How to Become a Great Leader: 4 Expert Tips for New Managers

The transition from employee to new manager can be a tricky one. Find out the four most popular pieces of advice for struggling bosses from six business leaders.


The transition from employee to new manager can be a tricky one. Find out the four most popular pieces of advice for struggling bosses from six business leaders.

As many business professionals will attest, transitioning to a new management or leadership position is not always easy. Learning how to delegate, provide constructive feedback, and build a great team are just a few of the challenges that new managers face.  

In fact, Forbes reports that “60% of managers underperform in their first two years on the job.” And this demanding transition doesn’t just affect the leaders. 

According to McKinsey & Company, the direct reports of struggling bosses have a 15% lower performance rating than those with a manager who is finding success. Theyre also 20% more likely to leave their organization.  

Obviously, new managers don’t want to fail. Why, then, are the statistics so negative when it comes to this role change?  

Below are some of the biggest hurdles people must overcome when stepping into a leadership role. 

The 4 Biggest Challenges New Managers Face 

  1. Learning How to Delegate: As an employee or solo entrepreneur, you’re responsible for your work. As a manager, you become responsible for your tasks, as well as your team’s. It can be difficult to let go and not micromanage someone’s else work. 

    Why Delegating Is Hard: Assigning work to a member of your team doesn’t mean you’re no longer responsible for the results, and trusting someone else to do a task “right” can be challenging. 

  2. Providing Constructive Feedback: It can be difficult to navigate the appropriate quantity of feedback to provide your team with and how to deliver it. You may be worried about stepping into micromanagement territory. Or, perhaps, you’re concerned that you’re not providing enough guidance. Whatever your concern, you know that providing tough feedback can sometimes be necessary as a leader. 
    Why Giving Feedback Is Hard: You don’t want to damage your working relationship with your team.

  3. More Tasks, Same Workday: You have your goals and responsibilities but now you must also factor in managing your team’s accountabilities. This can result in the feeling that you have less time in your day to get things done. 
    Why a Manager’s Workload Is Hard: Simply put, you now have more to juggle than you did before.

  4. Instilling Loyalty in Your Team: Regardless of whether you’ve hired employees for the first time, were promoted to management from within your company, or are new to the team, earning loyalty won’t happen right away.  
    Why Building a Loyal Team Is Hard: The grass is always greener and, according to Harvard Business Reviewsince the turn of the millennium, more employees are quitting their jobs than ever before. Find out how you can mitigate this phenomenon in our online guide: Tactics to Increase Employee Retention in a Competitive Employment Market. 

No wonder more than half of new managers are struggling! So, what can you do to ensure that you become an effective and capable manager for your organization – sooner, rather than later? 

We reached out to our network to see what advice CEOs, founders, and senior managers consider the best tips for new business leaders. Meet our panel below! 

Outback’s Panel of Business Leaders  

From tech to linen to law, and in both executive and senior management roles, our panel consists of six seasoned business professionals ready to share what they’ve learned about being a good leader. 

how-to-become-good-manager-adam-hempenstallName: Adam Hempenstall 
Position: CEO and Founder 
Company: Better Proposals 
Adam’s Top Tip for New Managers: 
A year or so ago, I introduced flexible working hours. That  
means that everyone can work whenever they want and as much as they want, as long as they get their jobs done." 


how-to-become-good-manager-andrea-loubierName: Andrea Loubier 
Position: CEO 
Company: Mailbird 
Andrea’s Top Tip for New Managers: 
“I try to stick to a very important rule: if I don't feel as if I am the absolute best person to do a job, then I will pass it on to someone else on my team.” 



how-to-become-good-manager-stacy-caprioName: Stacy Caprio 
Position: Founder 
Company: Growth Marketing  
Stacy’s Top Tip for New Managers:  
To create employee loyalty, first give your employees trust. This means not micromanaging them, and not mandating they can only work from the office. 


how-to-become-good-manager-chachi-floresName: Chachi Flores 
Position: Senior E-commerce Manager 
Company: Peacock Alley 
Chachi’s Top Tip for New Managers: 
“Managers must understand that employees are their businesses’ biggest assets and can show promising growth for the future.” 



how-to-become-good-manager-ciara-hautauName: Ciara Hautau 
Position: Lead Digital Marketing Strategist 
Company: Fueled 
Ciara's Top Tip for New Managers: 
Ensure that your feedback is constructive and actionable, and always explain to your report why they should approach a situation differently. 


how-to-become-good-manager-stewart-j-gussName: Stewart J. Guss 
Company: Stewart J. Guss, Attorney At Law 
Stewart’s Top Tip for New Managers: 
Don’t be afraid to be wrong. More specifically, I would urge up-and-coming business leaders and entrepreneurs to avoid being 'married' to an idea, just because it's your own. 


