How to say 'No' to your boss (like a boss)

At OSCON 2013, Deb Nicholson, Community Outreach Director of Open Invention Network, gave a talk on how to delegate, like a boss. She's returning to OSCON 2015 with a follow up talk on how to say no, like a boss. We caught up with Deb to get a preview of her upcoming talk, and we asked for a few tips on how to politely reject offers for additional work. If you have a chance to see her at OSCON, don't miss it—her talks are always a nice mix of entertaining, with a heavy dose of practical advice.

What inspired your talk?

I gave a talk a few years ago titled "Delegate, Like a Boss!" It was all about how to delegate. Its's something that busy, smart people aren't always good at, and free software builders are as prone to this as any other field. Last year, I ran into someone who had seen the original talk and as we chatted, she told me what she really needed now was "a talk on how to say no, like a boss!" It stuck with me and I realized that there are probably plenty of free software folks who could also benefit from that talk. The titles for both talks were inspired by the Lonely Islands song.

What are a few good questions we should ask ourselves when we're deciding whether to take on a new project or assignment?

When I used to work in politics, you would always measure your success based on how many votes it produced for your candidate. We'd have volunteers who wanted to stand around with signs, and we had to gently explain that it wasn't very effective. Even worse, it was a time-suck for the campaign staff to get in the car and deliver signs to people. So the question you want to ask yourself is, "Will the resources I (or we) expend produce the results we want?" To answer that question, you need to know what your goal is and you've got to have a metric for measuring what's "worthwhile," whether that's money, volunteers, new users, contacts, etc.

If I want to tell my boss "no," what can I do to prepare myself for that discussion so I enter it with confidence?

The more research you've done, the more confident you'll be. You'll want to look at both internal and external factors. Sometimes, your company or project has been doing things the way they have for a while because of an unstated goal that you may not be aware of when you take on a new role. You need to find out why colleagues are telling you, "We've always done it this way." Oftentimes, it isn't as simple as it appears. There could be a personal relationship with a vendor or some side effect—like camaraderie—of doing things slowly that people have come to really enjoy. Other times, the outside landscape has changed and something that used to be cheaper to do in house is cheaper to outsource now. The more completely you understand the impact of what you're saying "no" to, the better your counter proposal will be received.

If I'm willing to add to my workload—but for a price—how can I raise the "raise" issue in the discussion?

Again, I think research is going to be your best strategy. In this case, you'll want to know what the going rate for the new work is, or what your company would likely end up paying to outsource it. You'll want to look at websites like salary.com and talk to colleagues about what they get paid. If your company has a direct competitor and you can figure out what they're paying for the kind of work you're taking on? Well, that's definitely worth knowing, even if you aren't interested in switching companies.

Without giving too much away, what are a few of the best takeaways your talk attendees will have?

It's critical to think about your work goals in advance because it's really easy to say yes to assignments, jobs, or ideas in the moment if you aren't prepared. For instance, freelancers can build their professional networks by referring potential clients to friends and colleagues instead of saying yes to work they don't really want to do. But you've got to know who's looking for new clients, because otherwise your referral will end up feeling like a brush-off. Asking your boss questions about the scope and time commitment involved with new tasks before accepting them goes a long way toward keeping them from taking over your work day. That means being in the habit of always asking for clarification, even when you feel a little overwhelmed. If you attend this talk, I can't promise that your job will become perfect overnight, but I do think you'll leave with some new tools for saying no at work.

This article is part of the Speaker Interview Series for OSCON 2015. OSCON is everything open source—the full stack, with all of the languages, tools, frameworks, and best practices that you use in your work every day. OSCON 2015 will be held July 20-24 in Portland, Oregon..