Challenges Faced By Leaders and How to Overcome Them

A leader’s job is tough. Leading the strategic vision of the organization to building a high performance team comes with multiple unknowns and challenges along the way. There’s no rule book or a predefined path to face these challenges. Navigating each one requires exercising courage and conviction without falling apart. 

Experience and knowledge does come in handy when dealt with difficult circumstances, but what matters more is the attitude—how close are they to reality, are they looking for the right solutions or trying to be right, how do they leverage their team and how quickly are they able to respond with an action plan that fixes the problem in the short-term while not losing sight of the future.   

While many of these challenges are external—they are outside one’s control and the best way to deal with them is to face them head-on as they occur—others are internal and can be prevented by proactively taking action and putting measures in place to fix problems before they turn too big. 

But this requires initiative and hard work—a burning desire to build a strong organization that rises above the challenges. 

Leadership takes work. It takes time and energy. The effects are not always easily measured and they are not always immediate. Leadership is always a commitment to human beings.
— Simon Sinek, Leaders Eat Last

These 5 challenges are crucial to achieving success as a leader: 

Staying close to reality 

Leaders who distance themselves from their people lose sight of the real issues that plague their team’s productivity and performance. Time constraints and the usual busyness excuse can make them deprioritize connecting with people as multiple other important things vie for their attention. But keeping  themselves busy with other work priorities while not making time for their team is a costly mistake. 

The real challenge isn’t keeping up with team members who report to you, but the invisible members below in the hierarchy who often do all the real work.  

Every step up the ladder takes you farther from these people. What you think you see and what you often hear may be less grounded in reality and far from truth. The only way to bridge this gap is to stay connected to people in your organization who don’t directly report to you. 

Keeping communication lines open with your indirect reports who are managed by your managers enables many things:

1. Gives you an opportunity to hear about their real problems.
2. You can learn how employees feel about their managers. Knowing how your managers are doing enables more relevant feedback.
3. Gives everyone a channel to voice their concerns. People feel heard and supported from leaders in the organization. 

A great way to stay connected and closer to reality is to do regular skip level meetings. Schedule a one-on-one with each of your indirect reports every few months. Making it a recurring meeting is the best way to remove the burden of decision-making and ensure it doesn’t get deprioritized. Find a frequency that works for you and your people and stick to it.  

Leadership is solving problems. The day soldiers stop bringing you their problems is the day you have stopped leading them. They have either lost confidence that you can help or concluded you do not care. Either case is a failure of leadership.
— Colin Powell, author of It Worked for Me

Make one-on-one with people in your organization part of your strategy to stay in touch with real problems. 

Navigating and communicating change

Change is complex because there’s ambiguity, uncertainty and risk involved. Multiple moving factors, interdependencies and conflicting signals can make change very hard to implement. 

When leading through change, leaders face many obstacles, but the biggest bottleneck isn’t the challenges along the way, it’s how change is presented and communicated to employees. 

There’s too much focus on strategy, execution and operational excellence and too little on ensuring effective communication. Communication which is the key driver of ensuring a smooth transition is mostly an afterthought. 

Effectively leading through change requires a communication strategy—right information must be communicated at the right time. Sharing too much information can leave employees feeling overwhelmed and too little can lead to resistance and disengagement.

You can’t get employees buy-in by enforcing change. You can’t let them play a guessing game. To lead through change, you have to be on top of your communication game.

Use these 5 strategies to lead effectively through change: 

1. Keeping important information away from employees as a measure to protect them usually backfires. Not having the answers distracts them from putting their time and energy into work. Instead of trying to shield them, share the context and give them clarity. Connect the change to the organization’s vision. Knowing the “why” of doing something is a powerful motivating factor. 
2. Every change is an emotional experience for employees. Not knowing how the change impacts them can lead to stress and anxiety. Addressing how the change impacts their day-to-day work or responsibilities or what might it mean for them is crucial to lead effectively through change. 
3. Keeping communication lines open with all employees is essential to lead through change. Despite your best efforts, not everyone may approve of your plan. This is where managers can step-in. They can work closely with their team members to address their worries and concerns. 
4. When you’re doing something worthwhile, fear naturally comes along for the ride. Instead of hiding that change is scary, leaders can use it as a powerful motivating factor. Acknowledge it without letting it get in the way of your decisions or how you move forward. 
5. Change is a great opportunity for your employees to put their thinking, problem solving and leadership skills to test. Promote bottom-up leadership by empowering your employees through the entire change process. 

