Blog Leadership & Management

How to deal with 17 common leadership challenges

By Maggie Wooll, MBA

July 13, 2022 - 24 min read

leadership challenges

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The 6 most common leadership challenges

10 other leadership challenges you might experience

4 tips to help you overcome any leadership challenges you face

Conclusion

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I remember my first leadership role. I was promoted from within a team and felt totally unprepared for what I was taking on.

Suddenly a whole group of people was looking to me for guidance. Colleagues who yesterday were my peers — and friends — now saw me as “the boss.”

All my carefully thought-through plans seemed unrealistic, I worried I was asking too much of some people and not enough of others. Every piece of feedback from my manager seemed like criticism and I felt overwhelmed.

I was so concerned with being “the boss” that I responded poorly the first time someone questioned my decision-making.

Instead of exploring why they had questions and asking if they could see a better way, I shut down the conversation and resolutely stuck to my guns.

Happily, with experience, and the help of a good mentor and coach, I began to feel more comfortable leading others and became a more effective leader.

Research tells me my experience isn’t unique. Only 33% of leaders feel confident making business decisions yet companies need leadership at all levels more than ever.

Middle managers connect senior leaders with their front-line employees. This is why leadership training is critical even during these challenging times.

Leadership is developed through practice. With support, coaching, and mentorship, others like me can overcome the challenges of leadership and grow to be good leaders.

So, what are some common leadership challenges, and what’s the best way to manage them?

The 6 most common leadership challenges

1. Providing inspiration

As a leader, your team is looking to you to provide inspiration and motivation to complete their work. This can feel tough in a challenging work environment or if you’re not feeling motivated yourself.

To inspire others, help your colleagues to focus on the value their work creates. Share the vision for the team and make sure each of them can connect to how their piece of work makes a difference.

Helping your team find purpose in their work is critical for employee engagement. In fact, 90% of employees said they would trade traditional reward mechanisms — such as extra pay — for greater meaning within their work

2. Developing others

A key part of your role as a leader is talent and employee development. It’s important to search out the potential in your team members and encourage their growth. You’ll need to understand their hopes for the future and find ways to help challenge and stretch them.

Make sure you take the time to listen to your team. Create formal and informal opportunities to talk about how they want to progress in their career and support them to take those steps.

3. Leading change

Change can often feel scary or uncertain and leading a team through it is a significant challenge for today’s leaders. How we work is changing like never before and employees will look to leadership for guidance and reassurance.

It’s important to validate the feelings of your team and help them to feel their fears are heard. Helping them to find the positives of the change can lower resistance towards it.

4. Handling different perspectives

Workplace conflict can be extremely detrimental when handled poorly, causing stress to almost half (48%) of employees.

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There will be times as a leader when you have to manage conflict between team members or between yourself and an employee. Conflict can feel uncomfortable but you need to solve it before it upsets the team.

If the conflict is between two employees, try and facilitate them in solving the issue themselves by encouraging listening and compromise. If one of your employees disagrees with you, make sure you consider their point of view, and don’t be afraid to change your approach if theirs is better.

Given the diversity of employees within the workplace, it’s unsurprisingly that friction arises from individuals’ differing experiences, ideas, and perspectives.

The challenge for leaders is creating space for those ideas to be shared and ensuring that conflicting ideas are channeled into a productive discussion that allows for growth and shared understanding

5. Dealing with imposter syndrome

It’s common, especially for new leaders, to lack confidence or feel like they don’t deserve to be in a leadership position. There are a number of different types of imposter syndrome.

You might question your own skills or judgment which could lead to indecisiveness. Or you might feel like you have to tackle everything alone which could prevent you from asking for the help you need.

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To squash imposter syndrome, look for evidence of your capability in feedback from your line manager or peers. You were given the role for a reason! And continue to develop your own skills in areas you find most difficult.

6. Managing a team

When you become a leader, you’re either new to the team or you’ve been promoted from within it. Both of these things can be tricky. You’ll have to build trust with new colleagues or manage a new dynamic with old ones.

In collaboration at work and with your new team, take the time to set expectations with each other. Agree on how you’re going to work together, and how you prefer to communicate. If you’ve been promoted above your peers, don’t just ignore that. Talk to them about how that feels and work through any frustrations they might have.

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11 other leadership issues you might experience

While these six challenges above are among the most common you might face as a leader, there can be a number of others you may experience.

