Leadership isn’t about having all the answers —
It’s about asking the right questions.
At first, stepping into a leadership role feels like it’s all about strategy, execution, and results. But soon, reality hits. Leadership is about people. It involves navigating complex dynamics and handling unspoken challenges. You must make decisions in situations no playbook can fully prepare you for.
So, what are the biggest hurdles team leaders face? And more importantly, how can you overcome them? Here are 10 team leadership challenges and the critical questions you should be asking to tackle them.
1. Resistance to Change
You introduce a new process or tool, expecting it to boost efficiency. Instead, you find some employees eager to adopt it, while others hesitate or outright refuse. Instead of improving workflow, things slow down.
Why it matters:
Change resistance can stall progress and affect morale. Research by McKinsey & Co. suggests that 70% of change initiatives fail due to employee pushback and poor communication. Read more here.
💡 Question to ask:
Am I helping my team embrace change—or just expecting them to?
2. Uneven Workloads
One team member is overworked and constantly putting in extra hours. Another has lighter tasks but doesn’t step in to help. The high performer won’t complain—until burnout forces them out.
Why it matters: Overworking top performers can lead to high turnover. A study by Gallup found that burnout leads to a 2.6x higher likelihood of employees actively seeking a new job. Check the report.
💡 Question to ask:
Do I truly know who’s overwhelmed and who has capacity?
3. Lack of Psychological Safety
You ask for input in a meeting. Silence. Later, someone tells you they had an idea but didn’t feel comfortable sharing it. If people aren’t speaking up, how many good ideas are getting lost?
Why it matters: Studies show that teams with high psychological safety outperform others. Google’s Project Aristotle found that psychological safety was the #1 factor in high-performing teams. Explore their findings.
💡 Question to ask:
Do my people feel safe enough to challenge ideas?
4. Communication Breakdowns
You’ve explained the new direction in meetings, emails, and Slack. Yet someone still asks, “Wait, what’s changing?” Information overload doesn’t mean clarity.
Why it matters: Poor communication costs businesses an estimated $37 billion annually in lost productivity. See the report.
💡 Question to ask:
Are my messages being understood—or just heard?
5. Decision-Making Bottlenecks
One team is waiting on approval, but the person making the call is waiting on someone else. Meanwhile, progress is stuck in limbo.
Why it matters: Research by Harvard Business Review found that slow decision-making reduces organizational efficiency by 20-30%. Read more.
💡 Question to ask:
Are slow decisions costing my team speed and momentum?
6. Managing Remote & Hybrid Teams
A key decision is made in a casual hallway chat. A remote team member has no idea it even happened. Now, there’s confusion and misalignment.
Why it matters: Microsoft’s Work Trend Index reports that hybrid work has increased miscommunication and misalignment across teams. See the full report.
💡 Question to ask:
How can I make remote and hybrid teams feel equally included?
7. Misalignment on Goals
Marketing is focused on brand awareness, sales is pushing for revenue, and product is prioritizing user experience. Everyone is working hard—but in different directions.
Why it matters: Companies with high goal alignment see 3.5x better revenue growth, according to a study by LSA Global. Check the data.
💡 Question to ask:
Is my team aligned on what truly matters?
8. Low Team Engagement
You ask for input, but no one responds—cameras off, phones out, energy low. They’re showing up, but are they actually engaged?
Why it matters: A Gallup study found that only 36% of employees are actively engaged at work. This lack of engagement leads to lower performance and retention. Explore the research.
💡 Question to ask:
What’s quietly killing my team’s motivation?
9. Avoiding Tough Conversations
Two teammates aren’t getting along, and it’s starting to affect everyone. You keep hoping they’ll work it out. They won’t.
Why it matters: Avoiding conflict results in 57% of employees actively avoiding colleagues, causing drops in collaboration. See the study.
💡 Question to ask:
Am I avoiding a tough conversation that needs to happen?
10. Bridging the Skills Gap
You need someone to take on more responsibility, and they want to, but they don’t have the right skills yet. You don’t have time to slow down for training.
Why it matters: The World Economic Forum predicts that 50% of employees will need reskilling by 2025. Read more.
💡 Question to ask:
Am I prioritizing execution over development?
Final Thoughts
Great leadership isn’t about knowing everything—it’s about asking the right questions. If you want to grow as a leader, pay attention to the unseen barriers. Be prepared for the tough conversations. Address the gaps that hold teams back.
💬 Which of these challenges do you face most often?
Let’s chat! I offer coaching sessions designed to help team leaders create stronger, high-performing teams.
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