I recently spoke at an IT conference on transforming IT in our complex, fast-moving world. I hoped to enlighten attendees on prioritizing transformative work. While some may have taken away my core message on strategy, the most consistent feedback was how refreshing it was to hear someone articulate the common problems we face in IT with a frank dose of reality. It was a clear reminder of the importance of consistently conducting a “reality check” on our IT endeavors.

Say It Like You Mean IT: The Need for Candor

I’m rarely accused of holding back my opinions, and apparently, that candor resonated. Upon reflection, this feedback highlights a common issue in how IT often operates within a business: we aren’t always realistic enough.

IT teams and their business partners all face aggressive timelines, evolving scope, ambiguous needs, and demanding stakeholders. This is the nature of today’s business environment; our business colleagues challenge IT to move faster because their market demands it. But too often, IT departments or providers become passive “order takers,” accepting requests without sufficient pushback or collaborative refinement. This lack of upfront reality and strategic partnership diminishes trust, increases escalations, and ultimately lowers the value IT delivers.

It is IT’s job, and certainly the role of a strategic partner like a fractional CIO, to help the business understand what’s truly possible with technology, what trade-offs are necessary, and how everyone can collaborate to execute effectively.

Partner With and Truly Know the Business: What SMB Leaders Should Expect

Your business partners are generally open to hearing that trade-offs are needed. They understand choices must be made to ensure critical priorities are addressed quickly. In fact, they trust their IT leaders and advisors to stand up and illuminate those choices.

As an SMB leader, you need an IT function (whether internal or external) that:

• Challenges assumptions, not just accepts orders. Not every request is a “must-have,” and your IT advisor should be willing to push back respectfully to ensure true priorities are met.
• Delivers “good enough” for speed and learning, when appropriate. Not every solution needs perfect polish before it can provide value or feedback.
• Understands the problem before designing a solution. Your IT partner should always ask “why?” before building the “what.”

Reality Check Your IT: From Tech Delivery to Value Creation

Your IT organization or provider plays a significant role in delivering what really creates value for your business – whether that’s a product, a service, or a financial outcome. SMBs don’t make money from their IT; they leverage IT to make money from their core offerings. Therefore, IT professionals, and especially IT leaders like a fractional CIO, must understand your business ecosystem and proactively help you make sound technology investment choices.

We need more candid “reality checks” for our IT projects and strategies. Without this upfront realism, we risk merely delivering technology rather than tangible business value. Failing to speak up, challenge assumptions, or highlight potential pitfalls is like watching someone run full speed towards a cliff; we could have helped them change course with a difficult but necessary conversation grounded in facts.

What’s Next

It may not always be comfortable or popular to inject these “reality checks” into how your SMB approaches technology. But in the end, that dose of upfront realism, that commitment to ensuring IT initiatives are truly aligned with business value, might just be what makes your next project a resounding success.

Is your SMB’s IT function truly acting as a strategic partner, providing essential reality checks and ensuring technology delivers measurable business value? Or is it stuck in an order-taker mode? If you’re looking for an experienced fractional CIO to bring that critical, objective, and value-focused perspective to your technology strategy and execution, let’s connect with Succeed Sooner Consulting.