Seven pivotal conversations to have this week with colleagues and family

Seven conversations

Dear Friends,

Surreal and uncertain times call for deep attention to what conversations we have, with whom, and why.  Here are seven conversations you may find valuable having with your family, team, and colleagues this week while working from home.

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Master difficult conversations

Learn my best tips for staying cool under pressure and elevating your leadership in complex times.


When under stress, I turn to humor

Stephen Colbert did a monologue from his bathtub. My instinctual response was to create two things for the first time:

  1. A guide to mansplaining in an era of the coronavirus. Forget about me as the host of an interview series on women in leadership. Here I play the clueless and offensive mansplainer. Currently available only on request.
  2. A Public Service Announcement. This one I’ll share with you: “Six feet apart or six feet under. The choice is yours.”

Seven pivotal conversations to have this week with colleagues and family

1. “What matters conversations”

In stressful times, this is the one you’re most likely to skip. Please don’t. The “what matters conversation” involves slowing down and talking about what’s important to member of your family or team right now. Doing this has two benefits. First, it forces you—and everyone else—to pause and reflect on what you care about and what concerns you. Second, it helps you know what new worlds you are now speaking into. The child, spouse, or teammate in front of you today is in some ways a different person from the one of only a week ago. The key is to carve out time, say 30-60 minutes, go around the circle/screen, let each person share, and ask clarifying questions to understand.

2. “Possibility conversations”

This is where you explore “what if” scenarios without any pressure to commit. A few weeks ago, my wife and I had a possibility conversation around the question, “What if one of us had to self-quarantine for two weeks?” Last Thursday, we had one around, “What if we were to go to the mountain for the day for cross-country skiing?” In the workplace, you might have possibility conversations around scheduling daily 5 minute check-ins with each person on your team, canceling a planned initiative, or opening up a new collaboration with a division with whom suddenly you have vested interests. Again, this conversation is not a time to make requests or offer to do things. Stick with exploring “what if.”

3. New requests

Great, your team has had a positive possibility conversation around scheduling daily one-on-ones. The more you’ve listen, the more you like the idea. Now, you can take this possibility into action by making a new request: “I’d like to ask each of you, by 6pm today, to schedule a daily 5 min check-in with me between 8am and 5pm PST starting tomorrow and continuing through March 31.” Remember that an effective request has a clear What, When, and Why. And it only becomes a promise when the other person accepts. So consider ending your request by asking each person, “Would you be willing to do this?”

4. New offers

In a “what matters conversation” with your spouse, you realized that she really needs 2-3 hours alone in a quiet house. So you now look at your schedule, hers, and the kids,’ and make an offer. “Tomorrow, from 4 to 6pm, I’d be willing to take the kids on a long bike ride so you can have the house to yourself. Would you like me to do this?”

5. “You can say no or counteroffer”

If you want people to give real Yes’s, you have to make it safe for them to say No or propose a different timeline or outcome. I learned this when I was 22 years old and working for a senior health care leader—a guru of sorts who managed big budgets and testified before Congress. “Amiel,” he would say, “I’d like to ask you to do something. You can say no.” Hearing this surprising statement forced me to think—to not blindly agree but instead assess whether or not I could commit to what he was asking and the deadline. This gave me more freedom (which I liked) and raised the odds of my promises being reliable (which he liked). Every time we went through this, I matured a bit. The “you can say no or counteroffer” conversation is most important when making requests to people who have less authority than you and/or habitually say Yes.

6. Renegotiation of commitments 

Everyone has been moving face to face conversations to virtual.  Our family has also been shifting play dates to Zoom. These are examples of what I call “renegotiating commitments.” You can renegotiate the What and/or the When. Two tips:

  • Start with the phrase, “I’d like to renegotiate our agreement to___” because (a) it signals what’s kind of conversation you’d like to have and (b) it reminds you and them that your relationships rises and falls based on the quality of your commitments to each other.
  • End with “Would this work for you?” Just as it takes two to make a commitment, it takes two to renegotiate one.

 7. Cancellation of commitments with integrity

The past few days have witnessed the most momentous cancellation of commitments in my lifetime. Have you noticed that some people and organizations are better at this than others? Canceling commitments as soon as you realize you can’t deliver—and doing this skillfully—is important for two reasons: first, it allows the “customers” of these commitments to reassess the situation and explore other ways of getting their needs met; second, it preserves trust in the relationship. In my unpublished book Reliable Results (email me if you want a copy), I suggest three steps in canceling commitments with integrity

  • Explicitly cancel. “I will no longer be able to_____ as I had promised.”
  • Provide the context or rationale
  • Make it clear you are open to new requests now or in the future (to the extent this is true)

I hope these are helpful!

Cheerfully real,
Amiel Handelsman

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