Tag Archive for: #leadership

From Snake Encounters to Leadership Clarity

For the past seven weeks, I was working remotely from Australia. To stay in sync with my North American clients, I started my days at 4:00 a.m.—an experience that’s given me a deep respect for shift workers and a renewed appreciation for very strong coffee. But the real wake-up call came in my makeshift office beside the garage. One morning, after a heavy storm, I opened the door and saw what looked like a pile of oversized earthworms wriggling across the floor. Then I noticed the tiny scales. Not worms—baby snakes. Eighteen of them. Yes, I counted. And yes, I personally escorted each one out.

As unsettling as it was in the moment, it made me laugh later—and it reminded me of an important leadership truth: surprises will always find their way in. Sometimes they slither in quietly, sometimes they storm the room. Either way, leadership rarely unfolds in a perfectly straight line. The real question isn’t whether you can avoid the unexpected, but how quickly you can pause, reset, and refocus when it arrives.

Over the past few weeks, many of my conversations with leaders have centered on change—new structures, shifting mandates, and the added pressure of tariffs and an uncertain economy. Amid so much disruption, the risk isn’t just operational; it’s personal. Leaders often find themselves drifting away from the ‘why’ that drew them to their role and the leader they aspired to be.

If you’ve been feeling a little “off your game,” here are five ways to pause, reflect, and reconnect with clarity.

1. ASSESS YOUR CURRENT

LEADERSHIP LANDSCAPE

Leaders often jump straight into fixing problems without pausing to understand the bigger picture. Before making changes, start with a temperature check.

What parts of your role feel energizing and aligned?
Where are you feeling drained or stuck?
What signals are you getting from your team, your peers, or your board that you might need to pay attention to?

Insight: Think of this as your “leadership dashboard.” Just like a car, you need to know what’s running smoothly and what lights are flashing before you can chart the right course.

2. REVISIT YOUR INTENTIONS FOR YOUR ROLE

It’s easy to get caught up in quarterly targets and the day-to-day, but clarity often comes from going back to your original intentions.

Why did you take this role in the first place?
What did success look like in your first year?
How has that evolved—and does it still align with the leader you want to be remembered as?

Insight: Leadership drift happens quietly. By realigning to your original intentions (or deliberately redefining them), you shift from being reactive to being intentional again.

3. IDENTIFY YOUR STRENGTHS AND GAPS

Self-awareness is not a soft skill—it’s a strategic asset.

Where are you adding the most value and impact?
Where do you find yourself reacting rather than leading with purpose?
What skill, mindset, or behavior would raise your leadership game right now?

Insight: Don’t confuse being busy with being effective. The highest-performing leaders know exactly where they excel, and they actively close the gaps that hold them back.

4. CLARIFY YOUR STRATEGIC FOCUS

When everything feels urgent, nothing is truly strategic.

Where should more of your time and attention be going? What can you delegate, defer, or eliminate altogether? What critical conversations or decisions are overdue?

Insight: This is where leadership discipline shows up. Leading smarter doesn’t mean doing more—it means consistently directing your energy where it has the greatest impact.

5. DEFINE THE SUPPORT YOU NEED

Strong leaders don’t do it alone. They know when to ask for support.

What resources, coaching, or clarity would help you most right now?
What’s one action you can take this week to move back into your zone of influence?

What 30-day commitment can you make to yourself and your team?

Insight: Asking for support is not weakness. It’s what allows leaders to sustain performance through seasons of change and pressure.

WANT TO TAKE THIS FURTHER?

I’ve created a free Leadership Reconnection Worksheet to guide you (or your team) through these prompts in a more structured way. It’s perfect for an afternoon reset, a personal offsite, or as a tool in your next leadership meeting.

[Download the Worksheet Here]

LEADER’S CHALLENGE 

Set aside 30 minutes this week for a personal reset. Grab the worksheet, find a quiet space, and walk through the prompts. When you’re done, share one clear intention with your team—something they can see you commit to over the next 30 days. Small resets often spark the biggest momentum.

57!

