Modern Leadership: Thriving Despite Challenges

Globalization, significant technological advancements, environmental challenges, evolving needs of employees, and industry uncertainty – these are all challenges modern businesses face.

The business environment is constantly changing; we know this. But how is leadership adapting to these changes? How do business leaders keep up with the evolving challenges that come with modern leadership?

As a leader, you need to adapt to the continually changing business environment, including the technological advancements and economic forces that directly impact your business strategy.

Before stepping into any management role, it’s essential to know the potential leadership challenges. Especially in the current post-2020 climate, a host of new leadership and management challenges may pop up.

The global pandemic, paired with technological advancements and economic challenges, has changed the commercial landscape. 

Here are a few of the significant challenges that modern leaders face and how to overcome them. But first, let’s understand what makes a great leader.

What makes a great leader?

When you think of the term ‘leader,’ you think of people in charge – high-ranking people like your boss, teachers, politicians, and CEOs. But, leadership isn’t really about a person’s position or ranking. Leadership is about having the skills and characteristics needed to lead people successfully.

But, what are the skills and characteristics needed to be a great leader?

There are many definitions of what makes a great leader and blog posts listing the top characteristics of good leaders on the internet.

The truth is, there are different leadership approaches and qualities necessary for effective leadership. As leaders, we all have varying experiences and perspectives, and not all environments require or respond to the same type of leadership style. So, it’s hard to define what makes a great leader.

Leadership skills and attributes

Successful leaders come in all shapes and sizes, but after reading through a few of the ‘characteristics of good leaders’ articles, here are some of the most common leadership skills and attributes:

  • Integrity
  • Passion
  • Ability to delegate
  • Communication and ability to articulate a clear vision
  • Self-awareness and self-reflection
  • A desire to learn – constant personal and professional development
  • Responsibility
  • Strategic planning and the ability to think ahead
  • Empathy
  • Ability to embrace failure and learn from it
  • Positive attitude (while still being realistic)
  • Humility and a sense of humor
  • Courage and confidence
  • Mutual respect to and from the team
  • Regular transparent feedback

The below definition by Bhagi Rath, featured on Forbes, offers an excellent summary of what a good leader is:

“A great leader possesses a clear vision, is courageous, has integrity, honesty, humility, and clear focus. They are a strategic planner and believes in teamwork. Great leaders help people reach their goals, are not afraid to hire people that might be better than them, and take pride in the accomplishments of those they help along the way.”

While these are all necessary principles to lead teams, it all comes down to whether the leader is getting the job done at the end of the day. And getting the job done means building a team that is accountable and led to getting results. Without the team, there can be no real leadership – and a great leader understands and appreciates that. You can also learn more about what makes a great leader in our hand-picked collection of the best leadership books for entrepreneurs

Now onto the challenges that all leaders (great or not) face in modern leadership.

The challenges of modern leadership

81% of respondents in Deloitte’s 2019 Global Human Capital Trends report think that modern leadership has ‘unique and new requirements that are important or very important to their organization’s success.’ And that’s before they knew what was going to happen in 2020!

Topics like inclusion, fairness, social responsibility, understanding the role of automation, and leading in a network were not part of the leadership manifesto a decade ago. However, traditional leadership is changing, and with it comes a host of new challenges.

Here are five modern leadership challenges and how to handle them.

Leading in times of uncertainty

In uncertain times, employees turn to their leaders for guidance and reassurance more than ever before. But, when leaders may be just as skeptical themselves, how do they reassure their team?

RH International lists four key concepts when leading people during times of uncertainty

  • Inform: Leaders must candidly acknowledge the downsides and the unknowns. It is also the leader’s job to help people make sense of the changing conditions.
  • Connect: Generate a feeling of trust with your employees with a highly personal presence and connection.
  • Guide: Give steady guidance. Focus on the concrete steps on which all employees can align.
  • Unite: Celebrate who you are as a business community and emphasize your connectedness to your industry, company, customers, and one another.

Making hard decisions

Knowing how to make difficult decisions is a challenging part of leadership. Some decisions never get more manageable, especially when they involve people, money, and risk.

Sooner or later, you’ll need to make a tough call. Here are a few tactics to help you make challenging decisions:

  • Reduce decision fatigue by spending less time on small-scale decisions (like what to eat for dinner).
  • Take yourself out of the equation. Imagine that this isn’t your company and look at the situation from an outsider’s perspective.
  • Have a deadline and stop procrastinating.
  • Find a sounding board like a trusted colleague, coach, or mentor to chat through the decision. 
  • Own your decision. Once you’ve made your decision, stand behind it and let people know how and why you made that decision. You can still acknowledge the impact on the people around you and show empathy, but try not to appear tentative or give the appearance that the decision is not final.

As a leader, it’s unlikely that you’ll always make the ‘right’ decisions. There will, undoubtedly, always be someone who disagrees with your decision. But that’s life, and everyone has their perspective on things.

Dealing with conflict

Dealing with conflict is never easy. When there are many changes in a business strategy, the conflict will bubble and flare up, driven by disagreements, personal grievances, or misunderstandings.

