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5 Tips to Be Successful with Your New Boss

communication leadership relationships
woman working on computer with her new boss



By John Millen

We all know the importance of first impressions. They can make or break a relationship.

This is particularly true if you have a new boss, are in a new company or even a new assignment in the same company.

We are at a unique moment in history with more people than ever moving into new jobs. Recent college graduates are also starting their careers with new employers.

I have a lot of clients and friends who have gone through big transitions during the past year, changing jobs or positions, and have found the transitions challenging. 

Their success is not guaranteed. In fact, some research studies conclude that nearly 50 percent of new hires fail in the first 18 months. 

There will be many opportunities and landmines in your new position that will contribute to how you fare. But your relationships will ultimately determine your success or failure. 

And no relationship will be more important than the one you nurture and maintain with your boss. While her perception will be influenced by the reputation you develop with people in the culture, ultimately, she will decide whether you have won or lost.

When I counsel clients or friends in new assignments, the book I most often recommend is The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter, which The Economist calls “the onboarding bible.” 

This book gives you the tools you need to create and execute a 90-day plan for success in any new assignment. It applies to everyone from senior leaders to new college graduates.

I find author Michael Watkins’ analysis of the five most essential discussions with your supervisor to be right on point. He goes into detail about how to handle these transition-related discussions.

Even if you are not in a new job, these discussions could be valuable for helping to reset the relationship with your current boss.

Watkins warns not to treat these discussions and individual interactions as separate meetings: 

Your relationship with your boss will be built through ongoing dialogue. Your discussions will begin before you accept the position and continue into your transition and beyond.

In practice, your dialogue about these subjects will overlap and evolve over time. You might address several of the five issues in a single meeting, or you might work out issues related to one subject through a series of brief exchanges.

These are the five conversations Watkins recommends. I’m including only brief insights into his much more detailed analysis of each discussion area. The quotes are from Watkins.

  1. The situational diagnosis conversation. 

To achieve success, you’ll need to understand the facts of the situation you’re facing. But more important will be knowing how your boss perceives the environment and your role in change. “Your view may differ from your boss’s, but it is essential to grasp how she sees the situation.” 

  1. The expectations conversation.

This talk is aimed at not only understanding but also negotiating your boss’s expectations. What is most important for you to do in the short- and medium-term? What does your success look like, and how will you be measured? “You might conclude that your boss’s expectations are unrealistic and that you need to work to reset them. Also…keep in mind that it’s better to underpromise and overdeliver.”

  1. The resource conversation.

This is your negotiation for critical resources. This could be funding, people or specific support you’ll need from your boss within the organization. “Key here is to focus on the benefits and costs of what you can accomplish with different amounts of resources.” 

  1. The style conversation.

It’s also important to focus on how you and your new boss can best interact. What communication form does he prefer, including urgent matters, and how often? Face-to-face? Phone? Email? Text? “How do your styles differ, and what are the implications for the ways you should interact?”

  1. The personal development conversation. 

Watkins recommends that you have this discussion after a few months when you feel your relationship is reasonably well established. “[Y]ou can begin to discuss how you’re doing and what your developmental priorities should be. Where are you doing well? In what areas do you need to improve or do things differently?” 

As I’ve written before, success in life is all about relationships

And in a new position, no relationship is more important than the one with your supervisor. Giving early thought and time to nurturing that relationship will yield priceless benefits throughout your career.


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