Yesterday, on July 1st,  I turned 57—a number that feels both humbling and motivating. As I write this on a birthday weekend getaway in Whistler, honestly, I can hardly believe it. I am turning that big a number tomorrow. Most days, I still feel like I’m in my late twenties, until I catch my reflection in the mirror and do a double-take. Each year is a reminder to pause and reflect on the lessons that shape how I live, lead, and connect.

In my work with leaders across industries, I’ve seen again and again that it’s never about perfection; it’s about showing up with intention and courage, every single day. Over the past few decades, I’ve learned that the fundamentals don’t really change. Whether you’re guiding a team or trying to be your best self, it comes down to a few core practices that, when done consistently, make all the difference. 

So to mark another lap around the sun, I’d love to share a few reflections and practical ideas. Below you’ll find five tips for leading your best life and seven tips that can help you be an effective leader—insights I’ve practiced, taught, and seen transform people and teams. I hope they inspire you wherever you are on your journey.

5 Tips for Leading Your Best Life

  1. Get clear on what “enough” looks like.
    Take the time to define what success means to you—not what the world says it should be. When you know your own benchmarks, it’s easier to let go of constant comparison.
  2. Guard your energy like it matters—because it does.
    Pay attention to where you feel drained versus energized. Protect your time and say “no” more often to things that don’t align with your priorities.
  3. Take care of your health, even when life gets hectic.
    Small choices—going for a walk, eating well, getting enough rest—add up. Your future self will thank you.
  4. Do a weekly review and preview.
    Set aside time each week to reflect on what went well, note your wins, and assess whether you accomplished your most important priorities. Then look ahead: decide what matters most in the week to come and set your focus. This simple practice keeps you grounded, intentional, and clear.
  5. Keep learning.
    Whether it’s a new skill, a fresh perspective, or an old hobby you’ve set aside, growth keeps life interesting.

 

7 Must-Do Tips for Being an Effective Leader

  1. Be clear about what good looks like.
    People do their best work when they understand what’s expected. Spell it out—don’t assume it’s obvious.
  2. Listen fully.
    When someone comes to you, give them your full attention. Being present is one of the simplest ways to build trust.
  3. Walk your talk.
    If you expect accountability, model it yourself. If you value respect, demonstrate it in how you treat others.
  4. Give feedback often.
    Don’t save it for performance reviews. Share observations in real time, whether it’s to recognize progress or offer guidance.
  5. Celebrate progress.
    Acknowledging small wins keeps people engaged and motivated. It doesn’t have to be complicated—a simple thank you goes a long way.
  6. Take care of yourself.
    Leading well starts with self-awareness and self-care. If you’re exhausted or stretched thin, it shows up in how you lead.
  7. Make time to reflect.
    Ask yourself regularly: What’s working? What needs to change? What can I do better? This practice fuels growth and better decisions.

From the Fairway to the Office: Leading Through Tougher Conversations

This month, I dusted off my golf clubs and kicked off another season of Nine and Dine at Musqueam Golf Course. I’ve been playing in this league for eight years with two dear friends, and I look forward to it every spring. While my swing hasn’t exactly improved (in fact, I think my game has plateaued!), I keep coming back—for the laughs, the fresh air, and the guaranteed connection with people I enjoy. It’s a weekly ritual that recharges me.

What I love most is that it’s consistent. It gets me outside, fills my cup, and reminds me how important it is to create space for the things—and people—that give us energy. And that has me thinking about leadership too. Because when work gets messy or relationships become strained, it’s tempting to pull back. But the best leaders stay present. They show up. Especially in the hard moments.

This month, we’re exploring a topic every leader will encounter at some point: how to navigate difficult people and conversations. Whether it’s a team member, a peer, or a client, challenging personalities test your emotional intelligence and leadership maturity. The good news? With the right tools, you can lead through these moments with clarity, empathy, and confidence.

Here’s to strong leadership, better conversations, and just maybe, a slightly better golf swing this summer.

 

Dealing with Difficult People: Tools That Work

 

1. Understand Before You React: Leverage the DISC Framework

In my work with executive teams, the Everything DiSC® model is one of the most powerful tools I use to help leaders better understand themselves—and others. Often, what we label as “difficult” behavior is actually just a clash of natural communication styles.

