6 Tips on Making it Through a Difficult Conversation With Your Boss

manager, workplace difficulty, conversations

The other day I was reading the latest issues of Fast Company and came across an interesting article around leadership entitled Do You Pass the Leadership Test? Essentially, the article discussed opportunities where leaders have taken on a new job or venture and how they managed their staff and themselves amongst the chaos of the transition. Interestingly enough, additionally evaluation was provided on how the leader faired with the transition by integrating feedback from experts at DDI.

Much to my surprise, many of the leaders discussed in the article were on the right direction with their transition as a leader – well, according to some of the feedback provided by the DDI experts (and I would agree with most, adding my commentary, as well). However, what caught my eye as a dug through the article was a statistic DDI provided based on a survey the company conducted. According to DDI, 20.4% of employees dread difficult conversations with the boss more than:

  • Receiving a speeding or parking ticket
  • Having a cold
  • Paying taxes
  • Doing housework
  • Getting a credit card bill

Reading the data that an employee in some instances would rather pay taxes or get a speeding or parking ticket than have a difficult conversation with your boss was shocking….well, at least to me. Why is it so hard to have a difficult conversation with your boss that isn’t always “good” news? The answer:  it is different for each person, but most of the time it is because we do not like to self-reflect or hear constructive feedback/criticism. Hey, I get it, it is human nature for us to react in some situations like this, but how are we supposed to develop if we cannot face the reality that not everything is with “rose colored glasses”?

How to Have Difficult Conversations With Your Boss at Work

So, if you had to have a difficult conversation with your boss at work right now, would you prefer to have the conversation or take one of the options listed above?

If you took the latter option (one of the options listed above – hopefully not a cold or getting a speeding/parking ticket), here are some suggestions on how to approach those difficult conversations with your boss:

  • Listen and Be Open – as we all know in the communication cycle, communication is a two way street:  one person speaks, the other listens and vice versa. Therefore, when your manager is providing information to you, sit back, listen, and reflect on what is being stated. I know it can be difficult to take in information you do not want to hear, but be open to the information. Closing yourself immediately off to what is being stated breaks down the communication cycle and no one will win.
  • Evaluate the Feedback Rationally – anytime we obtain feedback that isn’t always good to hear, it is human behavior for one to react. However before you react, take a minute to evaluate what was stated. If needed, repeat what your manager stated to ensure clarity and evaluate the feedback as a whole based on what you know of the situation specifically. But as you do this, remove the emotion. It is easy for us to add in emotion and take something personally – we are human, it is natural – but to ensure the conversation stays smooth, keep it to the facts.
  • Respond Professionally – part of being human is to sometimes respond immediately to information someone tells you. Depending on the situation, it may elicit immediate feedback. In other situations, it may not elicit immediate feedback. When you are facing that difficult conversation with your manager, do not immediately respond. Remember the point above – Evaluate the Feedback Rationally? This is all part of how you respond professionally. Take a minute to evaluate the feedback, remove the emotion, and then respond based on the facts. Providing an immediate response with minimal thought pulls back in the emotion, which sometimes can come across as unprofessional.
  • Take the Good with the Bad – to think that every conversation we have with our boss is going to be good is crazy! Again, if you are thinking that every conversation is going to be good, then you have on your “rose colored glasses”. Therefore, it is important we take the good conversations with the bad conversations. Chaulk the difficult conversations up to something you can learn and develop from.
  • Again, Don’t Take it Personally – I know I already mentioned above that removing the emotion and personal from the feedback is necessary, but I wanted to reiterate this because if you are like me, I do take it personally. That is just me – I will own it, I do not like the difficult conversations, but hey, who does. What I do take from these situations is it is a learning opportunity for me not to let it happen again. I see it as another tool that I can add to my toolbox to make me an even more effective leader.
  • Ask for Advice – a difficult conversation does not mean you cannot solicit advice. Some of the best learning I have garnered through my career is obtaining advice from someone more experienced. Consider it a form of mentoring. As the saying goes, “there is no stupid question” and I certainly do not always have all the answers – although I wished I did :). So be sure to take the opportunity to ask for advice. How would they handle the situation or what else could you have done to make the situation better?

At the end of the day, I most certainly did not cover every suggestion to make a difficult conversation with your manager easy; however, I hope I at least provided some insight so you would rather have the conversation versus getting a cold or speeding/parking ticket. Again, I know difficult conversations are not easy, but if you take it step-by-step, I promise you will make it through.

What Other Advice Can You Offer to Others

What is your advice or suggestion to the readers on how to approach that difficult conversation? Do you find yourself sometimes preferring to pay taxes, get a cold, or get a parking/speeding ticket?

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Chris Ponder

Chris Ponder II is a human resources professional who has harnessed his human resources knowledge and experience across the casino, retail, and service industries, while pushing the extreme in: talent acquisition, employee engagement, training and development, human resources information systems, employee relations, process development and redesign, performance improvement, project management, and human resources analytics. Chris shares his knowledge and experiences at his contributor blog, Performance I Create. You can also follow him on Twitter at @ChrisPonder.

Reader Interactions


  1. Wendy MacIntyre says

    Did you mention not to take it personally??? It is so true. I too work at not taking it personally… and it is a difficult task. I love my work and take my performance seriously (and much of it to heart), so I know I have this tendency. Nice to hear someone else out there is like-minded! Thanks.

  2. Chris Ponder II says

    Hi Wendy,

    Not taking it personally can be a difficult task, but as you point out, it is necessary for us to continue to grow. It is just hard when you are passionate about your work!! Thank you for the feedback! – Chris


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