Lori Freitas Houghton

Lori Freitas Houghton


Erika Edwards

HR leader

Fadme Young

HR leader

Updated : 01/12/2021

Typically, it’s easy to say yes to your boss.

After all, that’s the way things work. You were hired to follow his/her lead. And you most likely are fairly attached to being employed, getting a paycheck, and all of that. So it can be quite uncomfortable when you need to say no to your boss.

But sometimes those moments happen.

Now–to be clear–if you need to say no because this is a harassment issue, then things get complex. Be smart and get legal advice if necessary–sooner is preferable to later.

1. How and When to Say No to Your Boss

But assuming this isn’t a harassment issue, perhaps you need to say no for one of these reasons:

It’s labeled as a “great opportunity,” but seems like a no win situation.
Too many tasks, too many hours – if you don’t get some sanity soon, you’ll walk away.
The issue is politically sensitive. Maybe, for example, your leader’s boss will not be happy with this choice.
Based on your expertise, the proposed plan is the wrong one. Your leader is suggesting something that you consider ineffective, unhelpful, or even unethical.
✓ Your boss wants you to do his/her dirty work and you need to draw the line.

These are all real dilemmas. You don’t want to weaken your working relationship or jeopardize your employment and the possibility for advancement. How do you decline a request from your boss both professionally and gracefully?

2. Read the Situation and the Relationship

Some situations require a direct–even blunt–conversation, while others are easier to finesse.

As you establish your relationship with your boss, it’s important to create respect between you.

Part of that process is proving your credibility in your subject matter expertise, says HR leader Erika Edwards. In a healthy working relationship, your boss will come to depend on you for your professional opinion. “When they’ve come to know that they can rely on what you say, then you have their respect and can push back when necessary,” says Edwards.

When to Have an Upfront Conversation

Perhaps your leader has just asked you to do something obviously unethical or damaging to others or to your company. This situation requires a frank conversation. It’s better not to assume any motives; sometimes people are blind to the damage they might be doing or they’ve never given it enough thought to recognize it’s unethical. Have an honest conversation to help your boss see the pitfalls of going that direction.

Don’t make an enemy of your boss. Maintaining respect will strengthen your powers of persuasion. But if you think a proposed action is destructive or wrong, you need to be upfront. Your leader may appreciate your candor and come to see the situation through your lens. But if s/he doesn’t, you will have demonstrated your character and be able to maintain your self-respect.

Getting experience if you’re just starting out

When to Use Conversational Finesse

Other situations don’t require a frank conversation and might be better handled with finesse.

For example, your leader is requesting something that is politically sensitive. Maybe your leader’s boss doesn’t want you to do what’s being requested. That’s a delicate situation and shouldn’t necessarily be addressed directly with your boss. Sometimes you can skillfully replace your leader’s proposal with a better one, while persuading him or her to feel s/he originated the idea. Or another example when there’s value in being indirect might be if you feel your leader’s suggestion is silly–you see a much better way to do it. It’s unnecessary to address this head-on. But by asking good questions or making your case, you might be able to turn your boss to your way of doing it.

3. How to Say No to Your Boss Without Arguing

Even if you’re determined to say no, take a cooperative tone.

Collaborative and inquisitive are two attributes to keep in mind as you navigate this situation, advises HR leader Fadme Young. If you say no right away, likely your leader will shut down. It’s important to assess your leader’s end goals and the reasoning that’s gone into this request.

Understand the End Goal

Find the underlying reason for the request.

Make sure you understand your boss’s objective, what s/he is trying to achieve. Young notes, “The leader may just be trying to get from A to B – and not seeing the challenges” of what s/he has proposed.

Assuming your boss hasn’t crossed some offensive line, there’s no need to damage your working relationship unnecessarily. You don’t want to create a contentious or confrontational dynamic, notes Edwards.

What if your boss has a more autocratic style? What is s/he isn’t interested in collaborating? Then you might want to stall for time.

Getting experience if you’re just starting out

Plan Your Approach

Time is your ally. Ask for some. Then, do your research.

Young emphasizes the importance of articulating when you’ll get back to your leader, but it’s okay to ask for a little bit of time.

Perhaps you say something like: “That sounds like a great idea, but I just want a little bit of time to assess this. Then I can give you a better response. Can I get back to you this afternoon?”

This will give you an opportunity to check-in with trusted team members or colleagues, learn more, and get informed/reinforced. If that’s not an option, do your own research, Young advises. Data and supporting facts usually produce better decisions and have a lot of persuasive impact.

Find Solid, Relevant Reasons

When it’s within your line of expertise and you need to push back, you should have solid reasoning behind it, Edwards emphasizes. Maybe you create a presentation or run some financial models to demonstrate your reasoning for saying no. Remember the expertise for which you were hired and be accountable to that. “That’s what you were hired to do,” explains Edwards. “Occasionally you need to stand toe-to-toe.”

If you’re uneasy about it, but your boss still wants what s/he wants, document it all.

Even when you’ve effectively justified an alternative, sometimes your leader may be inflexible and won’t listen. Ultimately, you may need to concede, Young explains. ”This is my recommendation, but the call is yours.” If you’re uncomfortable with the decision, Young recommends documenting the process. This may be needed not only to protect yourself and your role in it, but the organization as well. Ask advice from someone who will be wise and discreet and will support you. This might be another leader, an HR advisor, or someone outside the situation.

You can navigate most of these situations and still retain a positive relationship with your boss. But if these challenging situations become frequent, it might be worth considering another position, where you will feel more comfortable with the direction your leader is taking you.

About the Author

Lori Freitas Houghton

Lori Freitas Houghton


In her 15+ years in human resources, Lori Freitas Houghton has worked on both sides of the hiring equation. She’s experienced as a recruiter and partner with hiring managers. She is also a proven career coach with a high success rate at helping job candidates create breakthrough resumes that gain them interviews. With a BA in English and a Master of Organizational Behavior (MBA) degree, Lori also has considerable experience writing and editing HR content.

Erika Edwards

HR leader

Erika Edwards is a senior HR leader who has shaped high-performing cultures at Fortune 500, startups, and major growth brands for 20 years. She has particular expertise in attracting and retaining high potential talent.

Fadme Young

HR leader

Fadme Young is a seasoned HR leader with 15 years of experience in the banking and financial services industry. She thrives in the investigative aspects of HR and is passionate about mitigating risks.

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