The DiSC model breaks down behavior into four key tendencies:

• D – Dominance: Direct, results-oriented, strong-willed, and forceful
• i – Influence: Outgoing, enthusiastic, optimistic, and lively
• S – Steadiness: Even-tempered, accommodating, patient, and humble
• C – Conscientiousness: Analytical, reserved, precise, and systematic

When people with different styles work together—especially under stress—it’s easy to misread intentions. For example, someone with a Dominant style may push for fast decisions, while someone with a Steady style wants to build consensus first. Without awareness, this can create tension. With awareness, it opens the door to deeper collaboration.

Pro Tip: Understanding your own DiSC style—and those around you—can improve communication, reduce conflict, and build a more emotionally intelligent culture.

If you’re interested in bringing DiSC assessments or a customized DiSC workshop to your team, I’d be happy to support you. These sessions are eye-opening, energizing, and often a turning point in team connection and performance. For more information, please reach out to me jenny@jennyreilly.com.

 

2. Ask More, Assume Less

One of the fastest ways to de-escalate tension is to stay curious. Instead of labeling someone as difficult, ask yourself:
“What might they be experiencing that I can’t see?”

Here are three ways to lead with curiosity:

• Ask open-ended questions: “What’s most important to you about this?”
• Use neutral language: “Help me understand your perspective.”
• Listen for what’s not being said: Silence often signals stress, not disengagement.

Pro Tip: Curiosity doesn’t mean avoiding accountability—it just keeps you open long enough to uncover the real issue.

 

3. Focus on Impact, Not Personality

When a behavior affects the team, it needs to be addressed. But the most effective leaders separate the person from the pattern. I often coach clients to use the SBI model (Situation – Behavior – Impact):

“In yesterday’s meeting (situation), I noticed you interrupted two colleagues (behavior), which made it difficult for others to contribute (impact).”

Then pivot to solution-building:

“How can we make space for everyone’s input going forward?”

Pro Tip: Avoid blame. Stay focused on behavior and outcomes.

 

4. When Coaching Isn’t Enough

If someone continues to be difficult after you’ve coached, clarified, and given feedback—it may be time to set firmer boundaries.

Here’s how:

• With a direct report: Reaffirm expectations and consequences.
• With a peer: Address patterns directly and propose a reset in how you collaborate.
• With a client or stakeholder: Revisit scope, tone, and professional expectations clearly.

Pro Tip: Boundaries protect relationships, culture, and performance. They’re a leadership necessity—not a last resort.

 

Final Thought:

Leadership isn’t about keeping things comfortable—it’s about creating clarity, especially when the conversation is hard. Whether you’re managing a team or working cross-functionally, how you handle tough personalities will define the tone of your leadership more than any project plan or KPI.

And if you’re ever unsure how to approach these conversations—or want to explore how your team can use DiSC to create more trust and connection—I’d love to help.

From a Week in London to Weekly 1:1s: Strengthening Teams Through Connection

Why Weekly 1:1 Meetings Are Important

When conducted effectively, 1:1 meetings are a valuable tool for both the supervisor and the team member. They provide the staff member with a dedicated space to clarify goals, voice concerns, and receive guidance. For the supervisor, these meetings help reduce interruptions and ensure the employee has a clear plan for the week ahead. By committing to regular 1:1s, you empower your team member to succeed and demonstrate your dedication to fostering an aligned and efficient team.

Scheduling a 1:1 every week creates an uninterrupted time to connect both professionally and personally. During this time, the focus should be on the employee—they should speak at least 80% of the time, while you listen, guide, and support. This meeting is primarily for them, offering an opportunity to raise any concerns that might impact their performance or well- being, ensuring they feel heard and empowered.

Setting the Tone for Productive Conversations

Starting your 1:1s with a quick check-in is essential. This moment allows you to assess your team member’s mental and emotional state before diving into work-related discussions. By understanding where they are, you can tailor the conversation to offer the right support. As we know, an individual’s mindset directly impacts their performance, so if they’re struggling, addressing personal stress or challenges identifying this early in the meeting can make all the difference in how productive the meeting will be.

Start with a Check-In:

Take a moment to ask how they’re doing both professionally and personally. This helps you gauge their emotional state and mental readiness for the conversation ahead.

