Your single source for new lessons on legal technology, e-discovery, and the people innovating behind the scenes.

Confessions of a Recovering People Pleaser: How to Set Standards, Say No, and Stay Kind at Work

Sam Bock

Do you ever find yourself apologizing for making a perfectly reasonable, painstakingly polite, entirely role-appropriate request of a colleague?

Do you struggle to say “no” when receiving an unreasonable, impolite, role-inappropriate request from a colleague?

Are the phrases “whenever you have a moment,” “if it’s not too much trouble,” “happy to help in literally any way I can,” or “no rush!” common refrains in your emails?

Are the phrases “gosh I hope I worded that okay,” “I wonder if this person is mad at me,” “calm down, they’ll understand,” or “I guess I could take on one more thing” common refrains in your self-talk?

If you answered “yes” to any of the above questions, you might be a people pleaser.

Super sorry about that. If it’s any comfort, you’re not alone: I’m one, too.

If my professional growth has taught me anything, it’s that getting comfortable with pushing back is not just essential to doing your job well—it’s essential to feeling capable, in control, and comfortable in your everyday work.

Of course, we must note that it isn't always an option to decline assignments or requests in this field. But that makes it even more important to learn how to prioritize tasks and take on only what's appropriate and proportional whenever you have the option, doesn't it?

So whether you’re new to your role and hoping to overcome the pain of that effort, or an experienced professional hoping to set a healthier example for your colleagues and direct reports, take a few moments to reflect on the following ideas and see how you can help yourself push back as needed.

Build—And Then Blame—The Documentation

The key to delivering a negative answer and leaving a positive impression is to make it very clear that your pushback is professional, not personal. One simple way of doing that is to point to a rulebook that essentially dictates the decision for you.

When we launched The Relativity Blog more than a decade ago, we did so with the simple intention of sharing our team’s expertise on our software with our user community. We wanted to publish creative solutions for common e-discovery challenges, tips and tricks on making the most of Relativity, and some news about what our company was up to now and then.

But as our team, our platform, and our community grew, we outgrew that very simple mission. The blog has since set its ethos around becoming the legal tech community’s go-to resource for industry insights, technology tidbits, and professional peptalks.

As editor of The Relativity Blog, I have the honor and delight of collaborating with authors from across the Relativity community to execute on that vision. But this role also requires saying “no” to pitches and ideas from time to time. It's how we ensure we’re presenting a cohesive, on-brand publication that delivers helpful insights to our readers.

And you, dear reader, are likely a legal and/or technology professional who also has to find the strength to say “no” when necessary—to impossible deadlines, poor user experiences, unnecessary fire drills, unwise case strategies. You must also hold yourself and others to the exactingly high, but ethically and legally required, standards of your field.

In my case, a defined set of brand standards and strategic requirements for The Relativity Blog provides context around why a proposed piece of content is determined not to be a good fit. Not only does this illustrate the objective reasoning behind a rejection, it empowers collaborators to come up with new ideas that are better suited to meet publication standards.

Crafting official, accessible documentation and formal processes for your function can give you the operational support and authority you need to say “no” to a colleague with clarity and confidence. It can also turn those hard conversations into learning opportunities for said colleague, and arm you with the resources necessary to coach them on a better approach or a more realistic set of expectations for next time.

Show Honesty and Humanity

When confronted with a request or idea you must decline, a people pleaser’s best first step is to gather your thoughts and document your reasoning for refusal. The second is to figure out how to deliver this response professionally, in a way that remains true to your propensity for kindness—but does not drift into that wishy-washy sea where overly gentle rejections get bobbed around and turned into accidental acceptances.

Take the time you need to compose your response thoughtfully (but please take care not to torture yourself overthinking this step!). As you put it together, incorporate these tips:

Be Honest

Write out the words you want to say as you instinctively would. Then go back, read it through, and look for qualifiers—the things that actually negate or undercut your own answer, or suggest the possibility that it could or should be different. These may include sentiments like:

  • “I’m very sorry about this.”
  • “I wish I could help!”
  • “It’s a great idea, though.”

