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Like a Boss: “I have to have my first tough conversation with an employee who’s underperforming.”

September 30, 2019

Welcome to Lattice’s new advice column for new managers, “Like a Boss.” I’m your host, Jennifer Romolini. I’m an editor, an author (of the career guide “Weird In a World That’s Not”), and, yes, a boss who’s been managing other humans for the past dozen or so years at companies both giant and tiny, at quick and dirty startups and multi-layered corporations, with remote and in-office teams ranging from five to 45. I’m also a speaker who talks about succeeding at work even when you feel like a freak. And, sometimes, I give advice, like right now.  


Dear Boss,

I’ve been in my current position for the past six months, it’s the first time I’ve ever been a manager and I have to have my first tough conversation with an employee who’s underperforming. What’s your best advice for how to not screw this up? I’m nervous. 

Feeling Like I Just Cannot


Dear Feeling,

Let’s be honest with each other up front: No one likes critical feedback — not the giver, not the receiver (and certainly not the innocent adjacent friends/partners/strangers on the street who’ve been forced to listen to you vent ad nauseum about the situation). I can think of approximately 16,437 things I’d rather do than give negative feedback to another human and these things may include my taxes and removing black mold. 

However, some version of “How do I give feedback?” is the most common question I’ve ever been asked. This is because, while these conversations are challenging, they’re obviously necessary, the capital A adult requirement of any management job, the reason you’re getting paid all those giant manager dollars™. When done well, feedback sessions have an enormous payoff — taking the air out of toxic office tension, helping you align vision and goals, and even, in the best cases, turning an underperforming employee into one who is prized. (I’ve seen it happen!)

So what do you need to be an effective leader giving effective feedback? Let the following serve as a guide. 

Set your goals

 Before you even schedule the talk, sit down and, in a moment when you can be calm and focused, assess what you need to communicate in this conversation and, ideally, what you’d like to see come out of it. Is this an isolated issue, i.e. the employee is late to work all of the time and you want this behavior changed? That’s a simple conversation. Or is the problem broader or more nuanced: an interpersonal challenge or a work quality issue or maybe you need the employee to stop being an obstructionist pain in the ass? How can you specifically, fairly communicate your concerns? Do you think the employee can turn around? If so, what is the timeframe for which you’d like to see change and what does that change look like? To organize your thoughts, plot out simple formulas:  What I need from a person in this role is ______, ______, ______. What I’m not getting is _____. Success looks like: by _____, I need to see _____, _____, and _____.  Try not to project a negative outcome, try not to decide in your brain how the employee will react. You want the person receiving this information to be open to change, and that requires the same openness from you.

Have a plan 

Create a private itinerary for the conversation which includes all of your findings from step one. Make it concise and to the point. Don’t roll out an old-timey scroll of complaints, a rap sheet detailing each of the employee’s flaws. Pick the most urgent things, pick specific examples of problematic work that encapsulate behavior trends and address those head on. If relevant to the conversation, mention positive things first. Show how the employee is doing well, show how you’ve noticed them making an effort, tell them about aspects of a project you liked. It’s OK to be human here — this emotional generosity will go a long way.

Schedule the meeting ASAP

To the best of your ability, schedule the meeting as soon as possible. This shows respect and consideration, it shows good faith, and helps build employee loyalty and trust. Don’t book it a week or two weeks out; even if you’re slammed, squeeze it in, and do not cancel it. If you can, avoid telling an employee on a Friday, “We need to talk on Monday” thereby planting an anxiety bomb that will tick away every hour until, when the person finally meets with you, they are so reactive and ready to explode with “getting-in-trouble” rage/fear they can no longer pay attention to anything you say. Remember: Even if it might feel like it some days (being a boss can be lonely and sucks!), you’re not at war here. So be respectful of schedules and try to keep things chill. You can also use your weekly 1:1 meeting (and schedule it in a tool like Lattice). Then you can record notes from the meeting, and track them in one place. 

