Does your team have the courage to ask tough questions to management?

Most organizations say they want honest feedback, but employees still hesitate to challenge leadership. Why? Because they fear negative repercussions or believe nothing will change even if they do speak up. Leaders must do more than invite feedback —they need to facilitate, and model tough questions.

Organizational psychologist Adam Grant emphasizes the critical importance of creating environments where individuals feel safe to “speak truth to power”. He argues: “What stops us from speaking truth to power is not a desire for harmony. It’s a climate of fear and futility. When leaders fail to make it safe and worthwhile to be honest, we bite our tongues. Weak leaders stifle dissent and leave themselves weaker. Strong leaders welcome dissent and make themselves stronger.”

When employees stay silent, leaders lose visibility into real issues happening on the ground. This creates a dangerous gap between decision-makers and those getting the work done, leading to poor strategic decisions, misaligned priorities, and a culture where bad news is hidden until it’s too late.

The Volkswagen emissions scandal, often referred to as "Dieselgate," serves as an example of the consequences when employees lack the courage to ask tough questions to management. In 2015, it was revealed that Volkswagen had installed software in millions of diesel vehicles to cheat emissions tests, making the cars appear more environmentally friendly than they were. This deception eventually led to a $14.7B settlement for the company. Investigations indicated that a culture of fear within Volkswagen prevented employees from speaking up about unethical practices. Bernd Osterloh, a member of VW's supervisory board, wrote "We need in future a climate in which problems aren't hidden but can be openly communicated to superiors”.

So how can leaders facilitate and model tough questions? Here’s 4 habits organisations can adopt:

“Ask Me Anything” (AMA) sessions. Hold regular “Ask Me Anything” (AMA) sessions, where employees can submit and ask questions directly to leadership. These sessions should be live (virtual or in-person) and promote transparency, while leadership addresses concerns candidly. Companies like Zappos hold open Q&A sessions to build trust and reinforce their culture of transparency. To implement this effectively, organizations should allow employees to submit questions either in person or anonymously, rotate leadership participants, and record and share key takeaways to ensure accountability and follow-through.

Feedback platforms. Another approach is implementing a dedicated anonymous feedback platform where employees can submit questions or concerns without fear of repercussions. Organizations like Netflix, known for their radical candor, use open feedback channels to encourage constructive criticism at all levels. This can be achieved through tools like Slido or Google Forms, allowing employees to voice concerns, anonyously, and in a structured way. Leadership can then regularly review submissions and provide timely responses in company-wide updates, including what changes are happening and what are not happening, demonstrating that feedback is valued and leads to clear action.

Modelling vulnerability. Leadership needs to lead by example, by modelling vulnerability. Leaders can openly acknowledge their mistakes and talk about what they learned. This sets the tone that failure isn’t punished, but rather a growth opportunity. By admitting when they got something wrong, leaders normalize vulnerability and encourage employees to do the same. For example, Satya Nadella, CEO of Microsoft, transformed Microsoft’s culture by shifting from a “know-it-all” to a “learn-it-all” mindset, frequently admitting what he doesn’t know and reinforcing that mistakes is what drives learning.

Braintrust meetings. Instead of waiting for employees to challenge decisions, leadership should start meetings by asking: "What are we missing?" and “What concerns do you have?" For example, Braintrust meetings are a feedback-driven meeting format pioneered by animation company Pixar to encourage open, candid discussions and improve creative decision-making. It is a collaborative review process where a team of experienced individuals—often directors, writers, and key creatives—analyze a project, identify problems, and suggest improvements without hierarchy getting in the way. Everyone is encouraged to speak freely and challenge ideas without fear of offending others. The goal is to make the work better, not to protect egos. Even junior team members can challenge senior leaders. Titles don’t matter—only the strength of the ideas.

Final Thought

Encouraging tough questions isn’t just about permission—it’s about facilitating and modeling them. Organizations need systems that make challenging leadership a habit, not an exception. When employees feel safe to speak up, when they have the channels to do so, when leadership asks the tough questions and follows through, tough questions stop being uncomfortable—and start driving better decisions.