Leadership is hard: A guide to navigating relatable leadership challenges

Leadership is not a destination or a task to be mastered. It’s an ongoing journey, and you are not alone.

Leaders want to know they are “not alone” and that what they are experiencing has also been experienced by others. We support ourselves better when we acknowledge that leadership is hard. Everyone, even the most confident leaders, suffer from a bit of imposter syndrome. As a coach, these are the types of realities we help leaders accept and grow from. And when we work with a leader that has grown up in the same organization for many years, these insights have different and sometimes deeper impacts.

When I met my co-author Emily, on the surface, things appeared to be going well — great even. She had been quickly promoted over a 10-year period and was operating in a senior leadership role at a Fortune 100 company. Smart and ambitious, she had become more comfortable acknowledging these attributes, but, despite her growing confidence in some areas, she experienced significant growth pains in others. Throughout our coaching, I guided and supported Emily as the reality that “leadership is hard” caught up with her. She was forced to abandon behaviors that once assured her success but no longer served her as well as demonstrate resilience and vulnerability well beyond what she ever considered necessary as job requirements.

Our work together inspired us to share the following learnings in hopes of normalizing some of what Emily experienced for the benefit and comfort of other leaders and to provide the assurance that you are not alone.

Emily’s leadership reflections

Reflecting on the past 10 years, the journey seems immense — finding my way as an individual contributor to a supervisor, then as a leader of leaders while sitting on an executive team with peers at least a decade more experienced than me. The challenges I faced seem like an obvious consequence of the significant leaps in scope and scale in such a short period of time. I transitioned from working independently to leading a team and being responsible for the work of others. Colleagues, who were formerly peers, were now working for me. I was an ambitious late 20s, then 30-something leader trying to figure out my place, drive impact and perform in a way that was consistent with what the organization wanted to see from me and what I wanted to see from myself.

Perceived or real, I felt those around me questioning my trajectory, and, to be honest, in the early years, I questioned my own readiness. After each leap in scope and scale, I found myself working twice as hard to avoid disappointment from my champions and advocates and to prove, to myself too, I was capable and deserving.

At the time, and maybe even now, I did not fully grasp the accelerated leadership growth these sharp upward movements in my career would demand of me. I offered myself little to no grace. When I met my executive coach (and co-author), Lacey, I felt alone and frustrated, working myself into the ground to deliver the best results, be a good leader and maintain some semblance of a balance in my life. I remember being excited, nervous and generally uncertain of what to expect, but grateful that the company viewed me as worthy of the investment.

Throughout our time together, I learned a lot about the benefits and obstacles of quick progression within the same organization. These learnings helped me realize and establish who I am as a professional and a leader. Reflecting on our coaching journey, we share three critical tools below to help early-career leaders navigate these relatable challenges.

1. Communicate/ask for what you need

One of the biggest misconceptions I held early in my progression was that asking for help, support, guidance and resources was an admission of weakness, defeat or failure. For me, this meant subscribing to a leadership fallacy and a mindset where there was never enough time, patience or people to accomplish the goals in front of me. I now know that part of a leader’s role is to understand and ask for what you and your team need to deliver on your goals. Here are some things I learned to ask for along the way:

  • A mentor/coach/advisor. When you grow up within the same organization, you can identify individuals you look up to and proactively seek out their advice and feedback during key career transitions. If the relationships are no longer appropriate based on organizational structure or you have outgrown the mentorship, find new role models and mentors you can learn from in other parts of the organization. Also, consider an executive coach. Working with Lacey provided me with a confidential outlet to share my challenges, frustrations and successes and develop skills to manage issues more effectively.
  • Resources. At one point in my career, I found myself stretched very thin, providing direct leadership to a large team responsible for significant goals. Instead of asking for help, I neglected to speak up, concerned that asking for more resources meant I could not do the job successfully on my own. The real failure was working myself and others to death and not having the courage and maturity to redesign my team’s structure. Once I finally spoke up, not only was I personally relieved, but my team was also much better positioned for success. Part of the role of a leader is being realistic about the resources required to deliver on your team’s goals. If there is a misalignment between the available resources and what is required, it is up to me to communicate that and ask for what I need. Being asked to do too much with too little can impact your ability to motivate, inspire and empower and can lead you and your team to feeling overwhelmed, stressed and burned out.
  • Patience and empathy. As leaders, we hear repeatedly the importance of extending empathy to those we lead. I was so focused on figuring out how to do that effectively that I could not see my own need for empathy. When stepping into a new role or leading a new team, growth, risk and failure are a natural and expected part of those transitions. One of the benefits of being promoted internally is there is broad recognition that you are in a new role and, in some cases, a stretch position. Chances are you have built up goodwill and a reputation that supported your promotion in the first place. Remind yourself you are surrounded by people who want you to be successful, and ask for their patience and support as you find your footing.

