Are You Ready to be a Leader? Here’s How to Know
By: Suzan Bond
Tags: Leadership, Startup, Work, Careers, Management

Libraries have always felt like home. As a 12-year-old, I preferred reading to kickball. Getting lost in stories helped me escape to worlds beyond my suburb that abutted Detroit. The weekly trip to the library was my favorite. I consumed every book I could tearing through the stacks at a ferocious pace. I read it all — I even read the encyclopedia. One day I discovered a new shelf. Tucked all the way in the corner by the window, it held a treasure trove of books on great leaders. Each week I’d race over to that sunny corner to explore their lives: Martin Luther King Jr, Abraham Lincoln, JFK, Susan B. Anthony. I wanted to understand how they led movements, made important decisions and what drove them to serve others. I wanted to be like them — making a difference in the lives of others.

In college, my obsession with leadership led me to study psychology, sociology and organizational strategy. I was sure I knew what it meant to be a leader. I did not. Books about leaders are quite different than the experience.

In my career, that desire to be of service led me to take on more responsibility, often being promoted quickly. Eventually this culminated in a role as a COO. I got a few things right but wow did I get others so wrong. Later when interviewing other leaders, I learned that like me, most found the reality much different. We weren’t prepared for the reality of making hard decisions, juggling numerous priorities and running an obstacle course of human behavior every day. We didn’t understand what it really meant to be a leader and the cost it can exact. We knew it will be challenging, but don’t anticipate how hard or the ways in which it’s hard.

Leadership can be a meat grinder, just not always in the ways you expect. The hardest stuff isn’t always tangible things that show up on spreadsheets. The most challenging part revolves around human nature. Despite a desire to add value, leadership can be an energy sucking vampire. It can push edges you didn’t even know you had. Leading can also be incredibly fulfilling. If you’re considering a career leap, here are five things you want to consider.

Five ways to know you’re ready for leadership

You’re willing to battle imposter syndrome

People are often promoted because of their performance but leadership is not more of the same. Up to this point you’ve been rewarded for getting the work done. It’s such a well worn muscle it’s automatic. A problem crops up, you dig in to solve it. Rather than the fuel that drives the core engine, as a leader you’re accelerant. Shifting from execution to influencing at a strategic level is tough for most. This sounds small, it’s not. Focusing on execution can actually get you fired. To be effective, leaders have to know how to influence, what to delegate, how to empower, and build capacity in the team. For most, these are completely new skill sets. Learning something new is uncomfortable for everyone — even for the experienced. Imposter syndrome lurks at the corner of every new learning opportunity. While it might seem counter-intuitive, most leaders have battled imposter syndrome, especially during their first year or two in the role.

Are you uncomfortable learning new skills, especially in front of an audience? This should give you pause. If you are willing to face the discomfort of failing while you master new skills, leadership just might be for you. Imposter syndrome is sure to arise— have a strategy to handle it.

You’re ok with imperfect decisions

Be prepared to make a dizzying array of decisions. Sometimes the decisions come easily. Other times chaos reigns, especially as you sort through the variables and possible routes. You have to know how navigate perfectionist tendencies to avoid analysis paralysis that threatens to delay decision making. Be prepared for sleepless nights wondering if you made the right choice. You might even hope for a fabled time machine to go back and make a new one. Complicating it, when you become a leader you join another team made up of peers. Decision making becomes more complex. You have to consider multiple points of views and the business as a whole. Working across areas requires a different kind of skills and understanding. The best decision for the company might add strain to your team. Sometimes the leadership team gets it wrong, having a negative effect on the whole company. Regret might follow, the team might start questioning your choices. You have to accept imperfect decisions — they’re just are part of leadership.

Don’t mind making imperfect decisions? OK knowing you’ll get it wrong sometimes? If so, you might find the role fulfilling.

You can put the team first

If your ego needs oxygen like you need air to stay alive, leadership will be tough. Centering your needs might work…for a while. Sooner or later this breaks down as the team struggles to get their needs met. Rather than a ruler or monarch, leaders find themselves more like facilitators, sometimes even feeling like a therapist to the team. When the team struggles with changes or uncertainty, it falls on you to create a conducive environment. This might not be easy when you’re facing your own challenges or doubts. To lead others means putting others first more often than yourself. This requires tremendous amounts of self management. Emotion management is draining, especially without good boundaries or support. When working with people, you have to put your ego aside — over and over. Trying to be right or insisting on your way creates friction, draining everyone. Eventually those speed bumps ground everyone to a halt, a death knell in business.

