Do you ever have face-to-face meetings with your boss, just the two of you? Do you feel that they are giving you value? Are you reaping the benefits or do you feel that the meetings have been largely inefficient?

One on one meetings between you and your boss are very important.

Having these regular meetings helps you achieve more success in your role, makes you feel more positive about your work, makes you feel closer to the organization and to your manager, and provides you with an opportunity to give feedback to your boss and get heard.

Source: SoapBox

Source: SoapBox

Despite all the potential benefits of one on one meetings, many of them are not as productive or successful as you would expect.

According to a survey report by SoapBox, only 58% of employees leave one on one meetings feeling motivated. Ironically, 75% of managers feel that their direct reports leave one on one meetings feeling motivated.

Source: SoapBox

Source: SoapBox

While the statistics paint a not so great picture, the good news is that is possible to have productive one on one meetings with your boss, where you keep on topic and everything is optimized to ensure a successful meeting.

The best part is that you don’t have to leave everything in your boss’s hands.

There are things you can do as an employee to ensure your one on one with the boss is successful.

Read on to find out what how you can make one on one meetings with your boss more successful.


When it comes to one on one meetings, most employees choose the path of least resistance, which is passivity.

During meetings with their boss, they let the boss take the lead and engage with the boss according to the boss’s agenda. If the boss does not have anything much to say, then the meeting is over rather quickly.

This is not the way to get noticed at work. It is not the strategy of employees who get promoted to positions of authority in the organization.

What bosses are looking for in their employees is initiative.

You don’t have to be a mere rubber stamp – you can have ideas too. Don’t be afraid to bring them up.

Therefore, you must have an agenda for your own-on-one meeting with the boss. Don’t wing it, or go with the flow. Instead, prepare adequately.

Figure out beforehand what you want to discuss with your boss during your one on one meeting. This ensures that you can guide the conversation towards matters that are of importance to you.

This will also ensure better productivity because there will be less opportunity for rambling when you know exactly what you want to say and the exact questions you want to ask.

A clarity of agenda gives the one on one meeting a more precise structure that ensures it’s a professional meeting, not a chat.

If you want to impress your boss even more, you can send them the agenda of your meeting to them in advance. This demonstrates initiative, planning ability, and courtesy.

Being an employee who takes initiative is one of the sure ways to ensure your boss does not forget your name.


One on one meetings with the boss are meant for communication. You have to ensure the boss is on the same page as you, so you must keep him or her abreast of your progress.

Are there any important updates about the work you did last week?

Are there any important updates about the work you are doing this week?

Is there an update for a project you were working on – what’s your progress, have you completed the project, or how far have you reached and what challenges are you facing?

You must remember though that the boss is a busy person and their time is valuable – as is yours.

You are not here to chat. You do not have to tell the boss everything that is going on with your work. Be highly selective when picking to tell the boss.

Ensure that you are only sharing the important updates, particularly the ones you already know the boss wants to be kept abreast of.

Furthermore, even sharing important updates can lead to time wastage if you do not prune your words to the most necessary. In other words, be brief. Don’t belabor the point.

The assumption is that the boss is intelligent enough to understand things if you give the bullet points. If the matter is a bit complex, you can explain a bit more.

Another thing to consider is that not everything has to be discussed on your one-on-one meeting. Save for your one-on-one only those things that you cannot share through other means of communication such as email or Slack.

To determine the course you should take concerning a particular update, ask yourself the following questions:

Is it Urgent?

Some updates can’t wait until the next official meeting.

Some updates are time-sensitive, and next time you have a meeting could be too late because events will have moved on.

Not communicating urgent updates to the boss in a timely fashion can even lead to disasters.

If the update is time-sensitive, don’t wait for your next meeting.

Communicate with the boss in real time to ensure everything goes smoothly. You might decide to send an email or communicate on Slack, telephone, one-on-one, or whatever you deem the best communication method for the situation.

Is the Update Complicated?

When an update is easy and quick to express, you don’t have to hold a one-on-one meeting. You can inform the boss via email.

However, if you the update is complex, for instance when you realize the email is getting too long, it is better to convey the message in person.

Is There a Win You Can Share?

Don’t be too humble when it comes to your wins at work.

The boss is busy and may not even be aware of them. You should not be afraid to share your wins with the boss or manager.

This will ensure the manager sees the progress you are making and acknowledges it.

The supervisor or manager can then share the same with higher leadership in the organization who you may not have the opportunity to interact with.

