How to start awkward conversations

Begin the transition planning conversation by keeping it tight. Ask to have an initial conversation about transition planning at some point in the future and encourage others to speak up about their vision for success.

Written for Progressive Dairy and originally published January 1, 2024 issue. 

Transition planning for a family dairy is not easy, and the stakes are high, not only for the business but also for the family.  Even if it isn’t verbalized, there is often a powerful desire to get transition planning over with but not a strong desire to go through the process.  After all, the daily tasks of running a dairy are fun, while transition planning is a big unknown.


I’ve noticed that the most likable people with the strongest family ties often struggle to start the process.  The younger generation wants to be respectful, while the older generation is nervous about what could happen to family harmony.


Successful transition planning begins with a first formal transition conversation and how the first conversation often sets the stage for the entire process.  Get off on a good foot, and the entire process is smoother.  I’ve developed a three-step process for getting this first conversation off to a good start.


This process is similar to herding cattle and is subtle but effective.  Cattle don’t like surprises, and neither do people.


It works best if the senior generation introduces the transition topic and starts the process.  In a sense, they are giving the nod to move ahead.  But what can be done if nothing is happening? How do you have a successful start?

1. Ask for a small yes, not a big commitment.

No one can force anyone else to have a conversation they don’t want.  Instead, go for a small yes to have an initial conversation about transition planning.  You can get this small commitment by alerting them you want to have a transition conversation.  Here is the subtle part.  You aren’t asking to have the conversation right now, but rather asking IF they are open to having the conversation at some specific time in the future.  Here is an example.


“The other day, I was thinking of the future of the farm and transition planning.  I want to share my thoughts and I want to hear your thoughts.  Would you like to visit sometime next week?”


One of two things will happen.  They will either say yes to having the conversation, or they will not commit to the conversation.  If they hedge or waffle, they aren’t ready to have a transition conversation.  No amount of prodding can force the issue.  Give it some more time and ask again.  


2. End the first meeting with a question.

When you have the meeting present your initial thoughts.  Then ask for their thoughts.  An example might be, “This is what I’m thinking, but I want to hear your thoughts.” Then, listen to them without interrupting or debating.  Sometimes, asking a genuinely curious, open-ended question is all it takes to start the dialogue and build trust.


3.  Don’t solve it all.

During the first conversation, you want to keep it light.  Get everyone to speak up about what’s important to them and what a successful transition looks like.  Resist the temptation of brainstorming specific tactics too soon or setting appointments with attorneys.  If things go well, define and commit to a process, pool of advisors, and timeline.  If the conversation seems tense, it might be that people are still nervous about your intentions.  Don’t push it, but do take notes and get a commitment and date for a future meeting.


Each meeting will build commitment and momentum towards finally having the discussions on everyone’s mind.  As always, if you get stuck along the way, reach out to experienced and competent advisors to guide the process.  Get that first conversation off to a good start, and you’ll have crossed a major hurdle that keeps good families from starting their transition planning.

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