Handling difficult conversations

A single orange rose

We’ve talked a bit about some of the reasons that corrective feedback conversations feel scary to people: we worry about how our feedback will be received, we worry that they’ll take it personally, we worry that we don’t have the full picture and therefore don’t have the “right” to deliver the feedback. Other kinds of difficult conversations carry their own fears: fear that we’ll undermine the other person’s trust in us, fear that we’ll lose credibility if we admit that we messed something up, fear that the information we have to share will negatively impact their lives… the list goes on. Adding the word “manager” to your title doesn’t mean you lose those fears, and it doesn’t mean you can ignore them, but it does mean that you don’t get to let the fear have the last word.

As an example of a difficult conversation that isn’t necessarily about corrective feedback, let’s talk about money. Most managers, especially in impact-driven organizations, will need to have a difficult conversation with a report about money within the first year or two of being a manager. Sometimes, that’s responding to a prospective hire who’s disappointed with the initial salary offer when you don’t have much flexibility; other times, it’s letting an existing employee know that the raise or promotion they requested isn’t going to happen.

Thinking about that kind of conversation might have already made you feel a little uncomfortable. That discomfort can make it really tempting, particularly when you’re dealing with an existing employee, to put the conversation off as long as possible. You might worry that telling your report that you weren’t able to get them the salary they’re looking for will make you look ineffective. You might even hope that the problem will resolve itself eventually.

Here’s how that problem will resolve itself if you don’t address it directly: your employee or prospective hire will get frustrated and lose faith in your ability to get things done. You will look ineffective. Not only that; you will be ineffective. Your report might start looking for other jobs, and your prospective hire will likely lose interest. It’s imperative that you, as a manager, initiate tough conversations when the need arises.

So how do you go about working through that discomfort and making the situation clear for your direct report?

There’s a common customer-service approach for times when a customer has asked for something you really can’t deliver: start by sharing what you can do for the customer to meet the same set of underlying needs, even if you can’t do the specific thing they’re requesting. I find it helpful to approach difficult conversations with the same framework: understand the set of needs that the employee is hoping to meet with a higher salary, and see if there are ways that you can help them meet those needs in another way.

You don’t have to guess at what those needs are, nor does your employee have to tell you specifically why they need more money; the end goal is “more money,” and that’s clear enough to make a plan. As you prepare for the conversation, it can be helpful to come up with a few ideas of how to make things work and be open to considering other ideas they might have. Think of some questions you can bring to the conversation (not all of these will be appropriate for every money conversation, and some of them are trickier than others, but they’re a start):

  • Do they need to build a certain skill set to be a good candidate for a promotion to something that’s in line with their salary needs?
  • Are there professional development opportunities like classes or conferences that you can help them identify/take advantage of at lower cost to the organization than the salary raise?
  • Would changing some of their responsibilities make their current salary feel fairer, or would that feel punitive?
  • Do they need a little more flex time to work on a side gig?
  • Are their personal growth goals better suited to opportunities outside your current organization?

As you ask these questions, be ready to apply your active listening skills so that you can fully understand the problem you’re trying to solve.

For the sake of clarity, it’s important to think about the first thing you say in the conversation; you don’t want them to shut down before you go into problem-solving mode. You could start the conversation with something like “I want to talk about the raise we discussed last week; while I can’t make the (full) raise happen, I’d like to talk about what we can do to make your compensation work for your needs – whether that’s an adjustment of hours, more flexibility, a different set of responsibilities, or something else that I haven’t thought of yet.”

If you’re still feeling apprehensive or fearful about the conversation, I’d encourage you to examine that fear and identify, as specifically as you can, what you’re afraid of. That’s not to say “there’s nothing to be scared of” but rather, “identify what you’re scared of, because that can help guide the way you approach the conversation.” If you’re afraid of not being clear, you can write down what you need to say ahead of time. If you’re afraid of seeming callous or “corporate” in delivering bad news related to money, practice the conversation with a friend, or better yet, a therapist. (They’re confidential and usually emotionally perceptive.)

I promise there will still be hard conversations. But you’ll be better equipped to feel in control of the situation if you can approach the conversation from a reliable framework, and from a problem-solving or problem-mitigation perspective. In fact, this isn’t really all that different from the feedback structure we talked about in an earlier post:

Initiating difficult conversationsInitiating corrective feedback
Clearly present the issue.State the behavior.
Be explicit about wanting to identify and solve for (or at least mitigate) the underlying problem.Discuss the impact of the behavior. (The impact is the underlying problem you’re trying to solve!)
Identify some ways you could use your existing resources to address the underlying problem.Identify some possible requests for future changes to the behavior.
Allow space for the other person to identify solutions you hadn’t thought of.Ask questions to gain additional context.

