How much should leaders share with their teams? Is full transparency always the right move, or are there times when keeping decisions private is necessary?
These are questions I recently explored with Justin Smith, CEO at Contractor Plus, in an episode of Wisdom From Wizards. Our conversation tackled a central tension that many scaleup leaders face as they try to build trust while navigating complex, high-stakes decisions.
When asked whether he would prefer complete transparency or keeping some decisions behind closed doors, Justin did not shy away from acknowledging the nuance. He admitted that certain decisions, such as those involving legal and compliance issues, cannot be shared openly. That is the practical reality of running a business.
Yet despite those limits, Justin described himself as a firm believer in radical transparency. In his words:
“I am a proponent of radical transparency.”
He explained that for a company to truly flourish, transparency is not optional. Leaders need to say what they mean and mean what they say. Teams need to see the honest, authentic version of their leaders. Stakeholders deserve to be on the same page at the same time.
Justin shared a simple but powerful principle that guides his leadership:
“You get what you give in life.”
This mindset shapes how he runs Contractor Plus. By offering trust and openness, he expects the same in return. The payoff is alignment across the company, where people are more willing to buy in, take ownership, and work toward shared goals.
For CEOs of tech scaleups, this perspective is especially relevant. Rapid growth often strains communication and alignment. Without clear, authentic leadership, silos and confusion can take root quickly. Radical transparency can be a counterweight to those risks, but it requires deliberate choices about when and how much to share.
At Wisdom From Wizards, these are the kinds of conversations we prioritize. We feature real decision-makers talking about the real challenges they face so that other leaders can take away practical insights.
Wisdom From Wizards is brought to you by Caribou Strategic, helping tech scaleups stand out and succeed.
If you are a CEO looking to drive clarity, conviction, and growth in your business, I invite you to connect with us. Let’s talk about how you can sharpen your strategy and lead with confidence in the next phase of your company’s journey.