Communication challenges

1. Keeping everyone on the same page. In a fast-paced, changing environment it can be tough to keep everyone up to date with what’s going on in the organization, or even in the team. Schedule quick, regular one-on-one meetings to check everyone is receiving and understanding key information.

It’s important to keep communication frequent and open so that everyone is on the same page. Developing a culture of feedback within a team is an essential way to ensure they can really progress together and individually.

2. Staying honest. As a leader, you’ll sometimes have to communicate difficult things to your team. It’s important to share tough news or information as clearly and as honestly as possible. Prepare what you’re going to say and make sure there’s a chance for you to answer any questions.

3. Celebrating the wins. In the rush to make sure that work is being done, sometimes it can feel hard to make time to celebrate success. But it’s key to keeping the team motivated and making sure their efforts are recognized.

It’s critical to celebrate your employees' successes, however big or small. Making sure your team feels recognized is an important way to ensure they are motivated and want to contribute more.

Competency challenges

4. Making hard decisions. There will be times when you have to make hard decisions. It might mean making an unpopular choice or taking an action that upsets someone but is best for the business overall.

In those moments, you can feel alone and unprepared for the task ahead. Take a deep breath and remember that doing the right thing doesn’t always mean doing the easy thing.

5. Managing resources. This can be especially tricky if you’ve got a great team that everyone wants to work with.

Make sure you’re clear on everyone’s workload so that you know what requests for support you can accommodate and what you can’t. Prioritize work coming in against the core purpose of your team so you make sure you say yes to the things that create the most value.

6. Delegating. In your eagerness to be successful in your new leadership role, you can end up micro-managing everything.

It’s important to learn to delegate, both to demonstrate trust in your team and also to free up your time to concentrate on the most important things. If this feels hard, focus your attention on the most impactful tasks and ask for regular updates on those. Let the rest go.

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7. Seeking feedback. It can feel strange to ask for 360-degree feedback from those you’re leading but it’s absolutely key to your success.

Feedback is an opportunity to learn where you can continue to develop but is also a way to hear what your team does appreciate about your leadership. Set up your feedback mechanism to allow this and make sure to respond positively to whatever feedback you receive, it can take a lot of trust for employees to offer feedback in this way.

Internal challenges

8. Staying positive. Things won’t always go to plan and staying positive in the face of disappointment is a real challenge for leaders. But it’s important to move on, especially if the team is also feeling down and looking to you for motivation. Acknowledge the disappointment and identify what you can learn from it. Then use it as fuel to do better next time.

9. Wanting to be liked. There’s no rule that says those of us with a tendency to people-please can’t be leaders. But it does mean that sometimes things are going to feel a little uncomfortable.

Some of the decisions you make as a leader may upset or frustrate people but that doesn’t mean they’re wrong. Do show empathy for the feelings of others but remember that, while being liked is nice, it is more important to gain respect for your leadership skills.

10. Staying calm. It’s likely you’ll experience times where you’re under a lot of pressure in your role or you’re having to lead through a crisis. During those moments it can be difficult to remain calm and focused on the task.

Even if everything feels hectic, give yourself time and space to process information so that you can make decisions from a place of clarity, not chaos. Learning skills for emotional regulation is important, especially as a leader.

11. Learning to trust. While it’s undeniably a manager’s role to support and coach their team to help them perform at the best of their abilities, there’s a fine line between managing and not giving people the space to do their work.

A common misconception when becoming a manager is that they suddenly have to control and oversee everyone’s work, double-checking what’s been done and acting as a sort of quality control.

But this can quickly become stifling for the team and can breed distrust. Employees won’t feel autonomy over their work — and leaders risk losing trust and psychological safety.

7 tips to help you overcome leadership challenges you face

1. Look after yourself

Leading others can be challenging. There may well be times when you feel daunted or overwhelmed by the responsibility. You’ll need to be able to keep yourself motivated, deal with the stress that comes with uncertainty, and avoid emotional exhaustion and burnout.

Make sure you take the time to really switch off from work. Try to focus on maintaining work-life balance. Tempting though it is, don’t read and reply to emails and messages outside work hours. It’s exhausting for you and sets an expectation for your team to also work when they shouldn’t.

At work, try prioritizing a break in the day to eat and move. Self-care is important. Keep a bottle of water on your desk so you stay hydrated and try and take a screen break every hour or so to give your eyes (and brain!) a chance to rest.

2. Get clear on your role

Make sure you know exactly what you and your team are responsible for, and what you’re not! This really helps with managing resources and making sure you don’t take on too much work and stretch yourself, and your team, too thinly.