Keep your feelings out of it 

Don’t personalize the situation (“You made me feel X when..”), don’t bring up how you think the employee was feeling when they did inappropriate thing X or how they were obviously being spiteful over behavior Y. Avoid catastrophic phrasing: “everyone thinks” “you always” “you never.” Use basic, non-blaming therapy language, that focuses on the impact and effect of the behavior: “When the project wasn’t completed last week, it meant that X and X happened, which…”  It might seem airy fairy, it also helps. 

Ask for feedback 

Ask the employee: What do you need from me? What’s getting in your way? How can the company do better? Then quietly sit back and listen. Give the employee space to tell you how she feels and what she thinks would make her job easier. Let her take her time. Even if you’re mad, even if you feel, in the moment, like everything she’s saying is total baloney, appear patient and receptive. Try not to get defensive or need to prove you’re “right”  — remember you’re modeling the correct way to receive feedback. Thank the employee for telling you whatever they tell you and move on.

Schedule a follow up

A follow-up meeting serves two purposes: 1. Employee accountability and 2. Your acute attention and care. Set this at the end of the meeting. In this first feedback session, keep things positive and hopeful. Be clear about your expectations for meeting two. Type them up in gentle, neutral —but still firm and clear — language. Read over your email and make sure you haven’t softened the message so much that you’ve lost the initial intent. Send to the employee for reference and also as a document for if this all goes south. (Pro tip: If you set it up in a tool like Lattice, you should also record your expectations in the notes from the meeting.)

Take care of yourself 

These kinds of conversations take a lot out of us!  It takes real energy to give to another person, to review their performance calmly and carefully. It takes it out of you. That’s why so many bosses avoid it. Practice some self-care: exercise, meditate, drink a shot of whiskey. Bask in the courage and the sensitivity it took to do something that made you feel uncomfortable and know that, even if it doesn’t work out long term, you showed up thoughtfully and intentionally and made an investment in another person. No matter the outcome, that’s the best we can do.  

Library
Articles
Managing People

Like a Boss: “I have to have my first tough conversation with an employee who’s underperforming.”

But when done well, feedback sessions can turn an underperforming employee into one who is prized.

Welcome to Lattice’s new advice column for new managers, “Like a Boss.” I’m your host, Jennifer Romolini. I’m an editor, an author (of the career guide “Weird In a World That’s Not”), and, yes, a boss who’s been managing other humans for the past dozen or so years at companies both giant and tiny, at quick and dirty startups and multi-layered corporations, with remote and in-office teams ranging from five to 45. I’m also a speaker who talks about succeeding at work even when you feel like a freak. And, sometimes, I give advice, like right now.  


Dear Boss,

I’ve been in my current position for the past six months, it’s the first time I’ve ever been a manager and I have to have my first tough conversation with an employee who’s underperforming. What’s your best advice for how to not screw this up? I’m nervous. 

Feeling Like I Just Cannot


Dear Feeling,

Let’s be honest with each other up front: No one likes critical feedback — not the giver, not the receiver (and certainly not the innocent adjacent friends/partners/strangers on the street who’ve been forced to listen to you vent ad nauseum about the situation). I can think of approximately 16,437 things I’d rather do than give negative feedback to another human and these things may include my taxes and removing black mold. 

However, some version of “How do I give feedback?” is the most common question I’ve ever been asked. This is because, while these conversations are challenging, they’re obviously necessary, the capital A adult requirement of any management job, the reason you’re getting paid all those giant manager dollars™. When done well, feedback sessions have an enormous payoff — taking the air out of toxic office tension, helping you align vision and goals, and even, in the best cases, turning an underperforming employee into one who is prized. (I’ve seen it happen!)

So what do you need to be an effective leader giving effective feedback? Let the following serve as a guide. 