I recommend asking open-ended questions or, if you’re unsure where to start, using either the 1-5 scale or the Red-Yellow-Green scale as a simple tool to check in at the start of your meetings. These scales will give you insight into how your team member is feeling, setting the stage for a more effective and supportive discussion before diving into work-related topics.

1-5 Scale Check-In:

Professional: “On a scale of 1-5 (one being low and five being high), how are you feeling about work today?”

5 = High: Highly motivated, focused, and accomplishing objectives
4 = Good: Focused, meeting objectives, and having positive momentum
3 = Average: Getting things done, but could improve focus or effort
2 = Below Average: Some progress, but facing challenges and feeling less motivated

1 = Low: Struggling or disengaged

Personal: “On a scale of 1-5 (one being low and five being high), how are you feeling personally today?”

5 = Balanced: Content and energized
4 = Good: Stable, healthy, and feeling positive
3 = Average: Generally okay, but could be better
2 = Below Average: Some personal stress, but manageable

1 = Low: Struggling or stressed

Stress Level: “On a scale of 1-5 (one being low and five being high), how would you rate your current stress level?”

5 = Very High: Overwhelmed, with significant stress
4 = High: Feeling stressed, however, managing under pressure

3 = Average: Moderate stress, and handling everything okay
2 = Below Average: Mild stress, not overwhelming
1 = Low: Calm, and under control

Red-Yellow-Green Scale:

Alternatively, you can use the Red-Yellow-Green scale to quickly assess someone’s mental state. This simple tool helps you gauge how the other person is feeling, allowing you to adjust the tone and focus of your conversation accordingly.

To start, you can ask:

“On a scale of Red, Yellow, and Green, how are you feeling today?”

Red indicates you’re struggling, stressed, or overwhelmed.
Yellow means you’re experiencing some stress, but it’s manageable. Green means you’re feeling good, focused, and energized.

Alternatively, you can phrase it as:

“To help me better understand how you’re feeling today, can you rate your current state as Red, Yellow, or Green?”

Once they respond, this gives you a clearer understanding of their emotional state. If someone is feeling Red, you may want to explore the sources of stress or frustration more deeply and provide additional support. For someone in the Yellow range, you can still offer guidance while checking in on any concerns they may have. When they’re in the Green zone, it’s a good time to focus on progress, growth, and upcoming challenges.

This simple scale helps you adjust the direction of your conversation. If someone is feeling Red, the conversation may need to be more empathetic and supportive. If they’re in the Yellow zone, keep the conversation constructive, and for Green, focus on momentum and positive outcomes.

Ask Open Ended Questions

One of the keys to a successful 1:1 meeting is encouraging your direct report to open up about their experiences, progress, and challenges. By asking open-ended questions, you create a space for them to share their thoughts in greater depth, rather than just providing yes or no answers. This approach fosters a collaborative, two-way dialogue that promotes trust, transparency, and deeper insights into their needs and mindset.

Consider asking questions like:

“What have you been working on since we last met?” This gives them a chance to share updates on their tasks, projects, and accomplishments.

“What went well this week?/What were your wins?” Celebrating successes helps reinforce positive behaviors and boosts motivation.

“Did you have any challenges? If so, please provide details of the situation, the action you took, or potential solutions you’re considering?” This question promotes problem-solving and encourages them to think critically about how to overcome obstacles.

“Were there any actions that you committed to, but didn’t address as planned? If so, what were the reasons?” This helps you identify potential barriers or roadblocks while also creating an opportunity for constructive feedback and learning.

“What can I do to support you?” A direct invitation for them to express their needs, showing you’re invested in their success.

“Are there any roadblocks you are encountering that you need assistance with?”  This provides insight into challenges that may be hindering their productivity and opens up a space for you to offer support.

“Are there any other items that you would like to discuss today?” Ending the meeting with this question gives them the opportunity to bring up any concerns or topics that may not have been covered.

By asking these types of questions, you create a supportive environment where your team member feels heard and valued. This approach not only helps you understand their progress and challenges but also enables you to offer meaningful guidance and support.

 

How to Ensure a Successful 1:1

 

1. Be Fully Present:

This meeting is dedicated to your team member, so it’s important to be fully present and engaged. Avoid distractions such as checking your phone or email. The goal is for your direct report to feel that their time with you is valuable and respected.

