consider splitting a hard conversation into several conversations to make them all easier

Great leaders assign themselves hard conversations. Instead of a weary expectation that hard conversations will at some point end up in their laps / inboxes, they seek them out. They hire themselves as proactive Chief Clarity Officers.

And! The most skillful leaders I’ve encountered know when a hard conversation seems hard because it’s actually several conversations. They make some hard things easier on everyone with wise pacing and parceling. They have more than one conversation.

If you were hiring this hard conversation, what is the job you’d be asking it to do? What is this conversation for

Often when considering the hard conversations this way, you’ll find you want the conversation to achieve multiple emotionally fraught objectives. What if you narrowed down to just one of those objectives and scheduled a separate conversation (or two) to handle the others? 

A recent case study: a shrewd leader ran a talented pool of candidates through a robust work trial. Many of these candidates performed well but only one met the high bar of excellence this leader had in mind. He had to reject several good people who did little that was “wrong” or “bad”, objectively speaking, in their interviews. 

This leader felt conflicted about how to write a sincere, credible, and useful rejection email. He wanted to convey multiple ideas, including:

  1. You didn’t get the job. There were candidates we thought were a better fit. 

  2. We appreciate you and all the effort and insight you put into these interviews and the trial.

  3. We hope (in a genuine, non-bs way) there’s a way we can work together in the future.

  4. We think it would be valuable to stay in touch (in a genuine, non-bs way)

  5. We’d like to make good on 4) by scheduling a follow-up meeting a couple months from now (acknowledging that you may have another gig by then or not be interested in this).

  6. If you don’t want to engage further with us, no hard feelings at all and we won’t think any less of you. Door remains open to engage with us.

This is a lot to convey in one email, especially one with such an emotional cherry bomb at the beginning (“you didn’t get the job”).

A clever, compassionate path out was splitting this email into two. The first email contained ideas 1,2, 3 and 6 and a preview that a second, totally optional email was coming with ideas for staying in touch. 

Both emails felt way easier to write. They were only really doing one job each. 

  • Email 1: We’re rejecting you

  • Email 2: We’re inviting you to stay in our network and find opportunities we can help each other

It can be easier to see how this works with an email, because you can literally split it into two with your enter key. Same idea applies to a live convo. See if you can handle one important item. Preview another convo is coming, book it, then handle the business of that one when it’s time.

-Eric

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