How to Have Uncomfortable Conversations at Work

Oct 28

Nine business leaders share how they stay productive, without getting awkward.

They say the two inescapable facts of life are death and taxes, but we’d add a third — uncomfortable conversations.

They’re hard enough in our personal relationships, but they’re even more fraught in the workplace, where you’re balancing office politics with your own needs and feelings. Whether you’re negotiating for more money, asking to make your job permanently remote, or even putting in your two-weeks’ notice, the only way to get what you want is to communicate it clearly and effectively. But that’s not always easy.

Whether you’re the type who starts sweating at the mere thought of a chat like this or you sometimes find yourself getting a little too overzealous about confrontation, it’s frustrating to leave a conversation feeling like it got personal instead of productive. To learn how to optimize these tricky but necessary moments, we checked in with a batch of inspiring CEOs and business founders to learn what they do when it’s time to address something that’s been bothering them at work.

Give yourself time to decide what you really want to communicate.

“What I’ve found to be most helpful is writing down what I want to say. I compose two drafts: First, I write down all my feelings on the subject. I then put that draft aside for at least an hour, preferably an entire day. I then re-read my words and take out the emotions and deliver facts on what needs to be improved upon — what happened, why it was done incorrectly, and how the issue can be supportively corrected. Uncomfortable situations can never be approached reactively or with too much pathos.” – Rachel Krupa, founder of socially-conscious convenience store The Goods Mart

Keep your emotions in check.

“Research indicates that men are allowed a broader emotional range at work. If a man loses his temper at work, it’s just a Tuesday, right? If a woman loses her temper work, everybody’s talking about it. If she cries, you’re talking about it for ages. It’s a fascinating, counterintuitive rule that men can be more emotional and women can’t, even though women are supposedly more emotional. So my advice is — and I don’t love that I have to give it — try to only have uncomfortable conversations if you can do it from a place of little emotion.” – Sallie Krawcheck, co-founder and CEO of Ellevest, a financial wellness company devoted to getting more money in the hands of women

Know your boundaries—and what you’ll do if things don’t go your way.

“I handle uncomfortable conversations by actually having them, by never procrastinating them, and by being honest when I do. To be a successful business owner, leader, employee, partner, and just a person in the world, you will absolutely have to confront people and give tough feedback, probably on a regular basis. I usually prepare by setting an intention, outlining the conversation, and knowing what my minimum viable next move is if things don’t go my way. During the conversation, I remain firm on my boundaries, and I remember that I’m not responsible for other people’s feelings. But most importantly, I am brave, honest, and vulnerable.” – Rachel Rodgers, CEO of Hello Seven, a coaching firm for female entrepreneurs looking to take their business to the million-dollar mark

Don’t bottle up your frustrations.

“Someone once told me that we are all one uncomfortable, 10-minute conversation away from all our hopes and dreams. I think it’s very important to be upfront with co-workers about what is working and what is not. I just casually ask, ‘Are you open to some quick feedback?’ I don’t let things pile up. It’s best to address issues in real-time, and it’s absolutely possible to give feedback in a very kind way that considers people’s feelings. There are many different types of leaders, but my chosen style is definitely compassionate leadership.” – Katerina Mountanos, founder and CEO of Kosterina, a high-quality, organic brand of extra virgin olive oil

Remind your colleague that you’re on the same team.

“It has to start with the working relationship as a whole and a level of trust that each person is coming from a good place, sharing feedback for a productive purpose, and with good intent. I try to pre-frame tough conversations by first getting on the same page as to the desired outcome — that we’re on the same team and have a shared goal, so the intention behind sharing this feedback is to achieve that end. It helps create safety and a more productive environment for tough topics.” – Kaylin Marcotte, founder and CEO of JIGGY Puzzles, a jigsaw puzzle brand promoting the work of emerging female artists

Be kind, even when something needs to change.

“I try to lead from a place of honesty and compassion. That means that feedback should always come from a productive framework. Honesty can sometimes be uncomfortable, but I truly believe in building a culture of transparency where people understand that while we can always improve and evolve, we are rooted in being kind to one another.” – Nikki Eslami, founder of Wild Elements, a purpose-first platform that aims to restore symbiosis between humanity and nature

Make it a two-way conversation.

“I always start by highlighting the other person’s strengths, passions, and recent achievements to set the tone of the conversation. I want them to feel valued and appreciated, both as a person and an employee, before addressing the constructive criticism. With negative feedback, it’s important to be fair and straightforward, then put the focus on improving future performance as opposed to dwelling on the past. I keep questions open-ended to engage in a conversation instead of keeping it one-sided. Like any relationship, you also have to be open at work to asking for and receiving feedback on yourself as well.” – Elisa Marshall, owner of the French bakery Maman

Look for resolution, not confrontation.

“Instead of coming at it from a place of, ‘You suck, you did the wrong thing, you’re bad, you’re messing up,’ come at it with, ‘Here’s what happened, here’s how I interpreted it. Am I interpreting it the right way? How can we move past this? How can we put in place ways of communicating that allow us to grow from this?’ Those conversations that start with an assumption of respect and generosity are game-changing for your business and your work relationships.” – Shiza Shahid, co-founder and co-CEO of Our Place, an innovative cookware brand fostering human connection through food

Be empathetic, but put your business needs first.

“I’ve always been a straightforward, no-nonsense kind of person, but backed with a lot of empathy. If you’re able to understand the human side of challenging conversations, that removes a lot of difficulty. Trust me, if I have to let somebody go, I’m definitely up at night thinking about it. But as somebody who’s responsible for the performance of a business and has to answer to investors and other shareholders, you have to sometimes make challenging decisions and execute on those decisions without allowing it to affect how you’re operating day to day.” – Lo Bosworth, founder and CEO of Love Wellness, a total body care company for women