Set your goals

 Before you even schedule the talk, sit down and, in a moment when you can be calm and focused, assess what you need to communicate in this conversation and, ideally, what you’d like to see come out of it. Is this an isolated issue, i.e. the employee is late to work all of the time and you want this behavior changed? That’s a simple conversation. Or is the problem broader or more nuanced: an interpersonal challenge or a work quality issue or maybe you need the employee to stop being an obstructionist pain in the ass? How can you specifically, fairly communicate your concerns? Do you think the employee can turn around? If so, what is the timeframe for which you’d like to see change and what does that change look like? To organize your thoughts, plot out simple formulas:  What I need from a person in this role is ______, ______, ______. What I’m not getting is _____. Success looks like: by _____, I need to see _____, _____, and _____.  Try not to project a negative outcome, try not to decide in your brain how the employee will react. You want the person receiving this information to be open to change, and that requires the same openness from you.

Have a plan 

Create a private itinerary for the conversation which includes all of your findings from step one. Make it concise and to the point. Don’t roll out an old-timey scroll of complaints, a rap sheet detailing each of the employee’s flaws. Pick the most urgent things, pick specific examples of problematic work that encapsulate behavior trends and address those head on. If relevant to the conversation, mention positive things first. Show how the employee is doing well, show how you’ve noticed them making an effort, tell them about aspects of a project you liked. It’s OK to be human here — this emotional generosity will go a long way.

Schedule the meeting ASAP

To the best of your ability, schedule the meeting as soon as possible. This shows respect and consideration, it shows good faith, and helps build employee loyalty and trust. Don’t book it a week or two weeks out; even if you’re slammed, squeeze it in, and do not cancel it. If you can, avoid telling an employee on a Friday, “We need to talk on Monday” thereby planting an anxiety bomb that will tick away every hour until, when the person finally meets with you, they are so reactive and ready to explode with “getting-in-trouble” rage/fear they can no longer pay attention to anything you say. Remember: Even if it might feel like it some days (being a boss can be lonely and sucks!), you’re not at war here. So be respectful of schedules and try to keep things chill. You can also use your weekly 1:1 meeting (and schedule it in a tool like Lattice). Then you can record notes from the meeting, and track them in one place. 

Keep your feelings out of it 

Don’t personalize the situation (“You made me feel X when..”), don’t bring up how you think the employee was feeling when they did inappropriate thing X or how they were obviously being spiteful over behavior Y. Avoid catastrophic phrasing: “everyone thinks” “you always” “you never.” Use basic, non-blaming therapy language, that focuses on the impact and effect of the behavior: “When the project wasn’t completed last week, it meant that X and X happened, which…”  It might seem airy fairy, it also helps. 

Ask for feedback 

Ask the employee: What do you need from me? What’s getting in your way? How can the company do better? Then quietly sit back and listen. Give the employee space to tell you how she feels and what she thinks would make her job easier. Let her take her time. Even if you’re mad, even if you feel, in the moment, like everything she’s saying is total baloney, appear patient and receptive. Try not to get defensive or need to prove you’re “right”  — remember you’re modeling the correct way to receive feedback. Thank the employee for telling you whatever they tell you and move on.

Schedule a follow up

A follow-up meeting serves two purposes: 1. Employee accountability and 2. Your acute attention and care. Set this at the end of the meeting. In this first feedback session, keep things positive and hopeful. Be clear about your expectations for meeting two. Type them up in gentle, neutral —but still firm and clear — language. Read over your email and make sure you haven’t softened the message so much that you’ve lost the initial intent. Send to the employee for reference and also as a document for if this all goes south. (Pro tip: If you set it up in a tool like Lattice, you should also record your expectations in the notes from the meeting.)

Take care of yourself 

These kinds of conversations take a lot out of us!  It takes real energy to give to another person, to review their performance calmly and carefully. It takes it out of you. That’s why so many bosses avoid it. Practice some self-care: exercise, meditate, drink a shot of whiskey. Bask in the courage and the sensitivity it took to do something that made you feel uncomfortable and know that, even if it doesn’t work out long term, you showed up thoughtfully and intentionally and made an investment in another person. No matter the outcome, that’s the best we can do.  

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Like a Boss: “I have to have my first tough conversation with an employee who’s underperforming.”

But when done well, feedback sessions can turn an underperforming employee into one who is prized.

