Communicating Up: Tips for New Supervisors to Succeed

As a new supervisor, I didn’t struggle much with managing my team. I’m a people person. I could coach, delegate, and support. But when it came to talking to my boss, especially about difficult issues, I froze. My Navy background taught me to respect the chain of command, but it also made me nervous about challenging authority or reporting problems too early. I didn’t want to sound like I was complaining or incapable.

Over time, I learned how to “manage up” in a way that was clear, respectful, and strategic. This chapter is for every supervisor who finds it harder to talk up the ladder than across or down.

Speak with confidence, even when the conversation feels hard.

Why Communicating Up Matters

You can be a great supervisor, but if your boss doesn’t understand your team’s needs, your priorities, or your progress, it can cost you:

• Budget

• Resources

• Approval for new hires

• Respect
  

Communicating up isn’t just about updating your manager. It’s about showing that you have control of your role, clarity in your direction, and the ability to escalate the right things at the right time.

Why It’s So Hard (And How to Get Past That)

1. Fear of Looking Incompetent. No one wants to admit a problem. But your boss would rather know early than be blindsided later. Phrase it like this:

“Here’s what we’re seeing. Here’s what we’ve done. Here’s what we plan to do. I wanted to keep you in the loop.”

2. Intimidation.

If your boss is formal, high-ranking, or not very approachable, you may hesitate to speak up. That’s why documentation and structured communication help. Have a bullet list or a short summary ready to present.

3. Lack of Practice. If you’re used to peer communication or field work, formal upward communication can feel stiff. Practice writing short emails that follow this structure:

• What’s happening

• What we’re doing

• What we need (if anything)
  

What to Communicate Up (and When)

Not everything needs to go to your boss. But here are situations when you should escalate:

• Major delays or roadblocks that affect deliverables

• Resource needs that you can’t solve on your own

• Team issues that could grow into HR concerns

• Budget concerns or potential overspending

• Early wins that deserve celebration
  

Bosses don’t want surprises. Tell them early. Tell them simply. And be solution-oriented.

How I Overcame My Upward Communication Struggles

I’m someone who likes to think things through. So I used to delay sending updates until I had every answer. But by then, the problem had grown, and I’d lost the chance to get input early.

I eventually learned to:

• Send weekly summaries even if there’s not much to report

• Ask for feedback on style (some bosses want bullets, others want visuals)

• Use a review buddy, send someone detail-oriented, to look over emails and reports before I send them
  

The point is: I built a system that worked for me.

Practical Tips for Communicating Up

1. Use the Right Format

Some bosses like Slack updates. Others want formal reports. Ask what they prefer.

2. Be Brief but Complete

Use bullet points and avoid unnecessary detail. Focus on outcomes and decisions.

3. Own the Problem AND the Solution

“This is what’s happening, and here’s how I’m handling it. I’m flagging it in case you want to weigh in.”

4. Anticipate Their Questions

Always come prepared to answer:

• What’s the impact?

• What are the options?

• What do you recommend?

  
  

5. Know When to Push Back

If your boss gives a directive that won’t work in practice, say:

“Here’s a concern I have about that approach. Can I show you another option?”

Pep Talk for the Nervous Supervisor

If upward communication makes your palms sweat, breathe. You’re not being judged—you’re being trusted.

Your boss needs you to speak up. They need your visibility. They need your voice.

And you can do this. Whether you write it, say it, or draft it with help first, what matters is that you don’t go silent.

Show up. Keep them informed. Speak clearly.

Because one day, someone will be reporting up to you. And you’ll know exactly how to support them, too.

What You Can Try Today

• Draft a weekly summary email using this format:

  • Wins

  • Worries

  • What’s Next
    

• Ask your boss how they prefer updates: email, meeting, report?

• Find a “review buddy” to help you polish hard emails

• Role-play an upward update with a peer to get more confident
  

Call to Action

If communicating with your boss still feels uncomfortable, you don’t have to figure it out alone. Learning how to manage up is a skill, and you can grow it.

Try:

• Neighbor Chat to talk through real workplace scenarios

• Next Step Coaching for personal guidance on upward communication

• Peer groups to practice and learn from others in the same boat
  

We’re here to help you be heard—at every level.

JOIN A GROUP