Leadership requires two things: a vision of the world that does not yet exist and the ability to communicate it…People don’t buy WHAT you do, they buy WHY you do it.
— Simon Sinek, Start with Why

The biggest leadership challenge to successfully implement any change isn’t coming up with a solid strategy or an extensive execution plan—though those things are important in their own ways—it’s how the change is communicated to employees.

Getting honest feedback 

Feedback is a crucial part of growth. If you don’t know how you’re doing, it’s impossible to take corrective actions and improve. 

Many leaders fail at this. They either do not explicitly seek feedback or the way they ask for it only boosts their ego by getting feel-good praise about what they’re doing well without surfacing the actual areas where they’re falling short. 

There are lurking gaps in how leaders view their actions and how others perceive them leading to inadvertent blind spots. Without getting the criticism they need, they keep repeating the same mistakes over and over again. Not taking the time to reconcile reality perpetuates disconnect and dissonance. 

As a leader, making your employees comfortable to criticize you isn’t easy. Getting honest feedback is a big challenge. Don’t expect them to walk over to you and give you the feedback unless you take the first few steps in seeking it. 

Done right, feedback can be a great tool to get rid of behaviors that are damaging to yourself and the success of your organization and its people. 

To get clear and actionable feedback, follow these practices:

1. Don’t create the faulty image of a perfect leader without flaws. Set real expectations that you are learning and growing much like everyone else.
2. Frame your questions in a way that makes it easy for the feedback giver to share useful inputs. Use open-ended questions. 
3. Seeking criticism is uncomfortable and if you’re nervous about it, it will show up in your voice and in your body language. Practice stepping out of your comfort zone regularly. It will make your feedback conversations less scary. 
4. Most importantly, don’t seek feedback if you’re not willing to put it into action. If you keep collecting feedback but never act on it or your team sees no change in your behaviors and actions, they will assume that their suggestions don’t matter much. 

Don’t be defensive. People will be reluctant to share feedback if they are afraid of hurting your feelings or having to justify their perceptions. Listen carefully. Relax and actively listen to understand what the other person is trying to tell you; be sensitive to how your nonverbal communication is affecting the other person’s willingness to share with you. Suspend judgment. Listen, don’t judge. 
— James M. Kouzes, The Leadership Challenge

If you’re a leader, ignoring your ignorance is not an option. Be courageous. Face your fears. Get the feedback you need.

Building a resilient team 

No strategy can help an organization thrive if the people in the organization aren’t resilient to change and chaos. Setbacks and challenging situations – a missed deadline, a lost deal, a failed project, a bad strategy – are everyday affairs at work, and only those who learn to get past them can grow professionally and personally. 

A resilient mindset is essential to bounce back from challenging situations at work.

“Fail fast, be agile, be resilient.” Many leaders repeat this to their team with the hope it will not paralyze their team when faced with a setback and prevent them from moving forward. But simply telling people to be resilient doesn’t work. 

Irrespective of how much you tell your team to move past failures and learn from mistakes, accepting a failure is never easy. The expectation to do well at work makes people believe that failure isn’t an option.

By adopting these 4 techniques, you can improve your team’s ability to succeed in difficult situations by bouncing back from failure:

1. When dealing with failures and setbacks, building resilience isn’t about ignoring emotions and trying to be rational. It requires accepting those emotions while staying rational. It requires giving people space and time to process, reconcile and come to terms with what just happened.
2. Don’t try to be nice or say things to make them feel good. State facts. Share feedback as they need to hear. Building resilience requires facing reality, not denying it. People need to feel in control of their situation. 
3. Encourage a fail fast mindset by helping your team see the value in taking small steps and using that to build the courage to take bigger risks.
4. Don’t let finger pointing and blame games get in the way of finding solutions. Hold your entire team responsible for failures and help them find solutions to move forward as a group.

Those who are excellent at their work have learned to comfortably coexist with failure. The excellent fail more often than the mediocre. They begin more. They attempt more. They attack more. Mastery lives quietly atop a mountain of mistakes.
— Eric Greitens, Resilience

Develop a sense of realistic optimism in your team without displaying toxic positivity. Help them see that failure is a part of life and not an excuse to stop trying, avoid risk or ignore challenging circumstances. 