Like working to solve thorny people problems that don’t have easy answers? Leadership is likely a good fit. If you find people problems draining, you might want to reconsider. Look at a senior individual contributor role instead. You’ll still have influence but have much less people management tasks.

You’re prepared for scrutiny

Leadership is like constantly being on stage. The microphone live, the spotlight always on you. Every move you make observed. Your day flooded with decisions, you won’t always get them right. People won’t like your decisions — count on that. They may think you’re heartless, or incompetent. They might believe power has gone to your head, that you’ve become selfish. In leadership, praise is often scarce, criticism abundant. Making reviled decisions can make you doubt yourself and cause stress, especially if you want people to like you. It’s hard when the team criticizes your mistakes or gossips about you. Leaders aren’t so different from others, they want to be liked too. To get through the pressure gauntlet, you have to have a thick skin. You have to learn how to put distance between the team’s opinion of you and your opinion of you — without completely detaching from them emotionally. It’s far trickier to do that it sounds.

Do you struggle with criticism? If so, the role will likely be stressful. Your decisions will be analyzed to your face, but also in DMs and in closed slack channels. Yes, it will happen no matter what you do. If you’re ready to get better at handling criticism and scrutiny leadership is a good choice, your growth will accelerate rapidly. Just be prepared for gossip and criticism crush you when it comes. Embrace the lessons and leave the rest.

You don’t mind meetings

Leaders are well-known for schedules with back-to-back meetings. It’s an obstacle most can’t seem to get around. Some companies have been successful at curbing the meeting habit, even reducing it to less than 10 hours a week. Most leads spend the better part of their weeks in meetings, some even more than 25 hours a week. It’s true most companies need to seriously curb the meeting habit. Still, if you want to be a leader, you have to tolerate meetings. More importantly, you have to be deft at finding time for the deep thinking required for strategic planning and departmental level deliverable work. This might sound like a fun problem to have — it’s not. Meetings are draining for everyone. Packed schedules mean working extra hours to focus on critical strategic issues, pushing leads closer to becoming workaholics damaging themselves and the team. Worse, these days most are done via Zoom, requiring even more energy than in-person meetings.

Do you loathe meetings? This role will be difficult unless you find a company rigorous about reducing the meeting load. Even if you’re ok with meetings, make sure the company’s expectations match your own. Ask questions about the primary mode of company communication, the average number of meetings and the expectations of leaders.

Two reasons not become a leader

If you answered yes to all or most of these, you’re ready for a leadership role. Now go get that promotion or land that new job. But first, let’s talk about two reasons you might want to reconsider taking on more responsibility.

You want to make more money

If you want to make more money and you enjoy messy people stuff, great! Leadership is a good choice for you. If you come into the role expecting to have less people problems you’ll be disappointed. If you dislike messy people stuff, more money might not be enough. To get results, leaders need to work closely with the team and across the company. Leading requires tremendous amounts of influence, collaboration and self management — all which require deep people skills. People can be inconsistent, irrational, have lots of feelings, be resistant if they don’t like a decision, struggle with change. Every day is an obstacle course around human behavior. If you don’t love working through people problems, you’re likely to be miserable in the role, despite the extra cash. That misery will eventually translate to the team and multiply. Be very careful if money is the sole reason for wanting a leadership role.

You want more control

Being the boss sounds like you’ll have loads of control. As a leader, control is a mirage. Sure, there will be some decisions under your control but less than you think. You have to be willing to let go of dominating. High performing teams dislike command and control forms of leadership. Faced with lack of autonomy and a plethora of other choices, the team flees. Lack of control also translates to your peers. Running a business requires high amounts of collaborative work with other areas, diminishing full autonomy further. Too many stalemates at this level slows decision making, stalling the team, making it impossible to keep up with the market. Sure, you can make a play for more power. It probably won’t turn out well with your fellow leaders and most assuredly with your team. Unless you are the CEO, your quest for control will disappoint. Resist the urge, it doesn’t end well.

Seeking power is a pit of quicksand. You sink faster than you can get to the top.

If you have control issues and still want to be a leader, get a good therapist or coach immediately. It’s a must. Letting go of control reduces friction with the team and your peers — making everything easier. If you can learn to work with your peers you can create something marvelous, maybe even extraordinary.

P.S. If you want a leadership role to impress others, be careful. The title can lend credibility and open future career doors. Still, there are downsides to consider. That desire can be career fuel, just be sure it’s not the only reason.