Hard conversations are pretty much what they sound like. But, sometimes having a difficult discussion’s the difference between being unhappy and getting what you want. So while initiating one in the workplace isn’t fun, you could stand to gain respect, a promotion, or extra income—all good things. Emerging from the conversation unscathed comes down to three smart moves.
Use The Muse to find a job at a company with a culture you love. Select the career path that aligns with you:
First, never go into a difficult conversation unprepared. Think long and hard about what, exactly, you want to accomplish and how you want to use your energy. As my mother used to say, “Pick your battles.” Use your resources to address significant misunderstandings or problems professionally and thoroughly, letting the small stuff go.
Second, bring evidence. Does your boss think you messed up the department budget? Login to your budget system to show him where you stand as you talk through it, instead of just saying, “It’s fine! I did everything right.” Is your employee making the same design mistake over and over? Bring copies of the drafts and your notes from previous meetings.
Third, find your sense of calm, and keep your cool. This can be tough if you feel like you’ve been wronged or you’re really frustrated. But barging into someone’s office full of rage only exacerbates the problem. Consider the other person’s point of view. It’s unlikely she doesn’t have a single valid point. If you can find some common ground, you’re more likely to be taken seriously. Practice your talking points so you’re calm and collected when it’s time for the real conversation.
What does this look like? Read on for some templates you can use as a general guide in these tough talks.
Having a difficult or uncomfortable conversation with your manager can feel incredibly intimidating. However, there are times when it’s necessary to voice concerns, ask for what you need, or address problems directly. Avoiding challenging talks can lead to resentment, reduced productivity, and possibly even resignation.
In this comprehensive guide, I’ll provide tips and strategies to prepare for and navigate tricky dialogues with your boss. With the right approach, you can have constructive difficult conversations that strengthen your working relationship.
Why Difficult Conversations Are Important
It’s natural to want to avoid tension or rocking the boat with your supervisor But there are many valid reasons you may need to speak up
- Addressing issues impacting your work performance
- Resolving conflicts between team members
- Asking for a raise or promotion
- Voicing concerns about company policies
- Reporting unethical or inappropriate behavior
- Providing constructive criticism or negative feedback
Turning a blind eye to problems will only allow them to fester and worsen over time. Handled correctly, difficult discussions can lead to:
- Increased trust and understanding between you and your manager
- Solutions to workplace challenges and disagreements
- A more positive, transparent office culture
- Growth opportunities and improved employee retention
How to Prepare for the Conversation
Careful preparation is key to keeping difficult talks constructive Here are some tips
-
Reflect on your goals and motivations – Get clear on the purpose of the discussion and desired outcomes before going in. What do you hope to accomplish?
-
Gather relevant information – Collect data, records, examples or documentation related to the issue to support your perspective. Quantify the impact when possible.
-
Consider your manager’s position – Look at the issue from your boss’s point of view. Anticipate their potential reactions, concerns and objections.
-
Time it thoughtfully – Choose a day and time when your manager is less likely to be rushed or preoccupied with other priorities. Avoid ambushing them.
-
Plan your approach – Write an outline of what you want to communicate and practice out loud. Prepare for likely questions and responses.
-
Propose solutions – Providing potential solutions shows you’re invested in addressing the issue constructively, not just complaining.
Best Practices for Difficult Conversations
When it’s time for the discussion, keep these tips in mind:
-
Pick a private setting – Find a quiet, private space conducive to open, focused dialogue. Virtual meetings need strong connections and minimal distractions.
-
Establish a positive starting tone – Begin politely and positively. Thank your boss for their time and willingness to discuss the matter.
-
Communicate your goals – State upfront the reasons for the discussion and your desired objectives so you’re aligned.
-
Actively listen – Hear your manager out fully. Don’t interrupt or react defensively. Reflect back key points to show your understanding.
-
Find common ground – Look for shared interests, values or motivations around the issue. Highlight opportunities to collaborate.
