7 Tips for Setting Up a Successful Meeting with Your Boss

Find out what the boss wants and then give it to them!

Ever heard that term before? Are you working really hard, achieving exceptional things, and yet still somehow failing to move forward in your organization as quickly as you would like?

It may be that what you’re delivering isn’t what your boss expects. Managers and executives hoping to get ahead in the workplace often fail to deliver in ways that resonate with their managers and organizational leaders. Here’s a look at what you may be missing.

One of your most important objectives is to schedule a weekly time to meet one-on-one with your boss. Yeah, get that face time. Especially if you are not doing so now. These meetings should be scheduled for about an hour.

Why would you want to have a One-On-One Weekly Meeting with your boss?

The truth is the boss needs these meetings as much as you do. Yes, they do! Look at their life and schedule. This is an effective way for you to keep your boss informed and on top of things. Depending on their need for detail, this may be a generalized loose update or a more formal detailed interaction. Either way, you both gain from it.

The boss gets buried in meetings and responsibilities. This weekly meeting becoming a best practice brings the ability for the boss to stay plugged into more than what is right in front of them. Believe me, it gives them a level of comfort, knowing what is going on from someone else’s perspective.

If you know of something going on in the organization, let them know about it. NO! I’m not talking about snitching or gossiping, That will make you a pariah with your peers. What I’m proposing is keeping them informed on issues that are maybe getting overlooked.

Let me share a story from when I was a boss

One time a direct report came to me during one of our meetings and let me know about grumblings going on with one particular team regarding the microwave in the breakroom.

You see this team all went on lunch break at the same time. There were fourteen of them. Most brought their lunch to work. We had one microwave. Due to the lack of microwave capacity, they had to wait in line behind each other to gain access to the sole heating device.

This was making the ones at the end of the line to have to rush their meal once it was warm. Was this the most important thing for us to be focused on at the moment. Yes! Taking care of your employees is always a priority. The problem is you don’t always know what they need. Most will never complain to you. they will silently disengage and that is a detriment to your organization.

So I really appreciated this heads up. It was an easy fix, a few hundred bucks and we had 3 extra microwaves in the breakroom by the end of the day. On top of that, we had a team of fourteen who realized we cared about them in even the most simple way. Of course, I allowed him all the credit for the idea and he was much appreciated for that act. The fact is I would never have known about this and thus never would have done anything about it.

So keep in mind, the boss is busy. Many won’t suggest scheduling a meeting because their schedule is full. You have to bring it up and make an effort. Most bosses are willing to take the time if you are committed to making it valuable.

As for enhancing your career, when you start having one-on-one weekly meetings with your boss, you will find far more motivation to focus on “Big Picture” projects, which have a direct impact on the increased department and organizational growth and success. Isn’t that what the boss wants?

You should leave these meetings with the feeling that your plans, including your time allocations, are crystal clear to you, and you are on the same page as your boss. Now you are giving them what they want.

So often, direct reports avoid this interaction due to FEAR. False Expectations Appearing Real. Hey, if you are not confident enough to suggest and schedule this with your boss, then honestly, you are really not willing to commit to what it takes to advance your career.

The Truth is, a one-on-one meeting each week between you and your boss is essential to you making the best of your career

Why? There are several reasons you want to be a meeting with your boss. All have a benefit to you, and most have a benefit to your boss.

From my experience, the time I spent with my boss during these meetings was extremely beneficial to my education. I received an MBA from simply discussing business. We would discuss current issues that were specific to the business like sales, people, projects, and other challenges.

Sometimes we would simply discuss business in general. What was happening in the economy, news, and with competitors? During these interactions, I was able to not only learn business terms and philosophies that I was not well versed in but was also able to form a far more informed opinion on business-related topics.

Learning from their experiences and opinions was invaluable to me in my own development. The truth is I probably would have never gone out to seek some of the topics on my own. My curiosity peaked just being brought into a conversation. I loved this.

We also built a much better professional relationship.

Here are some ground rules for setting up your meeting.

No Cancelling or Rescheduling Weekly Meetings with Your Boss

It is your job to tactfully but assertively advocate for your spot on your bosses’ weekly calendar for your one-on-one meetings. These meetings should not be canceled unless there is an emergency or one of you is sick. If you or your boss is out of town on business, it is easy to hold these meetings over the phone or video-conference.

You must have a Weekly Meeting Agenda

For these meetings with your boss to be most effective, each meeting should include the following five agenda items for discussion:

1.Review the status of Project Plans for which you are responsible

2.Reprioritize your “To-Do” list for the projects and assignments within your areas of responsibility

3.Review people on your team. High performers and developing members

4.Review recurring items

5. Address new items – update on any new item about you or your department that you feel should be shared with your boss

Prepare for the Weekly Meetings

Your weekly meetings will not be as effective as they could be if you don’t prepare for them. Make sure you invest some time before the meeting to update your status report for your Project Plans and your To-Do list and to get prepared to discuss recurring and new items with your boss. The biggest benefit to many is you will drop far fewer balls. You will be on top of your game all the time! 