Are you sorry? (If the rejection is not due to an individual failure on your part—which it probably isn’t, unless you’ve spent the last six hours on Instagram and have simply run out of time in your day to meet this request—there is no need to apologize.)

Do you wish you could do this thing?

Was it a great idea?

If “yes,” then it may be alright to leave that sentiment in your response. But if you answered “no”—don’t lie. And if qualifying your response could invite the recipient to challenge you or attempt further persuasion, it might be smartest to avoid the qualifiers altogether.

Be Human

Minimizing or eliminating qualifiers doesn’t automatically turn you into a robot, although changing your natural language in this way might feel a little cold at first.

Turning this:

This is a great idea, Jess, and I’m so sorry to throw a wrench into it, but I’m afraid I can’t move this forward right now. Could we look at [this] and [that] resource, which might help us reframe it so I can help after all? Apologies again for the trouble!

into this:

Jess, I can’t move this forward for you as-is—but I can direct you to [this] and [that] resource. Referring to those guidelines might help you adjust the request to better fit our operational requirements. Let me know when it's ready for another look!

is not unkind. It’s direct, professional, and polite.

And you can inject more personality or positivity into your messages without undercutting your own statements. For example:

Jess, unfortunately, I can’t move this forward for you as-is. That said, I recently put together [this] and [that] resource to help set you and your team up for success on requests like this, so they fit operational requirements and help us move more quickly. Let me know if you have any questions on how to use them. Otherwise, feel free to send this back once you've gone over those to make some adjustments, and I'd be happy to take another look.

Depending on the topic, you can and should leverage things like humor, positive feedback, and linked examples your colleague can reference for next time.

Say “But” When You Can

I know, I know—I already told you to “avoid the qualifiers.”

But, sometimes functional qualifiers are helpful.

I’m not talking about emotional qualifiers that make you seem small. I’m definitely not talking about negative qualifiers that disparage your ability to do your job.

We’re not looking for “No, and I’m super sorry about it,” or “No, but I wish I could.”

I’m talking about the type of “No, but…” answers that can improve a nugget of an idea into something wonderful, open up a stretch opportunity, or invite collaboration.

For instance, when you receive a well-meaning request or suggestion from a teammate, can you improve your response with feedback? Invite someone to hone a new skill? Point them in a more helpful direction?

Some examples of what this might sound like:

  • “We can’t pursue that idea as-is, but it could be the start of something great—could you incorporate some information from [this] resource and we’ll see if we can make it work another way?”
  • “I don’t have the bandwidth to do that right now, but if you’d like to try it out on your end, I can set up a quick video call to go over the basics with you.”
  • “No, my team doesn’t have plans to take on something like that—but I’ve heard Joy’s department talking about a similar idea. Maybe your groups could tackle it together?”

Professionally declining a request or idea does require establishing confident boundaries, but that doesn’t mean you can’t bounce some thoughts back and forth. Putting in a bit of effort to help your teammate achieve what they’re looking to do—even when you can’t do it for them—is an important way of staying true to your friendly, collaborative, and welcoming qualities without sacrificing your own goals.

What lessons have you learned as a people pleaser in a high-demand profession? Share your favorite tips on LinkedIn using #ConfessionsOfAPeoplePleaser—we can’t wait to hear them!

Graphics for this article were created by Kael Rose.

How to Stay on Top of Tech Trends if You're Not a Technologist

Sam Bock is a member of the marketing team at Relativity, and serves as editor of The Relativity Blog.

The latest insights, trends, and spotlights — directly to your inbox.

The Relativity Blog covers the latest in legal tech and compliance, professional development topics, and spotlights on the many bright minds in our space. Subscribe today to learn something new, stay ahead of emerging tech, and up-level your career.

Interested in being one of our authors? Learn more about how to contribute to The Relativity Blog.