Really understanding your role allows you to focus on the things that only you can do and delegate tasks that others can tackle amongst the team. Delegating shows you trust your team to get things done and can help develop their skills. And it frees up your time to concentrate on where you can add the most value.

3. Be authentic

There are lots of different types of leaders, and theories on the best ways to lead. Don’t feel you have to fit into a certain mold. Develop your leadership skills and leadership style by trying different approaches to situations but don’t try to be something you’re not. Part of effective communication is being able to express yourself authentically, so keep that in mind.

Being an authentic leader is important, no so more than ever.

Research says that employees value authenticity in leaders. It’s ok to be human and look for support when things are challenging. In fact, it lets your team know that it's ok to be vulnerable and ask for help if they need it.

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4. Find support

We all need help at times, and sometimes, leadership can feel lonely. Make sure you get the support you need so you can do the best job possible. Speak to your line manager or see whether a coach or mentor can help you develop your skills.

Coaching and mentoring can be extremely helpful for both new and experienced leaders. Coaching creates space to think things through and finding a mentor whose experience you can lean on can also be helpful.

5. Use feedback to your advantage

Invest in making your company culture one that empowers feedback.

First, you need to teach your leaders how to give feedback. This will help them feel more comfortable giving their team members input on their work. This is especially important when addressing an issue. Remind them that giving constructive feedback isn’t a negative, but is a way of helping their team reach their full potential and be more efficient.

Encourage managers to be open to upward feedback, which will have two benefits. On the one hand, it will help to grow the culture of feedback within the team by setting an example.

If individuals see their manager is open, they will feel more inclined to share themselves. On the other hand, it shows the manager has a desire to improve and learn. To further support this you can run leadership reviews, so that you as HR have the data you need on how well your managers are performing.

While the word feedback may have a negative connotation, there’s positive feedback, too. Employee recognition goes a long way. And it can be as simple as a hand-written thank-you note.

Look at your internal recognition programs and what you’re doing to encourage this mindset. Ensure managers are aware of what is available to them and support them when needed.

Consider how BetterUp can help your organization thrive during change and uncertainty. BetterUp customer WarnerMedia shares how they leverage virtual coaching to help address some of its challenges.

6. Set clear expectations

Before someone starts in their new role, set expectations with clear communication.

Let’s say you’ve just hired someone new to manage a team below you. Their role is to enable the team so they have the space to complete their assignments while helping them make progress as individuals and take ownership of their development.

This means supporting their schedules so they can get their work done, helping them to prioritize, and acting as the buffer between the team and upper management, amongst other things.

Ensure this is known to them. You might consider clearly outlining expectations in a document, like a 30-60-90 day plan. Frequently bring up leadership expectations in things like one-on-one meetings, too.

One thing to be mindful of: avoid micromanaging. There’s a difference between setting expectations and hovering over your employees’ shoulders. If you show your leaders that you trust them, you’ll be better equipped to set up the team for success.

7. Communicate often

Ensure the company goals and values are clearly communicated at all levels of the organization. These company-wide goals and company core values need to be particularly clear to managers. Then take the time to connect the dots between initiatives and these goals.

This might be done through regular company-wide meetings, posters, or information sessions with smaller groups. No matter how it’s done, it has to be clear so managers can further communicate them to their team and give them direction.

8. Invest in a leadership development program

Effective leadership does not happen overnight. It takes time and experience to develop the hard and soft skills needed to become a better leader. That said, professional development programs can add structure to the learning process. Through this structure you’ll set goals, work through difficult scenarios, and delve deeper into the root causes of many leadership challenges.

Embracing leadership challenges

As a leader, you may face many challenges but it can also be extremely rewarding. We’ve described some of the most common leadership challenges and offered some solutions and tips to deal with them.

The environment for leaders is just getting more complex. Developing emotional intelligence and staying close to your values is helpful when everything else is changing fast. And, just like athletes, entertainers, CEOs, and other top performers, ongoing support from highly experienced coaches can help you adapt and take on whatever the next challenge is. For those times, everybody can benefit from having someone in their corner.

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Develop your leadership and strategic management skills with the help of an expert Coach.

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Leadership & Management

Published July 13, 2022

Maggie Wooll, MBA

Maggie Wooll is a researcher, author, and speaker focused on the evolving future of work. Formerly the lead researcher at the Deloitte Center for the Edge, she holds a Bachelor of Science in Education from Princeton University and an MBA from the University of Virginia Darden School of Business. Maggie is passionate about creating better work and greater opportunities for all.