Fostering Trust in the Tax Function: How Better Questions Create Better Conversations

Executive Summary

Tax professionals are under increasing pressure to deliver technically sound, timely, and strategically aligned outcomes in today's complex corporate landscape. But beyond the spreadsheets and regulations, a human element often gets overlooked: how we communicate. When conversations shut down—whether in meetings, reviews, or cross-functional discussions—it’s rarely because people lack knowledge. More often, it’s because they don’t feel safe to speak up. This blog explores how professionals in the tax function can encourage openness and collaboration by replacing closed or pseudo questions with genuine curiosity and open-ended dialogue. The result? Stronger relationships, clearer insights, and better business outcomes.

Replacing Control with Curiosity in High-Stakes Conversations

As a tax professional, you’ve likely been in a situation like this: You’re having a serious conversation—perhaps about a technical tax position, a review issue, or a missed deadline—and the person across from you goes quiet or suddenly shifts the topic.

Something just stopped them from opening up. More often than not, that something is fear.

• Fear of being misunderstood.

• Fear of saying too much.

• Fear of judgment or consequences.

While tax is a technical discipline, success relies heavily on collaboration and communication. If fear is present, people retreat. Key insights, root issues, or even innovative ideas stay buried when they do. The antidote is simple, but not always easy: authentic curiosity.

Curiosity Requires a Mindset Shift

To be truly curious, we must acknowledge that we don’t know what’s happening with someone else. In fast-paced corporate environments, we often walk into conversations with an agenda or assumptions about what’s wrong and how to fix it.

But genuine curiosity requires us to suspend judgment and focus on understanding, not solving. One of the most effective tools to build connection and understanding is the type of questions we ask. Unfortunately, we often fall into unhelpful patterns:

• Closed-ended questions: “Did you review this with the external auditors?” “Have you flagged this to leadership yet?”

These are efficient, but they limit the conversation. They can signal a checklist mentality rather than genuine interest.

• Pseudo questions are statements in disguise: “Do you think the issue is that you’re not pushing back enough?” “Is this happening because you didn’t escalate early enough?”

These can come across as judgmental or controlling, even if well-intended. They often close people down.

Open-Ended Questions Invite Openness

The most productive conversations happen when people feel safe sharing their whole perspective. To create that space, we must use open-ended questions that encourage reflection, invite context, and acknowledge emotion.

Examples include:

• “How are you approaching this new reporting requirement?”

• “What’s been the biggest challenge with the implementation so far?”

• “What concerns do you have about the upcoming audit?”

These questions allow the other person to guide the conversation and express themselves in their own words. They're especially effective in one-on-ones, performance feedback, and cross-functional meetings where alignment and trust are essential.

And a quick note—avoid questions that begin with “Why...” even if they’re open-ended. For instance, “Why did you structure it this way?” may sound like a genuine inquiry, but can feel like a demand for justification. Instead, try: “What led to this approach?” or “How did you decide on this structure?”

This subtle shift moves the conversation away from blame and into exploration.

To create that space, we must use open-ended questions.....These questions allow the other person to guide the conversation and express themselves in their own words

Avoid the Advice Trap

Even in supportive environments, one of the fastest ways to shut someone down is to jump into advice-giving, especially unsolicited.

Interpersonal dynamics experts David Bradford and Carole Robin caution against advising in emotionally charged or vulnerable moments. Why? Because advice can:

• Reinforce power imbalances

• Miss the context entirely

• Discourage the other person from developing their thinking

For example, compare these two responses:

A: “Arguments are the worst. Whenever I disagree with my colleagues, I go for a walk. It works every time. You should try it.” B: “I’m sorry you argued. You seem upset. What do you think triggered it?”

Response A is advice. It’s well-meaning but assumes sameness. Response B is empathy paired with curiosity. It invites ownership and reflection.

We often default to solution mode because we’re trained to fix problems. But sometimes, the most powerful thing we can do is listen and ask a thoughtful, open question.

One of the fastest ways to shut someone down is to jump into advice-giving.....Sometimes, the most powerful thing we can do is listen and ask a thoughtful, open question.

Practical Examples: What to Say Instead

Let’s walk through a few real-life scenarios and explore how to shift the conversation:

• If a team member misses a filing deadline, instead of asking, “Did you just forget about the filing?”, try: “What came up that made it hard to meet the deadline?”

• If a colleague resists a process change, instead of asking, “Why are you so against this?” try, “What’s your biggest concern about the change?”

• If a cross-functional colleague hasn’t responded to a request, instead of asking, “Did you even read my email?”, try: “How are you currently prioritising the requests we’ve sent over?”

These simple shifts can turn a tense moment into a productive exchange, grounded in respect rather than resistance.

Final Thought: Better Questions Build Better Culture

Great tax functions don’t just manage risk—they also manage relationships. How we communicate, especially under pressure, influences whether people feel safe speaking up, admitting uncertainty, or bringing solutions.

The next time you're in a conversation that feels stuck, ask yourself:

Am I trying to control, or am I trying to understand?

Choose understanding. Choose curiosity. And most importantly, choose questions that open doors instead of closing them.