Asking Bold Questions: Assertive Communication Techniques for Leaders
Updated: Sep 22
by Stephanie Bickel
Have you ever been in a meeting where you weren't the subject matter expert?
Perhaps the conversation moves into unfamiliar territory. Others seem to know the answers, and you're wondering how you can contribute.
You may feel uncomfortable speaking up because you don't have the same technical knowledge or experience as everyone else in the room.
But you don't need to have all the answers to add value.
Sometimes, the most valuable contribution you can make is asking the right question.
Assertive communication involves expressing your ideas, asking thoughtful questions, and participating confidently in conversations. It also requires curiosity, particularly when you're navigating complex decisions or unfamiliar subjects.
One of the most effective ways to demonstrate assertive communication is to ask BOLD questions.
These questions help teams identify problems, understand their significance, assess risks, and make informed decisions.
And they can help you contribute to important conversations, even when you're not the expert.
What Are BOLD Questions?
BOLD questions are thoughtful, direct questions that challenge assumptions, uncover important information, and move conversations toward meaningful outcomes.
They help leaders understand what is happening, why it matters, and what needs to happen next.
When you ask BOLD questions, you demonstrate your communication skills while drawing on your experience and judgment.
You also help accelerate decision-making and problem-solving for your team.
The art is knowing which questions to ask and when to ask them.
Some questions require significant thought or research before they can be answered. Give yourself and others the time needed to explore them.
The sequence matters, too.
Before jumping to solutions, you need to establish whether a problem exists, understand its significance, and determine what success would look like.
Here is a three-step approach to asking BOLD questions.
Step 1: Ask Questions That Prove the Problem Exists
Before investing time, resources, or energy into solving a problem, make sure you understand what is actually happening.
It's easy for teams to move directly into solution mode.
Someone identifies an issue, and the conversation immediately shifts to what needs to be done.
But what if the problem hasn't been clearly defined?
What if the team is responding to an assumption rather than evidence?
Asking questions that establish the facts can help everyone develop a shared understanding of the situation.
Questions to ask:
What evidence do we have that this problem exists? How do we know it is happening?
What is happening?
Where is it happening?
When is it happening?
Who specifically is telling us it is happening?
Which groups are affected?
Who specifically is affected by this?
These questions help clarify the problem before the team begins discussing solutions.
For example, imagine someone says, “Our customers are unhappy with the new process.”
Rather than immediately recommending changes, you might ask:
“What evidence do we have that customers are unhappy?”
“Which customers are experiencing the problem?”
“When did we first notice this?”
The answers may reveal that the issue affects a specific customer segment, occurs during one stage of the process, or is based on limited feedback.
By asking thoughtful questions, you help the team focus on the actual problem.
And you contribute valuable perspective without needing to be the subject matter expert.
Step 2: Ask Questions That Establish Significance
Once you've established that a problem exists, the next step is understanding how important it is.
Not every problem requires immediate attention.
Some issues have a limited impact. Others affect multiple departments, create financial risk, or prevent an organization from achieving an important objective.
As a leader, you need to understand the significance of the problem before deciding how to respond.
Questions to ask:
What is the size of this problem?
What is the scope?
Why is this important?
How urgent is this? Why now?
These questions help your team move beyond identifying the issue and begin evaluating its impact.
Consider a situation where a team discovers that a project is behind schedule.
Before recommending additional resources or changing the timeline, ask:
“How much of the project is affected?”
“What happens if we don't address this immediately?”
“Why is resolving this issue important right now?”
You may discover that the delay affects a critical customer commitment.
Or you may learn that the team has enough flexibility to adjust the schedule without creating a significant problem.
Understanding the size, scope, and urgency of an issue helps leaders prioritize their attention and resources.
It also helps prevent teams from treating every challenge as an emergency.
Step 3: Ask KPI Questions That Define Success
Once you understand the problem and its significance, it's time to talk about results.
This is where you do the math.
Leaders need to understand the cost of inaction, the opportunity associated with solving the problem, and how success will be measured.
Without clear measures of success, teams can spend significant time working on an issue without knowing whether their efforts are producing the desired outcome.
Questions to ask:
What is the cost if we do nothing?
What is the opportunity if we solve this?
How will we know we have been successful?
When do we need to resolve this?
These questions help connect the conversation to measurable business outcomes.
For example, imagine your organization is considering investing in a new technology platform.
Rather than immediately discussing vendors or implementation plans, ask:
“What is the cost of continuing with our current process?”
“What opportunity could this new platform create?”
“How will we measure whether the investment was successful?”
“When do we need to see results?”
The answers can help the team evaluate the business case, establish priorities, and define accountability.
You don't need to know every technical detail of the proposed solution to ask these questions.
You need to understand what the organization is trying to accomplish.
That's how BOLD questions can help move a conversation toward a decision.
How Do BOLD Questions Improve Assertive Communication?
Assertive communication is often associated with speaking up, expressing an opinion, or making a direct request.
Those are important skills.
But assertive communication also involves knowing how to ask questions that advance a conversation.
You don't always need to enter a meeting with a recommendation.
You can contribute by identifying an assumption that needs to be examined, clarifying the impact of a problem, or helping the team define what success looks like.
BOLD questions can be particularly valuable when:
You're participating in a meeting outside your area of expertise.
Your team is evaluating a complex problem.
You're discussing a significant investment or business decision.
You need to challenge an assumption without creating unnecessary conflict.
You're leading a conversation with multiple stakeholders.
You're selling consulting services or discussing a larger client engagement.
In each situation, thoughtful questions can help you contribute with greater confidence and purpose.
They also demonstrate that you're listening, thinking critically, and focused on achieving the right outcome.
How to Ask Assertive Questions Without Sounding Confrontational
Asking a direct question can feel uncomfortable, especially when you're speaking with senior leaders or challenging an idea that others seem to support.
Your delivery matters.
The objective is to create a productive conversation.
Start with genuine curiosity.
Rather than assuming someone is wrong, invite them to explain their reasoning.
For example, instead of saying:
“We don't have enough evidence to make this decision.”
You might ask:
“What evidence do we have to support this recommendation?”
Instead of saying:
“This project isn't worth the investment.”
Ask:
“What opportunity would solving this problem create?”
And instead of saying:
“We need to move faster.”
Ask:
“How urgent is this, and what happens if we don't address it now?”
These questions allow you to raise important considerations while keeping the conversation focused on the issue.
You can be direct and respectful at the same time.
Give people time to answer. Listen carefully. Ask follow-up questions when you need additional clarity.
And remember that some of the most important questions may require more than a quick response.
As you advance in your career, you'll find yourself participating in conversations that extend beyond your technical expertise.
You may be responsible for leading cross-functional teams, evaluating unfamiliar business challenges, or making decisions that affect multiple departments.
You won't always have the answers.
But you can learn to ask questions that help others find them.
BOLD questions assess risk.
BOLD questions make us accountable.
BOLD questions surface what's important.
BOLD questions get results.
The next time you're in a meeting and feel uncertain about how to contribute, consider what the conversation needs.
Does the team understand the problem?
Have you established why it matters?
Do you know how success will be measured?
Start there.
Don't leave a conversation without asking the BOLD questions.
Continue Improving Your Leadership Communication
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