Perhaps more importantly, you’ll be better equipped to handle difficult conversations equitably for all the members of your diverse team, which in turn will lead to more equitable growth opportunities and increased effectiveness – in short, to a better team.

Active listening for managers

a purple echinacea flower in a vase, seen from above, a clear focus of attention.

In last week’s post, we talked about the importance of cultivating empathy and curiosity as foundational principles of an inclusive team, and we discussed the fact that one key skill that enables people to act out empathy and curiosity at work is active listening. This week I want to go deeper and get practical: how do you go about exhibiting that key skill to your team?

In remote settings, making it clear that you’re listening requires some intention and preparation. Before your next meeting, take a look at your setup and identify your most frequent distractions. (If your most frequent distractions are other humans currently quarantining with you, I am the wrong person to give you focus advice, and the next couple of paragraphs are probably going to sound ridiculous – but hopefully they’ll help you develop some good meeting habits that you’ll be able to stick with in days when a more controlled environment is feasible.)

In my remote-meeting setup, I generally have two monitors, one where I keep my video meeting at full-screen (tip: make this the monitor with your webcam on it for a better “I’m paying attention to you” experience for your colleagues) and the second where I’m taking notes, presenting slides, or keeping reports handy for reference. If I have my email or chat apps easily visible on the second screen, I’m likely to get distracted by incoming requests, typically things that aren’t actually urgent or important to deal with in that moment. Most of us are now conditioned to pull our attention immediately to any sort of notification icon; arrange your notification settings and browser tabs to minimize their impact on your physical and virtual meeting space.

I’m also a fidgeter. If I’m not taking notes, I’m likely to be messing with whatever object is nearest my keyboard or kicking at fidget devices at my standing desk. For the other person in the meeting, it looks like I’m not paying attention if they don’t know that it’s a focus tool for me. To preempt that feeling that my fidgeting can bring up, I try to remember to say it explicitly when I start meeting with someone new, and I try to keep my fidgeting out of frame as much as possible. Because I know this about myself, I also try to keep my phone in a place where it isn’t likely to be “the object nearest my keyboard” so that I don’t turn it into my fidget device; engaging with my phone will actually take my attention away from the meeting.

Once you’ve established an environment that allows you to pay attention to your colleague, create space for them to tell you what’s going on by asking open-ended questions. By this, I mean questions that don’t lead your colleague to any specific answer, that ideally give them a chance to describe a situation in detail, and that prompt them to say more than “yes” or “no.” (Yes-or-no questions often contain a hint at the answer you expect. Sometimes you need to do this to nudge someone toward a solution! But that’s not “active listening” mode, which should be your default.) 

The goal of your open-ended questions is to get at issues underlying any challenges or obstacles that your team member might be facing. Often, that will mean that you need to (gently) push them to consider the challenge in a new way with questions like “What do you think is causing that?” (This is a wordier way of asking “Why?”, which can sometimes make people feel defensive; “why do you think that is?” also works here.) In a relationship where you have some measure of trust already built, and the element of defensiveness is less of a factor, you can go to the “toddler tactic”: continue asking “why?” until you get to the thing that feels like the real root of the problem. (You’ll sometimes hear this described as “the Five Whys” method, generally attributed to Taiichi Ohno, the author of Toyota Production System: Beyond Large-Scale Production.)

As your report describes a situation, you may identify moments where you think there’s more to be said. Listen to your instincts there; the phrase “do you want to say more about that?” is my go-to when I want them to elaborate, without inserting my interpretation of what they mean. I’ve often made a guess about what they mean before asking them to say more; asking in this way allows me to check my guess before it becomes an outright assumption.

Part of active listening is getting comfortable with moments of silence in a meeting. While your report is talking, avoid the temptation to formulate your response in your head; thinking about what you’re going to say next while someone else is talking is inaudibly talking over them. Give them space to finish talking, allow a moment or two of silence while you formulate your own response, and then continue the conversation. Nodding while you do that is a subtle way to indicate that you’re still engaged in the conversation, and I also like to be explicit that a little silence in a meeting is a good thing and doesn’t mean you’re wasting time.

