Managing People

Like a Boss: “How do I have tough conversations with a struggling employee during this crisis?”

May 28, 2020
November 7, 2023
Jennifer Romolini
Lattice Team

Welcome to Lattice’s 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 have an employee who I know is going through some hard times and feelings through this COVID-19 situation, and it's starting to affect her work. She tells me she's having a hard time with motivation and I've spent a lot of time talking her through it. But at what point and how do I start asking her to step back up? Is there a way to do that when I know everything is hard right now?

Trying to Make It Work

Hello there Trying,

Real talk: There’s not a manager on Planet Earth who enjoys addressing an employee’s performance issues. We don’t like it in the normal times and it certainly feels unpleasant and even unseemly now when we’re living through a collective trauma — when evaluating how well a person is doing their job can seem petty, if not downright absurd. As goals-oriented leaders (and humans), we like order and control. We like tidy, formulaic ways to measure our success and the success of those around us. But with the messiness of the pandemic and with so much of our lives upended, it’s harder to know how to assess performance and even harder still to correct course if someone seems to be heading off the professional rails.

Your instinct here is to be generous and empathetic — which is big-hearted and wise — but you must be sure you’re not confusing empathy with enabling. By continuing to give your employee a pass, you won’t solve the problem, but you may create new ones, including eroding your relationship, building resentment, and negatively impacting team morale. The most compassionate thing you can do right now is to responsibly address your concerns and empower your employee to sort out what it will take to get back on track. 

TL:DR: There’s a compassionate way to discuss performance issues AND stay true to your values. Here’s how.   

Step 1: Think Before You Act

Where all this is headed is a tough conversation, but before you schedule it, give yourself time to architect the meeting and plan the message you want to convey. This is your moment to get focused, gather information, and examine your feelings. Your goal is not only improved performance, but an employee who is reengaged with her work. And that will take careful maneuvering. 

Ask yourself:

  • Have you set the employee up for success? 
  • Have you clearly communicated your expectations? Do they reflect any recent changes? 
  • Are you giving regular feedback? 
  • What benchmarks are you using to gauge her performance? Are they reasonable/fair?

For some companies, our new remote reality is uncovering organizational weaknesses managers may have never seen if their teams were still huddled around a conference room table. Clumsy instruction, confusing systems, or grandfathered-in workarounds that were efficient enough pre-COVID may all be a hindrance in our current world order, impacting how employees feel about — and do — their jobs. Before you set a time to talk, examine areas where working conditions could be improved and come up with a few tentative solutions. 

Before the check-in meeting, make a few lists (I like to handwrite these, it’s good for your brain!): 

  1. Tasks you need your employee to complete each day, week, and month. 
  2. The areas where you feel she’s coming up short. 
  3. A series of questions to ask during your meeting, including: Does she understand her job? Does she have what she needs to do her job well? If not, what does she think she needs to be more motivated/engaged?

Step 2: Get Out of Your Feelings 

Before you set the meeting, you may want to interrogate your feelings about this employee and her needs. This may be an uncomfortable exercise. It’s still worth doing. Ask yourself:  

  • Is your employees’ neediness triggering? 
  • Are you having a hard time showing up for her because you’re struggling with your own mental health?
  • Are notions about work ethic or unhelpful (but hard to shake!) messaging about “sucking it up at all costs” causing you to judge her more harshly? 
  • Are there parts of this situation that you’re projecting or over-inflating due to your own biases?

Once you are able to identify and acknowledge your own feelings in all of this (with kindness and sensitivity to yourself — you’re doing great!), you’ll be better positioned to look at it calmly, and to advise and lead.  

Step 3: Have a Tough Conversation

Okay, so now is the time to take your lists, check your emotions at the door, and show up fully for this Zoom call. Keep in mind, and make sure to communicate, that conversation is not a punishment, you know this is not easy for anyone, and you want her to succeed. That’s why you’re here. 

Acknowledge and validate her struggles at the start of the conversation and continue to do so throughout. Tell her you’re here to help tackle the issue together. Remember that you cannot solve this problem for her, you can only help lead her to the solution. Ask a lot of questions! Really listen to the answers. Where is she struggling most? Does she need more guidance or check-ins? What feels reasonable/doable?

By the end of the call, set at least one new deadline and one new benchmark for improvement. Make sure she knows that mistakes are okay, that you just want to see growth and engagement, that you’re here to help. Because you are. After the call, take your notes and look for creative ways to keep the conversation going. 

At the end of all this, It may be that the relationship won’t work out, that the employee is not up for the job — things that are out of your control. But cross that bridge when you get to it. For now, put in the kind, thoughtful effort to make it work.