Tough Discussions

Tuesday, May 24 2022

By Judy Preszcator – Deciding to sell is the first step of a journey that can be either predictable or fraught with roadblocks. The outcome will depend largely on how well you plan and how honest you are with yourself, other stakeholders, as well as your employees. This decision can result in the need for tough discussions about the business.

Why Are You Selling?

Knowing why you’re selling is the foundation for the decisions and conversations that follow. It may be that:

  • Competition is too strong.
  • Someone is pushing you to sell.
  • The right buyer has come along offering the right price.
  • You’re tired or want out for your health.
  • Your vision for the business or your future has changed.

Use Planning to Mitigate Tough Discussions

Once you decide to sell, timing communication and choosing what to communicate is important. Be clear that you will share what you can, recognizing that people sense when change is coming. They notice shifts in behaviour or routines: the time you spend at work; strangers showing up for meetings; and some topics that might be getting avoided.

Communication needs to come from you. Watercooler gossip will take over if you don’t get ahead of it. Talk with the senior leadership team first, then arrange meetings with employees. Anticipating common questions will help promote respectful conversations and minimize difficult ones.

Individuals want to know:

  • Will they still have a job?
  • Might they need to move?
  • Is there going to be a different boss?
  • Should they expect to take a pay cut?

When you can, be prepared to answer:

  • Who is buying the business?
  • Why are you selling?
  • What about our benefits and perks?
  • Will things stay the way they are?


No matter how good they are, your communication skills are going to be challenged. Take the lead. Be clear and show empathy. If you don’t have the answer, say so. Explain that they can trust you to share particulars when you are able. Anticipate emotional reactions that can make it difficult to keep a cool head. Acknowledge sensitive topics with grace. A great strategy will still falter if facts are not clearly conveyed, and feelings are ignored. Plan your conversations. Be approachable. Change is scary, especially when it’s imposed. Your employees need to believe that you are being truthful with them.

It’s always a good idea to reach out to a business coach if you feel you need support with these conversations.

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