Difficult conversations at work: A how-to

Difficult conversations at work header

Most of your office life can come back to difficult conversations at work. Feels like it would be good to talk about what those tend to be and how to handle them, right?

Let’s start with a couple of basic concepts around the umbrella idea of difficult conversations at work. These concepts tend to create said difficult conversations:

Management isn’t actually intuitive for many people: What do I mean? Well, you typically get promoted for a specific set of reasons — often around being good at tasks or deliverables. People almost never get advanced to managerial levels based on interactions with people, which is very flawed (but interactions with people are harder to track and more subjective in the eyes of most senior leaders, and/or those senior people don’t really care about people and view them as interchangeable). Because management isn’t intuitive, and thus people are becoming managers without a good understanding of people, difficult conversations at work often arise.

Work isn’t logical; it’s emotional. We want work to be logical, which is why we throw process at everything (BPO, baby!). Work isn’t actually logical. It’s made up of people, so, uh, it’s inherently emotional. But again, we tend to promote and advance people who are good at the process side, because that side is more visual and controllable — and people like those things. Just because you’re good w/process doesn’t mean you’re good with people, and that creates a lot of difficult conversations at work.

Many managers feel uncomfortable even talking to their employees: This has been borne out time and time again in research, including around notions of managers feeling like they “don’t have time to respect” employees. The sheer fact is … most managers don’t really even enjoy talking to employees — it makes them feel uncomfortable — and obviously that’s going to lead to a ton of difficult conversations at work.

And now we’ve arrived at a good segue point!

Difficult conversations at work: Research!

Here’s an article on Harvard Business Review about work conversations we dread, and we’re going to have some fun with a couple of visuals now.

Let’s start with this one:

Difficult Conversations At Work: Preparation

This is about how people prepare for difficult conversations at work. There’s a number of batshit crazy elements here, although let’s acknowledge the good stuff first: it does seem people are more likely to prepare for these difficult conversations at work than anything else. (Yay!) Of course, the highest “very unlikely” on this chart is “warn the other person about the conversation,” which leads me to believe a lot of managers are blitz-krieging hapless rank-and-files at the once-a-year performance review and screeching about “accountability!” Because the rank-and-file only gets evaluated once a year and probably had no idea this conversation or feedback was coming, the whole thing is a total mess and waste of time.


Also: this “direct and concise” area seems very important around the idea of having difficult conversations at work, which is logical. That’s classic managerial training in a nutshell, right there. In reality, most managers probably assume they’re being direct and concise and they’re meandering around like a jackass in Compliment Sandwich Territory. (I think that’s somewhere in Oregon.)

Here’s the second visual:

Difficult Conversations At Work

The most difficult conversations at work seem to occur around salary, which is logic: absolutely no one truly understands what their salary even represents. One of the funniest things on this visual is that the lowest rating for “very uncomfortable” is “lack of clear direction,” which is a problem almost every organization has — i.e. a complete lack of organizational priority. Despite that being the problem that drives almost every other problem, people apparently don’t freak out about discussing that with others. Interesting.

And the trifecta visual:

Difficult Conversations At Work: Supervisors

Look at the highest ranking for “completely dissatisfied” in terms of difficult conversations at work.



It was probably one of these worst types of managers, honestly.

Difficult conversations at work: Knowing this, how do we improve them?

This is obviously hard. Communication is a challenge for a lot of people, and it’s especially a challenge at work — work is supposed to be all about ‘what’s measured is what matters.’ Communication doesn’t fit into that boat.

You can Google around the topic of ‘effective conversations at work’ or ‘office communication’ or ‘best practices for listening at work’ and get about 19.2M results. Here’s a dirty little secret: it’s all buzzwords, bullshit, and fluff. It’s basically inherently meaningless.

Difficult conversations at work aren’t easy, and they’ll never be easy. But there are a couple of tips.

Embrace awkwardness: Embracing awkwardness is actually really important, because it can humanize the situation at hand. Take a discussion about salary. No one wants to discuss money. The middle class was essentially brought up on the idea that you can’t discuss money, sex, or failure. Conversations about salary will always be awkward, but go ahead and lean into that awkwardness. Open with something like “Well, this is always hideously uncomfortable.” Get a laugh. Whatever. It’s better than making it more awkward by diving right into the deep end of this type of conversation. “Listen Paul, you’re just not a 120K per annum guy, OK?” Now Paul has 1.5 feet out the door of this company, and Paul might be the only guy who knows how to analyze data — so when he leaves, you’re uber-fucked as the CEO screeches about data as a competitive driver. “Uh, chief? We just lost our only good data guy.” Now your ass is on the line too, and it’s all because you fumbled the snap around difficult conversations at work. So, lean into awkwardness. It can help.

Offer context on both sides: One of the worst things about any workplace is that people tend to withhold information down the chain, either because they believe it’s proprietary or they just want to hoard information so that people have to seek them out for it … in turn increasing their own sense of ‘purpose’ or ‘relevance.’ When information is clustered and silo’ed, no one really has a good, complete picture of what’s what. This is actually a huge factor with salary: there’s almost no transparency at most organizations about who makes what and why they make that. As a direct result, very few people understand how earning potential works and tend to assign it out to long-held, traditional factors like “Sam’s a go-getter!” No. That’s part of it, but the real deal is that Sam kills it on the 1.2M dollar clients, and that pleases the top dogs — or that Sam has a MBA, or whatever the fuck. Without context and information, difficult conversations at work become even more difficult. So offer some. “Here’s how our finances look and here’s how we tier salaries via experience and performance,” etc. It’s amazing what transparency can do for a relationship at work, you know?

Offer some fault on your side: This has made me want to shatter a glass window with my bare fist at most gigs I’ve had. Tons of managers assume that hierarchy vetted them to the point that formal power means they never have to show weakness, which is a fucking train wreck because some of these people are probably vaguely familiar with the Bible, and … uh … um … er … Jesus? Leaders are actually better when they show failure and weakness, but because work is a massively complex game of “I’m Not Incompetent!” that doesn’t often happen. This creates the most difficult conversations at work — some manager basically gave you no context or background on a project or client, and suddenly you’re under a bus and the bus is being backed up over you 191 times. “Fall on the sword, Greg!” OK. Maybe Greg did a few things wrong, but you know what? Greg’s manager probably did about 27 things wrong in the process too. Greg’s manager should admit that. But he’s likely not going to. And there you have the root cause of most difficult conversations at work.

Difficult conversations at work: The power of failure

Simply put, we should talk about failure more openly at work — and if you just hurled yourself off a 17th-story elevator en route to a Q2 metrics stand-up, let me explain why. First off, failure happens. It happens in every organization, and it’s not going away. There’s no way to manage around failure; you need a strategy for dealing with it. And if you have that strategy in place? It can actually be a driver of success, and that’s backed up by stock market data!

Look, work can suck. Work can be awesome. But regardless of where you come down on that continuum, difficult conversations at work will arise. How would you handle them?

Ted Bauer

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