Are You Failing Your Team? How to Recognize and Address Leadership Challenges

As a business leader, the success of your team is directly tied to your ability to lead effectively. But what happens when deadlines are missed, tasks pile up, and your team struggles to deliver results? While it’s easy to blame external factors or even the team itself, the root cause might be closer than you think—it could be you.

In this post, we’ll explore actionable insights shared by leadership expert Jennifer Conaway on the Workergenix Mastermind Podcast. Jennifer delves into the signs that indicate leadership issues, common mistakes business owners make, and practical steps to build a stronger, more effective team.

Recognizing the Signs of Leadership Challenges

Jennifer identifies three red flags that indicate leadership may be the issue:

Recurring Hiring Issues – If you consistently find yourself saying, “This person doesn’t understand my voice,” or “They’re not delivering what I expected,” the problem might not be the hire—it could be the hiring process or your communication. Leaders must examine their expectations, hiring practices, and onboarding strategies to ensure clarity and alignment.
Becoming a One-Person Bottleneck – Are tasks consistently delayed because they’re waiting on you? A leader who can’t delegate or prioritize effectively creates unnecessary chaos. This doesn’t just hinder progress but also demoralizes the team.
Blaming the Team for Mistakes – If every misstep is framed as a failure on the team’s part, it’s time for a reality check. Leaders who fail to take responsibility erode trust and undermine morale, leading to disengagement and even turnover.

Actionable Strategies to Improve Leadership

Once you’ve identified the challenges, it’s time to take action. Jennifer outlines these steps to help business owners turn things around:

Evaluate and Delegate Tasks

Not every task on your to-do list needs to be done by you. Assess your responsibilities and determine what can be delegated to capable team members. Trusting your team fosters collaboration and frees you to focus on high-value leadership activities.

Streamline Your Workload

Many leaders face overwhelm from a bloated task list. Jennifer recommends revisiting your list and asking:
- Is this task still relevant?
- Can it be eliminated or delegated?
Reducing unnecessary tasks clears mental space and allows you to prioritize effectively.

Establish Boundaries to Enhance Focus

Distractions are inevitable, especially when working remotely or managing multiple responsibilities. Jennifer suggests:
- Turning off notifications and placing your phone in another room.
- Setting clear expectations with your team for uninterrupted work periods.
- Using physical or virtual “Do Not Disturb” signs to signal focused work time.

Improve Communication and Set Clear Expectations

Effective communication is the cornerstone of strong leadership. Jennifer recommends using the “Five W’s” for every task:
- What: What needs to be done?
- When: When is it due?
- Why: Why is this task important?
- Where: Where will this task or its output be used?
- How: How should it be completed?
Including the “why” gives your team context, empowering them to innovate and troubleshoot without constant oversight.

Rebuilding Trust and Accountability

Accountability starts with the leader. Jennifer emphasizes the importance of:

Owning Mistakes: When something goes wrong, instead of pointing fingers, ask, “How can I make my expectations clearer?” This shift fosters trust and a collaborative problem-solving culture.
Encouraging Feedback: Create a safe environment where team members feel comfortable providing honest feedback. Junior employees, in particular, may hesitate to share their thoughts unless explicitly invited to do so.

Preventing Leadership Burnout

Being a leader doesn’t mean doing it all. To prevent burnout, Jennifer highlights the importance of:

Allocating Time for Grounding and Reflection: Take time to prepare mentally before tackling big tasks.
Using Tools to Delegate Effectively: Software like project management platforms can help you track progress without micromanaging.
Leveraging Support: Partner with consultants or coaches to enhance your leadership skills and provide an external perspective.

The Cost of Poor Leadership

Unchecked leadership issues can lead to talented team members leaving. Jennifer warns that high-performing employees will often look for opportunities elsewhere if they feel undervalued or unsupported. Retaining top talent requires creating an environment where team members can thrive and feel respected.

Resources to Become a Better Leader

To help leaders improve, Jennifer offers a free resource called the “Be a Better Boss Starter Pack.” This toolkit includes:

The 10 Commandments for Better Leadership: Daily reminders to guide your leadership approach.
Curated Books and Podcasts: Learn from experts who have successfully navigated similar challenges.
Practical Tips: Actionable advice to implement immediately for long-term impact.

Conclusion

Improving leadership is not just about addressing the struggles of your team; it’s about evolving as a business owner. By recognizing your shortcomings, taking accountability, and implementing Jennifer’s practical strategies, you can transform not only your team’s performance but also your business’s trajectory.

If you’re ready to step into your role as an exceptional leader, start by downloading Jennifer’s Be a Better Boss Starter Pack and begin creating the trust, collaboration, and efficiency your team needs to succeed.