2. Schedule in Advance and Stick to It:

Set a consistent time for your 1:1s and make them a priority. Scheduling in advance demonstrates your commitment to this process and shows that you value the time you spend with your team member. Avoid rescheduling unless absolutely necessary.

3. Talk 20% of the Time:

The purpose of the 1:1 is to listen, provide feedback, and offer support, not to dominate the conversation. Make sure your team member does the majority of the talking. Use the time to guide the discussion, offer feedback, and share insights, but let them take the lead.

4. Ask Open-Ended Questions:

Encourage your direct report to share their thoughts, successes, and challenges by asking open-ended questions. This fosters a deeper conversation and helps you better understand their progress, goals, and any obstacles they might be facing.

5. Provide Feedback and Recognize Wins:

Use this time to acknowledge both successes and areas for improvement. Offer positive reinforcement and constructive feedback. Celebrating wins boosts morale and helps motivate your team member to keep moving forward.

6. Set Clear Next Steps:

Always end the meeting by summarizing key action items, setting clear priorities, and confirming who is responsible for what. This ensures alignment and accountability, making it easier to track progress and follow up on commitments in future meetings.

By investing in regular 1:1 meetings, you are not only strengthening your relationship with your team but also creating an environment where open communication, growth, and accountability thrive. These meetings are a critical tool for supporting your direct reports, aligning goals, and addressing challenges before they become larger issues. I encourage you to prioritize these sessions, ensuring consistency and focus.

Your commitment to making these meetings a success will not only help your team members perform at their best but also contribute to the overall success of the team and organization.

Please reach out if you have any questions or need further guidance on conducting effective 1:1s.

Jenny Reilly, MBA | Phone: 604-616-1967 | Email: jenny@jennyreilly.com

How Town Halls Strengthen Teams & Trust

Why Town Halls Matter

A town hall isn’t just a meeting—it’s an opportunity to reinforce company culture, provide clarity, and engage employees at every level. When done well, it can transform how a team feels about leadership and the organization’s direction.

Key Takeaways:

  • Strengthens trust and credibility between leadership and employees
  • Aligns the team with company goals and values
  • Creates a space for real dialogue and employee feedback
  • Helps prevent confusion and workplace rumors before they spread

The Power of Communication in Leadership

Leaders who communicate effectively create teams that are more engaged, productive, and invested in the company’s success. But communication isn’t just about talking—it’s about listening, too.

Ways to Strengthen Your Leadership Communication:

  • Make your message clear, direct, and consistent
  • Create opportunities for employees to ask questions and share concerns
  • Use storytelling to make complex ideas more relatable
  • Reinforce the company’s mission and vision regularly, not just at big meetings

What You Can Expect from a Well-Run Town Hall

A town hall isn’t about checking a box—it’s about creating a meaningful experience for your employees. When done right, the impact is tangible.

Signs of a Successful Town Hall:

  • Employees leave with a stronger sense of clarity and direction
  • Engagement levels increase because employees feel heard and valued
  • Alignment improves between leadership and teams, reducing silos
  • Transparency increases, leading to a more open and accountable culture

Best Practices for Running an Effective Town Hall

It’s not just what you say—it’s how you structure the conversation that makes all the difference. Here’s how to maximize impact:

Practical Steps to Improve Your Next Town Hall:

  • Keep the agenda focused and intentional—don’t overload it with updates
  • Have senior leadership present and actively engaged in the discussion
  • Make it interactive—allow Q&A, polls, or breakout discussions
  • Follow up after the meeting with key takeaways and action items

Final Thoughts

  • Communication is the foundation of strong leadership, and town halls are one of the most effective tools to bring teams together. If you’re not using them strategically, you’re missing an opportunity to build trust, clarity, and engagement.
  • How are you using communication to strengthen your leadership? I’d love to hear your thoughts. Please connect with me to discuss strategies for making your next town hall more impactful.
  • Whether you’re seeking executive coaching, strategic business consulting, leadership retreat facilitation, or a dynamic town hall host, I’m here to help.

  • Reach out today—I’d love to discuss how we can work together. Phone: 604-616-1967 | Email: jenny@jennyreilly.com