Chicago Tech Leaders Share Their Top Challenges | Forte Group

ITA Leadership Summit Recap: technology leaders share their top frustrations

Leading a technology organization is a tough job. Struggling to deliver value, adapting to changing business needs, dealing with massive turnover and staffing issues, all while driving innovation—these are just some of the daily challenges tech leaders face.

So, we figured, what better way to address some of these frustrations than to meet up and talk about it? On October 10, Forte Group partnered with the Illinois Technology Association (ITA) to host the Fall Leadership Exchange Roundtable Dinner. The event was a discussion with some of Chicago’s technology leaders on the challenges they face and how they’re solving those challenges.

The night kicked off with an intro from Forte Group Managing Director and Partner, C.J. Montano. He asked, “What are some of your top frustrations? How do we solve them?”


We asked the CTOs and other tech leaders at each table to discuss and list some of their top frustrations. Here’s a summary of some of the common challenges they shared:

Consulting frustrations

  • IT consultants: A running theme, even from C.J., was that vendors and software delivery providers aren’t generally held in high regard. Poor-quality software, overshot budgets, and a lack of transparency are common. One person shared that most vendors don’t have to live with the fallout of the decisions they make. Rather than consult, they’re often order-takers.
  • Groupthink: In concert with the above frustration, vendors often assume the role of a “yes-man,” merely kowtowing to the point-of-view of the person paying the bills. Without appropriate data points or differing perspectives, it’s easy to fall into a “groupthink” culture that prioritizes hours worked, not organizational value created.
  • A lack of resources: Often, when consultants attempt to advise in the right direction, they don’t have enough clout or budget to convince C-level executives that their suggested course is the correct one.

Management frustrations

  • “Bike-shedding;” the Law of Triviality: Small, trivial change requests that take time and effort to develop, alter the scope of a project, and don’t produce much value.
  • Getting influencers on board: Creating organizational alignment between business and IT that focuses on value.

Leadership frustrations

  • Give credit where credit is due: Often, those who submit the exceptional ideas don’t get the credit.
  • Get out of maintenance mode: The burdens of layered or unwieldy systems can make innovation a struggle.
  • Attrition: Constant staff churn can inhibit the continuity of a project.
  • Quality and consistency: Establishing predictable, valuable delivery from product and engineering teams is a constant challenge.

Overcoming technology frustrations

Vendor frustration was a recurring theme throughout the evening’s discussion. The evaluation of a software delivery partner is one of the most crucial decisions a technology leader can make. In fact, C.J. shared that he so disliked the consulting industry’s approach that he decided to start his own practice. Whatever your path to building software, an outside resource should establish predictable, value-driven software delivery with full transparency. If your software vendor isn’t making you better, they’re making you worse.

Related resource: In a recent white paper, we outlined some guidelines for evaluating your delivery partner.

How does your organization tackle some of these challenges? Get in touch with us on LinkedIn or send us your feedback directly, and we’ll share the results in future articles.

Steve Brown

by Steve Brown

Steve is a writer and editor who works with Forte Group’s practice leads to share our insights on best practices, tips, and trends in software design and development.

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