You will be asked to do the impossible.

⚠ Proceed with caution. ⚠

Saying “Yes” to everything is a great way to let others down while also burning yourself out. 👍

On the other hand, simply saying “No” a lot doesn’t solve your problems either. It may make more. At one company early in my management career, my Director pulled me aside. He shared that amongst the leadership team, I had earned the reputation of Dr. No!

I wondered, How could this be?! I was responsibly focusing on the details and alerting leadership to risks. I imagined myself courageous for protecting my team, and even the person asking for the impossible, from the inevitable consequences of unrealistic expectations.

I failed to realize that people weren’t intentionally asking for the impossible. They just wanted to know if I could help them solve a problem[0] and asked in the best way they knew how. Cast in that light, my repeated Noes suddenly felt less noble.

One thing that helped me was the “yes, and…” approach. Note, this is intentionally not the “yes, but…” approach. While similar, “yes, but…” sounds close enough to “No” that it will risk putting your listener into a defensive frame of mind.

Putting it into practice

So how does the “yes, and…” approach work? It’s simple. For example, let’s say it’s Monday. Your team’s work is scheduled for the next two weeks. Then the Boss walks in.

Boss: A customer reached out to me and wants to know if we can have feature Y delivered by Friday. Can you do that?

You: Yes, and can we discuss tradeoffs? The team is already working on feature X. We’ll need to take at least one person off of that project. That will push back delivery by two or more days. Are you and the other stakeholders comfortable with that?

The conversation changes from a yes/no question, which can feel adversarial, to what is hopefully a more productive discussion of informed options.

How might it turn out?

Boss: I think they were randomly throwing a date out there. I’ll let them know we can schedule the work for our next two-week cycle.

Or maybe it will be something more like this.

Boss: I understand. However, this is a blocking issue for the customer. We need to invoice them this quarter. Who are the stakeholders on feature X? I’ll talk to them.

So there you have it. It may not always feel easy, but it is simple.

I would strongly recommend that you follow the conversation with an email. Use it to avoid misunderstandings later. For example, Did I accurately capture what we decided?

Wrap up

Will this one handy linguistic trick solve all your problems when it comes to impossible asks? Yes, and… well, actually, No. It won’t. You will still have to say No at times. And it will be critical that you do. But save them up for when it will count most.

Side note, the “yes, and…” technique will also come in handy if you decide to dabble in improvisational comedy.

[0] Unfortunately, this will not always be true. Some will prove to be bad actors, intentionally asking for the impossible.