How to Have Difficult Conversations at Work

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Difficult conversations are often dreaded and sometimes even avoided, but hey, let’s be honest, these are conversations that we need to have. Before I became Lauren’s sidekick (AKA Executive Assistant), I was in sales. I’ll be honest, I would find myself occasionally avoiding difficult conversations, sometimes at all costs, but that’s not going to help us grow and get results. LB was joined by four amazing ladies on a panel talking about how to overcome the temptation to avoid a conversation, how to prepare for the talk, and what to expect. 

Our panelists included:

Shianne Sampson who has been working with great startups and technology companies across the U.S. to help build out world-class sales teams. She’s currently the VP of Sales & Customer Experience at PetDesk in San Diego as well as a freelance consultant.

Wendy Mitchell-Covington, National Vice President of Sales Success at TriNet, who is a high-energy, polished strategist who builds and scales sales organizations. Wendy has spent the last 20 years in the HR outsourcing space funneling her expertise into helping America’s businesses improve and thrive.

Brenda Roper who is the VP, Global Sales Enablement at Thomson Reuters based in Minneapolis. She’s also held many sales leadership roles but her passion is seeing behavior change as a result of training – and she’s trained over 15K sales people!

Natalie Servino who is the VP of Marketing for Chorus.ai. where everyday she gets to help B2B sales professionals win more. She oversees all marketing and sales development for Chorus, including product marketing, demand generation, and communications.

What Mistakes Are You Making When Having These Conversations?
  1. People don’t address the situation or the problem – they address the person and sometimes it feels like a personal attack. Our job is to help them understand how to do it right the next time.
  2. Delaying the conversation – this is never going to help the situation as it can continue to spiral and get worse.
  3. Not setting clear expectations up front on what you are asking of them.
  4. Managers should not have the conversation on the fly – instead think about what you want to say, plan the conversation, and the desired outcome.

Lauren used the Factor 8 COACHN Model framework as a guide. This model is used for all sales manager meetings to help leaders provide consistency and embody coaching best practices. For difficult conversations, it’s called the E-COACHN Model

The “E” reminds us to maintain an employee’s self-esteem. It also reminds us there are four legs of research to do:

  1. A private location
  2. Ample time (double your best guess)
  3. Data or examples
  4. Desired goal 

Once prep is done, we can follow the COACHN Model to guide the conversation:

  1. Clarify Expectations: one sentence intro for the meeting – the “problem statement”.
  2. Observations: Talk about behavior you have observed, data you’ve seen. Not hearsay. 
  3. Asking questions: can the employee explain what’s going on?
  4. Committing to action items – this is where the employee decides and commits to fixes.
  5. How can I help? Great managers offer to get involved where appropriate.
  6. Next steps – nailing down when we check back and what will be done.
Download the E-COACHN Model here.
Tips & Tricks For Having Difficult Conversations

The panel shared so many awesome tips and stories. Here were a few that stood out:

  1. Make sure that you are ending the conversation helping them come up with a solution for the problem. We can show our faith in them and be encouraging. This helps maintain esteem.
  2. Follow-through is critical. Get next steps on the calendar and be accountable for your own actions AND measuring their progress and actions.
  3. The most difficult conversations that you encounter aren’t just performance conversations. When we enter them with the intent to help and learn, they will turn out OK – even the really embarrassing ones!
  4. Don’t expect to have all the answers. It’s smart to ask HR, a mentor, or a boss for guidance and to practice before having the difficult conversation. 
Now for some GREAT Q&A between the audience and our panel:

1. How do you give feedback up the ladder? To superiors, leadership, or your boss.

Always start with your end in mind. What outcome are you seeking? Prepare, have an outline, have someone you trust review and practice. Ask your boss if you can have an open conversation to help propel the business, relationship or whatever it is further. Tell her or him that you have been hesitant to bring this up (if that is true) and that you are seeking to improve whatever it is you are going to discuss AND then go for it! 

Remember, your boss can’t read your mind. Everyone is human and makes mistakes. Be prepared to hear feedback that you may not want. How will you react? Do your best to take the feedback as a gift, even if it is something that doesn’t make you feel good.

“Feedback is a gift” – This came up many times during the webinar. What an amazing perspective to help all parties navigate giving and receiving feedback. 

