How a Bad Boss Turns One on One Meetings Into Torture

by Jason Evanish, CEO Get Lighthouse, Inc.

One of the single greatest tools at the disposal of any manager is their one on ones with their team. Used well, it can help drive top performance, boost morale, and fix problems when they're small.

Unfortunately, most bad bosses make one on ones miserable, discouraging experiences. They become an event on the calendar everyone learns to dread, instead of being the powerful, positive meeting they should be.

Today, we explore how a bad boss ruins one on ones, and what you can do instead if you're guilty of some of these bad habits.

bad boss keeps cancelling one on ones dilbert knows

How a Bad Boss Turns One on Ones into Torture

Having bad one on ones can lead to a variety of issues with your team like:

  • They avoid you: They seem to spend the minimum amount of time communicating with you.
  • They go around you: They go to other people when they need something.
  • They're disengaged: They seem unhappy, but you don't know why, and won't tell you when you ask.
  • Surprise turnover: A good person quit, and you didn't see it coming.
  • Poor accountability: Your team isn't hitting their goals, meeting expectations, or keeping promises.

Fortunately, with a commitment to making a few changes, these are all fixable. Let's dive into some of the most common habits of a bad boss that ruins their one on ones for them and their team:

  1. You cancel one on ones more than you have them
  2. You make your one on ones status updates
  3. You're not prepared for your one on ones
  4. You fail to keep your promises
Bad boss don't know what David Cancel does about the value of 1 on 1s

Bad Boss Habit #1: You cancel one on ones more than you have them

There are many seemingly "good reasons" to cancel one on ones: you may get pulled into other meetings, travel a lot, or feel like you constantly have to tackle emergencies.  While this may be okay every once in a while, making it a common occurrence is very damaging.

If you go to your team member and say, "you didn't have anything important to talk about, did you? I really need to do X," it's very hard for them to say "No, I really need to talk." If they did, now there's pressure for any issue they bring up to be bigger than your "emergency." They lose whether they push you to have the meeting or let you cancel again.

If this happens repeatedly, it will discourage your team from coming to you with any organizational issues that aren't hair on fire bad. This only traps you further in a reactive management mode, as no one will tell you about anything until it's a big problem. Anyone would be a bad manager when that happens.

And if your boss keeps cancelling one on ones, then you probably know that it leads to...

A bad place to work.

No one enjoys working on a team that is in constant crisis mode, nor one that is forced to hold in everything bothering them.

This is why Ben Horowitz, investor and former CEO of Opsware, was willing to fire a manager, and his boss, because the manager was not having one on ones with their team. As he recalled this conversation in his book, The Hard Thing about Hard Things: (emphasis is ours)

"Ben: "In good organizations, people can focus on their work and have confidence that if they get their work done, good things will happen for both the company and them personally...These things make their jobs both motivating and fulfilling.

"In a poor organization, on the other hand, people spend much of their time fighting organizational boundaries, infighting and broken processes. They are not even clear on what their jobs are, so there is no way to know if they are getting the job done or not. In the miracle case that they work ridiculous hours and get the job done, they have no idea what it means for the company or their careers. To make it all much worse and rub salt in the wound, when they finally work up the courage to tell management how f*#@ed up their situation is, management denies there is a problem, then defends the status quo, then ignores the problem.”

Steve: "OK.”

Ben: "Are you aware that your manager Tim has not met with any of his employees in the past six months?”

Steve: "No.”

Ben: "Now that you are aware, do you realize that there is no possible way for him to even be informed as to whether or not his organization is good or bad?”

Steve: "Yes.”

Horowitz then summarizes simply why this is so important when he later wrote:

a bad boss may not realize how their bad habits can sink their company

What to do instead: 

Never go more than a month without having a one on one with everyone on your team. If you're having trouble sticking to a schedule try one of these tactics:

  1. Set aside a day or two for them: Block off a large chunk of your day and plan to not be available for anything else. It's harder to cancel 4 or 5 one on ones than talk yourself into canceling one. It's also an easier argument to others trying to get you to cancel by saying, "This is my one day to meet with my team, can we meet another day?"
  2. Schedule your next one on one during your one on one: If you travel a lot it can be hard to have a simple recurring schedule for your one on ones. However, you will often know your availability the next few weeks. Don't let yourself leave the meeting without scheduling the next one on one to fit around your travel.
  3. Reschedule instead of cancel: Emergencies happen. The best way to signal to your team that they are important to you is to reschedule for as soon as possible after your cancellation. You don't want to be distracted in the one on one thinking about a real emergency, and by rescheduling, you show your team they're still important to you.