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Library
Articles
Managing People

Like a Boss: “I have to have my first tough conversation with an employee who’s underperforming.”

Prefer Podcasts? You can listen on iTunes, or here:

Welcome to Lattice’s new advice column for new managers, “Like a Boss.” I’m your host, Jennifer Romolini. I’m an editor, an author (of the career guide “Weird In a World That’s Not”), and, yes, a boss who’s been managing other humans for the past dozen or so years at companies both giant and tiny, at quick and dirty startups and multi-layered corporations, with remote and in-office teams ranging from five to 45. I’m also a speaker who talks about succeeding at work even when you feel like a freak. And, sometimes, I give advice, like right now.  


Dear Boss,

I’ve been in my current position for the past six months, it’s the first time I’ve ever been a manager and I have to have my first tough conversation with an employee who’s underperforming. What’s your best advice for how to not screw this up? I’m nervous. 

Feeling Like I Just Cannot


Dear Feeling,

Let’s be honest with each other up front: No one likes critical feedback — not the giver, not the receiver (and certainly not the innocent adjacent friends/partners/strangers on the street who’ve been forced to listen to you vent ad nauseum about the situation). I can think of approximately 16,437 things I’d rather do than give negative feedback to another human and these things may include my taxes and removing black mold. 

However, some version of “How do I give feedback?” is the most common question I’ve ever been asked. This is because, while these conversations are challenging, they’re obviously necessary, the capital A adult requirement of any management job, the reason you’re getting paid all those giant manager dollars™. When done well, feedback sessions have an enormous payoff — taking the air out of toxic office tension, helping you align vision and goals, and even, in the best cases, turning an underperforming employee into one who is prized. (I’ve seen it happen!)

So what do you need to be an effective leader giving effective feedback? Let the following serve as a guide. 

Set your goals

 Before you even schedule the talk, sit down and, in a moment when you can be calm and focused, assess what you need to communicate in this conversation and, ideally, what you’d like to see come out of it. Is this an isolated issue, i.e. the employee is late to work all of the time and you want this behavior changed? That’s a simple conversation. Or is the problem broader or more nuanced: an interpersonal challenge or a work quality issue or maybe you need the employee to stop being an obstructionist pain in the ass? How can you specifically, fairly communicate your concerns? Do you think the employee can turn around? If so, what is the timeframe for which you’d like to see change and what does that change look like? To organize your thoughts, plot out simple formulas:  What I need from a person in this role is ______, ______, ______. What I’m not getting is _____. Success looks like: by _____, I need to see _____, _____, and _____.  Try not to project a negative outcome, try not to decide in your brain how the employee will react. You want the person receiving this information to be open to change, and that requires the same openness from you.

Have a plan 

Create a private itinerary for the conversation which includes all of your findings from step one. Make it concise and to the point. Don’t roll out an old-timey scroll of complaints, a rap sheet detailing each of the employee’s flaws. Pick the most urgent things, pick specific examples of problematic work that encapsulate behavior trends and address those head on. If relevant to the conversation, mention positive things first. Show how the employee is doing well, show how you’ve noticed them making an effort, tell them about aspects of a project you liked. It’s OK to be human here — this emotional generosity will go a long way.

Schedule the meeting ASAP

To the best of your ability, schedule the meeting as soon as possible. This shows respect and consideration, it shows good faith, and helps build employee loyalty and trust. Don’t book it a week or two weeks out; even if you’re slammed, squeeze it in, and do not cancel it. If you can, avoid telling an employee on a Friday, “We need to talk on Monday” thereby planting an anxiety bomb that will tick away every hour until, when the person finally meets with you, they are so reactive and ready to explode with “getting-in-trouble” rage/fear they can no longer pay attention to anything you say. Remember: Even if it might feel like it some days (being a boss can be lonely and sucks!), you’re not at war here. So be respectful of schedules and try to keep things chill. You can also use your weekly 1:1 meeting (and schedule it in a tool like Lattice). Then you can record notes from the meeting, and track them in one place. 

