We all work for someone and sooner or later it’s necessary to have a meaningful conversation.

It could be about concerns related to work hours, types of assignments, team dysfunction, negative work environment, desired pay increase, approval for hiring extra staff, personal career path opportunities, transferring to another department, conflict management concerns and a host of other issues.

Sounds easy enough…until it isn’t. Bad experiences from the past talking to a boss come up, worries that the concerns you have aren’t valid, fearful that you’ll be viewed as weak, a trouble-maker or at the very least shining a spotlight on yourself for immediate and future scrutiny are common.

It just feels awkward.

In today’s article…

We will flesh out 5 ways to approach your boss which take the awkwardness out of the experience. And the bonus is that generally these are ways that work for other important conversations that matter whether it’s with a boss, contractor, co-worker, mentor, teacher, spouse, partner or friend.

Let’s take a look…

Way #1- First, request a specific amount of time.

Simply request a specific amount of time to meet and talk. Do you have 10, (15 ,20, or 30 ) minutes in the next day or so? Schedule it and respect the time agreed to by being on time. When time is up, stop. You can ask if 5 minutes more is possible if needed. Regardless, at time’s end, smile, say thank-you and leave.

You can follow up with a brief email of thanks and/or conclusions/next steps reached.

Way #2- Use time productively and clearly state what you’re wanting. Tie it to the organization’s mission.

Review the mission of the organization. Link your issue with the mission if possible. It’s critical to be prepared with your message, stating clearly what you are wanting from your boss. Finish the sentence stem, I would like for you to… consider, know, approve funding, etc.

Outline it before the meeting. Practice it out loud. Keep your discussion productive with only one or two issues during a short period of time.

Hint: Think about how you want the conversation to end. That can help instruct your content.

Way #3- Let your boss’ preferred style of communication influence yours.

If your boss likes supporting documentation, like an article, website address or book, provide it. If your boss needs bullets rather than long explanations, cut out the extra words/descriptors.

Your boss may have a pretty good sense of humor. Remember small talk matters and being too serious is counterproductive. Relax. Join the lightheartedness. Then, introduce the topic.

If your boss is a talker and talks on and on maybe providing an outline prior to the meeting will help the boss focus. Provide an outline with simple phrases describing the issue and the action requested.

Way #4- Always let your professionalism rule.

Report the facts of the situation first. It’s better to stay with the facts and limit subjective comments. Own your assessment and/or judgments if you must share them.

Emotional reactions need to be controlled. If you’re aware of a lot of emotion, please do yourself a favor and get it out of your system before the meeting and certainly before you ever put anything in an email or brief.

Writing is my best friend for those times. I pour out my heart, uncensored. I type quickly. I walk away and return and take the thoughts, clean them up and describe the facts of the event. My emotional turmoil is not for the public, however, the raw truth expressed within the emotion is often what needs to be articulated objectively and descriptively.

At an earlier time in my career as a manager, I sometimes became teary when addressing an issue, particularly when integrity and respect were at stake. Surrendering to this possibility (I didn’t want it), I’d let my boss know at the start of our meeting that I have a tendency to tear up at times and that I didn’t want that to stop the conversation. I probably called it becoming passionate.

I don’t remember any negative reaction and frankly, because I was accepting of my trait, others were too. Isn’t that the way it usually goes? The acknowledgement alone usually kept the tears at bay.

For me, the cost of not sharing was much greater than the risk of a few tears. I don’t tear up these days…looking back, that was a younger, tender part of myself. It wasn’t weakness. A good boss would know that.

Way #5- Recognize the larger context.

Another important part of your conversation should be some acknowledgement of the larger context for your boss, not only your reality. Often a simple statement of, I’m aware I may not have all of the information will show you as a considerate, mature employee who isn’t just looking out for your interests.

Even better is some thought given to the larger scope for your boss and incorporating that awareness into your conversation.

The takeaway is…

Speak up and let your boss know what is important to you as a responsible, engaged employee who cares about the organizational effectiveness and efficiency. Taking an approach that supports consideration of mutual interests and rationally presents alternatives is key. Everyone benefits.

I’m interested in learning, What helps you successfully discuss concerns?

Give me a quick notification of your interest in a Love My Work Strategy Session.  It’s a no cost opportunity for us to meet and talk about your next steps towards making your work what you’d truly find meaningful.  Reach out to me today.