October 25, 2022

  • 10 MIN READ

Five tricks for having productive conversations with your boss

Blog Team

Having an important conversation with your boss isn’t as intimidating as it seems. It’s less about what you say than how you say it

Office politics – who loves them? The stakes, tightropes and power structures can be overwhelming, but that’s no excuse to avoid (or mess up) an important conversation with your boss.

Your work relationships are just like any other relationships: they rise or fall depending on your communication skills. Managers and workers are on the same side, but have to balance maintaining what’s often a hierarchical arrangement with making sure that everyone’s satisfied and productive.

At UpTeam we know that classic, top-down talks from bosses aren’t productive any more. So here are five tips for getting the most out of these discussions and making sure your needs get met.

1. Use collaborative language

This is probably the most important piece of advice on offer. If you want to make a suggestion, frame it as an add-on to the direction your boss is already taking. When you speak, talk about your problems as potential solutions – this will make your manager more open to what you have to say because you’re not being seen as adding to their to-do list.

A classic strategy is replacing the word “but” with “and.” This frames objections as contributions and doesn’t get peoples’ guards up as much. So go from a yes-man or -woman to an and-man or -woman.

2. Know what you want to get out of the conversation

“I hope you understand what I’m saying.”

They won’t. Not unless you understand what you’re saying first. Some people thrive on thinking out loud, but this can be frustrating for a boss who’s used to treating their time as a valuable commodity. So figure out what you’d like to get out of your talk with them and be upfront.

That means no beating too much around the bush. Saying what you need to, using unambiguous language, not only speeds the process up but it also gives the management another reason to treat you with respect. They can’t read your mind, and they don’t want to be guessing what you’re trying to say.

3. Affirm that you’re a human being with legitimate needs

Many bosses treat their workers purely as a resource: they come in, do their work, get paid and take vacation every now and again. But we at UpTeam know there’s far more going on under the hood, and employees shouldn’t be afraid of standing up for their boundaries in a respectful way.

It’s not that managers don’t treat workers as human, but that there are sometimes so many tasks on their plate that they can get a little utilitarian. When speaking with them about a boundary or a need, affirm that this is what you need to continue working productively and frame it as a solution to help generate a better office culture.

4. Respect power and work within your limits

The absolutely worst thing you can do with a boss in a conversation is to undermine them. Offering criticism doesn’t have to be done on egg-shells, but frame any issues you have in a way that allows everyone involved to save face and prove their dedication to your common goal.  

That doesn’t mean that you don’t have power in this kind of situation – your power comes from the value that you bring to the company. So if you’re contributing something extraordinary, this gives you a bit of leverage. Like mentioned in the first point we made above, though, leverage works best when you’re looking for collective solutions for a common future.  

5. Show that you’re attentive

If you want your boss to take note of you, show them that you’re paying attention. If you’re asking for time to present your ideas, for a role on a new team or even for a raise, mentioning the concrete ways these will bring value to the company will help your case.

If your managers have been presenting about their vision in company meetings, reference that. Take notes whenever you come across something important. Refer to company figures. Bring your top tier game and your bosses will know you’re someone to take seriously.

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EU: Nicu Bordea


US: Michael Philip

Group CEO & Founder