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How Confident Are You in Handling Tough Conversations?
Discover how confident you are in handling tough workplace conversations. This quick quiz will assess your strengths and provide actionable insights to improve your leadership communication skills. Take it now to start leading with confidence!
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An employee has been showing up late consistently over the past two weeks.
How do you address the issue?

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Schedule a one-on-one meeting to understand the cause and set clear expectations.
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Avoid mentioning it for now and hope it improves.
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Mention the lateness casually in passing but don’t schedule a discussion.
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During a team meeting, two employees openly disagree, and the discussion becomes heated.
What do you do?

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Let them resolve it on their own and move the meeting forward.
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Acknowledge the disagreement, suggest a private conversation, and follow up with both parties afterward.
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Step in to diffuse the situation but avoid choosing sides.
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You need to provide negative feedback to a high-performing employee about their communication style, which has been upsetting the team.
How do you approach this?
How do you approach this?

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Give feedback indirectly and hope they adjust.
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Avoid addressing it to avoid damaging morale.
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Set up a private meeting, provide specific examples, and suggest ways to improve.Type Answer Here
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An employee reacts defensively during a feedback session, interrupting you and denying the issue.
What’s your response?

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Apologize and change the subject to avoid further conflict.
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Acknowledge their feelings, restate your point calmly, and steer the conversation back to solutions.
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Reiterate your feedback firmly without inviting further discussion.
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You’ve noticed an ongoing issue with missed deadlines from one team member.
What do you do?

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Schedule a private meeting to discuss the missed deadlines and agree on an improvement plan.
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Assign deadlines to someone else to avoid further delays.
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Bring it up during a team meeting to address it publicly.
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You overhear an employee making a comment that could be perceived as discriminatory.
What’s your next step?
What’s your next step?
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Mention your concerns to the employee casually later.
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Speak with the employee privately, explain the potential impact of their comment, and reinforce workplace expectations.
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Ignore it since it wasn’t directed at anyone.
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An employee often interrupts others during team discussions.
How do you address it?
How do you address it?
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Say nothing, assuming others will eventually manage the behavior.
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Ask them to stop interrupting during a meeting.
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Speak privately, explain the impact of their behavior, and suggest alternative ways to contribute.
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You’re asked to mediate a conflict between two team members who both feel they’re “right.”
How do you handle it?
How do you handle it?
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Meet with each party individually first, then bring them together to discuss solutions collaboratively.
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Meet with them together, ask each person to explain their perspective, and decide who’s correct.
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Avoid getting involved and let them work it out themselves.
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You’ve assigned a task, but the employee keeps asking for clarification and seems unsure.
What’s your next step?
What’s your next step?
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Break the task into smaller steps, ensure they understand, and check in periodically.
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Reassign the task to someone more experienced.
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Explain the task again and ask if they have any questions.
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A new hire has been underperforming during their first month.
How do you approach the situation?
How do you approach the situation?
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Provide informal feedback but avoid a formal discussion.
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Wait longer to see if they adjust on their own.
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Set up a meeting to provide structured feedback and identify any challenges they’re facing.
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You Are a Hesitant Leader

You’re hesitant to address tough conversations, often avoiding them altogether. This may lead to unresolved issues and strained team dynamics.
As a leader, you prioritize harmony and avoid confrontation, believing it’s better to sidestep awkward situations than risk making waves. While your approach fosters a pleasant day-to-day environment, the long-term consequences can include simmering tensions, unmet expectations, and missed opportunities for growth.
Your team likely values your supportive nature and calm demeanor, but they may also feel frustrated by a lack of clear communication or direction when issues arise. By avoiding difficult conversations, you inadvertently send the message that problems don’t need to be addressed—or worse, that you don’t notice or care about them.
The good news? Your natural inclination toward empathy is a strength, and with the right tools, you can turn this into a superpower for navigating tough conversations. By learning to address challenges head-on with confidence and kindness, you’ll strengthen your relationships, inspire trust, and create a more cohesive, high-performing team.
3 Tips to Build Your Confidence Today
1. Shift the Narrative:
Instead of thinking, “This is going to be awful,” try reframing the situation. Tell yourself, “This conversation is an opportunity to strengthen our understanding and solve a problem together.” A small mindset shift can do wonders for your confidence.
