How To Talk To Your Boss

Let's look at how turn what might otherwise be a rocky relationship with your boss into a stable and healthy connection.
conversation at work between boss & employee

How to talk to your boss

Talking to higher-ups can be a tricky road to navigate. At the same time, learning how to talk to your boss is a core component to succeeding at your job — if you don’t learn how to do it effectively, you may not benefit from the bonuses, promotions or opportunities you deserve. 

What’s more, if you decide eventually that it’s time to leave your job, you’ll want to have an honest, heartfelt and productive conversation with your boss… and that simply won’t happen if you don’t possess the tools to communicate and advocate for yourself. 

Fortunately, there are several ways to improve your relationship with your boss through practice and effort. Consult this list of tips to turn what might otherwise be a rocky relationship with your boss into a stable connection that benefits the both of you.  

How to talk to your boss

1. With a hands-off boss: dispense with doubt and avoid over-communication 

Are you constantly checking in with your boss to make sure you’re doing your job right? If that’s the case — and your boss is the more laid-back, macro-managing type — it’s time to dispense with your self-doubt and start taking matters into your own hands. 

It might sound strange not to tell your boss what you’re up to, but doing so to a boss who already trusts you can actually erode some of that confidence. For bosses who aren’t too concerned that you’re going to do a poor job, your constant check-ins might telegraph to them that you’re unsure of what you’re doing. Nobody wants that — least of all you! — so when it comes to a hands-off boss, it pays to simply get the job done, and ask questions later. 

2. With a hands-on boss: focus on what you want (instead of setting boundaries)

With a very hands-on boss, it can feel stifling to try and get work done in their presence. Anything you do gets scrutinized, looked at and picked over… it’s enough to drive anyone a little crazy. So, what can you do?

The short answer is: avoid setting boundaries around your workflow. That might sound counterintuitive, but the truth is that boundaries will actually inhibit your ability to work well with your boss. That’s because when you set a boundary — such as telling your boss not to check up on you unless it’s absolutely necessary — it means you’re diverting a significant amount of energy into preventing your boss from interrupting you. 

Unfortunately, when you spend a lot of time and energy telling someone what they shouldn’t do, it keeps you from chasing the things you do want. All of us want productive, fulfilling careers with enjoyable work, but if we’re always focusing on stopping our bosses from screwing things up, we won’t spend any time on actually making our careers happen. 

That’s why it pays to flip the narrative with a hands-on boss. Instead of putting up a million boundaries regarding your communication, tell your boss what you do want out of your relationship. 

Expressing to your boss that trust, open communication and space to complete your work is important to you will inform your manager how you like to get the job done. To go one step further, tell your boss that having those things in your day-to-day experience will actually help you produce better work than if you don’t have those things. 

Once your boss gets the message that your preferred work-style leads to better results for the company, your working relationship is bound to improve. 

3. With all bosses: accept that communication problems are usually thinking problems 

Learning how to talk to your boss might sound like a communication challenge. However, most communication problems actually start as thinking problems. In other words, while we often think that our communication skills aren’t polished enough to influence others, the reality is that our words begin as thoughts, and having faulty thinking is the initial barrier to great communication (not the words themselves). 

Instead of approaching your relationship with your boss from an adversarial standpoint, consider all the ways in which your communications with them could go right instead of wrong. What’s stopping you from speaking to your boss in a way that they can understand? What’s preventing your relationship with your boss from improving? 

Asking yourself questions like these will help you reconsider and examine the way you show up for your boss — and soon enough, your boss is going to notice.  

It’s possible to learn how to talk to your boss 

Your boss might be in control of your day-to-day workflow, but they’re not in control of your career. Only you can decide how you want the future of your relationship with them to play out… would you rather invite a tense, difficult working relationship into your life, or would you prefer to have easy, smooth, simple communication? 

The beauty is that the power to change your relationship with your boss lies within you. Sometimes, however, it takes a little help to unlock that power — which is what we’re here for. We’re a team of coaches who work specifically with highly driven professionals, executives and leaders who are dedicated to succeeding in their careers. 

If you feel like you’re at an impasse with your boss, we highly recommend getting in touch with us. After all, breaking down communication blockades between bosses and employees is exactly the kind of work we excel at.   

Looking for more?

Check out our article on The Benefits of Executive Coaching.

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