Keep your feelings out of it 

Don’t personalize the situation (“You made me feel X when..”), don’t bring up how you think the employee was feeling when they did inappropriate thing X or how they were obviously being spiteful over behavior Y. Avoid catastrophic phrasing: “everyone thinks” “you always” “you never.” Use basic, non-blaming therapy language, that focuses on the impact and effect of the behavior: “When the project wasn’t completed last week, it meant that X and X happened, which…”  It might seem airy fairy, it also helps. 

Ask for feedback 

Ask the employee: What do you need from me? What’s getting in your way? How can the company do better? Then quietly sit back and listen. Give the employee space to tell you how she feels and what she thinks would make her job easier. Let her take her time. Even if you’re mad, even if you feel, in the moment, like everything she’s saying is total baloney, appear patient and receptive. Try not to get defensive or need to prove you’re “right”  — remember you’re modeling the correct way to receive feedback. Thank the employee for telling you whatever they tell you and move on.

Schedule a follow up

A follow-up meeting serves two purposes: 1. Employee accountability and 2. Your acute attention and care. Set this at the end of the meeting. In this first feedback session, keep things positive and hopeful. Be clear about your expectations for meeting two. Type them up in gentle, neutral —but still firm and clear — language. Read over your email and make sure you haven’t softened the message so much that you’ve lost the initial intent. Send to the employee for reference and also as a document for if this all goes south. (Pro tip: If you set it up in a tool like Lattice, you should also record your expectations in the notes from the meeting.)

Take care of yourself 

These kinds of conversations take a lot out of us!  It takes real energy to give to another person, to review their performance calmly and carefully. It takes it out of you. That’s why so many bosses avoid it. Practice some self-care: exercise, meditate, drink a shot of whiskey. Bask in the courage and the sensitivity it took to do something that made you feel uncomfortable and know that, even if it doesn’t work out long term, you showed up thoughtfully and intentionally and made an investment in another person. No matter the outcome, that’s the best we can do.  

Library
Articles
Managing People

Like a Boss: “I have to have my first tough conversation with an employee who’s underperforming.”

Prefer Podcasts? You can listen on iTunes, or here:

Enjoy the presentation? Download the deck

Oops! Something went wrong while submitting the form.

Welcome to Lattice’s new advice column for new managers, “Like a Boss.” I’m your host, Jennifer Romolini. I’m an editor, an author (of the career guide “Weird In a World That’s Not”), and, yes, a boss who’s been managing other humans for the past dozen or so years at companies both giant and tiny, at quick and dirty startups and multi-layered corporations, with remote and in-office teams ranging from five to 45. I’m also a speaker who talks about succeeding at work even when you feel like a freak. And, sometimes, I give advice, like right now.  


Dear Boss,

I’ve been in my current position for the past six months, it’s the first time I’ve ever been a manager and I have to have my first tough conversation with an employee who’s underperforming. What’s your best advice for how to not screw this up? I’m nervous. 

Feeling Like I Just Cannot


Dear Feeling,

Let’s be honest with each other up front: No one likes critical feedback — not the giver, not the receiver (and certainly not the innocent adjacent friends/partners/strangers on the street who’ve been forced to listen to you vent ad nauseum about the situation). I can think of approximately 16,437 things I’d rather do than give negative feedback to another human and these things may include my taxes and removing black mold. 

However, some version of “How do I give feedback?” is the most common question I’ve ever been asked. This is because, while these conversations are challenging, they’re obviously necessary, the capital A adult requirement of any management job, the reason you’re getting paid all those giant manager dollars™. When done well, feedback sessions have an enormous payoff — taking the air out of toxic office tension, helping you align vision and goals, and even, in the best cases, turning an underperforming employee into one who is prized. (I’ve seen it happen!)

So what do you need to be an effective leader giving effective feedback? Let the following serve as a guide. 

