Learning from Failure: How to Overcome Leadership Challenges

Last updated: Jan 17, 2023

As a workplace leader, you’re called on for more than just spearheading projects and assigning tasks. Your employees lean on you to foster a positive, structured workplace that promotes productivity and success. Unfortunately, building a healthy workplace presents some of the greatest, most complex leadership challenges you may face. If you’re like most leaders today, you’ve had your fair share of struggles and failures.


With so much uncertainty, disruption, and negativity in the workplace, the trials you encounter have probably never been greater. The key is to learn from your failures and grow as a leader. If your leadership struggles are hurting workplace morale, bringing down results, or costing you employees, it’s time to find out how to overcome the challenges you’re facing.


Struggling to Resolve Workplace Conflict

It goes without saying that these are polarizing times. From politics to the pandemic to social unrest, there’s no shortage of topics to drive a wedge between even the kindest of coworkers. Although you can’t avoid all office squabbles, you can adopt some policies that help you move past them:

  • Don’t assign blame.
  • Pick the right time to address the conflict.
  • Set clear workplace rules.
  • Don’t let major conflicts continue.
  • Remember that healthy conflict helps you grow.

Conflict is a two-edged sword. Yes, it can cause some discomfort and emotionally charged situations. But it can also show you and your team new ways to solve problems. Instead of avoiding conflict altogether, instead think about how you can better manage it and channel that discord into some creative solutions.


A male and female coworker writing on a board  trying to solve work related problems.

Difficulty Leading in Times of Crisis

If you held a leadership role during the start of the pandemic and managed to guide your team through it unscathed, congratulations. You’re the exception. For everyone else who struggled to adapt, COVID-19 ushered in an unprecedented period of fear, uncertainty, and change that we still haven’t totally recovered from. Fortunately, there are concrete steps that can help you lead through times of crisis:

  • Stay calm: Maintaining your sense of calm will help you see solutions, as well as reassure your team that everything will be OK.
  • Add some structure: By definition, times of crisis throw your whole workplace into a tailspin. A steady routine can help restore a sense of normalcy for everyone.
  • Surround yourself with other strong leaders: These supportive colleagues will give you someone to lean on and remind you where to focus when tough times hit.
  • Take care of yourself: If you’re overworked, frazzled, and burnt out, your leadership will suffer. Make sure to care for yourself during the challenging times.
  • Stay flexible: The pandemic has forced everyone to adapt to a new way of working, living, and thinking about the world. The leaders who can best accept these changes are the ones most equipped to pull their teams through.


Failing to Motivate Employees

Keeping your employees motivated can be challenging, even in the good times. If your office is running smoothly, you may be tempted to think everything’s on auto pilot. This can lull you into believing that your employees have it easy, too. It’s common to overlook all the hard work your team members pour into their role, particularly if you’re not involved in the day-to-day operations.


It can also be difficult to keep your employees motivated during challenging times. Sure, results may be down, but that doesn’t mean your team isn’t doing all they can to turn it around. Unless you tell them otherwise, team members may feel personally responsible for outcomes that are beyond their control. What’s worse, it can be financially challenging in these lean times to reward strong employees with bonuses, promotions, and raises.


Although you may not be able to motivate employees with monetary recognition, you can use appreciation to keep your team happy. Instead of throwing cash you don’t have their way, it simply takes a little more time and effort on your part as a leader:

  • Listen to your team when they come to you with suggestions and complaints. This signals that your employees have a voice in the direction of your company and shows that you value their input.
  • Notice the contributions of your team. And this doesn’t just mean the big stuff. Take the time to look for the small, day-to-day efforts of individual employees and let them know it hasn’t gone unnoticed.
  • Check in with employees on a regular basis. This will show that you’re concerned with them, as well as provide an opportunity to elevate any concerns.

Lack of employee motivation often stems from an employee disconnect with the mission and results of a company. By using these tips, you will illustrate how vital they are to the team.


Losing Valuable Employees

When employee motivation suffers too much, employee turnover isn’t far behind. The “great resignation” has exposed much of the discontent in the workforce, and many of the reasons that employee resign are the same as why they feel demotivated, just ratcheted up a few levels.


To get to the root of why so many of your employees are handing in their letter of resignation, ask yourself some important questions:

  • Do my employees feel valued?
  • Does my team have all the support they need?
  • Does everyone know the greater mission of this company?
  • Do employees feel like their voice is heard?
  • Have I offered opportunities to grow?

If the answer to any of these questions is “no” or “I don’t know,” you have a problem. Some employee turnover is natural, but a rash of resignations may indicate some deeper issues in your company, communication, and leadership style that need to be addressed. The important thing is to remember that retaining great employees takes effort on your part.


Weakening Team Cohesion

Over the past 18 months, building a cohesive team that works well together has never been harder. If your workplace went remote due to COVID-19, the physical separation of employees probably put a damper on the sense of teamwork. Without the time to talk before meetings start, quick greetings in the hallway, and breakroom chats, informal encounters that used to bring your colleagues together have evaporated. Add to that the higher-then-usual number of employees who may have left your team and it’s easy to see why everyone may feel just a little more distant.


You never want your employees to feel like they’re just clocking in for a job. You want them to feel invested in their role, and a huge part of that is enjoying the colleagues they work with. Sure, much of that starts by picking the right people during the hiring process, but you can also take steps to build team cohesion during these tough times:

  • If you’re a larger organization, divide your employees into teams that are responsible for their own success, and give them the autonomy to complete work as they see fit.
  • Encourage the formation of informal teams that can solve issues as they arise without going through an official project assignment process.
  • Allow time for cross-training, which will give employees a greater appreciation for the contributions of their colleagues.
  • Support your teams with a dedicated place to meet, time allotment to get together, and budget (when necessary).

The benefits of a cohesive team include stronger trust, greater motivation, higher productivity, and more success. Plus, you’ll be rewarded with greater employee autonomy, which may take some pressure off of the leadership to solve challenges and assign work.


A group of employees having a meeting discussing how to overcome leadership challenges.

Get the Leadership Support You Need

If you’ve struggled with any of these elements of leading a team, you’re not alone. It takes an entirely new skill set that few people naturally possess. Fortunately, USF offers leadership and management training that can help you overcome your struggles and gain the skills you need.


From communicating to leading multiple generations of employees to recognizing your strengths and weaknesses, our programs offer the specific leadership skills that will help your team succeed. Learn more about our certificates today.


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