One last key component of active listening as a manager: once you have the root of a challenge, work with your report to identify action items, and make sure that they happen. There are contexts where simply listening to someone is enough to support them; a manager/report relationship is not one of them. You need to take action to help them address the issue. If you plotted “behaviors of a good friend” and “behaviors of a good manager” in a Venn diagram, it would have a lot of overlap, but would not be not a circle, and listening just for the sake of listening would only land in the “behaviors of a good friend” section.

Modeling this skill is a critical part of your work as a manager of an equitable, effective team. As a leader, your organization has placed an implicit value on you and your behavior; modeling active listening as a means to empathetic, curious collaboration shows your team that those behaviors are valued in your organization and encourages them to do the same. In addition, think about how you can ask them to show this skill in their own work and measure their progress against it. (That’s a sneak preview of next week, where we’ll talk about ways to measure your team on skills that can show “potential” for more senior roles or increased responsibility.)

Improving work relationships: the Empower Work coaching model

This week’s post is a collaboration with the Empower Work team – head to their website to learn more about their peer counseling services, to volunteer, or to donate.

With some time on my hands after joining the ranks of those impacted by COVID-19 layoffs, I decided to sign up as a volunteer peer counselor with Empower Work. I’d been following their efforts for some time and thought that the model showed promise as a way to help address many of the issues that I’ve seen my friends and colleagues encounter at work. Having been through the training program, I can confidently say that I was right.

Throughout the training process, volunteers are encouraged to bring what they’ve learned during training to their everyday lives, and I couldn’t agree more. Empower Work conversations are unique in a lot of ways: they’re anonymous, they’re completely about the person seeking help, and the peer counselor has only as much context about the situation as that person shares. This makes it absolutely essential to rely on a few skills in particular that are easily overlooked in our “real life” work relationships, but that can be especially valuable in a challenging conversation – say, one between a manager and their direct report.

While I’d recommend this for just about any work relationship, this kind of approach can be especially helpful for managers who are new to their team, or those who are starting to oversee the work of team members who are well established in their roles. Those folks don’t need their manager’s help learning to do their job – their manager may not even know how to do their job as well as they do – but they often need their manager’s help overcoming obstacles and getting through difficult situations. These are skills that can help the manager be an asset to their team, even when the details of the individual report’s work aren’t the manager’s best area of expertise.

Be aware that you don’t have the full context – and that’s okay.

By nature, an Empower Work peer counselor can’t possibly have the full context of the situation that a person texting in is facing. When we face difficult conversations with the people we work with, we have much more of the context, and can often establish a shared understanding of the situation before a difficult conversation happens… but it’s never complete.

As employees, it’s common to assume that our managers know everything about our work. As managers, it’s common to assume that what you see of your direct report is all that there is. When we make these assumptions, we lock ourselves into an idea of what any given problem is that may be wildly off base. That’s not because we were hopelessly wrong or are bad at understanding things! It’s because we never know the whole story. Ideally, it should be up to the manager to recognize when there isn’t enough context to make a decision or a plan, but there are times when an employee needs to take the reins (sometimes called “managing up”). 

Once you know that you don’t have the full context, how do you get enough to form an action plan? You…

Ask open-ended questions.

As your colleague describes a situation, you may identify moments where you think there’s more to be said. Listen to your instincts there; the phrase “can you say more about that?” is my go-to when I want them to elaborate, without inserting my interpretation of what they mean. I’ve often made a guess about what they mean before asking them to say more; asking in this way allows me to check my guess before it becomes an outright assumption.

Open-ended questions open possibilities for your colleague and that give them a chance to describe a situation in detail. The goal is to get more context, not drive advice or a solution. 

Aim to understand the impact of the issue on the person

Often, if someone is raising a problem to us that we weren’t previously aware of, it’s not because we didn’t know that the situation existed – it’s because we weren’t seeing it as a problem. That is to say, we didn’t understand the impact that the situation was having on our colleague. This is a key part of the context that we’re often missing.

It can be tough to recognize when we’re missing this part of the story. Some indicators that there’s more for you to understand about the impact on the person:

  • The question “what’s the big deal?” is sitting at the front of your brain. Find a way to let them answer that question earnestly, such as “how is this impacting you right now?”
  • Your colleague is from a marginalized identity group that you aren’t part of. Our identity shapes our experience in ways that may be difficult to communicate, so if they’re telling you about their experience, believe them.
  • You think you know what the impact is, but they haven’t said it. Say what you’re hearing to be at stake for them, and ask them how that lines up with what they’re feeling. 
  • You know how you would feel in their shoes, and are assuming they feel the same way. Let them have their own feelings!

