Tough Call Series TILE 1

There’s just no getting around it: you’re going to have to talk to your boss. And not just about their weekend or whether Disney+ is worth the hype (seriously though, is it?), but about the big stuff: your career goals, your growth plan, and what you need to do to get to where you want to be.

But just because we know we should be doing something doesn’t make doing it any easier. And that’s where we can help. As a company that’s built a phone system for every sized business, we’ve learned (a lot) about workplace conversations and more importantly, how to have smarter ones.

In this series, we’ll provide best practices for navigating those tough albeit important conversations, whether it’s having a 1:1 with your boss, cold calling into a prospect, or seeing eye to eye with a colleague.

Let’s look at our 7 tips to having better conversations with your boss.

#1: Actually Schedule a Recurring 1:1 📆

If you don’t already have a recurring 1:1 scheduled with your manager, that’s got to be your first step. Having a dedicated spot on their calendar that’s just focused on you and making sure that both of you are on the same page is h-u-g-e.

There’s no way to have an effective conversation if both of you are completely in the dark of how the other is feeling. Recurring check-ins remove that cloud of doubt, keep you on task, and help establish a healthy working relationship.

#2 Set An Agenda 📝

If you’re already nervous about talking to your boss, walking into that conversation with absolutely no idea of what you’re going to say is a recipe for disappointment. Setting an agenda for the conversation helps establish expectations and gives your manager a heads up if the topic is going to require more people or resources to be meaningful.

Not sure where to start? Try one of these suggestions from GetLighthouse:

  • Your Career/Growth Goals
  • Team Improvement
  • Self Improvement
  • Personal Topics
  • Interpersonal Issues

#3 Stick To Your Agenda (As Best You Can) ✅

So you’ve set an agenda and shared it with your manager—great. Setting an agenda is only half the task...sticking to it is the real challenge.

Remember that the time you get with your manager is precious and limited so it is important to keep yourself on track. Plus, having agenda items makes it easier to come out of the meeting with actionable next steps. Speaking of which, if your boss isn’t in the same location as you, having a tool that automatically captures your meeting minutes can be a game-changer to keeping you both aligned.

#4 Be As Transparent As Possible 👀

Unless they somehow developed mind-reading powers overnight, your manager actually isn’t as tuned in to how you’re feeling as you might expect. Much like how you’re in your own head about your day to day activities, your manager is in the same boat—multiplied by however many direct reports they have. It doesn’t mean they don’t care: it means they’re busy.

So that means it’s on you to be upfront and honest about what’s going on, whether you’re hitting your goals or hitting a wall. And of course, every company and manager is going to have a different definition of “transparent” so you’ll have to gut check yourself before opening up but isn’t there some saying about a squeaky wheel?

#5 Don’t Let Emotions Overrule Clear Thinking 🤯

As tempting as it can be, try to keep the conversations you have with your boss from going overboard on feelings. It’s ok to express emotions but do so in a productive way. The goal isn’t to vent to your boss until you feel better, it’s to make them aware of a problem that’s stopping you from growing and to come away with a proposed solution.

Tip: If you haven’t already, learn your (and anyone you work with) communication style and personality profile to break down communication barriers and have more effective discussions.

#6 Get Comfortable Asking for Help 🤝

🎶Help, I need somebody / Help, not just anybody / Help, you know I need someone, help 🎶

Asking for help is crucial in both your personal and professional development. There’s not a single successful person that hasn’t asked for some help along the way. It’s not a sign of weakness, but it’s important to understand that no person is an island, and you still get to hold the trophy even if others helped you win the race.

One study at Cornell University found that compliance—the rate at which people provided help to strangers that asked for it—was an average of 48% higher than the help seekers had expected. And those are strangers.

Your manager’s job is literally to help you get better. But they can’t do anything if they don’t even know you need it.

#7 Remember They’re Human 👱‍♂️👩

Believe it or not, but your boss isn’t some hobgoblin or an infallible super-being. They’re just someone who’s tasked with doing a job. And unless you’ve managed people yourself, it can be hard to truly appreciate where they’re coming from all the time.

So if they forget a meeting (which they will) or let something slip that they were supposed to tackle (which they also will do), just keep in mind that 99% of the time it’s because they’re busy and not because they’re trying to sabotage your success.

It’s also important to remember that just like you, they also could be coming into the relationship a bit nervous about how to lead, how to handle the responsibility of someone else’s career path, and what their boss thinks of them. So breathe, remember they were once in your shoes, and just talk to them like they’re a person. Because they are—a person who really does want to help you.


No workplace conversation is completely out of your grasp. Most of the time, it just takes a bit of understanding and patience to strike the right chord. And while this sounds trite, practice really does make perfect. The more at-bats you have with everyone: your boss, your colleagues, your prospect—the better you can be at learning how to navigate those conversations and the kind of impact they can have on your career.

At Dialpad, we aim to not just connect people but to share insights into how your conversations can shape the relationships you have with your colleagues, your managers, and your customers. To learn more about the ways Dialpad can help you learn more from your conversations, reach out to us today.