When your wins are known, it creates a narrative in the bosses’ minds about you, and when time comes to promote somebody, you will be in their minds and they will consider you for the promotion.


As an employee, especially if you are new in the company or in your current position, you are going to encounter situations you don’t know how to deal with, or situations that challenge you.

Even experienced employees encounter such situations, especially in jobs that have a high level of unpredictability, such as customer relations.

If you find yourself in such a situation, it is okay to ask your boss for advice or help during your one on one meetings. Doing so ensures you get a solution sanctioned by the boss and allows you take the next step forward with confidence.

Even if the boss doesn’t help you debug the problem, he or she can give you valuable feedback that can help you come up with a solution yourself.

That said, it is important that you don’t portray the image of an employee who has to be spoon-fed by the boss.

You have to demonstrate that you do have initiative, that you can come up with solutions by yourself.

Before you have the one on one meeting, brainstorm possible solutions and present these as options you consider viable.

It’s alright if the ideas you give are not completely baked, because the important thing is to show initiative.

It would be even better if you try out those solutions (unless it’s an urgent matter or one that is too sensitive to experiment on).

Remember that your boss might also be unfamiliar with the situation, or the boss could decide that he or she wants to see how you would tackle the problem.

That means you might still have to come up with the solution on your own, so you might as well start thinking of possible solutions in advance.


A one on one meeting would be unfruitful if it does not yield resolutions. What do you aim to do next?

One of the goals of a one on one meeting with the boss is to help you be more focused and productive.

The best way to do this is to verbally commit to doing certain things between now and the next check-in or meeting.

When you verbally make a commitment to do something, it places psychological pressure on you to deliver what you have promised.

Nobody likes to let their boss down. In this way, the act of verbalizing your resolutions or goals is a productivity hack that forces you to focus and put in the work and grit required to attain your objectives.

The boss can also commit to doing certain things that are helpful or necessary to your job performance.

For instance, your supervisor or manager might commit to sending you a report that will be useful to you.

These commitments are short-term goals and can function as a sort of to-do list, either for your day or week.

These commitments are definitely things you should add to your daily or weekly to-do list.


While short term goals are the main subject of discussion in one on one meetings, not all one on one meetings should focus on your short-term goals.

It is also important to look at your long-term goals. Without long-term goals, there is no direction. It means you are basically drifting around, merely reacting to daily events.

Having long-term goals is like being a ship captain with a destination in mind – such a ship captain will ensure the ship heads towards his or her predetermined destination, no matter which way the wind blows.

Long-term goals give you direction, and ensure you are the one in control rather than merely reacting to daily events.

Long-term goals put order where there is chaos – this is especially important in jobs that are unpredictable or non-routine in nature.

You can discuss these goals with your boss. Lots of these goals will pertain to your personal development, mainly capacity building.

For instance, are there courses you think will help you get better at your job? Are you thinking of enrolling as a part-time student in a college?


Your manager or supervisor has an aerial view of your performance at work, while you have a more limited view.

He or she can also see multiple dimensions because of a usually longer experience in the workplace or the fact that he or she is overseeing multiple workers or has access to high-level information that you do not have.

Put simply, your boss is able to see the big picture that you might not see, not because you are not capable or smart, but simply because you do not have as much information or perspective as he or she does.

It is therefore likely that when you think your performance is excellent, your boss could have an opposite opinion.

This is why it is very important to learn to seek feedback. In most cases, your manager or supervisor will only be too willing to give their honest opinion.

Being given an honest opinion or valuation of your job performance can be terrifying. It can feel shattering to you if your boss does not gush over your performance.

However, this is the cost of growth.

To grow and build capacity, we need to swallow hard truths, we need to listen to honest feedback and apply it to better ourselves.

When your boss gives you feedback, do not complain or argue or try to justify yourself.

This is the reaction most of us have when we are given feedback, but it’s wrong. Instead, take time to introspect on what the boss has said and see what you can do to improve.

Asking for feedback will put you a cut above the rest. It is easy to get complacent in your job and not put much effort into bettering yourself.

Many employees fall into this trap, and therefore the best way to stand out is to you ask for feedback and then instantly implement it.

Implementing feedback will cause a rapid improvement in performance and within no time you will be so good at what you do that it will be impossible for anyone to ignore you.

Merit is often rewarded. Your show of initiative and grit will mark you as a prime candidate for promotion and give you good favor with your boss.


