Making a Manager: The Early Struggles of Leadership and How to Overcome Them

Key takeaways:

• 65% of managers regret stepping into a leadership role at least occasionally, while 56% would give up their title as long as their salary stayed the same.

• 28% of managers have suffered an anxiety attack following a difficult conversation with a team member, while 24% have grown apart from work friends.

• 55% received mere days of training before stepping into management, while 84% had to teach themselves critical skills.

• However, 98% are now comfortable in the role, with 15% believing they’ve outgrown it.

• 43% turn to senior colleagues, 37% to family or friends, and 37% to leadership and self-improvement books to learn and grow as managers.

Moving into management is a natural step in many careers, but it can be a daunting one. One day, you’re focused on doing your own job, and the next you’re responsible for making sure everyone else is doing theirs. 

You’re tasked with delivering difficult feedback, handling team conflicts, and dealing with the demands of senior leadership – thrown into the deep end with little more than a firm handshake and a fancy new title.

Headway app surveyed 1,000 managers on the struggles and sacrifices of stepping into a senior role, and how they learned to lead with confidence.

Pay rises and resentment: Do managers regret taking the title?

Some 12% of managers admit they constantly regret their decision to step into the role, but for most, it depends on what lands on their desk each day.

Monday brings a difficult hiring decision, Tuesday a spreadsheet of figures that exceeded expectations, and Wednesday a sudden bout of illness that leaves you short-staffed. No two days are the same in management, and as stress levels rise and fall, so too does resentment, with 53% of managers admitting they occasionally regret taking the promotion.

Given the choice, however, most would take fewer responsibilities and an easier work life, with 56% willing to give up their leadership title as long as they continue receiving a leadership wage.

The title tax: The personal burden of being the boss

Once you’re responsible for making sure everyone is pulling their weight, handing out constructive criticism, and making tough calls, being ‘one of the team’ isn’t always easy. The pay rise often comes at a social cost, with 24% of managers admitting that stepping into management caused them to grow apart from their work friends. 

For some, maintaining those relationships takes priority over managing performance, with 38% of managers admitting they’ve softened or avoided giving feedback to an employee they were once friends with.

Rather than managing conflict, 39% of managers have avoided it entirely, leaving issues unaddressed because they couldn’t face giving critical feedback, issuing a warning, or firing a member of their team.

Unpleasant conversations are part of the job, but no manager gets satisfaction out of having to criticize or discipline those they work with every day. In fact, 28% admit they’ve suffered an anxiety attack following a talk with a team member, 25% have experienced migraines, and 19% have shed a tear or two during a difficult day at the office.

Learning on the job: How prepared are managers to lead?

The problem is that a small step up the career ladder can often feel like a leap off into the unknown. Less senior roles don't necessarily prepare people for the realities of leadership, and 55% of managers receive just a few days or less of relevant training, with 17% given only a few hours and 15% starting the job without any preparation whatsoever.

For most managers, it’s a case of learning on the job – 84% have had to look up and figure out critical skills themselves, including handling conflict (46%), navigating employment law (37%), delivering negative feedback (36%), and firing team members (26%).

Greener grass (and greater pay): The search for something better

In between leadership meetings, client calls, and disciplinaries, 47% of managers are actively searching for a new role – and while the pressure plays its part, it's not the main thing pushing them out. Most are chasing greener grass: better pay and a clearer path forward.

While regret and self-doubt might occasionally throw a spanner in the works, most aren’t searching for a way to escape management altogether, but for a role that offers more in return for all their hard work.

Some 55% of those seeking a new role say they’re currently underpaid, for instance, while 38% see no clear path to progression, and 32% feel let down by those above them.

Many may have started as inexperienced managers, learning the ropes through trial and error (and fighting back tears during their lunch breaks). But after weathering leadership’s steep learning curve, most have emerged as confident, capable leaders, with 83% believing they’re in the right role and 15% feeling they’re ready for the next step.

Untrained and undeterred: The methods confident managers used to grow

Practice makes perfect... or at least less terrifying. Some 57% of managers admit they’ve scripted or rehearsed a tough conversation with a junior colleague in advance.

As technology advances, many managers are hiring a modern assistant: artificial intelligence. 

Some 33% have used AI to write feedback or prepare performance reviews, 31% have turned to it to resolve team conflicts, and 27% have used it to craft uncomfortable messages – putting algorithms in charge of the tasks they least enjoy.

Soon, many managers predict, AI might even be ready to take on a management position. 

Some 76% believe it’s already capable of handling part of their role, with 22% convinced it could successfully take on half of their workload, and 6% confident it could manage three-quarters or more.

But for all AI can take off their plate, becoming a better manager still comes down to something more human. Experience, empathy, and hard-won advice continue to prevail – managers pick the brains of senior colleagues or former managers (43%), turn to friends or family for advice (37%), or settle down with a good book written by a leader who's been there, done it all, and has plenty of success to show for it.

After all, no matter how high you climb the corporate ladder, there’s always something more to learn. Your job isn’t to have all the answers, but to know who to ask and where to look for them.

About the Headway app

With over 50 million users in 170+ countries, the Headway app is the world's most downloaded book summary app. It offers 15-minute audio and text summaries of nonfiction bestsellers, as well as daily microlearning sessions and gamified challenges. 

The app is designed to help people achieve their self-development goals. Headway received the Editor's Choice award from the US App Store and constantly hits the App Store home screen as App of the Day.