Set your goals

 Before you even schedule the talk, sit down and, in a moment when you can be calm and focused, assess what you need to communicate in this conversation and, ideally, what you’d like to see come out of it. Is this an isolated issue, i.e. the employee is late to work all of the time and you want this behavior changed? That’s a simple conversation. Or is the problem broader or more nuanced: an interpersonal challenge or a work quality issue or maybe you need the employee to stop being an obstructionist pain in the ass? How can you specifically, fairly communicate your concerns? Do you think the employee can turn around? If so, what is the timeframe for which you’d like to see change and what does that change look like? To organize your thoughts, plot out simple formulas:  What I need from a person in this role is ______, ______, ______. What I’m not getting is _____. Success looks like: by _____, I need to see _____, _____, and _____.  Try not to project a negative outcome, try not to decide in your brain how the employee will react. You want the person receiving this information to be open to change, and that requires the same openness from you.

Have a plan 

Create a private itinerary for the conversation which includes all of your findings from step one. Make it concise and to the point. Don’t roll out an old-timey scroll of complaints, a rap sheet detailing each of the employee’s flaws. Pick the most urgent things, pick specific examples of problematic work that encapsulate behavior trends and address those head on. If relevant to the conversation, mention positive things first. Show how the employee is doing well, show how you’ve noticed them making an effort, tell them about aspects of a project you liked. It’s OK to be human here — this emotional generosity will go a long way.

Schedule the meeting ASAP

To the best of your ability, schedule the meeting as soon as possible. This shows respect and consideration, it shows good faith, and helps build employee loyalty and trust. Don’t book it a week or two weeks out; even if you’re slammed, squeeze it in, and do not cancel it. If you can, avoid telling an employee on a Friday, “We need to talk on Monday” thereby planting an anxiety bomb that will tick away every hour until, when the person finally meets with you, they are so reactive and ready to explode with “getting-in-trouble” rage/fear they can no longer pay attention to anything you say. Remember: Even if it might feel like it some days (being a boss can be lonely and sucks!), you’re not at war here. So be respectful of schedules and try to keep things chill. You can also use your weekly 1:1 meeting (and schedule it in a tool like Lattice). Then you can record notes from the meeting, and track them in one place. 

Keep your feelings out of it 

Don’t personalize the situation (“You made me feel X when..”), don’t bring up how you think the employee was feeling when they did inappropriate thing X or how they were obviously being spiteful over behavior Y. Avoid catastrophic phrasing: “everyone thinks” “you always” “you never.” Use basic, non-blaming therapy language, that focuses on the impact and effect of the behavior: “When the project wasn’t completed last week, it meant that X and X happened, which…”  It might seem airy fairy, it also helps. 

Ask for feedback 

Ask the employee: What do you need from me? What’s getting in your way? How can the company do better? Then quietly sit back and listen. Give the employee space to tell you how she feels and what she thinks would make her job easier. Let her take her time. Even if you’re mad, even if you feel, in the moment, like everything she’s saying is total baloney, appear patient and receptive. Try not to get defensive or need to prove you’re “right”  — remember you’re modeling the correct way to receive feedback. Thank the employee for telling you whatever they tell you and move on.

Schedule a follow up

A follow-up meeting serves two purposes: 1. Employee accountability and 2. Your acute attention and care. Set this at the end of the meeting. In this first feedback session, keep things positive and hopeful. Be clear about your expectations for meeting two. Type them up in gentle, neutral —but still firm and clear — language. Read over your email and make sure you haven’t softened the message so much that you’ve lost the initial intent. Send to the employee for reference and also as a document for if this all goes south. (Pro tip: If you set it up in a tool like Lattice, you should also record your expectations in the notes from the meeting.)

Take care of yourself 

These kinds of conversations take a lot out of us!  It takes real energy to give to another person, to review their performance calmly and carefully. It takes it out of you. That’s why so many bosses avoid it. Practice some self-care: exercise, meditate, drink a shot of whiskey. Bask in the courage and the sensitivity it took to do something that made you feel uncomfortable and know that, even if it doesn’t work out long term, you showed up thoughtfully and intentionally and made an investment in another person. No matter the outcome, that’s the best we can do.