Before you start delving into the challenges you are facing, it is wise to start with letting your boss know of a success you have had recently in your job. It could be a task you have completed, a new client you have acquired, a deal you have closed, and so on.

Just make sure you start with successes rather than problems.

When you start off with challenges, it sets a bad tone for the meeting.

Remember that your boss has several employees under him or her and they too bring their challenges or problems to boss.

That can be overwhelming. It is therefore good to start off with sharing success as this is sure to set an uplifting tone for the meeting.

It also alters the boss’s perception of who you are and what you are saying. If you start off with the challenges you are facing, the boss will most likely see you as a complainer reciting a litany of woes.

On the other hand, if you start with sharing a win, the boss will most likely see you as a capable individual who is facing challenges but who will eventually triumph over them.

Put simply, the win makes you look like a winner, while starting with challenges can make you look like a whiner.

This is all just psychology.

We are all human, including our bosses, and our minds are susceptible to such illusions.

You must therefore be careful how you present your case to your bosses and avoid portraying yourself in a bad light.


If you want to move into the next level of your career, you have to prove that you are an employee who takes initiative.

This is very important, because individuals who are given authority in an organization tend to have more responsibility.

That means there are aspects of the organization you will be responsible for that are more sensitive than what you are currently responsible for.

To prove that you are capable of handling such responsibility, you must demonstrate an ability to increase productivity, wellbeing, revenue, and so on.

Presenting your ideas during your one on one meetings to show your boss that you are constantly thinking about the overall wellbeing of the organization, rather than just what you are tasked with.

Of course, for you to have a constant flow of ideas, you must always ensure you are up to date on the latest developments in your field. Read widely, especially articles that pertain to your field.

Note that some of the top CEOs like Warren Buffet and Bill Gates are avid readers.

The more you read, especially in your field, the more ideas you are going to have.

Today, ideas are the most valuable currency in the workplace. Ideas run the world, as can be seen in the rise of scruffy startups like Apple and Facebook into the most valuable companies in the world.

Ask yourself questions like: What can we do to improve our performance as a team? What can help me improve my performance?

If you have an idea, don’t be afraid to present it to your boss during your one on one meeting.

Be very respectful as you do so to avoid giving the impression that you are bashing the existing way of doing things.

You can suggest that the idea gets tested on a small scale before it is adopted to prove if it’s viable. If the boss does not warm up to the idea, do not insist, lest you appear rude and belligerent.

Suggesting ideas is always a risk, since you do not know how your boss will react to it.

However, if your boss likes the idea, this will shine a spotlight on you as the kind of brilliant, hands-on, innovative, initiative-taking person the organization cannot do without.

If the idea is implemented and proves to be a success, the boss will always remember you as the person who came up with that idea.


We live in a highly distracted world.

During the one on one meeting, you must ensure that nothing distracts your discussion.

For instance, it might be a good idea to put your phone on silent during the meeting – that is if shutting it down is not an option.

You should also avoid things like snacking during the one on one meeting, unless you are holding your one on one meeting in a restaurant.

Put simply, you want all attention, yours and the boss’s, to be on what you are discussing.


You and your boss should set the day and time of your one on one meeting in advance. It should not be an impromptu kind of thing. This will give you ample time to prepare for the one on one meeting.

Time is of the essence, and no boss will be thrilled having theirs wasted by their employee. Once you have set a time for your meeting, you should ensure that you are there on time and ready to start the meeting.

Never, unless it is absolutely necessary, cancel your one on one meeting.

That communicates a lack of organization on your part. It might also imply that you do not have your priorities in order, or worse, that the one on one meeting with your boss is not a priority for you.

If the boss cancels on you, take it in your stride. However, ensure you both agree on the exact time and date to which you will postpone the one on one meeting.


One on one meetings with your boss are very important, and if you follow the tips shared in this article, you will see an improvement in the effectiveness of your one on one meetings with the boss.

Before I go, however, there is one thing I need to say.

The most important thing to having successful one on one meetings is implementation of what you have agreed upon in the meeting. The success of a one on one meeting is measured by its fruit, not by how much was discussed.

Even if you put all everything you have learnt in this article into practice and have a very fruitful discussion, but then fail to implement what has been discussed, the one on one meeting will not have achieved any success.

Therefore, following through with what you have discussed during the one on one meeting is key.

How to Have a Successful One-on-One With Your Boss

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