Did He Blow It? Coaching Our Executives Through Difficult Conversations

We experience them at home. In the boardroom. At parent/teacher meetings. Difficult conversations are par for the course. They are simply part of life.

What’s more – stress in the workplace is inevitable. Conflict and/or difficult conversations are to be expected when we’re dealing with an unexpected influx of new customers or a major drop in clientele. It certainly rings true when we’re dealing with a merger or acquisition or trying to do some succession planning.

Ever have one of your top direct reports absolutely blow it? He’s your top direct report. You trust the guy. He’s good. I mean, really good. After all, that’s why you put them on this major project.

But he’s are also human. Unless he knows how to handle difficult conversations (I mean the really tough ones), he might not come out unscathed. Worse, he might even screw things up.

Below are some tips for coaching your executives through learning the ropes of difficult conversations. Consider showing him why each of these is so important (it will help drive things home)

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  • Avoid trying to force someone to listen to you. It’s the fasted way to get them to tune you out
  • Avoid defending yourself. I know it’s hard to resist, but it’s not necessary most of the time. It usually throws the conversation off kilter
  • Let the other person save face. Is it really necessary to hit below the belt?
  • Avoid bias. Remove blame in the words you choose
  • Avoid shooting the messenger
  • Seldom is there a need to use the word ‘but’ in a difficult conversation. It only negates everything that was said prior to uttering the word
  • Using words like ‘no’, ‘never’, or ‘not’ don’t need to be used as often as they tend to be during a difficult conversation. Try reframing the words you choose to deliver the same message without causing the other person to naturally turn up the defense [/message] [su_spacer]

And most of all… refrain from responding at all at least and until you’re at a comfortable (and fair) plane. Click here to read more about creating a workplace culture where difficult conversations aren’t such challenging endeavors. Lead your workforce into learning how to transform difficult conversations into productive opportunities.

Difficult conversations can be so productive because they serve as a catalyst for growth. Displacing blame is one of the most powerful advantages you hold during a challenging conversation because you are exuding genuine interest in discovering a resolution.

But knowing how to conduct them can mean the difference between a constructive conversation and a path to nowhere.

What has been the cost to your company when the real issue isn’t addressed?


Dr. Jennifer Beaman
Dr. Jennifer Beaman
FOR over 25 years, Jennifer has served as an executive consultant helping organizational leaders streamline processes and strategies by enhancing skills and practices. Serving as a strategic consultant to industry-wide businesses throughout California, she soon recognized the unparalleled value of human capital. In turn, she introduced leadership and executive development services, thereby providing a more holistic opportunity for clients. Cornerstone to helping leaders recognize the power of their actions and behavior, she weaves the art of emotional intelligence into all interactions, thereby promoting thorough value to the entirety of organizational systems. Joining ranks as a business owner in 2004, she partnered in a California-based sign manufacturing business. This business served a variety of clients, primarily larger corporations, franchises and Fortune 100-500s. In 2008, she participated in partnership in southern California specializing in project management and leadership development services. This corporation served clients ranging from Fortune 50-100s. The Association for Leadership Practitioners is a subsidiary of a parent company opened in 2010 and serves clients ranging from small businesses to Fortune 500s. Dr Beaman also serves as a partner at Chasing Limitless, Inc., providing strategic consulting and executive leadership development services to catapult organizational revenue and growth and primarily serves Fortune 500 companies. She holds a Doctorate in Management with a focus in Organizational Leadership; Master's degree in Organizational Management; and Bachelor's degree in Organizational Development. She is an active member is several professional affiliations and volunteers on a consistent basis helping entrepreneurs and doctoral students working toward publishing their dissertations.

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  1. The best way to have a difficult conversation with a person is to have non difficult conversations with that person first. Once you’re used to each other, a difficult conversation is easier and more impacting.

    Then again, I believe in practice – practice – practice – for success.

    • Ahh yes! Great point Chris! Building that relationship first creates a barrier, so to speak, so that when a difficult conversation becomes necessary, the foundation of the relationship and the familiarity can not only serve as a buffer, but a catalyst toward positive change.

      There is nothing that can replace the importance of practice. With practice, we can create a loop in our brains that will be busy helping us along the way, hence making things easier for us during the process~

      Thank you for chiming in and engaging 🙂

  2. I have found that the words “never” and “always” are seldom accurate or even desirable. That is particularly true when embroiled in one of those difficult conversations.

    One should always leave the receiver of a tough conversation a back door to save face and self-respect. Without that, you have probably done more damage than good.

    • Exactly! Well said Ken and thank you for engaging with me here regarding the message in this article. I have found that for many, the effort to remove ‘never’, ‘don’t’ and other negative words/terms is a tough transition — but the rewards are certainly worth the effort.

      There is never a reason to hit below the belt and while we may be on the receiving end of that, to preserve our integrity and self-respect — I am 110% in agreement with your assertion – let the other person save face. After all, they are human, too~