So You Want to Be a Manager, Part 2: Challenges and Real Talk

Are you thinking about becoming a manager or new to the role? It's a challenging yet rewarding position. Last time, we explored the core responsibilities and skills, but the real challenge lies in navigating day-to-day realities. Today, we're delving into the challenges of people management, giving you a realistic look at what to expect. I'll share some of my own management struggles and failures and what I learned from my stumbles, so you can learn from them too.

New Managers

Let’s start with some of the common issues that new managers face. 

Delegation

New managers often struggle with delegating work. You may have been a top performing individual contributor with high expectations, and you find it hard to trust anyone else to do things the same way that you would. It feels simpler to just do things yourself, and that way you know it will be done to your standards. Or if you’re like me, you feel guilty putting work on someone else’s plate. Effective delegation is a crucial skill for managers, freeing up time and empowering your team.

To overcome your resistance to delegating, keep in mind that in addition to lessening your workload, you are creating opportunities for others to have new experiences and build skills. Be clear about the expectations for the assignment, ensure your report receives the right training and support, and check in regularly with your report. And resist the urge to micromanage!

I have struggled with delegation, even as an experienced manager. However, I’ve found that despite my concerns that I might be burdening the delegate or making them unhappy by assigning new work, my fears have never actually materialized. In fact, I’ve been pleasantly surprised to find that they are happy to help and have the chance to gain visibility or learn a valuable new skill. And if they are already stretched thin, I’ve been able to work with them to reprioritize their work.

Transition from peer to manager

Transitioning from peer to manager can feel awkward for both parties, especially when you're new to the role or after a team restructure. Your new report may react negatively to the change. Managing reports who are older or more experienced than you can trigger imposter syndrome. Remember, you were selected for your role based on your capabilities, not because of your age or tenure. Taking the time to  earn trust and credibility with your team and demonstrating your commitment to their best interests will help to ease the transition.

In my first management role, I worried that my peer – also a friend – would be upset to get me as their manager. I had an honest conversation with them and acknowledged that I was a little uncomfortable but was committed to doing my best. Things turned out fine, and when it happened in my next job, I was better equipped to adjust.

Time management

New manager responsibilities often involve a wider scope of work, including various administrative tasks. Prioritize ruthlessly and manage your time effectively. Tools like the Eisenhower matrix, time blocking, or the Pomodoro technique can be helpful. As your responsibilities expand, assess your tasks, identifying those only you can handle, and delegate the rest. Distinguish between urgent and non-urgent tasks. If your to-do list becomes overwhelming, focus on your top 3 to 5 priorities.

During busy periods with tight deadlines like performance reviews or annual planning, I use time blocking and timeboxing; I review my calendar to see where I can create more time within my normal working hours and skip non-essential meetings, minimizing the need to work evenings and weekends.

Beyond managing your own time, you'll also need to adapt to various individual and situational challenges

Adapting to Individual People and Situations

When it comes to managing humans, a one-size-fits-all approach usually won’t cut it. Effective managers understand the context they are operating in and adapt to the unique needs of the situation. Here are some common examples:

Personal Hardships

At some point, your employees will face difficult situations that affect their ability to focus or perform at their usual level, including medical conditions, mental health struggles, relationship issues, personal loss, and impact from current events. Even if employees don't openly share personal difficulties, offer empathetic support and ensure they know about resources like leaves of absence, workplace accommodations, and EAP benefits.

Having experienced both my own personal struggles (like burnout) and supporting employees through theirs, I've learned the importance of empathy and a long-term perspective. People matter more than temporary work disruptions.

Managing Low Performance

At some point, an employee may not meet their job expectations. Unmet expectations often stem from lack of experience, skills, or clarity. Avoid labeling someone a 'low performer,' as this can be limiting. Instead, provide feedback, identify barriers, and explore solutions. If performance doesn't improve despite your efforts, take appropriate action, remembering that some roles simply aren't the right fit for everyone. Act with empathy but don’t let feelings get in the way of doing the right thing and wait too long to take action, as low performance can negatively impact the entire project or team. 

One of the toughest challenges is recognizing when someone, despite their best efforts, isn't the right fit. In such cases, an honest conversation about their happiness and potential fit elsewhere can be beneficial. I’ve never gotten to the point of firing someone who turns out not to be the right fit for a role – fortunately, they were always able to find another position, and have been happier in the long run. 

I’ve also made my share of mistakes. Once, I reacted emotionally to a new team member's error, damaging our relationship. I've learned the importance of pausing before reacting and remembering that everyone makes mistakes, including me.

Career Development

As you’re mentoring and coaching your team members, schedule time for career conversations so you can gain a deeper understanding of their values, strengths, motivators, and goals. Which of their skills are currently underutilized? Which skills are they interested in developing? This allows for personalized support and development opportunities. 

I like to have career conversations at least twice yearly to check in on progress toward development goals and also be aware of shifts and changes. This is a great time to practice your coaching skills. It’s also important to make sure you are providing equitable opportunities across the team. We discussed low performance, but it’s equally important to make sure those who are performing strongly have opportunities to keep growing and stretching when they are ready.

Interpersonal Conflicts  

Conflicts are inevitable. When addressing them, listen to all perspectives before taking action. I’ve made the mistake of jumping to conclusions after hearing only one side of the story, and as a result, didn’t approach the other party with an open mind. My lack of objectivity wasted valuable time and effort. Focus on finding solutions that meet everyone’s needs, not on where the fault lies. However, you do need to address egregious behavior; for example, if you become aware of harassment or abuse, you may be liable as a manager to report it to HR or another mandated authority.

Other challenges

These are just a few of the challenges that managers face. Other common challenges include navigating organizational change, maintaining confidentiality for sensitive information, delivering difficult messages, managing both up and down, leading distributed teams, and protecting your own well-being. Prioritize your own self-care and seek out mentors and other support systems. I’ve found it helpful to lean on a network of peer managers that I can for advice, encouragement, and commiseration.

My goal is not to discourage you but to provide a realistic picture of management. It truly is a rewarding role, somewhat akin to being a parent or caregiver, but you should be aware of both the benefits and drawbacks so you can decide it’s right for you. If you’re considering this path, explore opportunities to practice management responsibilities before committing.

Despite the difficulties, I find management incredibly fulfilling. It’s a chance to bring out the best in your team by creating an environment of trust, empowerment, and challenge so you can leverage each person’s talents and enable them to thrive and grow. Nothing beats hiring a team of great people who are smarter than you, creating a strong team culture, and letting them do what they do best.