How to Help Others Through a Difficult Transition

“I don’t want to go to ski class!” Sophia, my four-year-old daughter, was crying. I knelt down on the snow so we could be at eye level and asked her why.

“I just don’t want to go,” she whimpered.

I didn’t want her to skip class. She was already skiing well — turning and stopping on her own — so I knew she could do it. Plus she’d asked for lessons and we’d committed with the instructor. I wanted to teach her that she needed to follow through on her commitments. Finally, I had seen this before: she’d cried while learning to ride a bicycle, but when she finally learned, she was tremendously proud of herself.

I tried to comfort her, reason with her, convince her that, in fact, she liked class and at the end of it she would smile and tell me she had fun.

But she was still crying when we walked up to her ski teacher. She hugged me, then hugged me again. I walked away but when I heard her continue to cry, I came back and hugged her more, telling her again how the class would help her ski better, how she would have fun, how it wouldn’t be so bad.

Finally, after twenty minutes of trying to comfort her without success, I tore myself away.

Later that morning I was on the chair lift with two teenagers and their mother. I asked the mother what she would do in my situation.

She didn’t hesitate. “Drop ’em and run!” She laughed. “Remember?” She looked at one of her sons. “I would put you on the floor at daycare and 10 seconds later you could hear the tires screeching as I pulled away.”

Now we were all laughing and I realized she was right. My mistake? I prolonged the agony.

A few weeks ago I extolled the virtues of transition time, arguing that if we only built in a little extra time before a meeting, call, or event, we could use that time to prepare.

It’s incredibly valuable when the transition time is used to make the subsequent activity more useful, more productive, maybe even shorter.

But there in some situations transition time isn’t the solution. It’s the problem. As long as Sophia was in the transition, she was miserable. And by trying to comfort her through it, I prolonged her misery. I kept her in the pain of the transition.

We do this in organizations all the time. We decide on a change and then spend a tremendous amount of energy trying to get everyone to feel great about it before they have a chance to experience it. We try to get them to want it.

But sometimes, too much preparation can be a bad thing.

Imagine you’re on a cliff overhanging a river and you’ve decided you’re going to jump into the water. Would you be better off standing at the edge, looking down, convincing yourself it will be OK? Or would you be better off just jumping without thinking about it?

Sometimes it’s better to shut your eyes and jump. Especially if you feel anxious about your next step.

I know a large company that moved offices from New York City across the Hudson River to New Jersey over a period of a year, a move many people were dreading. Some departments opted to move immediately to secure space and get it over with, while others stayed in New York City as long as possible, trying to delay the pain.

The delaying strategy backfired. The departments that stayed in New York started to feel the pain right away — in their anxious anticipation of the move — and continued to feel it right up until they actually moved. Then the pain continued for a few months until they adjusted to their new reality.

The departments that moved early started their adjustment period right away, cutting out many months of trepidation. The reality of being in New Jersey just isn’t as bad as people fear.

When we fear something, we often complain about it. And when we complain about something, we rile ourselves up and convince ourselves that our fears are justified. The more we complain about a decision that’s already been made, the more frustrated we become. And the more we resent being in the situation.

So if there’s something you need to do that you find difficult — writing a proposal, having an unpleasant conversation with someone, or doing any work you consider unpleasant — try doing it first thing in the morning so you minimize the time you have to think about it.

And if you’re in a position to help others through a transition? Here are three steps that may quicken the transition:

  1. Listen fully to their concerns. Repeat back what you hear them saying and ask if you got it right. Once they agree that you understand their issues, move to step 2.
  2. Share your perspective. Once. Check for their understanding, not their agreement. You want to make sure they hear your view.
  3. Don’t repeat. This is the critical step to moving them through the transition to the other side. If you’ve done step one and two effectively, you’re done. Any more just lengthens the transition — and the dread.

I knew Sophia was going to class so I needed to move her out of contemplating the change and into living it as quickly as possible. I should have hugged her and left.

“She cried for the first few minutes of class,” her ski teacher told me at pick up, “but then she was fine.”

I knelt down to Sophia and asked her how she liked it. She stared at me intently, looking angry, like she was about to cry again.

We stayed like that, looking at each other, without saying anything, her face stern, for several seconds. Then she broke into a wide smile. “It was fun,” she said, and fell into my arms.