2. How can you use difficult conversations with clients as an opportunity to strengthen the relationship?

Many difficult conversations with clients occur because the company that you work for can’t or won’t fulfill something the client wants or needs. Sometimes these occur because expectations were not met. 

Honesty and timely communication will actually strengthen a relationship, versus harm it. The worst thing anyone can do is avoid the crucial conversation.

3. What is the best way to have these conversations with your boss. For example if you disagree with an approach or need to “manage up”.

This one is tricky because it really depends on what type of boss you have, you’ll need to gauge your boss’s openness to feedback and these types of conversations. That being said, start with clear expectations. I use a simple format of expectation setting which is: Here is what you should expect from me, and what should I expect of you? They will almost always say the right things: support, transparency, accountability, etc. If not make sure they cover what you need by asking the right questions. Then, once expectations are clear you can use those expectations to align on feedback, similar to the roleplay we did in the webinar. Let them know where expectations aren’t being met and be specific with examples, then provide actionable solutions. The most important part of managing up is for YOU to come with solutions, don’t just come with issues and expect them to solve. If you disagree with their approach it means you are not aligned on what protocol/expectations should be, so start there.

4.  Do you have any tips on having difficult conversations remotely, e.g. via Zoom?

Eliminate distractions and make sure you plan as you would for face-to-face. Then always make sure that your video is eye-level and that you maintain eye contact. The rest conveys just as well through video as it does in person. If this is a conversation that is HR-related or could end in termination, you should have HR present or record the session for documentation.

5. How do you acknowledge a counter argument and listen without agreeing?

Depending on the situation, you might not have to agree, but you likely need to address the disagreement and how to move forward. So to start, you need to be OK with disagreement. If the disagreement is done the right way it can actually be productive and build trust! There is a time and place for rude and blunt disagreement, for example at political rallies and debates, however, for business professionals, the polite and respectful approach is always the right way to go. Here are some tips to make this type of difficult conversation productive:

  • First, you need to understand that your argument is stronger when you acknowledge an opposing side! It shows that you have thought deeply about your argument or position. 
  • Be respectful and listen intently. Before you disagree make sure you listen and ask clarifying questions. Sometimes the idea being discussed is good, but the articulation of the idea is not good. Either way, you must actively listen to the other person, don’t just be thinking about your response. Note: it is important to be aware that active listening can give the other person the impression that you agree with them even if you don’t.
  • Mirror the person who is disagreeing. A technique you can use is to respond by repeating what he or she has said. word for word. “Correct me if I’m wrong, but what you are saying is…” This helps people feel as though you have heard and understood them. This puts them in a position to listen more carefully to what you have to say.
  • Validate the person who is disagreeing. Another approach is to express that you understand what they are saying (but not that you are agreeing). “It makes sense to me that…”. This approach helps to lower people’s defenses so that they are more open to what you have to say. 
  • Finally, be prepared to articulate how you can both “agree to disagree”. This shows that you are willing to recognize the other person’s point of view, but you do not agree.

6. How to disagree with your boss without getting fired.

We already know the complexities and tips to improve difficult conversations, but initiating one with your boss might be intimidating. However, it doesn’t have to be! If you have a good manager, disagreeing should not be an issue, it should just be another constructive conversation that you have. However, if you do not have a manager that is open to others’ opinions, here are a few additional tips. 

  • First, pick your battles wisely… you can’t and shouldn’t fight every battle!
  • Carefully consider the time and place before you set up a meeting to discuss. If you believe your manager is not going to be receptive to your view, pick a time that is not stressful for him / her. Remember it is not just what you say, it is also about when you say it.
  • Tread carefully and don’t make it personal. Stay positive, address the issue and focus on the facts.
  • Use “I” statements. For example, “I see where you are coming from, but I am concerned about…
  • Ask questions! This will foster a collaborative discussion, rather than just your point of view. It is important that the conversation is not one sided. Questions are crucial for making your opinion more of a suggestion or request, rather than a mandate.
  • Be prepared to confidently articulate the benefits of your position. You will likely be asked this so be prepared and be concise.
  • No matter what, respect the final decision. Go into the conversation knowing that your boss does have the final say and be prepared to let it go and support the final decision if it does not go your way.

I hope you found these tips helpful!

If you’d like to watch the recording for our webinar on “Having Difficult Conversations With Ease”, just fill out the form below!


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