-
Back up claims – Provide concrete data, records and examples to support your assertions versus relying solely on emotion.
-
Suggest solutions – Offer potential remedies that will resolve the issue, not just blow off steam. Be open to compromise.
-
Agree on next steps – Define action items, responsibilities and timelines to continue progress. Schedule follow-ups if needed.
-
Conclude positively – Recap agreements made and express appreciation for a constructive discussion.
What to Avoid When Talking to Your Boss
Just as important as what to do is what NOT to do when navigating tricky talks:
-
Don’t ambush your boss or breach their trust by escalating issues without coming to them first.
-
Don’t assume the worst of your manager’s intentions. Avoid accusatory language that puts them on the defensive.
-
Don’t beat around the bush or become overly emotional. Stick to facts and concrete examples.
-
Don’t dwell on problems without proposing solutions. Suggest remedies that will help you and the organization move forward.
-
Don’t expect overnight change or miraculous agreement. Have patience through ongoing dialogue.
-
Don’t become combative or issue ultimatums like quitting. Keep the discussion professional, not personal.
-
Don’t share private convos with the team before agreed next steps are taken. Uphold discretion.
Helpful Phrases for Tricky Talks
Language matters greatly in high-stakes conversations. Here are some helpful phrases to use with your boss:
-
“I wanted to discuss something privately with you that’s been concerning me…”
-
“My intention is to improve our team’s productivity and success, not to criticize…”
-
“I’m having a hard time reconciling this situation with our company values…”
-
“What factors should we take into account to make sure we find the best solution?”
-
“I may be missing key information from your perspective. Help me understand…”
-
“Here are a few ideas that I think could resolve this issue effectively…”
-
“I’m committed to making this better. What role can I play moving forward?”
-
“Thank you for hearing me out and being open to my concerns…”
When to Bring In Mediators or HR
If private discussions with your manager have failed and the issue remains unresolved, you may need to expand the conversation. Consider involving:
-
Internal Mediators – Many companies provide neutral third-party mediators to facilitate conflict resolution. This is less formal than involving HR.
-
Human Resources – HR can objectively investigate concerns around discrimination, harassment, safety, or ethical breaches. They also formally document issues.
-
External Mediators – As a last resort, third-party mediators not affiliated with your company may need to intervene. This is rare but can provide impartial insight.
Don’t take these steps lightly. Uphold discretion and give your boss a chance to address problems directly first. But if you’ve hit a wall, mediation may help.
Outcomes to Expect
Keep realistic expectations when going into difficult discussions. Outcomes may include:
-
Your boss gains greater awareness of your concerns and challenges.
-
You gain insight into your manager’s perspective that informs potential solutions.
-
Agreements are made to pursue certain action items or changes.
-
Next steps are scheduled for continued check-ins and reevaluation.
-
You agree to disagree but with greater mutual understanding.
-
The status quo remains but channels open up for future dialogue.
-
Your concerns get formally documented with HR in case issues persist.
The mere act of speaking honestly and respectfully can lead to progress, even if the ideal resolution isn’t immediately reached. Have patience.
Following Up Post-Discussion
Don’t let the conversation end once you walk out of the difficult talk:
-
Send a thank you email summarizing the discussion, agreements made, and next steps. This documents the conversation while it’s fresh.
-
Connect regularly to check in on action items and provide support. Hold each other accountable.
-
Evaluate progress at agreed intervals. Discuss what’s working and what still needs improvement.
-
Give it time to see how agreements and changes unfold before revisiting serious concerns.
-
Learn and improve by reflecting on how you can even more effectively handle difficult talks in the future.
Ongoing follow-up and collaboration is critical to realizing the positive potential of difficult conversations over the long-haul.
Constructive difficult conversations with managers, handled correctly, can transform work relationships and organizational culture for the better. With courage, empathy and commitment to win-win solutions, you have the power to drive positive change. What matters most is your integrity, skill and determination to express yourself and resolve issues. Going into tricky talks prepared and following up diligently will help unlock the full benefits challenging dialogues promise.
