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How to navigate a difficult professional conversation

How to navigate a difficult professional conversation

Sweaty palms. Stuttered starts. Finishing the meeting and thinking, “oh I wish I’d remembered to say that!”

We’ve all been faced with difficult situations at work, and for many of us, when we reflect on those times, they can come with regrets. What if I had known this thing beforehand? What if I had prepared more? What if I had remembered to include this important detail that I got too flustered to mention?

The good news is that a little preparation can go a long way. Whether you’re asking for a raise or providing critical feedback to a manager, there are guiding principles you can follow that can make for more valuable and mutually beneficial professional conversations, no matter how difficult they are.

4 tips for navigating difficult conversations at work

1. Write out all your thoughts. Then reframe them.

Sometimes, when we feel like it’s time to have a difficult conversation – whether it’s feedback to give, a raise to ask for, even quitting a job – it’s when we are at or near our most emotional about the situation.

It’s at these moments when it can be beneficial to just brain dump all of your thoughts and feelings onto paper (or type them in a Google Doc or the like). Write without judgment; let your stream of consciousness about the situation flow. When you’re done, take a step back and read what you’ve written. As you’re reading, assess your thoughts and feelings and look for some patterns. You might be enraged about one thing in particular, but maybe there’s a trend of behavior that’s more valuable to callout.

By doing this reflection, you’ll be able to approach these conversations from a more reflective place, and less instinctive based on a single circumstance.


2. Remember that it’s not about any individual. It’s about the business.

Conversations about work are inherently different than discussions in our personal lives. At work, it’s important to not center ourselves, but rather put the company, business, or business goals at the forefront.

It’s easy to say, “my manager isn’t letting me achieve my goals”, but it’s more valuable for the person on the other side of the conversation to hear you say “this level of micromanagement is impeding our ability to move quickly as an organization, and I’m worried our OKRs are at risk.” While a good manager or HR department will be concerned about your individual wellbeing, it is their job to be concerned about the organizational health.

Wherever you can, take a look at everything you wrote down in our first tip, and see how you can reframe in light of business goals. If you can tie your individual strife to those goals, you’ll have a much more compelling argument.

3. Ask yourself: what is the outcome you want to achieve? And be honest – is that possible?

This is perhaps the most essential point before deciding if you want to even engage in a difficult conversation. Have a clear goal in mind for that conversation, but also be honest with yourself if it’s even achievable. That is not to be meant in a self-deprecating way, but rather, if you feel you are underpaid in the market and you want to double your salary, but your company is tightening budgets and just did a big round of layoffs because of lack of funds, the outcome you want probably isn’t going to happen.

In that same circumstance, if the outcome you want to achieve is that you want an incremental raise with the promise of a review in six months, that might be a better starting point. Another way to consider this same situation would be to have a main goal in mind and a variance of flexibility in which you’d consider the conversation a “win.”

Going into a chat with black-and-white thinking (“it’s double my salary or I quit!”) will often lead to more rash decision-making on your part, and more often than not, an unsuccessful outcome.

4. Be nice and listen.

Difficult discussions at work are hard for you, and they are often hard for the person on the other side of the table.

When you need to give critical feedback, acknowledge that it is hard for the other person to receive it. You can consider level-setting a conversation with a question of consent, like “I want to discuss some constructive criticism, but first I want to ensure you’re in a good place to receive it.” If that sounds arduous or forced, just be present and attentive within the conversation itself. Be kind and be an active listener. If things feel like they are getting tough for you or the other person, pause and reset.

While our second tip tells us that business goals are paramount, that doesn’t mean that we aren’t all human. Opt for empathy whenever and wherever you can!

Here's something else you can listen to: These 5 side project podcasts

Time to navigate a difficult conversation! (Hopefully not)

Now that you’re feeling more prepared, it’s time to engage in that conversation. The good news is, you can put these tips to practice at work (asking for a raise, bringing to light a work issue, resigning) and at home – although Tip Two should be fully disregarded in all personal matters.

In no time, these tips will feel like second nature and you can say goodbye to all the woulda-coulda-shoulda and regret of engaging in difficult discussions!

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