Navigating Tough Conversations At Work

We’ve all been there — when you get to the point where you can no longer hold in your frustrations at work. You want to voice your concerns, but it’s such a risky move. You don’t want to piss anyone off, especially not the person who hired you, but if you don’t say anything you run the risk of remaining unhappy and having it affect your work. How do you manage those conversations to get your point across as smoothly as possible?

I recently read this article that says, For Women and Minorities To Get Ahead, Managers Must Assign Work Fairly. And while I identified with 100% of the points since I’m both a woman AND a minority, I still felt something was missing. Not only must managers do their part in any situation, employees must take action and speak up. Unfortunately, I’ve been in this position way more times than I’d like to count. But I’m okay with that because that lets me know I care about my professional development and personal stress levels enough to address my concerns head-on. Those who know me know I never let things slide if I feel bothered, and I’ve had a lot of practice with confronting my issues with others.

Here are some of my tips on how to navigate tough conversations in the workplace.


Take some time to identify the source of your frustration. What exactly is the problem? What were the incidents that got you to this point? Be proactive and try to anticipate the questions or rebuttal you’ll receive. It’s important to practice for confidence, but try to avoid being scripted. This way you won’t be thrown off if the conversation does not go exactly as you thought it would.

Ultimately, you have to think of this as a pitch; you’re presenting a case for why you deserve that promotion, that highly-visible project, to be treated with more respect, etc. With any presentation, you have to come prepared with facts and know your stuff. Difficult conversations at work are no different. If you can’t speak to the value you bring, how do you expect someone else to recognize it?

Use all of those notes to evaluate whether or not there was something you could have done differently to steer the situation in a different direction. Then narrow it down to a few key points to keep the discussion organized and productive.


Now it’s time to tailor your approach. Be ready to suppress your attitude, fix your face, and think before you speak. This is already going to be a touchy discussion, so you don’t want anyone to feel attacked, especially if they have the power to fire you. Timing and setting are important. You may not want to have this discussion in front of others (especially not around your instigating peers or your manager’s manager). Set up some time to grab coffee or lunch to reduce some of the tension that could possibly build up if you were to have this conversation in a stodgy conference room.

If you’re addressing something via email, take a step back to read through it all. If your email was forwarded to your CEO, would he/she be proud of your approach? If not, the ‘backspace’ key is your friend.


I’m not telling you to go demanding to have your manager’s job since you do all the work anyway. This is not the time to request a huge raise knowing you get to work and chat on GroupMe all day. Be honest with yourself. Do you deserve what you’re asking for in this tough conversation? Have you actually put in the work that would warrant that raise? That promotion? That increase in responsibility? Take this opportunity to garner some serious change that can truly impact your career. There’s a difference between practical aspirations and quixotic expectations.

By no means is this an exhaustive list of ways to handle situations like this one, and I’m not claiming to be an expert. I’m just sharing what has kept me from resulting to empty venting sessions with coworkers, and instead directed me towards desired results. I’d also suggest reading Difficult Conversations: How to Discuss What Matters Most if you would like to dive deeper.

Let me know below some of the methods you use when having tough conversations. I’m sure you all have some good ones!




  1. Ashley c
    June 5, 2018 / 1:11 am

    Important topics for professional women! Love this

    • Taneshia
      June 5, 2018 / 2:24 pm

      Thank you! We don’t talk about professional development enough. Always elbowing our way up, instead of sharing knowledge.

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