Identify what feels important to them

As you learn more about the impact on the person, you’ll also be learning about the things that are important to them. This can help shape your approach to future conversations in ways that can make it easier to communicate candidly, fluidly, and with trust. Seeing and acknowledging what matters to your colleague is one of the clearest ways to demonstrate that they matter to you, which will bolster your team’s trust in the long run.

Empower Work volunteers are trained to use these skills and more to suss out what’s important to the person connecting for support, understand what the impact of their situation is, and to identify the right moment to work with the person seeking help on achieving an outcome that works for them. As different as those conversations are from our day-to-day work relationships, they can share key approaches: Whether you’re in an anonymous, one-time conversation with a stranger or in your regular weekly one-on-one with your manager or direct report, being curious and ready to set aside assumptions about the other person’s context, values, and impact are critical to getting to the heart of just about any workplace issue.

Intentional culture

A bouquet of spring flowers viewed from above, against a white tabletop

Imagine it’s your first day on a new job. You’re excited about the role that you’ve taken on, you’re excited about the company – what you know about it so far, anyway – and you’re eager to get started.

How do you start to understand the culture of the organization? I’m not talking about the mission, vision, and values – although you should definitely also know what those are – but the concrete ways that those values play out (or don’t) in your relationships with your coworkers.

In a co-located space, you can rely on clues from the space around you, especially visual cues if you’re a sighted person and auditory cues if you’re a hearing person. Without consciously thinking about it, you can glean the answers to a lot of questions:

  • Is the unofficial team motto “work hard, play hard”?
  • Are people around you eating lunch at their desks or getting up to go outside for a walk?
  • Is there a lot of non-work “water cooler” chat?
  • Can you see the various office cliques that form around non-work conversations?
  • How are people dressed?
  • Are plans being made to spend time together outside of work? (Who is left out of those plans?)
  • When talking about work, are there a lot of silos and territorial approaches, or are projects approached more collaboratively and cross-functionally?

These are all cues about how we act and relate to one another that don’t exist if you’re working remotely (and, by the way, are a lot harder to pick up if you don’t have access to sight or sound, or if it’s difficult for you to read social cues for whatever reason). Often, we pick these kinds of things up organically, by observing how our more established coworkers interact with each other (and, if they are especially nice or have a good onboarding protocol, how they interact with us).

When we’re new to a remote environment, whether we’re used to physically working together in person or not, we have to build up those elements of culture intentionally as if we were asking those questions for the first time. Left to our own devices, remotely, most of us won’t initiate a conversation that isn’t directly relevant to work, so we lose some of the connections that we establish with co-located colleagues that way; plus, in work-related conversations, we have to learn how to convey our intended tone without always relying on in-person social cues.

As a manager, it’s important to ask yourself: how do you think questions like the ones I’ve framed above should be answered on your team? What are the answers to those questions that best reflect your company’s core values? Then, make that answer explicit and work with your team to figure out the best ways to enable it to happen. Some considerations that might come up:

  • How will you approach scheduling in a remote environment?
  • What channels work best for which types of communication?
  • Can you identify cliques that already exist and what impact they’re having on who has power and influence at work? (I promise there are cliques influencing power at work, and if you’re not thinking about who’s in them and why, they are very likely to leave behind your colleagues from minoritized and underrepresented backgrounds.)
  • How can you provide intentional space for non-work conversation in meetings that you run?

It will feel forced and awkward at first to do things like announce in your chat app that you’re going to lunch or stepping away to take care of your family: you are forming new habits, and if new habits were easy to form, we would all have impeccable flossing routines. Be candid about the fact that it feels forced and awkward, and encourage your team to let you know (maybe by means of an anonymous form they can fill out) if “forced and awkward” starts to cross a line into “uncomfortable and invasive.”

I’m not the first to observe that remote management requires a level of intentionality and focused communication that’s easy to let happen naturally in a co-located context. In this article by Juan Pablo Buriticá, and Katie Womersley, Buriticá writes “Remote teamwork doesn’t happen by accident, but through deliberate systems and practices around communication, coordination, collaboration, organization, operations, and culture.” Those deliberate systems and practices, I’d argue, are worth your time to create even if you think you’ll be fully co-located post-quarantine.

Establishing a culture that’s intentional, explicit, and focused on your core values is critical to the success of a remote team. When applied to co-located teams, it helps to ensure that the culture that develops among your staff is aligned with the values you want your organization to reflect and the mission you want to achieve. Even if your organization is entirely co-located, you shouldn’t be relying on teamwork happening by accident; instead, I encourage you to consider the ways you’ll do things now that you don’t get to rely on happenstance.