The 5 Mistakes New Managers Make When Communicating with Their Boss (And How to Fix Them)

I was probably two years into the engineering management phase of my career before I really learned the value of managing up. When I first got started, I thought it was my job to handle everything and only escalate to my boss when things were above my paygrade. Reporting to some hands-off managers only reinforced this belief—I figured I was on my own to manage my team’s work without much input or interest from above.

It wasn’t until I had a manager who was truly invested in my team’s success that I realized how important that relationship was. I learned that managing up wasn’t just about being micromanaged—it was about building trust, aligning on priorities, and nurturing the support system I needed to be successful.

If you’re new to management, you might be figuring this out for yourself. Here are five mistakes we've all made on our leadership journey—and how to avoid them.

1. Lack of Proactive Communication

New managers often assume that if something is important, their boss will ask about it. But in reality, your boss is juggling multiple priorities and won’t always know what’s happening on your team. Keeping them informed is not a sign that you can’t handle what’s going on – in fact, it sends a message that you clearly see what is happening around you, and that you have a plan for how to respond.

The Fix:

• Establish a regular update cadence—whether it’s a weekly email, a quick check-in, or a structured report.
• Be proactive in surfacing problems early rather than waiting for your boss to ask.
• Use a simple format like "Here’s what’s going well, here’s what’s at risk, and here’s where I need your input."

Your boss shouldn’t have to chase you for updates, and they should never hear bad news about your team or project from someone other than you. The more proactive you are, the more trust you build.

2. Providing Too Much Detail

Not all updates are created equal. Some new managers overcompensate by sharing every single detail about their team’s work, drowning their boss in information. This makes it hard for them to quickly grasp key takeaways and make decisions.

The Fix:

• Get to the point. Use structured, concise updates that highlight key issues and insights.
• Know your audience. Does your boss like to read, or do they want a verbal summary? Tailor your communication to their preferences.
• Use data selectively. Instead of explaining every step taken, summarize findings and provide data-backed conclusions.

Your boss is working at a much broader scope than you, and will value efficiency. If they need more detail, they’ll ask for it.

3. Not Understanding Their Boss’s Priorities

Many new managers forget that their boss is the first stop on aligning the team’s activities to the broader company goals. Not understanding your boss’ goals, pressures, and worries can lead to misalignment and frustration.

The Fix:

• Ask directly: “What’s top of mind for you right now?” or “What are you reading these days?”
• Connect your team’s work to company objectives. Instead of just reporting tasks completed, explain how they impact broader business goals.
• Pay attention to what your boss emphasizes in meetings. This gives clues about what truly matters to them. If your boss is using a new phrase, such as “focus on outcomes over outputs,” that is a guide for how you should be telling the story of your team’s work.

When you show that you understand and support your boss’s priorities, they’ll see you as a valuable strategic partner.

4. Overpromising and Under-Delivering

New managers, eager to prove themselves, sometimes commit to unrealistic deadlines or goals—only to struggle to deliver. This damages credibility and erodes trust. Make sure your “yes, we can do that” actually means something. 

The Fix:

• Be realistic from the start. If you’re unsure about a deadline, say, “I’ll check with my team and get back to you.” And say WHEN you will get back to them. 
• Flag risks early. If a project is slipping, inform your boss before it becomes a crisis—and offer solutions. Act on the principle of least surprise – no one yells about a slipped date when they’ve known for weeks that delivery was at risk. 
• Manage expectations. Instead of saying “We’ll get this done by Friday,” say, “We’re aiming for Friday, but I’ll confirm after our midweek check-in.” Use target dates rather than deadlines when you are talking about the future. These should get more concrete as the day draws near.

It’s better to underpromise and overdeliver than the other way around.

5. Expecting the Boss to Provide All the Direction

Some new managers wait for their boss to tell them what to do rather than taking initiative. This makes them seem overly dependent and slows down decision-making.

The Fix:

• Come with solutions, not just problems. Instead of saying, “What should we do about this issue?” try, “Here are two options—here’s what I recommend.”
• Anticipate your boss’s needs. If they often ask for certain updates, start providing them before they’re requested.
• Take ownership. Your team’s success is your responsibility, not something your boss has to define.

The best managers lighten their boss’s workload rather than adding to it.

Good communication with your boss isn’t about checking a box—it’s about building trust, showing leadership, and making their job easier. By avoiding these five mistakes, you’ll set yourself up for success, gain more autonomy, and become a more effective leader.

Moving from IC to EM? These communication skills are just one part of the transition. My 12-month IC to EM course is designed to help new managers build confidence, master key leadership skills, and navigate common challenges like delegation, prioritization, and managing up. If you’re ready to level up, let’s work together!