Consistency is a key part of healthy one on ones. By having them on a consistent basis, you will build a stronger, more trusting relationship with your team members, who will see you truly value the time. You also build momentum from one meeting to the next, as they can trust the meetings will happen.

Stop nagging your subordinates if you  want to avoid becoming a bad boss

Bad Boss Habit #2: You make your one on ones status updates

When you get busy and your team grows, it can be hard to keep track of everything going on. You may wonder who is working on what project and what the status is of everything. The busier you get, the more out of the loop you feel.

At this moment a temptation can creep in that will help you, while ruining your one on ones. You turn them into status updates. Don't be a bad boss that falls into this trap.

The peril of status updates in one on ones.

You should absolutely stay in the loop on what the latest is with all the important projects and tasks for your team. However, your one on one is not the place to find out. Here's why:

  • It's inefficient: If it's a common project discussion, others on your team would benefit knowing as well. If you're constantly updated individually, you make yourself a bottleneck for information across your team.
  • It wastes time: It's incredibly easy to fill your entire one on one talking about a project. It's safe and feels productive. However, that leaves no room for what you should talk about in one on ones like their career, problems, feedback, and coaching. There's no other time to talk about any of those things, which means they'll never get discussed otherwise.
  • It's selfish: One on ones are supposed to be for your team member. They work 40 or more hours a week for you. A one on one is the one hour you give to things important to them. A status update on a project is all about what you need.

No one looks forward to getting drilled on the details of every project and task they're working on. This is especially frustrating when the answer is likely already in a project management tool, or could have been communicated over an email.

a bad boss leaves elephants in the room
Status updates in one on ones leave elephants in the room

What to do instead: 

Try a project management tool like Basecamp so you can always look into the status of projects. You can also try stand up meetings, or status update email tools like IDoneThis, to get a daily snapshot of where everyone on your team stands on their work.

Once you have status updates out of your one on ones, you'll need to reset expectations on what your one on ones with them are about. The best way to do that is in your words and actions:

  1. Tell them: Make it clear you're changing the meetings to focus on them. Tell them what to expect in their one on ones.
  2. Bring good questions: If it's going to be their meeting, then asking good questions and listening is one of the best ways to break the ice and dig into what's important to them. These one on one questions can help.
  3. Talk about their career: Growth and development is the most commonly desired benefit of Millennials today. Taking some time to really dive into their career is a great way to spend your one on one and clearly demonstrate your investment in them as more than a task robot.

What you spend your one on ones talking about is as important as having the meetings. If you waste them on a status update, you're missing out on all the real benefits of one on ones.

a Bad boss don't take the actions to demonstrate they care

Bad Boss Habit #3: You're not prepared for your one on ones

We all know as a manager, your schedule can get crazy.  And of course, sometimes that’ll make it pretty hard for you to carve out time to thoughtfully consider what you want to talk about with your team members. 

Yet, if you don’t make some time to prepare, you risk having a completely unproductive and damaging  one-on-one. 

Lack of prep really is a tried-and-true recipe for bad meetings.

Not only will you struggle to figure out what to do in the meeting (making it easy to fill it with things like status updates), but you can also cause a lot of resentment. If you forget things that are important to them, and constantly have to waste time remembering what they brought up last time, don’t be surprised if your team is unenthusiastic about your 1 on 1 with them.

You waste everyone’s time and hurt your relationships if you’re unprepared.

Prep is essential for your most critical conversations. If you need to give constructive feedback to improve their performance, or want to boost retention and engagement by talking about your team member’s career growth plans, you cannot wing those conversations. It can make all the difference to prepare a few notes and thoughts for these kinds of discussions before you meet with them.

Avoid bad meetings by always coming prepared with notes.

A missed opportunity.

A friend of mine was performing well in their job and was eager to get promoted. They proactively asked their manager a few times, “what would it take to become a director?” While their manager was adamant they weren’t ready, they never took the time to explain why.

Over time, this became increasingly frustrating to them (something I heard about regularly when we caught up); they felt like the lack of a straight answer was to stall a promotion instead of a genuine reason. And since their manager never broke down things for them  to work on, my friend never learned where to channel their ambitions to improve themselves. 

