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.

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