How to Know Whether You’ll Succeed as a Leader Before You Take the Leap


How to Know Whether You’ll Succeed as a Leader Before You Take the Leap

Wondering if entrepreneurship is right for you? Here are some ways to test your leadership acumen before you go for it.

CREDIT: Getty Images

Are you ready to lead a company? Too many people move into leadership roles simply because it’s the next step in their career hierarchy. Or, worse, because they don’t have a better idea of what they want to do.

But not everyone is a good fit for leadership, even if you have the best idea ever for a company. It might make you miserable.

While you’re honing your skills in your field — whether you’re still in school or in the middle of your career — here are some ways you can try your hand at leadership before taking your career down a path you might hate.

1. Start a side hustle.

Before you go all in and start a company you have to lead, dabble with the idea as a side hustle. It’ll let you ramp up slowly, so you can try on all the hats of entrepreneurship one by one: managing projects, people, finances and creative ideas.

If you find that any of these are awful for you, you can always pull back.

As my fellow Inc. contributor Carol Sankar explains, starting your business as a side hustle helps you find what works (and what doesn’t) while mitigating risk: "Before you quit your job, use your ‘hustle’ hours as your exploratory time to make adjustments and changes. It is less risky during the side hustle phase to go through this process."

2. Volunteer.

In college, volunteering gave me some of my first leadership opportunities. Look for local non-profit organizations supporting causes you care about, and join the volunteer ranks for a couple of hours each week or month.

Once you’re oriented, look for opportunities to lead. The group might need coordinators to organize or recruit other volunteers. Or offer an idea for a whole project you could lead. From my experience, nonprofits love anyone who’s willing to go the extra mile.

Volunteering was especially helpful because it gave me a chance to try out both people management and project management, and see my natural strengths and weaknesses in each.

3. Run meetings at your day job.

I’ve got some natural leaders on my team, but they don’t all yet know they have that skill. They’re still intimidated to speak up at meetings, even with only a few people in the room. I encourage them to build that muscle by giving them time to prepare before calling on them in a meeting.

If you have opportunities like this, take them. Let your boss know leadership is a goal, and work together to find opportunities to dip your toes in.

Running a single meeting or owning a recurring meeting lets you step into that leadership role briefly, for 30 or 60 minutes a week. It’s safe, because no particular outcome rides on your performance; but still effective, because you have to learn how to navigate various needs and personalities to keep the meeting on track and ensure a productive use of everyone’s time.

4. Manage group projects.

Whether at a job, through your kids’ school or in your friend group, look for mini leadership opportunities to strengthen your skills and assess your interest.

Were you on fire coordinating your best friend’s bachelorette party? Or did you hate being responsible for everything, and fielding everyone’s questions and concerns about the night?

However unrelated to your career, these experiences can shed light on whether you’re a good fit for leadership before you take the responsibility of leadership to a team or company.

5. Become a mentor

Do people earlier in their careers often ask you for advice? This is a great opportunity to put on your leadership hat and see how you fare.

Surprisingly early in my writing career, newer bloggers and freelancers would ask me for guidance. I loved having these conversations and eventually started charging for them as a writing coach. Now, as a manager, I realize what a huge role coaching and mentorship plays in any kind of leadership, and I’m thankful for that early experience.

Before strapping yourself to a job or company that puts you in this position every day, make yourself available for smaller leadership moments. Connect with someone green in your field seeking a mentor. Or keep it even simpler, and just respond thoughtfully when someone asks you for advice.

These one-off conversations can help you see how you feel about the responsibility that accompanies being looked up to.

Published on: May 29, 2019
The opinions expressed here by columnists are their own, not those of
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