How To Ace A Conversation With Your Boss (or Anyone you Want to Impress or Please) | Handel Group

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How To Ace A Conversation With Your Boss (or Anyone you Want to Impress or Please)

Still wondering how to win friends and influence people?

We’ve been studying it for years and it’s easier (and in some ways trickier) than you may think! I know I am still learning myself. Below are 5 steps for how to ace any conversation with your boss, or anyone else you want to impress or please, that I discovered the hard way. Hopefully, you won’t have to.

Keep in mind the dialogue that hasn’t been going so well in your life, as I go through the steps. For me, it was with my boss.

My experience after my weekly phone meeting with my boss was often one of overwhelm. I’d usually go in nervous and come out bedraggled. Somewhere in the middle, we’d squabble, I’d fall behind in the conversation, lose her attention or just skip over stuff I couldn’t figure out on the fly. She often left the conversations weary too. She shared with me how frustrating it was to feel my resistance to her questions and concerns and noted we just weren’t having fun.

I let it go on this way for such a long time because I always got amazing coaching in these conversations and learned a ton from them, plus she is my boss and didn’t really feel like I had the power to change the dynamic. I just assumed the unpleasant feeling of the meetings was the cost I had to pay for all the benefits.

Not so!

Just like we teach our clients, WE have power in all of our relationships because every relationship has a dynamic and when one part of a dynamic changes, the whole dynamic has to change.

Other than the fact that we are both on a mission to make the world a happier place, my boss and I are about as different as can be. She is a visual learner, I am all auditory. I love details and precision, her strengths are making connections between people and ideas, cultivating team integrity, and holding a huge vision. She is an awesome delegator, I’m not. I love to read and write, she does not love to read emails. Therefore, our conversations are uber important and it’s very important that they go well. In order for any conversation to go well, you have to be aware of your differences and instead of thinking of them as a problem, think of them as an opportunity. If you can give someone what they need, they’ll give you what you need.

Learn from me so you don’t have to learn the hard/long way like I did. Here are the steps in summary:

1) Prepare
2) Set the agenda and send it in advance
3) Give context to each item on the agenda, know what you are asking for, be ready with data and your own opinion.
4) When things get rough, chant this mantra: “I am getting a gift, I am learning, I am growing, I am scoring points by getting through this.”
5) Care and assume your boss cares. Plan connection, not just on business items, and make the whole meeting fun, person to person.

Get a feel for how The Handel Method® could benefit you.


Now let’s drill down:


Before any meeting with your boss, review your notes from your last meeting, review the items you are working on and gather a list of open items and questions.


Nothing knocks a boss’ socks off more than your leadership. Show your boss you love your job and all your projects by reporting on them weekly in writing. Use your regular phone or in-person meetings to review what can’t be handled over email or memo. I send my boss the agenda the day before our meetings (this also forces me to prep in advance, which is great for calming nerves). I’ve recently started to categorize parts of the agenda to make it even more fun and organized. For example:

A) Personal vibe check (both ways): It’s always good to start off with “How are you?” and mean it. I also tell her how I am. Getting emotionally connected is never a waste of time. I told my boss I wanted to start every one-on-one meeting this way and she gladly agreed.

B) Updates (on any projects she is monitoring): Here is where I show her how her past advice has helped and all the good work that I am doing. It is also where I update her on areas of concern with which I need help.

C) Questions/Requests for Advice: Here is where I use her expertise and insight to assure that I am headed in the right direction and to brainstorm  ideas that I may not have come up with on my own.

D) Approvals: This is for proposals I have about things for which I need her approval.

E) Fun: Here is where we come up with fun quotes to put up on social media or new content for new offerings. It’s purely creative time and a great way to end the meeting.

Notice we don’t have an item F) Set the Next Meeting. This is because we have a standing regular meeting. Whether you are a boss or an employee reading this (or even a contractor) note the brilliance of setting aside time on a regular basis to empower and connect with your teammate(s). This is not only organizationally smart but it relieves stress on both sides and leads to increased efficiency.


Before you download an item on one of the above lists, explain the context of why it made the list. Your boss has as much or more on their plate as you do, so she/he may not (and probably shouldn’t) be fully aware of what you are talking about. It’s your job to briefly and effectively fill your boss in. Be ready with data about the project and try to anticipate what questions might be asked.  If you want help making a decision, come with your own opinion and be prepared to say why you have that opinion, preferably with supportive data. But also be ready to hear and ponder alternative analyses and solutions.


Chant this mantra: “I am getting a gift, I am learning, I am growing, I am winning by getting through this.”

I’ll admit it, I often squabbled with my boss in past meetings. I did a lot of defending, back pedaling and sometimes even crying. Later, things would get resolved and I always ended up better, smarter and more trusted than had the conversation never happened. My boss and I have the same mission and we know that. Now I am seasoned enough to know that if my boss and I squabble, it’s because we both really care about getting the best results. Occasionally, there will be rough times and growing pains. When we go through them together we actually build our bond and our own belief in what we’re working on. If I (or she) backed away from a disagreement, both sides would end up weaker. Our intellectual and emotional sparring helps us grow and learn. I truly believe this and chant it to myself (metaphorically) if things get heated.


Plan business items, but also make time to connect. Relationships are at the heart of anything that gets accomplished on a large scale. Cultivate a culture of caring–yes, caring what your boss’ experience is of life, his/her job, and you. Care how your boss thinks and feels and your meetings will go much better. How do you demonstrate this? Ask questions and listen to the answers. Say back what you heard to ensure you are really listening to her/him and not the voices in your own head or planning what you are going to say next. Even bosses need taking care of (it’s called “managing up”). Assertiveness on the job is an important asset, but the ability to listen well is a rare gift, that if extended to your boss, will be appreciated a great deal.

I hope in reading this you are getting valuable advice, not just for meetings with your boss, but for any meeting where you have an agenda which may or may not coincide with that of the other person or people involved. Learning and practicing how to effectively engage and influence people never gets old and never runs out of usefulness.

Love, Laurie