Listen to the full episode of the Workergenix Mastermind Podcast for more actionable insights from Joel Oliver on how to leverage podcasting for business growth

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Transcript

Harley Green
Welcome to the Workergenix Mastermind Podcast! Today, we’re joined by Jennifer Conaway from Conscious Business Answers. Jennifer specializes in helping business owners uncover whether their leadership style might be holding their team back. If your projects are constantly delayed or your team seems stuck in chaos, it might not be them—it might be you. Jennifer, thank you for joining us. How are you doing today?

Jennifer Conaway
Thank you, Harley. I’m doing great and appreciate the opportunity to be here. How are you?

Harley Green
I’m doing well, thank you. Let’s start by diving into your background. What led you to create Conscious Business Answers and focus on helping business leaders improve their team dynamics?

Jennifer Conaway
My journey started in a Fortune 100 company where I always felt like a square peg being forced into a round hole. While I struggled to fit into the traditional corporate mold, I was often given out-of-the-box projects. That’s where I discovered the transformative power of data—how presenting it in the right way could shift an entire organization. For someone who initially struggled with math, that was a game-changer.

Eventually, I transitioned into coaching and gained a wealth of experience in online business. I worked with one of the biggest personal development marketers in the country, running her internal mastermind. That role taught me a lot—it was essentially like running a business within a business. However, I noticed a critical gap. While the “business-in-a-box” model worked for many, it didn’t fit everyone, especially heart-led, purpose-driven entrepreneurs with unique needs. I felt the need to step out and create something tailored to those individuals, and that’s how Conscious Business Answers was born.

Harley Green
It sounds like you identified a very specific gap and created a solution to address it. So how did you come up with today’s topic—how business owners might unknowingly be failing their teams?

Jennifer Conaway
It’s a combination of observations from my previous coaching role and experiences with my current clients. Many business leaders have brilliant ideas and incredible visions, but they’re not taught essential management skills—like conflict resolution, human resources, or even general leadership. Whether it’s managing a single VA or a team of 15 in a multi-six-figure business, the challenges are often the same. I’ve been on both sides of this coin: as part of teams where leadership was lacking and as a leader who had to confront my own shortcomings.

Harley Green
That’s so relatable. What are some key red flags or early indicators that a leader might need to reevaluate their approach?

Jennifer Conaway
Absolutely. Here are three common signs:

Recurring Hiring Issues: If you find yourself repeatedly hiring people who “don’t get it,” can’t deliver, or don’t align with your expectations, the common denominator might be you. This often stems from unclear communication or hiring processes.
Becoming a Bottleneck: If your team constantly reminds you about unfinished tasks or projects stall because you haven’t completed your part, you’re likely the one holding things up. This isn’t micromanaging—it’s simply not getting your own work done.
Blaming the Team: If your default reaction to problems is to point fingers—“They didn’t meet expectations” or “They didn’t do it the way I wanted”—that’s a major red flag. As leaders, we hold ultimate responsibility for our teams. Blame undermines trust and morale.

Harley Green
Those are hard truths but incredibly valuable insights. So, for a business owner who identifies with these challenges, what steps can they take to start turning things around?

Jennifer Conaway
Here are a few actionable tips:

Delegate Strategically: Evaluate your task list and decide what you can hand off to your team. Trusting your team not only clears your plate but also empowers them to excel.
Purge Your Task List: Reassess lingering tasks. Are they still relevant or valuable? If not, remove them to reduce overwhelm.
Protect Your Focus Time: Set aside dedicated work hours. Communicate with your team that you’re unavailable unless it’s an emergency. Turn off distractions, like your phone or chat notifications, to stay productive.
Improve Communication: Use the “Five W’s” framework when delegating: What, When, Why, Where, and How. Clearly outlining expectations minimizes confusion and gives your team room to innovate.

Harley Green
I love the focus on the “why.” When your team understands the purpose behind their tasks, they’re better equipped to deliver results and even improve processes. What tools or frameworks do you recommend for fostering clearer communication and better team dynamics?

Jennifer Conaway
The “Five W’s” is a great start. Additionally, encourage open dialogue within your team. Create a culture where feedback is welcome and solutions are a collaborative effort. Trust is key—your team members need to feel safe enough to share their perspectives without fear of judgment.

Harley Green
That trust is essential for any team to thrive. Before we wrap up, could you share a little about your “Be a Better Boss Starter Pack” and how it can help leaders?

Jennifer Conaway
Of course! The “Be a Better Boss Starter Pack” is a collection of tools and resources designed to help leaders grow. It includes the “10 Commandments for Being a Better Boss,” a curated list of books and podcasts, and actionable tips to strengthen team relationships. The goal is to provide leaders with practical, personalized strategies that create lasting change.

Harley Green
Thank you, Jennifer, for sharing these invaluable insights and actionable strategies. I encourage everyone to check out the “Be a Better Boss Starter Pack”—we’ll include the link in the show notes. Jennifer, it’s been a pleasure having you on the podcast.

Jennifer Conaway
Thank you, Harley. It’s been a joy to be here.