The 4 Most Valuable Pieces of Advice for New Managers 

When asked what advice they would give new managers, our panel gave a variety of answers, but there were four similarities across the board.

1. Empower Employees

You don’t have to do it all! And sometimes there might even be someone who’s better for the task than you. 

Does that seem unlikely? For managers who are having trouble letting go of the little things, Andrea Loubier suggests, “Productivity will go through the roof when everyone is working on the projects for which they are best suited.” 

If you’re unsure of how to identify your employees’ different strengths, our team recommends Building Strategic Teams with StrengthsFinder. In this program, you will gain actionable insight into how to strategically leverage your group’s capabilities to build a strong team.

Chachi Flores recommends that you can empower your employees from the very beginning by offering a strong onboarding process. 

This will also give employees the confidence they might need to approach management with solutions for the team,” says Chachi. “This act of collaboration could end up being very resourceful and end up saving the company in the long run.”

“Have enough senseand lack of ego, to listen to your trusted employees and staff around you,” puts Stewart J. Guss simply. “Remember – you hired them for a reason.

Stewart goes on to say, “Some of the best innovations and improvements in my business and the service we provide our clients have come from my employees. You trusted yourself enough to hire them, make sure you trust yourself to listen to them and take their suggestions and input seriously – even if its different than what you were thinking.  

2. Provide Clear, Consistent Communication

When it comes to feedback and communication with your team, you likely know that it’s important to find the right balance. But what’s the best way to figure out what resonates with your employees?  

Ciara Hautau shares, "As a manager, it is vital that you deliver feedback to your direct reports as often as needed. You don't have to be blunt and you don't have to sugarcoat it but be direct and honest. 

Ciara also recalls that when she first started out as a leader, she thought she had to say “yes” to every request.  

“My manager at the time told me if you find yourself in a situation where you can't get a task done right away, it's okay to set expectations,” she says. “The best thing you can do as a manager is be honest and upfront with deadlines and expectations.” 

Our training and development program, Clear Communication, offers practical skills to help you and your team become more effective communicators. 

3. Use Productivity Tools 

If “more tasks, same workday” feels relatable to you, it’s time to take advantage of all the productivity tools you can find!  

For some leaders, that will be as simple as having an effective email tool 

“You'll need an email service that will not only offer the basic features, but will also integrate some of your favorite organizational apps, like DropboxAsanaSlack, and much more. Doing so can literally save you hours every single week, recommends Andrea. 

Ciara offers the below list of productivity resources that she’s found invaluable working in the tech industry:  

  • Trello for project managing your team. 
  • for bookmarking and easy navigation to highly used websites, documents, and tools. 
  • TextExpander for easy emailing and filling out forms. 
  • Slackbot for setting reminders - reminders for me are HUGE! Without 
    them, I'd be far behind! 
  • Also memorize keyboard shortcuts! You might find it tedious in the 
    beginning but it can make an insane impact on your productivity.

4. Offer Flexibility & Your Trust 

One of the best ways to foster loyalty on any team is by trusting your employees. We’re not suggesting you blindly jump into this. But building towards a relationship where trust and flexibility are the status quo can have huge benefits for you as a manager.  

For example, Adam Hempenstall offers his entire company the option to not only work remotely, but to keep flexible hours. 

“This was scary at first, but I realized how powerful it is when everyone started reporting how happy they are,” he says. “It’s fairly simple - I give out the tasks for the upcoming week and everyone has to make sure they do their part. Whether they do it in one, three, or five days is completely up to them. 

The result for Adam and his team? As I said, we have all benefited from this set up and my employees thank me every time because of the freedom they have in their jobs,” he shares. That makes me happy as the owner of the business as well!” 

Stacy Caprio has a similar philosophy. “To create employee loyalty, first give your employees trust. This means not micromanaging them, and not mandating they can only work from the office.”  

She continues, “Let them have the freedom to work remotely with your blessing and to figure out their own strategy and way to solve problems, and you'll find they will be happier, as well as get more done.” 

Team building can also be a great way to help build trust. This can be especially important for remote teams.  

For example, here at Outback, we have an annual retreat where we bring all of our employees together for some development sessions and team building activities to help build stronger bonds and working relationships. 

Training & Development for New Managers  

Looking to gain practical skills to help you become a better manager? If you’re still feeling uncertain about your new leadership role, here are four training and development programs that can help. 

  1. Coaching FundamentalsLearn constructive ways to nurture the people you’re accountable for.   
  2. Productive Feedback & Performance ReviewsFind out the best tactics to share feedback with employees in a more positive and impactful way. 
  3. Performance Management FundamentalsDevelop a foundation of simple and effective management skills. 
  4. Situational Leadership StylesIdentify your own inherent style and understand how your employees want to be led. 

Learn More About Training & Development Programs for Your Group 

For more information about how training and development programs can benefit your group, reach out to our Employee Engagement Consultants.   

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