Eventually, my friend got tired of waiting and left the company to get the promotion they desired.  

All their manager would have had to do was sit down one day and answer 3 questions:

  • What are the most important skills needed for the director role?
  • Which of these skills was my friend missing?
  • What are a few examples of those skills lacking in their work?

With answers to those questions, my friend’s manager could have sat down in a 1 on 1 and made clear what they needed to do. They could have then tracked progress over time and likely have retained my friend while eventually giving them the well-deserved promotion.

What to do instead:

Always have an agenda for your meetings, especially when they’re one on ones with your team. A little effort beforehand can make all the difference during the meetings, as well as the quality of the outcomes you have after. 

Now, keep in mind: this doesn’t and definitely shouldn’t take you all day to prepare. 

For regular meetings, as little as 10-15 minutes can be plenty to review some notes from last time, choose a few questions to ask this time, and note any other quick topics you want to cover. 

And then for more important meetings, like fixing issues with an underperforming team member, you may need a bit more time, but the time spent is worth it.  Would you be willing to find 30-60 minutes if it meant a team member doesn’t need to be replaced, or becomes twice as productive the rest of the year? 

Here are a couple of tips to make your one-on-one meeting agenda great:

  1. Start where you left off: Often, the best things to talk about is to pick up where you left off last time. This can be things like: Asking about something they shared with you (like a personal issue or concern), showing you kept your promises and commitments from last time and check in on their's, building on the previous discussion's topics (feedback or praise on work since issues discussed previously, next steps in their progression, etc).
  2. Prepare questions of your own. As Ben Horowitz wrote in “The Hard Thing About Hard Things”: “While it’s not the manager’s job to set the agenda or do the talking, the manager should try to draw the key issues out of the employee. The more introverted the employee, the more important this becomes.” That means picking out some questions to ask. Remember: If your team member has never had a good manager, they may not know what topics are safe to bring up. What you bring up signals to them they can bring it up in the future as well. 
  3. Leave room for your team members to contribute. Every one-on-one is a 2-way street; this is their meeting with you, after all. As you prepare, remember to leave room for them to bring up topics they want to discuss, ideally at the beginning of the meeting (or ask them to send it to you in advance). I've lost count how many times a team member shared something critical with me that was best to know before I bring up things I wanted to talk about.

Being prepared for your one on ones is one of the best ways to build confidence and trust in your team. When they see you're taking these meetings seriously, they will, too. You'll also get more out of the meetings, so you'll see your investment in preparation really pay off.

Further reading: 

Always prepare a meeting agenda so you get the most out of your meetings with your team

Bad Boss Habit #4: You fail to keep your promises

You just had a great one on one. Your team member opened up about something really important to them, and you listened intently. You may have even talked about possible solutions, and how you can help. But then it all fell apart.

You went back to your desk and got pulled into 27 other things. As you tackled other issues, you slowly forgot the next steps you'd do to help your team.

When you show up to your next one on one with them, it finally hits you that you completely forgot to do what you promised to.

How likely are they to want to tell you something important again? Not very.

Progress matters to your people.

If you fail to keep your promises multiple times, your people will start mailing in their one on ones. No one likes to have the same conversation over and over again without any progress, nor feel patronized by a bad boss that doesn't keep their commitments.

A little progress can make all the difference in how your people feel at work. It gives them a glimmer of hope that things are getting better. It prevents them from giving up hope and thinking to themselves, "nothing ever changes here," and starting to look for another job.

And this is more than a warm and fuzzy, emotional feeling. Researchers at Harvard and Stanford found that progress is one of the most important factors contributing to people's happiness and motivation at work. Teresa Amabile summarized her research best when she wrote:

a bad boss doesn't make progress in their one on ones

What to do instead:

If you want to remember what happened in your meetings and keep your promises, the easiest thing to do is make sure you take notes in your one on ones. This simple habit will help you give you something to reference when a discussion weeks ago is no longer fresh in your mind.

If you're worried about interrupting the meeting to take notes, try one of these tactics:

  • "That sounds important to you. Let me write that down." Use this phrase to let them know you're not checking email or anything else, and that you value what they just said. They will appreciate you writing it down, and the fact you said their words are important to you.
  • Use the Last 5 Minutes Method: Use the last 5 minutes of your one on one to go over what you think you heard and write it down. This takes advantage of active listening and ensures you don't miss anything important from the rest of the discussion.

