Why It’s Okay to Say ‘No’ to Your Boss

“No” is a much more important word in business than “yes.”

Being able to say “no” is important to your teams, your customers, and your partners. “No” sets the wooden edges around the sandbox in which you play. Without those edges, sand goes everywhere.

Here are a few methods to prepare yourself to deliver a “no” at work:

Ask the right questions

I tell my teams to evaluate requests in the context of sequence, priority, and resource constraints. To evaluate whether to move forward with a project or opportunity, consider the sequencing of things that need to come before or after. Is it the right time for this request, project, or initiative? And consider the priority. We live in a world of time and budget constraints: If everything is a priority, then nothing is a priority.

I also have a bias for action. If you ask for more resources, I will likely ask you what you’ve already accomplished with existing resources.

With that in place, it becomes easy to say “no” in a business context, because you have rules by which you’re making decisions.

DocuSign’s overhaul of our web experience in November 2015 is a great example of these principles at work. Instead of waiting for the messaging to be perfect and for the tech to be exactly right, we asked questions around sequence, priority, and resources up front. This helped us quickly identify which things to prioritize and which to turn down, and moved the project forward so rapidly that we doubled our web traffic within five months.

Delegate decision-making authority

Our engineering teams transitioned recently from a structure that was organized in silos around different pieces of the product to mission-based teams that empower people to say “no” when necessary.

There are still engineers who do the coding, product managers who figure out the features that will go into our platform, and customer experience people who will design the user interface and flow of the product. But they all work together with a unified end goal in mind. That means anybody in that group can raise their hand and say, “No, we shouldn’t be doing this,” because they understand the broader context of the project.

This creates an environment where “no” is common, so much so that everybody feels safe to stop the train if it’s going in the wrong direction.

Say it confidently

“No” isn’t about telling somebody, “Oh, you know, I wish I could do that. But I really can’t because I’m too busy.” “No” is about avoiding making excuses as to why someone’s idea or request isn’t going to work. Being unequivocal helps train people to understand that they are going to get a “no” if their request does not align with your stated principles.

I think this is where many businesses struggle. We’ve been trained to say “yes” to the customer no matter what. Our problem isn’t the word “no” itself. It’s understanding how to stop doing things that aren’t going to create value for the business or customers. And it’s figuring out how to refocus our resources on the right things.

For example, recently one of my teams said they thought a project they were working on was completely misguided, and wanted to reorient their efforts in a completely new and different direction. They didn’t ask me for permission; they knew the principles, understood what we wanted to do as a business, and they just went and did it.

They shut down the product development, moved all of those resources to the new product, and got started on the new project. With our shared beliefs and principles in place, they made the right decision and kept the business moving forward without the typical delays of bureaucracy or errant focus on something that wasn’t a key priority. They became motivated, inspired, and delivered an in-market beta version in record time.

That’s what happens when you have clarity. That’s the power of “no.”