2. Acknowledge the transition and the challenge

One day you are surrounded by good friends at work, and the next, you’re venting to your co-worker about how a leadership decision is completely inappropriate. Redefining relationships and setting new boundaries is a real and necessary implication when leading former peers and attempting to establish yourself as a peer to those you previously considered your bosses. The following mindset shifts were key in my personal transition:

  • Recognize some of your behaviors will need to change. Decide how you are going to set boundaries with prior friends and colleagues. Lacey encouraged me to seek out a mentor outside of my function. Managing a new and larger team, I needed someone I could talk to and confide in about my challenges and experiences, and it was no longer appropriate for me to do that with colleagues within my own function. Seeking out another leader within the organization, but in a different area of the business, gave me the benefit of a sounding board who knew the company but was removed from my direct team.
  • Remember that you were asked to do the job for a reason. When promoted internally, the decision makers’ confidence in your capabilities stems from your track record at the company. Take time to learn from your new peers and leadership team members, but let them learn from you as well. While you may be less experienced, you bring new ideas, personal strengths and unique perspectives to the group.
  • Decide how you want to show up. It is time to turn the chapter on who you were versus who you aspire to be going forward. Several months into our coaching engagement, Lacey guided me through an exercise for further clarity on who I am as a leader. I spent weeks reflecting on what I value, what I admire about other leaders, when I am at my best and when I am at my worst. Through that process, I discovered more clearly the unique value that I add as a leader and crystalized how I want to show up every day. Today, I am more transparent and authentic about who I am and self-aware about my weaknesses.
  • View feedback as an opportunity to learn and grow. Seeking feedback can be terrifying, especially when you know you are learning and will have some missteps along the way. Instead of fearing feedback, I have learned to embrace it as an opportunity to understand the impact I am having on those around me and how I can further enhance my contributions. As an ambitious “star” student, anything less than an A rating felt like a total failure to me. My worst fears were realized when I received closer to a C feedback from my direct reports as I was learning to lead my largest team yet. After a few days of tears and frustration, I unpacked the feedback in partnership with Lacey and went to work on applying the insights. Now, I seek feedback on an ongoing basis and formally every six to 12 months to check in with my key stakeholders to track and share my progress. Do not mistake your inexperience for weakness. Learning is an expected and ongoing part of the leadership journey.

3. Seek external perspective

As an early career leader who progressed within the same organization, I placed a lot of focus on what it meant to be successful within my current company and measured myself accordingly. As I’ve matured in my career, I’ve come to appreciate the value of understanding leadership in a much broader context. Seeking perspective outside of my existing company and industry through insights from articles, external networks and Lacey’s coaching gave me access to new role models and different styles. As I worked with Lacey to define my leadership aspirations and identity, I was able to do so with a broader appreciation of what good leadership means.

Leadership is a journey, not a destination

Every leader’s path is different. What Emily experienced, and the learnings that helped her most along the way, may not coincide with your own experience. However, if there is one thing we hope you take away from this article, it’s the validation that the demands of leadership and quick progression are very real.

While you may have excelled at everything up to this point in your career, taking time to work through these new obstacles and challenges is a natural part of growing and developing as a leader and deserves your understanding and attention. Even those with the best natural tendency to lead are faced with these challenges.

Don’t confuse growth and development that may feel uncomfortable and painful at times with failure. Stay focused and be purposeful in working toward your goals, both professional and personal, and seek help from others to support you in achieving them. Remember that asking for help and acknowledging the growth these transitions demand are not signs of weakness but an indication of maturity. Leadership is not a destination or a task to be mastered; it’s a continual journey, and you are not alone.