As the leader, it’s your responsibility to manage conflict in the workplace. Business strategies that deal with conflict management include:

  • Diagnose the conflict. Describe the conflict from your perspective as objectively, clearly, and precisely as you can. Then, talk honestly and directly to the people involved.
  • Maintain boundaries. A leader must assist and support others in maintaining boundaries while also keeping themselves from crossing the line.
  • Respect differences. A leader should respect the unique differences that each person in the team has.
  • Identify solutions. Come up with possible solutions that help everyone’s motives, goals, and agendas.

Working with a team

Managing a team has always had its challenges – from developing talent to not micromanaging. Now add in a shift to remote working and managing a team while navigating a pandemic, and you’re in a whole new ball game. Leadership and management styles have had to develop to suit the new working environment. 

Here are a few common challenges that leaders are facing with regards to a remote workforce and how to solve them:

  • Managing the productivity of your team. Resolve this by building trust between you and your team and using technology to your advantage by using project management tools.
  • You are staying on top of communication. Resolve this issue by figuring out the best tools for your team to use and setting guidelines around all communication methods. Also, schedule regular team calls and one-on-ones with your teammates.
  • Keeping the motivation levels up. Keep on doing team-building activities, host regular video chats, run online quizzes, and do wellness sessions.

Today’s businesses are also seeing a massive shift in the importance of demographics when building a team. As leaders, it’s essential to ensure that you’re hiring a diverse and representative team across all races, genders, and ages.

Imposter syndrome and burnout

Imposter syndrome and burnout are very real challenges for the modern leader. 

“I have no idea what I’m doing,” “I don’t deserve this position,” or “Who am I to be managing a team?”

No matter how hardworking and deserving we are of a position, imposter syndrome still gets to the best of us. Imposter syndrome is the struggle to internalize and accept our accomplishments and always doubting our deservedness and abilities.

Fortunately, leaders can combat impostor syndrome by actively revamping their organizational culture – including strategizing vulnerability, promoting problem-solving, and encouraging questions in the workplace.

Then there’s the burnout…

Burnout is another common challenge among leaders. Too many leaders push too hard, never rest, and work insane hours under the pretense of ‘leading their team.’ But, that only leads them (and often their team) straight down the path of burnout.

It’s tempting to be a superhero, but how can you lead and inspire others if you’re not taking care of yourself? You need to put your wellness (and sanity) first to manage a team effectively.

How to overcome the challenges

There are many bumps on the path of leadership. But every challenge is also an opportunity. An opportunity to learn something about yourself, improve your skills, and become a better leader.

While many challenges may be from external forces, our feelings and reactions to situations often create the most significant leadership hurdles. There are specific internal shifts that we can do to help us face these leadership challenges.

Adopting the below mindset shifts and internal processes can help.


Resilience is a crucial characteristic of high-performing leaders.

Resilient leaders can sustain their energy level under pressure, cope with disruptive changes, and quickly adapt. No matter what challenges get thrown your way, you’re able to bounce back up.

Being resilient allows you to overcome significant difficulties without engaging in dysfunctional behavior (like burning out).

Scenario planning and foresight

Underestimating the challenges of uncertainty can lead to business strategies that neither defend against nor take advantage of the challenges.

Scenario planning and foresight are both tools to use for better decision-making. It helps you explore the new trends and signals of change, create new strategic options, and inspire learning and conversations about possible futures.

Staying humble and human

It can be easy to let it go to your head a little when you’re in a leadership position, especially when things are going well. However, when you’re constantly receiving praise, it’s not uncommon to start believing that your team’s success is all because of you.

But, it’s not all about you. A successful leader is only as good as their team.

The best leaders are humble. They understand that leadership is about influence and impact, not authority. And they recognize the importance of their team.

Arrogance is not a good look on leaders. It only alienates a team, causes conflict, and encourages drama. 


As a leader you can’t (and shouldn’t) do everything yourself so delegating is essential. Delegating empowers your team, builds trust, and assists with professional development. It also helps you identify key team members who can assist in challenging times.

Now, delegating is easy. But delegating well is not. Successful delegation isn’t about simply ‘handing things over’. It’s about empowering others to do the work you’ve brought them on board to do.

Seeking feedback

Want to be a better leader? Ask for feedback and listen to it. 

Requesting feedback is quite possibly the single most impactful thing a leader can do to improve their performance. As a leader, seeking feedback increases mutual respect among your team members, improves dialogue and understanding, and enables continuous improvement. 

Management, leadership, and entrepreneurship are all filled with challenges. It’s part of the fun! Instead of seeing challenges as something to avoid, see them as opportunities for growth. By facing our challenges head-on, we’re more likely to come out of them stronger. Which will only make us better managers, leaders, and entrepreneurs, right?

No matter what you do to become a better leader, it’s better to do it alongside other entrepreneurs. Join the Deliberate Entrepreneurs community and get the best support for your growth! 

Many of the guests on the Beyond 8 Figures podcast share the challenges they’ve faced, including leadership challenges. Check out some of our latest episodes for insights on modern leadership.

Modern Leadership: Thriving Despite Challenges