You’ve Received Unfair Negative Feedback
Criticism always stings a bit, but unfair criticism flat out burns. Whether this happens during a formal evaluation or a less-formal chat with your supervisor, if it’s significant enough to impact your reputation or compensation, you’ve got to be your own best advocate.
It’s best to start by acknowledging that at least some of the feedback is helpful; when you address it, you’re demonstrating that you understand how to work on the issue. Once you’ve done that, you can segue into the feedback that needs attention. Bring supporting documentation (if you have it) and avoid getting defensive. Wrap up with a suggestion for avoiding such a misunderstanding in the future. Here’s how this conversation looks:
I’ve thought really hard about the feedback you shared with me regarding [something accurate]. I see where you’re coming from. I wanted to let you know that I [insert what you’re doing to address the problem here].
I also want to talk about [the feedback that you believe was unfair]. I was caught a bit off guard when you expressed so much concern. But, it occurred to me that [this particular thing might have contributed to the misunderstanding]. Here is [evidence supporting your argument that you are, in fact, doing your job well].
I thought it might be helpful for us to communicate a bit more regularly so that you are more aware of my progress on various projects. [Make a suggestion of how you can avoid such a misunderstanding in the future. A regular email? A short, weekly meeting?]
Your Boss Is Impeding Your Progress
Whether he’s a micromanager, can’t make a decision, or has a tendency to change his mind halfway through a project, your boss’s mismanagement is a problem for you. This situation obviously needs to be handled with kid gloves; accusations and demands aren’t productive, but neither is simply wishing for his management style to change.
Set up a meeting, practice addressing the topic in a composed manner, and then go into the appointment with confidence, armed with evidence. Begin the conversation graciously and acknowledge your desire to do good work. Then, in a respectful way, be honest about the problem and how it’s affecting your performance. It might also be appropriate to ask if there’s something that you’re missing.
For example, with a micromanager, you might ask if there’s a particular concern driving the frequent check-ins. Here’s how it might go:
Mike, thanks for making time to sit down with me. You know how important the product launch is, and therefore, how important it is to me. I’m really struggling to move forward, though, and part of the problem is [insert the issue, in a professional and non-attacking way]. I’d really like us to find a way for me to be as productive as possible. I have a couple of ideas and would love to hear your thoughts too. Could we talk about striking a balance that will keep you [whatever your boss needs to stay informed, to maintain some flexibility with clients, and so on], but be a bit easier for me to manage? [Insert your suggestion here and listen for your boss’ feedback. This will allow you to you wrap up with a concrete plan for improvement that addresses both of your needs.]
Bob Bordone Teaches You How to Have a Difficult Conversation with Your Boss
How to have a difficult conversation with your boss?
Empathy in tough conversations can make everything run more smoothly. If you’re worried about how to have a difficult conversation with your boss, you’re not alone. 20% of Americans are uncomfortable talking to their managers. But, preparing for the conversation can make the process a bit more manageable. Take a deep breath and relax.
How do you deal with a difficult boss?
Instead, prepare yourself in advance and figure out what you want to say. When it’s time to have the difficult conversation, talk about facts rather than highly charged emotions. It is possible to express discomfort without being hostile. By staying positive, you can also win your boss’s trust and have a productive conversation.
How do you manage difficult conversations with your employees?
Be Direct And Succinct Be direct and to the point with just the specific information that the conversation needs when you communicate with your boss or manager. Learn to value the time you are investing in that conversation. Being a leader, I always hate difficult conversations with my employees.
Should you have difficult conversations with your manager?
While having these conversations can be uncomfortable, they make it possible to increase the level of openness between you and your manager and reach a mutually agreeable resolution. Learning some key steps for how to have these challenging conversations can help them go better and make it possible for you to achieve your goals.
