5 Leadership Challenges That Determine a Team’s Success or Failure

Jessica Thiefels

19 August 2019

Leading a team of unique individuals has always been a challenging task. However, in the shifting landscape of a new digital workplace, it’s become ever-important and equally daunting for managers to be great leaders. According to Deloitte’s 2019 Global Human Capital Trends, 80 percent of workers rate leadership as a high priority, yet only 41 percent think their organizations are ready to meet leadership requirements.

When considering what it takes to be a better leader, and to overcome the many team challenges of the modern workplace, consider what Elaine Pulakos, CEO of PDRI and author, says are the three qualities that make up an effective team: adaptability, resilience and agility. 

"To be [a] successful, integrated, cross-functional team, [you] need to operate within an organizational climate that is characterized by ARA values,” she writes in a LinkedIn article. “These include authenticity, trust, flexibility, empowerment and collaboration—characteristics that are essential for teams to successfully manage disruptive, fast-paced change.”

Keeping these qualities in mind, consider these five common leadership challenges that hold leaders back, and how to overcome them. 

Challenge 1: Empowering Each Member of the Team

It’s essential you understand each team member and know how each of them works most effectively. Without this understanding, you’ll struggle to empower your staff and may run into challenges with agility. (If you don’t know who does what, how can you move quickly as a team?)

Kevin Sealey, VP of operations at EPOCH Student Living, defines a leader as, "Someone who takes time to understand and know the team members they are working with—what are their strengths, what are areas of development, how you can better support them? Every team member is going to be different, and it’s the leaders’ responsibility to know how each one works separately so that when they are put together, you create positive results."  

Solution: Take time to get to know each team member, and use Sealy’s suggestion to focus on what tasks or projects they excel at. Beyond that, you can ask them what they enjoy doing. Without this, employees may struggle to find their place, making your team weak.

Challenge 2: Engaging Introverts

According to Gallup’s State of the Global Workplace report, 85 percent of employees are not engaged in their jobs. Disengagement can be even more prominent with naturally introverted employees. Elena Carstoiu, co-founder and COO of Hubgets, explains why: 

“One of the most common challenges introverts face today is that most workplaces are built to stimulate collaboration and somehow seem designed for extroverts,” she says. “Starting from the large open spaces, up to the constant interruptions that shatter their focus at work. And let's not forget the endless meetings where they need to speak up in front of many people.”

Solution: The first step is awareness and understanding. Carstoiu advises, “Both introverts and extroverts will work best in an environment that complements their capabilities. Therefore, to be able to better connect with introverts, start by solving these challenges first.” Connect with introverted employees to discuss their preferred workflow and communication methods. Make sure they know you’re there to help them navigate the office culture, should they need it.  

Challenge 3: Knowing When Collaboration Is and Isn’t Necessary

Much of the conversation about collaboration in the workplace naturally arose from living and working in a hyperconnected world. While some collaboration is necessary, a good leader knows when it is and isn’t productive.

Rob Cross, a professor at Babson College, explains in this article by the Wharton University of Pennsylvania that an always-on collaborative organizational structure can be a drain on everyone’s time and resources. According to Cross, people are “emailed and meetinged to death,” which leads to “little time left over to perform individualized tasks.” 

Carstoiu also touches on this issue for the introverted team members when she advises, “Create a culture where ‘personal flow’ is respected. And design the internal communication in a way that caters for focus at work as much as for productivity.” 

Solution: When the time does call for collaboration, understand the best way to champion it. Lead by example and participate in the process yourself. According to that same Deloitte report, 83 percent of workers say their C-suite rarely collaborates with their teams or does so only on an ad hoc basis. Break that mold and get your hands dirty with your team.

Challenge 4: Tackling Issues Head-On 

Every manager will experience problems in their tenure, whether it be personality clashes among team members or poor staff performance. While it may seem easier to ignore the issue or take time assessing it from all sides, the best option is to acknowledge and rectify the situation as soon as possible. 

Most importantly, don’t wait for a quarterly review to bring it up. According to another Gallup report, employees are most likely to learn (and therefore grow) when feedback is immediate and specific. 

Solution: Leading people is not easy, and sometimes issues can be sticky and uncomfortable. However, in-the-moment actions yield better results in the long run. In fact, 83 percent of employees say they appreciate receiving candid feedback, whether it’s positive or negative, according to Officevibe’s State of Employee Engagement report. Don’t be afraid to assert yourself as a leader and tackle challenging situations head-on.

Challenge 5: Fostering an Environment of Trust Through Recognition and Feedback 

Trust fosters a successful and productive team. The Center for Creative Leadership explains in this article, “When trust is present, people step forward and do their best work together efficiently. They align around a common purpose, take risks, think outside of the box, have each other’s backs, and communicate openly and honestly.” 

Alternatively, “When trusting relationships are absent, people jockey for position, hoard information, play it safe and talk about—rather than to—one another,” explains the CCL.

Solution: The best way to foster a trusting culture is to offer specific and frequent recognition and feedback to your team. A recent study on feedback found that a supportive supervisor and a feedback-driven environment increases employee’s creative performance. What’s more, 72 percent of employees ranked recognition as one of the most important factors impacting their engagement in the workplace, according to a report by Achievers. Take the time to recognize your team’s accomplishments, offer your input when needed and be available for dialogue.

Overcome Team Challenges to Lead Effectively 

Leading a team is not an easy task; there are many complicated factors at play, which only get more complex as the workplace globalizes and digitizes. However, if you get back to the basics and focus on your team, you can build a productive, cohesive and ultimately successful culture. 

Jessica Thiefels

Jessica Thiefels is an entrepreneur and founder and CEO of Jessica Thiefels Consulting. She’s been writing for more than 10 years and has been featured in top publications like Forbes, Fast Company and Entrepreneur. She also writes for Business Insider, Virgin, Glassdoor and more. Follow her on Twitter @JThiefels and connect with her on LinkedIn.

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