Your baby is ugly

Dec 02, 2019

Successful leaders have to be able to deliver tough messages. Use these six strategies to navigate difficult conversations.

Before entering executive life, I worked several years as a finance lawyer. In that life, I had to capture the dreams of my clients and convert them into investment worthy business plans.

Part of that job included delivering tough messages few people wanted to hear. For example, I had to tell two company founders that their cherished project had been rejected by regulators because of their past poor handling of the agency relationship. I informed another client that despite his loathing of a customer, he had a contractual obligation to deliver a prototype or face being sued. Then there was conveying the accountant’s opinion that despite millions of dollars of private investment, the company didn’t qualify as a “going concern,” making it ineligible for a planned public offering.

I enjoyed lawyer work, even with the frank messaging part. It prepared me for executive life where you frequently have to deliver unwelcome messages. While they might not have an immediate impact on the life or death of a company, they nevertheless matter to business health. The issues arise from such situations as receiving feedback from an unhappy client about a team’s performance, a company executive’s industry group presentation that landed poorly, or a manager’s obnoxious behavior that is causing low morale and retention problems.

Successful leadership requires effective communication to motivate people to do their best work. That means providing candid feedback, positive and negative. While it’s easier to deliver praise, the cost of not giving negative feedback can be high. If people don’t know what they are expected to do and how they are doing, they will disengage, perform at a substandard level, or leave.

The outcome of a difficult conversation will depend on how you choreograph it. Here are six strategies:

  1. Know why you are in the room. Before entering into a potentially difficult conversation, know what you want to accomplish. Too often, the need to be liked takes precedence over solving the problem. While it’s nice to be liked and to alleviate momentary hostility, it won’t solve the business problem. If hurt feelings are involved, they can be addressed during the conversation.
  2. Use your indoor voice. Giving difficult messages is not the time to pull punches. Nevertheless, they must be delivered with the utmost care. It’s hard enough to say things others don’t want to hear. Coming across as judgmental or censorious will be counterproductive and make things worse. Open with a statement that establishes an even, objective tone. “I have received feedback from your team that I find concerning and would like to discuss it with you.”
  3. Validate up front. Acknowledging a difficult situation establishes credibility. “I know this has been a tough project and you’ve been working hard ...” opens a door that might otherwise be closed by defensiveness. Your compassion allows them to see you as a human being rather than a jerk or the reincarnation of a hated relative. It also says you are paying attention.
  4. Couch your feedback and goals in behavioral terms. Your job is to ask for a change in behavior, not personality. The latter would only impugn someone’s worthiness and be a futile undertaking. Frame your remarks in terms of the behavior you do and don’t want to see. “Your team members say they experience your communication style as angry and sarcastic. They find it demotivating. I’d like to hear your view of the situation and figure out how we can improve team motivation.”
  5. Don your detective hat. Successful conversations allow each person to tell their side of the story. It sets the baseline information and lets them clarify their perception of a problem. Listen to understand. That means remaining quiet to absorb information, however uncomfortable. Your goal is to integrate new information into how you can solve the problem, rather than fighting over it. Key to understanding is asking follow-on questions and confirming what you heard.
  6. Agree on a solution. With the benefit of new and clarified information, create a plan to address the problem. Be prepared to make compromises where new information supports them. It not only honors the conversation, it creates buy-in.

Candor and smart choreography of difficult conversations, hard as they might be, will lead to more productive results and justify the pain of getting there.

Julie Benezet spent 25 years in law and business, and for the past 18 years has coached and consulted with executives from virtually every industry. She earned her stripes for leading in the scariness of the new as Amazon’s first global real estate executive. She is author of the award-winning The Journey of Not Knowing: How 21st Century Leaders Can Chart a Course Where There Is None. Her workbook, The Journal of Not Knowing, provides a self-guided discovery mission to navigate the adventure of pursuing one’s dreams based on the Journey principles. She can be reached at

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