2. Practice the 3 R’s: Reflect, Rehearse, Relax:
o Reflect: Spend a few minutes thinking about the purpose of the conversation and the outcomes you want.
o Rehearse: Run through key points in your head or with a trusted friend or coach.
o Relax: Take a few deep breaths before the conversation to calm your nerves and settle your thoughts.
3. Be Direct and Kind:
Clarity is key in tough conversations, but kindness goes a long way. Start with a clear statement of your intentions, like, “I care about our working relationship and want to address something that’s been on my mind.” This sets a tone of respect and collaboration.
As a leader, you prioritize harmony and avoid confrontation, believing it’s better to sidestep awkward situations than risk making waves. While your approach fosters a pleasant day-to-day environment, the long-term consequences can include simmering tensions, unmet expectations, and missed opportunities for growth.
Your team likely values your supportive nature and calm demeanor, but they may also feel frustrated by a lack of clear communication or direction when issues arise. By avoiding difficult conversations, you inadvertently send the message that problems don’t need to be addressed—or worse, that you don’t notice or care about them.
The good news? Your natural inclination toward empathy is a strength, and with the right tools, you can turn this into a superpower for navigating tough conversations. By learning to address challenges head-on with confidence and kindness, you’ll strengthen your relationships, inspire trust, and create a more cohesive, high-performing team.
3 Tips to Build Your Confidence Today
1. Shift the Narrative:
Instead of thinking, “This is going to be awful,” try reframing the situation. Tell yourself, “This conversation is an opportunity to strengthen our understanding and solve a problem together.” A small mindset shift can do wonders for your confidence.
2. Practice the 3 R’s: Reflect, Rehearse, Relax:
o Reflect: Spend a few minutes thinking about the purpose of the conversation and the outcomes you want.
o Rehearse: Run through key points in your head or with a trusted friend or coach.
o Relax: Take a few deep breaths before the conversation to calm your nerves and settle your thoughts.
3. Be Direct and Kind:
Clarity is key in tough conversations, but kindness goes a long way. Start with a clear statement of your intentions, like, “I care about our working relationship and want to address something that’s been on my mind.” This sets a tone of respect and collaboration.
Before We Go Any Further – Let Me Introduce Myself
Hi there! I’m Michelle Mullen, founder and Cringy Conversations Confidence Coach at Higher Results. I’m here to help you tackle those uncomfortable workplace conversations that everyone else avoids. Think conflict resolution, leadership challenges, or personality clashes—I’ve got the tools to turn awkward moments into opportunities for growth.
With 29 years of experience, I specialize in coaching leaders through tough conversations so they can build stronger teams and get back to focusing on what matters most—creating a positive and productive workplace. Let’s make it happen!
Book a Free Strategy Session
In our session, we’ll dig into your specific challenges, identify what’s holding you back, and create a clear plan to help you approach tough conversations with confidence.
Pick a time that works for you at https://higherresults.com/letsmeet
Hi there! I’m Michelle Mullen, founder and Cringy Conversations Confidence Coach at Higher Results. I’m here to help you tackle those uncomfortable workplace conversations that everyone else avoids. Think conflict resolution, leadership challenges, or personality clashes—I’ve got the tools to turn awkward moments into opportunities for growth.
With 29 years of experience, I specialize in coaching leaders through tough conversations so they can build stronger teams and get back to focusing on what matters most—creating a positive and productive workplace. Let’s make it happen!
Book a Free Strategy Session
In our session, we’ll dig into your specific challenges, identify what’s holding you back, and create a clear plan to help you approach tough conversations with confidence.
Pick a time that works for you at https://higherresults.com/letsmeet
Schedule Your Session
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You Are a Developing Leader
As a developing leader, you’ve already made strides in tackling tough conversations—kudos to you! 🎉 You’ve shown you’re capable of stepping into challenging situations when needed, but there are still moments when hesitation creeps in. Maybe you feel more confident addressing certain topics than others, or perhaps you second-guess whether you handled a situation as effectively as you could have.
This inconsistency can lead to mixed results. Some issues get resolved, while others linger or resurface because they weren’t fully addressed. While your willingness to engage is a strength, refining your approach and building confidence across all situations will help you take your leadership to the next level.
By strengthening your consistency and sharpening your communication toolkit, you can turn difficult conversations into opportunities to lead with clarity, empathy, and authority—every single time.
3 Tips for Developing Leaders
Anchor Yourself in Preparation
One of the best ways to build confidence is to be prepared. Before entering a conversation, outline the key points you want to cover and practice how you’ll deliver them. Anticipate potential reactions and think through how you’ll respond. This preparation gives you a solid foundation and helps you stay calm and collected.
