8 Surprising Conversations You Should Have with Your Boss on a Regular Basis


Chances are you already meet with your boss on a fairly regular basis to discuss the usual things like your progress on projects or goals, any roadblocks or challenges you’re facing, performance reporting for your department or team, and of course any housekeeping issues that need addressing.

Performance check-ins like this are routine in nearly every type of position and organization, from entry-level to director, from the corporate world to the academy. But these are not the only types of conversations you should be having with your boss on a regular basis. Here are some additional important topics to cover with your boss at least once a quarter that will go far beyond the usual touchbase agenda items to build a much clearer, more robust picture of your contributions and help to forge a closer relationship with your boss.

1. Offer Big ideas

Every so often you should share any “big ideas” you have with your boss. Knowing that you need to think outside of your comfort zone and come up with new ideas on a regular basis is beneficial on three fronts: 1) it encourages you to be an innovative thinker, no matter how many years you’ve had in this field or position, and helps you to avoid falling into a rut or stagnating 2) it signals to your boss that you can see beyond your own role or function in the organization and that you’re invested and engaged enough to come up with interesting, new ideas and 3) you may actually hit on something that could be a game-changer for your organization!

2. Ask for help

Don’t be afraid to admit what’s not working and what you might need to be more productive or successful. Oftentimes in reviews or check-ins with bosses or leadership, we tend to put a positive spin on everything, focusing only on wins and not problems to avoid conflict, confrontation, or, worse, negative consequences.

But most bosses sincerely want to know the good, the bad, and the ugly of what’s going on throughout the organization so that they can face the issues head on and work with you to find solutions that make sense for everyone. Remember, if you don’t speak up and make sure the issues are addressed, they’ll very likely only get worse over time.

3. Discuss your career path

It’s important to communicate your own long-term career goals with your boss and spend a little bit of time a few times a year making sure your workload aligns not just with where you are at the moment, but where you’re going in the future.

Think of your career as a kind of roadmap. Every quarter or so, it’s wise to evaluate if you’re sticking to that roadmap or straying off course. A good boss who views you as a long-term asset for the company will be equally invested in your progress.

4. Do you need more resources?

Having the right resources is a key ingredient for success and can have an enormous impact on what you’re able to accomplish. Do you need some new tools or technology upgrades? Do your processes need updating? Is the strategy out of date? Should you define new benchmarks for how you define success? Take some time with your boss every few months to reevaluate your resources and processes to make sure you have everything you need to succeed… and that you’re measuring all this success with the most relevant, up-to-date approach.

5. Are you ready to learn?

Professional development is not only key to your own success, but a strong growth strategy for employees that drives a business forward. A few times a year, you and your boss should discuss how to close any skills gaps you have. Do you need more education? Training? Certifications? Online learning? Exposure to other disciplines or areas of the organization? Access to conferences, professional networks, or research tools?

Lifelong learning and growth should be a key part of your long-term career strategy, and the right employer will be eager to support you at every stage.

6. Don’t be afraid to “meddle”

Sometimes a little distance from a problem or situation can produce the best solutions. Do you see other areas of the business or organization that need improvement, and do you have clear, strong, actionable ideas on how to achieve it? Innovation can come from every corner of an organization, so don’t be afraid to offer ideas or solutions, even they aren’t directly related to your job title or department.

7. If you’re happy and you know it…

It’s important for your relationship with your boss that you don’t only focus on problems that need fixing, challenges you’re facing, or resources you’re lacking. If you’re happy at work, find time to communicate that to your boss. Employee job satisfaction is a big priority for company leaders, and they really do want to hear what makes you happy at work so they know what’s working and how to do more of it.    

8. What’s absolutely not working for you?

On the other hand, if there are serious issues you’re facing that are basically deal-breakers and have you considering leaving your employer, don’t suffer in silence and assume the only way out is to just “deal with it” or quit.

Perhaps you have a workplace conflict that’s beginning to affect your performance, or your workload is too heavy, or you are long overdue for a promotion or salary increase… whatever your grievance, if it’s serious enough to affect your job satisfaction and make you think of leaving, it’s time to bring the issue to your boss to see if there’s a solution that will benefit everyone. They can’t help you if they don’t know what it is, though, so it’s up to you to communicate the issue and do your part to collaborate on a resolution.

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