Investing the time before the meetings will result in presenting yourself at the meetings with a high standard of professionalism. So, do the needed up-front work necessary to make this meeting as efficient as possible.

Be Ready with Answers Before Hearing Your Boss’s Questions

At your weekly meetings with your boss, make a point of focusing your boss’s attention on any items in the Project Plan for which predicted results are not achieved. Taking the initiative to address these items directly is important so that your boss does not think you are hiding or ignoring weak results. NO SURPRISES!

Be prepared to answer questions about your Project Plan, such as the following:

• What are the measured results of the Project Plan or Tactic com¬pared to projected results?
• Are the projected results on track?
• If the projected results of the Project Plan are not on track, which Tactics are not being completed on schedule?
• What caused the below-expectation results?
• If a project is not on track, what is needed to get it back on track?
• If a project can’t get back on track, what should be the new track, and what is needed to stay on this new track?
• Do you believe that some of your Project Plan Tactics are over¬whelming and should be broken down into smaller, more manageable units? If this is the case, what can you recommend to make this happen?

Agenda Item Major Point: Review Your To-Do List

Your Project Plan is not the same thing as your To-Do list. The Project Plan lays out what is to be done for a specific plan. Your To-Do List identifies what you need to be doing next and when!

Your To-Do List

Every manager faces multiple tasks that need to be completed throughout their day. A To-Do list will help you manage this situation by identifying and prioritizing the tasks, activities, and decisions that you must accomplish. If you don’t utilize a to-do list, it is likely that your days easily become overwhelming and stressful.

Many find that following this approach and sharing the To-Do List with their boss prevents too much work being assigned to them by the boss. Ahhh, secret ninja trick! If the boss knows exactly everything you are working on they will be far more informed of your workload and less likely to pile more on. Nice! This sets you up to deliver expectations successfully

During your one-on-one meeting with your boss, ask for suggested changes to your To-Do List.

Your boss may suggest delegating tasks that are currently on your To-Do list to other members of your team. When you finish reprioritizing your To-Do list at each of your weekly meetings with your boss, the result should be alignment between you and your boss on how your time should best be used.

Then you have your NO GOs.

The negative traits you listed are now your “NO GOs.” When you are recruiting or interviewing someone and you detect any of these “NO GO” traits…STOP! Do not go forward with further considering them. EVER!!!

Learn from my mistakes. My optimism often talked me into hiring certain individuals that I believed I could live with, or that they could overcome some of these negative tenancies. Nope. Never worked and never will. Don’t do it. Don’t ever believe you can change what their maker baked into them. You might as well tell them to change the color of their eyes. It can’t happen, and you can’t make them.

These must become your standards for hiring. Live and abide by these, and you will, in short order, experience a huge improvement in your culture, work-life balance, productivity, and turnover.

Notice I did not list experience in this part. In my opinion, the experience is a nice to have.

I’d much rather take the right personality fit and train them for my company’s needs. Yes, the experience can be great, but it should not be the most important factor in hiring your next person. Sure, some positions will require a certain amount of experience. The point I want you to take away is, make experience secondary in the selection process, Choose the right human first and then use the experience as a secondary deciding factor.

 When you hire an employee, don’t underestimate the importance of hiring someone with whom you enjoy working.

Some reading this will question, how do I determine these positive or negative traits? The answer is in your interview technique and personality assessments.

You must use a behavioral-based interview approach that will uncover what you are looking for in prospective new hires and internal promotees. If you are unsure of those types of questions look like, check out this article on Behavioral Based Interviewing FAQs. You can also contact me through my website, and I will be happy to discuss behavioral-based interviews with you and send you some valuable tools.

Be very honest with yourself about your personality and motivations. A common mistake that many managers make is that they want to hire a self-directed individual, a problem-solver, and a motivator who has a dominant nature. The truth is, more times than not, a domineering behavior style may actually be better served by a more passive, easy-going, organized type of individual who takes direction well, does not rock the boat, and is more task-oriented than leadership-oriented.

What are some of the tools I can use?

There are many available tests and surveys that show such things as behavior or personality styles, motivations, and general intelligence, which you can use as part of the initial or pre-screening if permitted under the laws in which you operate. I utilize the DISC assessment as part of my training and coaching practice. I’ve used the DISC tool for close to 20 years. If you want more information on how to deliver and read a DISC profile contact me here for more information and a free 45-page DISC assessment for yourself.

Before you test your prospective new employee for behavior and personality style, it’s a good idea to test yourself first to find out your own style. Identify which type of style meshes best with your own style. More Information

IMPORTANT: Your Employee should complement your leadership style, but not be a mirror image of yourself. Know your own strengths and weaknesses, and hire those who fill the voids you have, without duplicating your own strengths.