Find Your Go-To Phrases
Having a few ready-to-use phrases can be a lifesaver in tricky moments. For instance:
To diffuse tension: “I want us to figure this out together—how do you see the situation?”
To refocus: “Let’s pause for a moment and revisit what we’re trying to achieve here.”
To clarify: “Can you help me understand your perspective a bit more?”
These phrases keep the conversation productive.
Reflect and Refine
After each challenging conversation, take a few moments to reflect. Ask yourself:
What went well?
What could I have handled better?
What did I learn that I can apply next time?
By treating each conversation as a learning opportunity, you’ll steadily improve and build the consistency you’re striving for.
You’ve already proven you have what it takes to handle the tough stuff. With a little more practice and focus, you’ll become the kind of leader who navigates every conversation with confidence and grace! Ready to dive deeper? Let’s book a strategy session and create a personalized plan to keep you growing! 😊
This inconsistency can lead to mixed results. Some issues get resolved, while others linger or resurface because they weren’t fully addressed. While your willingness to engage is a strength, refining your approach and building confidence across all situations will help you take your leadership to the next level.
By strengthening your consistency and sharpening your communication toolkit, you can turn difficult conversations into opportunities to lead with clarity, empathy, and authority—every single time.
3 Tips for Developing Leaders
Anchor Yourself in Preparation
One of the best ways to build confidence is to be prepared. Before entering a conversation, outline the key points you want to cover and practice how you’ll deliver them. Anticipate potential reactions and think through how you’ll respond. This preparation gives you a solid foundation and helps you stay calm and collected.
Find Your Go-To Phrases
Having a few ready-to-use phrases can be a lifesaver in tricky moments. For instance:
To diffuse tension: “I want us to figure this out together—how do you see the situation?”
To refocus: “Let’s pause for a moment and revisit what we’re trying to achieve here.”
To clarify: “Can you help me understand your perspective a bit more?”
These phrases keep the conversation productive.
Reflect and Refine
After each challenging conversation, take a few moments to reflect. Ask yourself:
What went well?
What could I have handled better?
What did I learn that I can apply next time?
By treating each conversation as a learning opportunity, you’ll steadily improve and build the consistency you’re striving for.
You’ve already proven you have what it takes to handle the tough stuff. With a little more practice and focus, you’ll become the kind of leader who navigates every conversation with confidence and grace! Ready to dive deeper? Let’s book a strategy session and create a personalized plan to keep you growing! 😊
Before We Go Any Further – Let Me Introduce Myself
Hi there! I’m Michelle Mullen, founder and Cringy Conversations Confidence Coach at Higher Results. I’m here to help you tackle those uncomfortable workplace conversations that everyone else avoids. Think conflict resolution, leadership challenges, or personality clashes—I’ve got the tools to turn awkward moments into opportunities for growth.
With 29 years of experience, I specialize in coaching leaders through tough conversations so they can build stronger teams and get back to focusing on what matters most—creating a positive and productive workplace. Let’s make it happen!
Book a Free Strategy Session
In our session, we’ll dig into your specific challenges, identify what’s holding you back, and create a clear plan to help you approach tough conversations with confidence.
Pick a time that works for you at https://higherresults.com/letsmeet
Hi there! I’m Michelle Mullen, founder and Cringy Conversations Confidence Coach at Higher Results. I’m here to help you tackle those uncomfortable workplace conversations that everyone else avoids. Think conflict resolution, leadership challenges, or personality clashes—I’ve got the tools to turn awkward moments into opportunities for growth.
With 29 years of experience, I specialize in coaching leaders through tough conversations so they can build stronger teams and get back to focusing on what matters most—creating a positive and productive workplace. Let’s make it happen!
Book a Free Strategy Session
In our session, we’ll dig into your specific challenges, identify what’s holding you back, and create a clear plan to help you approach tough conversations with confidence.
Pick a time that works for you at https://higherresults.com/letsmeet
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You Are a Confident Leader
As a confident leader, you’ve cultivated the skills and mindset to handle difficult conversations with clarity, composure, and purpose. You don’t shy away from addressing challenges, and your ability to tackle issues head-on has earned you trust and respect from your team. Whether it’s resolving conflicts, providing constructive feedback, or navigating sensitive topics, you bring a sense of calm and authority that inspires confidence in others.
