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Having difficult conversations at work

We’ve all had those moments – you’re sitting at your desk procrastinating that uncomfortable conversation. Maybe you’ve found yourself on the receiving end of workplace discrimination, or you have concerns about company culture, or maybe you want to push for more investment in equity, diversity, and inclusion in the workplace. Whatever the topic is, you have found yourself in need of having a serious conversation with a manager or supervisor about a workplace issue beyond your typical scope of work. You may find yourself staring blankly at your screen thinking, “just do it” while you mindlessly stall with distractions. Many of us have been there.

Author: Sophie Warwick

Having difficult conversations with colleagues and superiors is simply put, well, difficult. There’s that temptation to question whether you’re “nagging” (a word too often misused to describe women). Was the situation or concern really that problematic? Don’t undermine your value and underestimate the importance of a positive and inclusive environment. Not only for your own wellbeing (which is paramount), but also for the success of your company.

Note: A 2017 study titled “Doing Well by Making Well: The Impact of Corporate Wellness Programs on Employee Productivity” found that participation in an employee wellness program increased employee productivity between 5 and 11% - which is equivalent to a day of work a month. Your wellness concern is a company issue.

As with any workplace obstacle, setting a clear plan for success is step one. Here are my top 10 recommendations for tackling that difficult conversation head on and achieving a successful resolution.

1. Understand the concern and scrutinize why it’s important to you. I don’t mean this as questioning the importance, but instead validating and understanding it. Naming the issue will help you articulate it to your manager. Are you being talked over in meetings? Is this something that’s happening to other women, to junior staff, or to a certain team? Getting into the details will help rationalize what options would help solve your concern. You can’t solve a problem you don’t understand.

2. Be strategic and selective of your audience. Keep the group small, at least to start. Pick someone you feel comfortable talking to who can coach and support you in bringing your concerns to a larger group. Ensure this is a manager or mentor you trust, where you feel secure being candid. If you feel uncomfortable with this person, find someone else, as it may lead to withholding key information that is crucial to a resolution. In other words, it won’t help!

3. Pick an environment you feel comfortable in. Ensure you have the privacy you need to have a confidential conversation. Consider a private office if possible. However, in the world of open-concept offices and flat organizational structures, these can be hard to come by. A glass breakout room likely won’t offer the privacy you require. Instead consider options outside the office like a coffee shop or heading out to lunch somewhere you don’t anticipate being interrupted (don’t pick your colleagues “go-to lunch spot”). Leaving the workplace also creates a more relaxed environment that may lead to a more comfortable and honest conversation.

4. Go in with a clear outline of your key points. To some degree, this may be an emotionally driven conversation. Having a concise outline of your meeting will help maintain a constructive and pragmatic discussion. You don’t necessarily need to “stick to a script” but a well thought out plan will help organize your thoughts and keep things factual and informative. You can never predict how another person will respond, but at least you’ve presented all the information you wanted in a clear and controlled way. Planning is therefore key. I also suggest visualizing the conversation in advance. This will increase your confidence.

5. Be solution oriented, when possible. You don’t need to have the final answer, but by suggesting policies or support that would help prevent a similar situation in the future, you can help to keep the tone positive and forward thinking. It also shows that you are invested in your future at this company and have done your homework. Leaving is always an option, but by taking time to consider possible improvements you’re displaying that you care about company success. You want to stay, and you want to fix this.

Note: If you’ve been the victim of workplace discrimination, bullying, or any other traumatic or harmful experience, it is not your duty to solve the problem.

6. Keep notes on examples you can reference – and be specific. A single microaggression can be extremely harmful, but it’s often the sum that creates a larger, or cultural, problem. Having a list of examples will help showcase that your concern is a broader issue. It will also help communicate to your manager how the sum of these experiences made you feel. Even the best managers can sometimes be blind to the social dynamics of an office – this could be the first time they’re hearing about it.

7. Be strategic on timing. Try to avoid peak times during the week where most team members are busiest. You want your audience to have the energy and time to listen – and more importantly hear you. Look for quieter times in the week where you’re likely to get a more attentive ear. Avoid scheduling for first thing on a Monday morning – especially if you haven’t been able to give a heads up on the content.

8. If possible, give them some context for the discussion. You’ll want to avoid all the details in an initial email so you can control tone. Instead try to touch base in person or over the phone, if possible. There’s no need to get into the specifics at this time – it can be as simple as “I’d like to chat about that meeting on Thursday afternoon, I was a little disappointed with the outcome.” This will give your manager, or whoever you’re meeting with, a chance to prepare a little which should lead to a more productive conversation.

9. Be generous with the allotted time. This refers both to prep time to organize your thoughts and to the meeting time itself. You don’t want either party to feel the need to rush out and cut things short. Leave enough time for everyone to share their perspective and possible solutions. This will limit any uncertainty that may arise from someone rushing and being unable to finish their thought, or fully articulate their perspective.

10. Leave the meeting with a plan. You need a path forward. What are the actionable items, who’s responsible for delivering them, and when is the next check in? This may sound like all your other meetings. Surprise, this is no different. If it was a small problem that could be resolved by just expressing an opinion, you probably wouldn’t be in the meeting in the first place. A resolution and a plan are needed.

Note: An action plan may be as simple as a mutual agreement to monitor the situation and a timeline for a future check-in.

Always remember that you are valued, and so is your opinion. Discussing cultural or employee satisfaction concerns is important, and it is company business. Just because it isn’t listed as a task in your job description, it is still critical to your success and the company’s success. Likely, you’re not the only one who’s had this experience and bringing it to your employer’s attention will make everyone more productive in the future. You are important and so is this discussion. It isn’t a waste of time.

It goes both ways. Participate in creating a welcoming and approachable environment that’s conducive to difficult and constructive conversations. Retention is expensive. If there isn’t a means to bring forward concerns, people will leave before you even know there’s an issue. Relationships of all types sometimes need work. Invest in your team by checking in regularly and keeping an open dialogue. Provide a clear medium to bring up suggestions (these can be about new projects, markets, or employee concerns) and consider if an anonymous option is needed. Ensure to follow up if you see or hear of any concerns – have they been resolved? If your team feels supported by a foundation of trust, they will give you a chance to help solve a problem before they look elsewhere.


Bevacqua, J. (2019, September 17). The missing link of employee health and productivity. Retrieved from Rise:,a%20month)%20and%2011%25


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