You can get more ideas on how to take notes in your one on ones here.

Remember though, taking notes isn't enough. You also need to make progress. This is why you should end every one on one with a key question:

"What can we both do by next one on one to make progress on what we talked about today?"

This engages your team in thinking about how to tackle even the toughest situations and ensures you take advantage of the progress principle. Don't leave your team hanging. Be deliberate about setting expectations and ensuring you keep your promises with them.


There's a lot more that goes into leading and motivating your team effectively. However, the habits discussed above are some of the worst mistakes that can make an otherwise good leader run really bad meetings and turn into a bad boss.

Like most important things in life, it takes effort to succeed at having great one on ones with your team. By taking the time to prepare and take notes, keeping your meetings consistently, and keeping your promises, you can turn around even the most problematic one on one meetings.

One on ones don't have to be painful meetings, but failing to do those things will ruin any chance of one on ones being the awesome, motivating investment in your people they can be.

a bad boss will miss out on the amazing benefits of one on ones

Further Reading:

If you'd like to learn more about one on ones and how to make them awesome like Andy Grove believes they are, these links can help you avoid being a bad boss:

  • 150+ questions to ask in your 1 on 1s: Break the ice, spark new discussion, and gain insights you never would otherwise by mixing up what you talk about in your one on ones.
  • How to help your people grow: Career discussions aren't always easy to start, but this post can help you with a few different approaches to uncover and make progress on their career goals.
  • how to motivate an employee who is disengaged: One on ones are a great time to work on performance issues. This post gives you a step by step process many managers have used to save disengaged and underperforming team members.
  • How to have 1 on 1s like Andy Grove: Grove was the founder and long time CEO of Intel growing them from 0 to $20 billion in revenue. He has a specific process that he used and taught his Intel managers that helped them have great one on ones.

We also have a podcast episode dedicated to the power and importance of one-on-ones. Up your game with these amazing tips from expert leaders and leadership consultants like Mike Pretlove, Jeremy Brown and Valentina Thörner:

Are you and your managers wasting their 1 on 1s?

There is no greater investment to make in your team than having 1 on 1s. Yet, done poorly they’re a huge waste of time. 

That’s why we made the 1 on 1 Master Class. You and your fellow managers learn step by step how to supercharge these meetings to motivate your teams, fix problems, coach your people, and much more. 
You can learn how Lighthouse Lessons can help your leaders like we helped SeedBox Technologies by signing up here.

Are you and your managers wasting their 1 on 1s?

There is no greater investment to make in your team than having 1 on 1s. Yet, done poorly they’re a huge waste of time. 

That’s why we made the 1 on 1 Master Class. You and your fellow managers learn step by step how to supercharge these meetings to motivate your teams, fix problems, coach your people, and much more. 
You can learn how Lighthouse Lessons can help your leaders like we helped SeedBox Technologies by signing up here.

Testimonial 7 christine bad boss,boss keeps cancelling one on ones,bad meetings,bad boss habit

What are the signs of a bad boss?

Bad bosses come in many different shapes and forms. One of the best ways to see what someone is like as a leader is to look at how they approach their meetings.

Most bad bosses, for example, make their one on ones miserable experiences, by:

  1. Frequently cancelling them; 
  2. Using them as status updates;
  3. Not preparing thoughtfully;
  4. Failing to keep the promises made during their one on ones.

What is an example of a bad boss?

There are many examples of a bad boss. Some may waste their time (and yours) with pedantic micro-management, while others will cancel 1-on-1s more often than actually have them. A bad boss might use 1-on-1 meetings as status updates, instead of checking in with their team's well-being and taking the time to listen to their point of view.

What happens when you have a bad boss?

The consequences of having a negligent or dismissive boss are:

  • Team members may stop communicating with their bad boss, effectively avoiding them.
  • Employees may seek out other people in the company to confide in instead of their actual boss.
  • Employees become more disengaged. A bad boss may notice their team is unhappy, but they won’t understand why, and won't work to fix it.
  • Star employees might start leaving because of their bad boss.
Jason Evanish

Jason Evanish

As the founder and CEO of Get Lighthouse, Inc, Jason and the Lighthouse team have helped managers grow their leadership skills in dozens of countries around the world. They’ve worked with a variety of companies from non-profits to high growth startups, and government organizations to well known, publicly traded companies. Jason has also been featured in publications including NPR, the Wall Street Journal, and Fast Company.

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