However, even the most skilled leaders know there’s always room to refine their approach. The next step for you is maintaining this level of consistency while continuing to elevate your emotional intelligence, empowering others to handle challenges, and fostering a culture of open, constructive communication within your organization.
3 Tips for Confident Leaders
Empower Your Team to Handle Tough Conversations
Now that you’ve mastered handling difficult conversations, focus on mentoring your team to develop these skills too. Encourage team members to resolve conflicts among themselves before escalating to you. Provide guidance and support, but let them take the lead—it builds trust and strengthens their problem-solving abilities.
Fine-Tune Emotional Intelligence
As a confident leader, you already bring empathy and understanding to conversations. Take it a step further by honing your ability to read subtle emotional cues and adapting your approach to suit each individual’s needs. Ask yourself, “How can I better align my communication style with this person’s preferred way of receiving feedback?”
Cultivate a Feedback-First Culture
Confident leaders set the tone for open communication. Regularly model giving and receiving feedback with transparency and positivity. For example:
Share your own areas for growth to normalize vulnerability.
Create structured opportunities for feedback, like regular check-ins or team retrospectives.
Reinforce positive behaviors by recognizing when someone handles a difficult conversation effectively.
You’ve already built a foundation of trust and leadership through your composure and clarity. By mentoring others, fine-tuning your emotional intelligence, and creating a culture of open dialogue, you’ll not only sustain your confidence but also elevate your team to new heights. Keep up the amazing work—you’re setting the standard for leadership excellence! 🚀
However, even the most skilled leaders know there’s always room to refine their approach. The next step for you is maintaining this level of consistency while continuing to elevate your emotional intelligence, empowering others to handle challenges, and fostering a culture of open, constructive communication within your organization.
3 Tips for Confident Leaders
Empower Your Team to Handle Tough Conversations
Now that you’ve mastered handling difficult conversations, focus on mentoring your team to develop these skills too. Encourage team members to resolve conflicts among themselves before escalating to you. Provide guidance and support, but let them take the lead—it builds trust and strengthens their problem-solving abilities.
Fine-Tune Emotional Intelligence
As a confident leader, you already bring empathy and understanding to conversations. Take it a step further by honing your ability to read subtle emotional cues and adapting your approach to suit each individual’s needs. Ask yourself, “How can I better align my communication style with this person’s preferred way of receiving feedback?”
Cultivate a Feedback-First Culture
Confident leaders set the tone for open communication. Regularly model giving and receiving feedback with transparency and positivity. For example:
Share your own areas for growth to normalize vulnerability.
Create structured opportunities for feedback, like regular check-ins or team retrospectives.
Reinforce positive behaviors by recognizing when someone handles a difficult conversation effectively.
You’ve already built a foundation of trust and leadership through your composure and clarity. By mentoring others, fine-tuning your emotional intelligence, and creating a culture of open dialogue, you’ll not only sustain your confidence but also elevate your team to new heights. Keep up the amazing work—you’re setting the standard for leadership excellence! 🚀
Before We Go Any Further – Let Me Introduce Myself
Hi there! I’m Michelle Mullen, founder and Cringy Conversations Confidence Coach at Higher Results. I’m here to help you tackle those uncomfortable workplace conversations that everyone else avoids. Think conflict resolution, leadership challenges, or personality clashes—I’ve got the tools to turn awkward moments into opportunities for growth.
With 29 years of experience, I specialize in coaching leaders through tough conversations so they can build stronger teams and get back to focusing on what matters most—creating a positive and productive workplace. Let’s make it happen!
Book a Free Strategy Session
In our session, we’ll dig into your specific challenges, identify what’s holding you back, and create a clear plan to help you approach tough conversations with confidence.
Pick a time that works for you at https://higherresults.com/letsmeet
Hi there! I’m Michelle Mullen, founder and Cringy Conversations Confidence Coach at Higher Results. I’m here to help you tackle those uncomfortable workplace conversations that everyone else avoids. Think conflict resolution, leadership challenges, or personality clashes—I’ve got the tools to turn awkward moments into opportunities for growth.
With 29 years of experience, I specialize in coaching leaders through tough conversations so they can build stronger teams and get back to focusing on what matters most—creating a positive and productive workplace. Let’s make it happen!
Book a Free Strategy Session
In our session, we’ll dig into your specific challenges, identify what’s holding you back, and create a clear plan to help you approach tough conversations with confidence.
Pick a time that works for you at https://higherresults.com/letsmeet
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