Navigating a New Boss

By: Patty Prosser

 

One of my clients recently got a new boss and, in preparation (as she should), reached out for some advice on how she might get started off on the right foot. Successfully navigating a new boss relationship can produce both benefits and some potential pitfalls. Here’s what we discussed.

A new boss can be an opportunity to develop your own career, so focus on relationship-building and adopting a forward-looking mindset. New bosses will likely have their own ways of doing things and likely a different management style. So, it’s a good idea to stay flexible and be open to new ways of doing things.

And, it’s important to remember, this is less about trying to impress them and more about establishing trust, understanding expectations, and learning how to work well together.

Some Important Steps to Consider

Learn Their Leadership Style

Pay attention to how your new boss communicates, makes decisions, gives feedback, and handles problems. Ask questions such as:

• “How do you prefer to communicate—email, meetings, or quick check-ins?”
• “What information do you like to receive regularly?”
• “How do you typically like your team to bring problems to you?”

Clarify Expectations Early

Don’t assume your new boss has the same expectations as your previous one. Discuss:

• Your key responsibilities
• Priorities for the next 30–90 days
• How success will be measured
• Important deadlines
• What decisions you can make independently

Ask What Matters Most to Them

A particularly useful question is:

“What are the most important things you want me to accomplish over the next few months?”

This helps you understand their priorities rather than simply continuing to work according to the previous boss’s priorities.

Understand Their Pressures

Your boss is likely adjusting to a new role, new expectations, and perhaps pressure from their own leadership. Ask:

“What are the biggest challenges you’re facing right now, and where do you think I can be most helpful?”

This shifts the relationship from employee/boss toward partners working toward common goals.

Don’t Overload Them With Problems

When bringing a problem, whenever possible, bring some potential solutions as well.

Instead of:

“We’re having a problem with this project.”

Try:

“We’ve run into a problem with the project. I see two possible ways to address it, and I’d like your thoughts on which makes the most sense.”

This demonstrates judgment and initiative.

Establish Regular Check-Ins

Even a short weekly or biweekly conversation can prevent misunderstandings. A simple agenda might be:

• What I’ve accomplished
• What’s coming next
• Where do I need guidance
• Any emerging concerns
• Priorities that may have changed

Give Them Early Wins

Look for opportunities to demonstrate that you’re reliable. Follow through on commitments, meet deadlines, communicate proactively, and make your boss’s job a little easier.

Trust is usually built through a series of small, consistent actions—not one big accomplishment.

And Finally, Don’t Compare Them Constantly to the Previous Boss

It can be tempting to say, “That’s not how my old boss did it.” Even when you’re trying to provide context, that can unintentionally create resistance.

Instead, ask:

“How would you like me to approach this?”

In the End…

It’s important to give a relationship with a new boss some time. You don’t have to establish a close personal relationship immediately. Focus first on developing professional trust, mutual respect, communication, and reliability.

Focus on what you can do to make the working relationship successful! And let them know you are committed to their success! This will open the door to a very productive conversation and is a great way to set yourself up for success!

Have a Prickly Leadership Challenge?

If you have this or another “prickly” leadership issue you’d like me to address in future blogs, please reach out to me directly, and I promise to try to discuss it!

There’s more than one way to tackle a problem or issue. Sometimes you just might need a little help! And as always, if you or other leaders in your organization are facing similar challenges, please visit our website at The Center for Leadership Excellence, www.cleindy.com.

Patty Prosser, Co-Founder and Coaching Practice Leader at The Center for Leadership Excellence, 317-727-6464 or at pprosser@cciindy.com