Three Conversations You’re Struggling to Have with Your Boss and How to Make Them Easier

“Do you have anything for me?”

It’s a question most of us had from our boss. It often comes off as a generic way of checking to make sure we are “ok,” but ultimately it is uninviting and the risk of responding never seems worth the potential reward.

You’re not alone in sharing a fear of dealing with higher management. Whether it be apprehension about appearing needy or the concern for repercussion (even in age of the “Open Door Policy”), we all have hesitations at some point in our lives when being open and honest with our boss.

The first thing to remember is that if you’re having these serious concerns you might need to reconsider your current choice of employment. Working while in in fear of honesty and transparency at work probably isn’t the best way to earn a living.

In my experience, I have repeatedly encountered three types of conversations about which we are uncomfortable having with my bosses.

  • What I think
  • What I need
  • What I feel

The foundation to each of these conversations is trust. The way I prefer to build trust is by focusing on creating a great working relationship of support with my leader. If you’re thinking, “my boss doesn’t really do relationships,” have no fear. The best way to build trust in that scenario is to consistently deliver results and support your boss on his or her priorities. That means when your boss asks you to do something specific, your turn around time on delivering a high quality result should be as quick as possible WITH follow up. It’s hard not to trust someone who consistently delivers for you and makes you look good at the same time.

What You Think

If there is a topic on which we are all experts, it is our opinion. Am I right?

But how does this translate into casual conversation with your boss. Well after the relationship has been established this dialogue occurs by either he or she asking for or you offering your opinion.

If you are being asked, that’s good news. Your boss feels that your opinion matters. The trick to this is making sure you remove any and all emotion out of the conversation. As someone that struggles with emotion from time to time, it’s critical for you to be aware of how your opinion is being presented. An emotional opinion erodes your credibility because you appear to lack objectivity.

If you are volunteering what you think, you need to tread softly. Your ability to gauge the situation or simply the mood of your boss is critical. The most important thing to remember is to ask permission. Your boss may have had his or her mind completely made up. What you think might fall on deaf ears or make you appear out of touch. The second most important thing to remember is to present a solution if what you think challenges the status quo or might appear negative.

People love positive and solution oriented people. Be that person when expressing your thoughts.

What You Feel

Like it or not, we are in a world full of complex and difficult emotions. It seems like EVERYONE has them and no one knows how to communicate clearly about them. We somehow convince ourselves that letting our frustrations pile up over time is a better solution, but then we explode over the smallest issue rather than addressing it in the moment.

What you feel without doubt can be the most difficult conversation. No one wants to appear weak or frustrated. Having said that, feelings can make or break your experience. Negative feelings and emotions can cripple productivity and destroy team morale, but how do you approach your boss about it?

The key is vulnerability.


I know, the mere thought of this concept is nauseating in our culture. There is no room for weakness in our daily interactions and those that sense it usually pounce upon it either consciously or sub-consciously.

If you’ve never seen Brené Brown’s TED Talk on vulnerability, it is a must watch. It without doubt has influenced my life and the way I lead for the better. It’s also given me the courage to be upfront and open with my leaders. In my experience, I’ve found being up front with my bosses about how I’m feeling has opened up new doors and strengthened our relationships. Brené Brown alludes to the idea that humans simply crave connection and vulnerability is the key to unlocking that connection.

Similar to conversations about what you think, removing emotion from the equation is key. Crying (literally) to your boss over a situation is probably not the best approach. You can tell your boss how a behavior or action impacted you. There are all kinds of situations that may apply. Regardless of the situation, your feelings are valid and you’re likely doing everyone a disservice if you’re not expressing them.

Early on in my career, I had a major issue with remaining composed in intense situations. If you know me, you probably know that I am a very, um, expressive individual. While I felt on the inside I had a good handle of a problem, my non-verbals and tone of voice often gave the impression that I was not in control of the situation.

A trusted employee finally provided me the feedback that during those stressful situations, my reactions and behaviors caused the team be come hypersensitive the situation themselves. In other words, my stress was causing them distress and ultimately making the matter worse.

It’s a conversation I will never forget and it has impacted my filter on how I behave in situations that trigger my stress levels. This simple feeling that was expressed has impacted every team that’s worked for me since.

What You Need

What we need is easy when it comes to actual resources to do our job.

“We need more copy paper. We need faster computers. We need a better schedule. We need more meetings.”

*Side note – please don’t ask for more meetings unless you’re confident you can make them value added.*

What “I” need is much more complicated. When discussing what you as an individual need, you can’t hide behind the group’s desires. You run the risk of being needy or a complainer.

You don’t have to be – as long as your needs are reasonable. Remember, reasonable is relative and it’s important we do our best to filter our needs with reason.

We are NOT talking about wants.

An example of a need conversation might be based on your development. Time after time in developmental conversations with my direct reports I run into the same problem. I ask what they need from me, and  they say, “I need support.” I respectfully reject that statement and ask for specifics.

And that is the trick; be specific.

My motivation for this post has to do with a struggle I have with my boss. She is a wonderful, enthusiastic and passionate leader, but I found myself not getting the most out of my one on one connections with her.

I tell my direct reports and peers all the time, “I can’t fix your problem if I don’t know your problem.”

I spent some time reflecting and determined that what I need in my development conversations with her is structure. I need an advanced agenda about points she’d like to cover so that I can come prepared to speak intelligently on each topic. Last time I felt like I was going into a conversation for one thing, but felt like I was in a shooting gallery of topics. I didn’t feel prepared and I felt deflated after the fact.

And that’s my fault – not hers.

I had not appropriately expressed to her what I needed for my development. I was just as bad as every employee that had simply sad they need “support.” It’s silly that I was so apprehensive to talk to her, especially considering she’s so approachable. If I’m having trouble, I know some of you are as well.

When talking to your boss about your needs, it is CRITICAL to have the conversation mapped out (even written down) when you sit down to discuss them. A well thought out dialogue on what and why you need something from your leader is a recipe for success. If you’re need is reasonable and actionable, I wager you’ll walk away from that conversation feeling valued, listened to and more engaged than you’ve been in a long while.


At my current company, we leverage the Lominger Competencies. They are tangible and easy to understand ways to gauge and evaluate performance. Due to several discussions with my team and peers, I’ve gathered my thoughts into a statement that has become something of a mantra in my life. It is based on my new favorite of the 67 competencies discussed by Lominger – Informing. Every time I deal with someone that is frustrated or feeling challenged by a situation, I remind them of the following:

The quality of your experience, whether it be personal or professional, is directly correlated to the quality of your communication with those around you.

We have full control over how we interact with our environment, but our control is based on clearly communicating what we think, what we feel and what we need.

Practice with a trusted peer or loved one. Give it a try. You might be surprised with your results.


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