Seeking alignment across teams and functions 

One of the most powerful forces at work is teamwork. When team members learn to collaborate well, greater things are achieved—projects are completed on time without compromising on quality, business targets are met which makes the stakeholders happy and the joy and satisfaction from doing impactful work motivates the team to go after bigger and better things. 

But collaboration is one of the most failed efforts at work. Despite best attempts from leaders, collaboration continues to be a messy affair. 

As a leader, you cannot succeed without implementing effective ways to bring people together and helping them navigate the dynamics of a successful workplace collaboration. Adopt these 5 strategies and put them into practice:

1. When people in the team don’t have a clear end goal and a common success criteria to measure their results, they focus on individual goals and tasks which turns collaboration into a nightmare. Days working together are filled with blame games, complaining and emotional outbursts as everyone thinks their direction is right and others must be at fault. A well-defined end goal and a common measure of success is crucial to help your team members row in the same direction. It gives them a reason to work together instead of trying to do it all alone.
2. Disagreements and differences of opinion are unavoidable when a group of people from different backgrounds, experiences and expectations come together. Instead of viewing them as obstacles in path, team members need to consider them as opportunities to identify problems, find the best possible solution and course correct before it’s too late. 
3. Every team member will hit some roadblock as they work towards their goals. In such moments, getting help and support is important to make forward progress instead of staying stuck. Having team members around to guide, share their knowledge and expertise and encourage to not give up goes a long way in keeping the momentum and continuing to stay positive. Giving and seeking support is essential for effective collaboration and teamwork. 
4. When team members give undue attention to a destination while ignoring the path needed to get there, they lose opportunities to re-strategize, pivot and incorporate learning lessons from the process. Obsessing about the outcome also turns every failure into a disaster and minor disappointments into major setbacks. It makes them lose hope due to feelings of lack of control. Shifting their focus from outcomes to process can give them hope because the journey to reach the end goal is completely in their control. 
5. Communication problems, wrong assumptions and misalignment of expectations are the norm when multiple people work towards a common goal. Eliminating these problems is not the solution because it’s impossible to achieve. However, identifying them early in the process and correcting them is the way to go. Milestones are a great way to achieve this. They not only help in minimizing these problems, but delivering a tangible result—however small it may be—boosts team’s motivation and trust in each other’s contributions.

If you could get all the people in an organization rowing in the same direction, you could dominate any industry, in any market, against any competition, at any time.
— Patrick Lencioni, The Five Dysfunctions of a Team

If collaboration isn’t working in your organization, don’t be frustrated. Implement the right practices, review what isn’t working and make corrections as you go.  

Summary

1. Your people are your most important asset. Keeping them productive and performant is necessary to achieve business targets. However, you can’t do it if you never take the time to connect with people in the organization and hear their real concerns. Digging deeper by speaking to people who don’t directly report to you can give you insights into issues that otherwise remain hidden. 
2. Change is complex and change isn’t ordinary. Change also evokes strong emotions in people that are important to keep in check. While strategy and planning are important to lead effectively through change, making it work requires strong communication. Transparency, clarity, repetition and understanding are crucial. 
3. Leaders aren’t perfect and they need feedback to bridge the gap between how they view themselves and how they are perceived by their team. Getting honest feedback as a leader is tricky. You have to take the initiative, put on a brave face when feedback hurts and show willingness to improve. If you turn defensive or ignore feedback, your team will stop giving you critical feedback that you need to improve. 
4. Irrespective of how much your team plans, things won’t always go as expected. Surprises, challenges and obstacles will show up when they least expect it. Handling them with courage and conviction requires building a resilient mindset that doesn’t let minor disappointments turn into major setbacks and thinks of creative ways to turn obstacles into opportunities. Build a team that can bounce back from failures and succeed in difficult situations. 
5. The biggest bottleneck in meeting deadlines is getting everyone on the same page and making them work together as a team. Collaboration breaks down when everyone operates with their own agenda without regard for the common goal. A common success criteria with milestones, focus on the process and the right kind of support can prevent collaboration from turning into a nightmare.   

Recommended Reading