Leadership   //   April 5, 2023  ■  4 min read

‘It truly sucked’: The bumpy path to becoming a boss

Everybody fantasizes about being in charge — but actually running the show can be a sobering reality.

S. Mitra Kalita remembers well the worst year of her life — it was the year she became a boss.

“It was like someone had turned on a firehose, and I saw no end in sight for when it would turn off,” recalled Mitra, cofounder and CEO of URL Media Holdings, in an article advising new managers from the workplace insights firm Charter. In the two decades since, Mitra writes, “neither hindsight nor nostalgia has changed how I feel about that first year of management. It truly sucked.”

The first year of being a boss doesn’t have to be the worst of your career — rather, it can be most liberating, according to John Waldmann, CEO of workplace tech firm Homebase, who urges new managers to prioritize delegating responsibilities and then trust employees to carry them out. “Remember, there’s a big difference between being a boss and a leader,” he said. “A boss focuses more on the day-to-day activities of employees, while a leader provides purpose and direction.”

“When you step into that first management role, I think it’s natural to wonder, why me? Why am I suddenly managing these people who were just my peers?” added Traci Chernoff, senior director of employee engagement at the workforce tech firm Legion. “Even the most eager, natural born leaders are going to feel this way in the early stages, and that’s simply because change is hard for everyone.” 

Even though she’s been in HR leadership for nearly a decade, Chernoff still vividly remembers experiencing first-time manager anxiety. “The trick,” she said, “is not letting it stop you.”

Still, there is a learning curve for newcomers to the management ranks — something not every company takes into account. 

"There’s a big difference between being a boss and a leader. A boss focuses more on the day-to-day activities of employees, while a leader provides purpose and direction.”
John Waldmann, CEO of workplace tech firm Homebase.

“One of the common things we say to our clients when they look to promote people to management is, they may be great at their job, but that doesn’t mean they are ready to be a manager,” said Eric Mochnacz, operations director of strategic HR and management consultant Red Clover. “You can be a great technician in your role, but people management requires a whole different skill set, one that people may have never had the opportunity to demonstrate.”

Mochnacz points out that when his own company recruits employees, it gives them 90 days — or more — to adapt to their roles and become familiar with how the company operates. The same runway should be afforded new managers, he believes. “We can’t expect people to jump into a people management role and be perfect at it,” he said, advising top management to use tools like goal setting and check-ins for new managers just as they would for a new hire.

As for those new managers looking to conquer their role? Knowing thyself — strengths, weaknesses and everything in between — is an essential first step. 

“Ask yourself: What is my personality type? Am I outgoing or an introvert? Am I an anxious person? What motivates me? The answers to these questions will shape the leader that you will become in the future,” said Amy Rice, vp of corporate communications at workplace tech firm Workhuman. “If you don’t know what makes you tick, you won’t be setting yourself up for success in your career.”

“One of the common things we say to our clients when they look to promote people to management is, they may be great at their job, but that doesn't mean they are ready to be a manager.”
Eric Mochnacz, operations director of strategic HR and management consultant Red Clover.

It is also vital that new bosses understand that the successes and failures of their direct reports amount to their own successes and failures, she stressed. Frequent meet-ups with those you manage builds connection with your team and will help you be a more empathetic leader — something more of the workforce has come to demand in a boss. 

“It’s important to remember that each and every one of your team members is a human first — they need to be appreciated, feel balance in their lives, and have their own emotional needs met,” Rice said. “Creating a strong experience for them is going to help you become a leader that each and every contributor wants to work for.”

Ruling by fiat is so yesterday, after all, and bosses who rule with an iron fist may find that they won’t keep those employees very long.

“The best leaders I know use influence and relationships to motivate people to be highly productive,” said Tammy Polk, CHRO at workplace tech firm Formstack. “They use their power for good, to grow their teams, streamline processes and connect with customers. Influence is sustainable and will continue as you rise to the top.”

As for being a first-time leader? It “does not have to suck,” as Polk sees it. “It can be enjoyable and an adventure.”