50 Shades of Fail

Why tech implementations fail and how to avoid them.

Ken Akoundi
2 min readSep 30, 2020


By Ken Akoundi and Josh Smith

“I’m a very strong believer in listening and learning from others.”
- Ruth Bader Ginsburg

“We are not perfect, nor should we pretend to be.”
- Dr. Travis Bradberry

Most institutional investors have been or will be exposed to a technology decision at some point in their tenure. Those of you who have been involved in technology selection and implementation know these projects can be challenging and that vendors vary not only in software competency levels but implementation competency. The goal with this white-paper is to provide insights on potential challenges and best practices for preventing issues when selecting portfolio management and portfolio reporting systems. The insights and best practices in the paper were gathered through over 200 dialogs with various institutional investment over the past several years.

To go beyond the most common problems that plague projects[1] such as “Optimism Bias“ or the usual interplay between technology solution vendors and institutional investment organizations (hereafter to be referred to as “clients”) during technology selection, we began by asking investment offices specifically about the outcome of their most recent investment technology implementation. The answers were usually one of three outcomes: (1) successful, (2) failed or (3) inconclusive. We note that when an implementation “failed” to meet client expectations, the expression of frustration is very vocal and unconstrained. In these cases, no one seems to “own” the failure. To quote JFK, “Victory has a hundred fathers and defeat is an orphan.” We observed that the “inconclusive” implementations sounded like failures (or strategic denial), as the main component seemed to be basic unmet expectations.

Rather than a lengthy treatise on project failures, we chose to summarize our thoughts and findings into an actionable cheat sheet and checklist, intended for senior managers. We hope this paper can help you mitigate risk in future projects by identifying common pain points, offering tips for risk mitigation, and helping both vendors and the family office investment and operations teams better understand the others point of view.

This is meant to be a living document. As such we welcome all suggestions and comments.

[1] For a great podcast on this subject, please see “Here’s Why All Your Projects Are Always Late — and What to Do About It”, by Freakonomics Radio.

About Ken Akoundi PhD

Ken is the founder of Cordatius, Cordatius helps Long-term investors improve all technological and operational aspects of their investment office.

About Josh Smith

Josh Smith is co-founder and CEO of Solovis — the industry’s first true multi-asset class portfolio management, analytics and reporting technology platform focused on the unique needs of the limited partner community. Learn more at www.solovis.com.



Ken Akoundi

Leading Investment office digital transformation for all LPs.