How To Say No...To Your Boss!

3 Easy Steps To Say No When It Matters Most

The Art of No

The O’Daily has been dropping a lot of k-NO-wledge lately: how to decide if something is a yes or no and how to actually say no.

We saved the best for last. The pin-no-cle. Grand fi-no-le. A culmi-no-tion. (Ok, I’m done.)

Today we talk about how to say no to your boss…or anyone else who materially impacts your livelihood and well-being and you don’t want to piss off!  

Your boss mentions a project, asks you to own something, sends over an event for you to attend. Everyone’s familiar with this scenario. 

The reality is sometimes a direct “no” isn’t a good option. Here’s what I like to do instead. 

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3 Steps To Say No When It Matters Most

1. Ask about priorities. 

Put this request in the context of the other work you’re doing help the company. Explain what you’re currently working on and ask how the new item compares to those items.

Ways To Say It:

Here are the top 3 items I’m working on right now.

List items + relevant dates. Explain why. 

Where does <thing you just mentioned> land related to those? 

You may find that your boss is brainstorming, thinking about something 6 months from now, or realizes this project is not important compared to other things you’re working on. 

Or they may say that it’s the #1 priority. That’s cool. Proceed to Step 2…

2. Clarify timing and scope.

A “time sensitive” request could mean minutes or weeks. A “report” could be a Google Doc or might be a polished slide deck with hours of research. Make sure you understand what your boss is thinking regarding the amount of work and when.

Ways To Say It:

How quickly do we need this? 

Does next week work or do you need it sooner?

Will it include XYZ, only ABC, or something else? 

Once you know the extent of the new priority, it’s time for Step 3…

3. Align on tradeoffs.

Get super clear on what will not get done and get agreement from your boss on that plan. Including recommendations on how to rearrange can be helpful and show leadership.

Know your audience though. Some bosses do better with open ended questions and directly crafting the solution.

Ways To Say It:

I’ll push Project A to next week so we can tackle Project B this week - does that work? 

Do you have thoughts on how to decrease Project C to keep it on time with the new items? One idea is XYZ.

How should we reprioritize things?

What should we cut? I’d recommend A or B. What do you think? 

Your boss has helped you shape the new plan. No one ever had to no. You simply reprioritized, adjusted scope, and changed timelines. Woohoo!

But what if…

If you consistently get wishy-washy answers like

•  “Get it all done.” 

• “Everything is a priority.”

• “You figure it out.” 

Guess what? Your boss needs to work on their ability to say no! (Or not be a workaholic jerk.) They are not clear on priorities or unable to say no. The lack of focus is overflowing to you. 

Is this an issue across the organization or unique to your boss? A one-time exception or ongoing problem? Analyze the situation to see if it’s something you can change, live with, or need to move on from.

BONUS: 2 More Ways To Use This Prioritization Technique

1. With Customers

Two common customer scenarios where you can discuss priorities instead of saying no:

• Product roadmap discussions

• Project management planning or timelines

Customers often have great ideas that you hadn’t considered. It’s also enlightening when talking about tradeoffs to find out what they don’t care about.

2. For Your Own Clarity

I’ve used this framework when I’ve bitten off too much and need an outside perspective to help me reign things in.

Can you look at this list of projects and share thoughts, based on what you see in the business, on what I can drop or move to next quarter? 

Rigor CEO Craig Hyde could sort out in 10 minutes what I’d been agonizing over for a week.

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It Works!

Most startup CEOs and leaders are creative and ambitious, which leads to lots of ideas, projects, or improvements. 

When you dig in with an organized, collaborative approach, it’s quick and painless to discern what matters. No “no” required! 

I’ve used this technique successfully hundreds of times with leaders and CEOs and have encouraged my teams to use it with me. 

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How have you said no to a boss before? What has worked or not worked? Share your learnings!