.  Their remaining career at the organization will hinge on the success and adoption of the platform.  If the project is stopped or fails outright, their credibility as a business person will take a hit.

I admire Accidental CTOs.  I have seen a lot of them over my 20-year  career.  They are the corporate heroes of small and medium-sized organizations particularly when hiring a Technology Executive is not an option.  They will make a thousand critical decisions before their software project is finished:  Buy vs. Build, Vendor Selection, Product Selection, Onsite vs. Remote, On-prem vs. Cloud, Full Data Migration vs. Incremental, Development Methodologies, Change Management approach.  A long chain of decision points each feeding off of another, each difficult to reverse, with the potential to derail any software project.

This blog does not profess to have an answer to the high-end structural issues that continue to plague Enterprise Software projects.  Its goal, however, is to ease the pain and make the journey smooth for Accidental CTOs.  I aim to cover the myriad of topics involved in delivering software and share my experience and lessons learned, having launched and carried out hundreds of software projects throughout my career.

So congratulations my dear friends and Accidental CTOs, you have taken the path less traveled.  Yours is a journey of an entrepreneur.  You have waged long hours and your own credibility.  You have taken on a challenging software project, to improve your company, to serve your customers, and to make the life of your co-workers easier, and more productive.  Let this blog serve as your guide, as a verifier of your intuitions, as a tool you go back to and a checklist.  I want to congratulate you on deciding to be a hero.  Good luck on your project and keep in touch.


Martin Gruszka – Three Column Consulting LLC. –

Leave a Reply