Ok you guys. I’ve been pretty open about the fact that I’ve made so many negotiating mistakes. I was pretty much as bad as they get. Yes, even after taking classes on negotiation. I just didn’t understand exactly what I was supposed to say and when.

One of the things that used to confuse me the most was when to actually negotiate. All of the jobs that I had before going out on my own, had a very structured annual review process. It confused me

In December I’d do an assessment of how my year had gone and a few months later I’d have a meeting with my boss to hear what my raise and bonus was. If I wasn’t happy with my raise, I didn’t feel like I could actually ask then. It felt like it was too late. But there never seemed to be an opportunity during the meeting in December. We’d have formal mid-year check ins, but those also didn’t feel like the right time to ask for a raise.

I felt stuck. When should I ask?

Now that I hold workshops on negotiation, I realize that I’m not the only person confused by this. People reach out to me after a disappointing performance review, where they didn’t get the raise they wanted, and ask what to do. Unfortunately, starting this late in the game doesn’t lead to the best results.

If I can leave you with one piece of advice, this is it: start the negotiation process well before you think you should.

Whether you work in a very structured environment with annual reviews, you work at a company that has really loose policies (if any at all), or you work for yourself as a freelancer and need to negotiate with clients, the advice remains:

Start before you think you need to.

To illustrate what starting early looks like, I’ll break down how this would work in a traditional environment where you have annual reviews. This is also the same timeline and process that I use now that I have to negotiate rates and contracts with clients.

when should I ask for a raise

4-6 months out:

This is where you want to establish expectations for the upcoming review, even though it’s months away. Collaboratively set goals and expectations with your manager so that you both know what you’re working toward.

Don’t know how to start the conversation? Here’s an example:

“I’d really love to talk about my development plan for the remainder of the year. My goal is to take on more, be one of your strongest performers, and be promoted [given more responsibility, etc] next year. I’ve really enjoyed working on the new communications plan over the last few months and I see a big opportunity for the company to take that further. I’ve come up with some ideas to really knock this out of the park over the remainder of the year, and I’d like to get your feedback. I think this is something that can make a real difference to our group and I’ve outlined my ideas here. [hand over proposal of ideas] Do you think I’m on the right path with this and if I’m successful with this would you be able to support me with my goal?”

Another example:

“My goal this year is to create massive value for our team as well as get a ranking and raise that really reflects what I’ve done. I see a huge opportunity to create a social media training program, as this becomes a bigger and much more lucrative part of our business. I’ve come up with some ideas as to what this training program would look like and what I can create over the next 6 months. I’d like your advice on whether you think this is beneficial and how it can be as strong as possible. Do you think I’m on the right path with this and if I’m successful with this would you be able to support my goals?”

The key here is to actually write something up, share it, and get feedback on it. You want your goals to be aligned with your manager’s goals so that when you do the work and deliver on this, you know that they value it.

If you have a mid-year review, this is the perfect opportunity to bring this up.

2 months out:

Now’s the time to check in, remind them of what you’ve done, the progress, and get their input so you can course correct if needed. Come prepared to this meeting with the summary of the expectations you set with them at the 4-6 month mark. It should now be updated to include the progress you’ve made there, and any other exceptional work that you’ve done.

2 weeks out:

Practice, practice, practice. Oh, and practice. You’ve put in the work, you want that raise or promotion. Now, it’s almost time to ask for it. Get together a summary of what you’ve done and go over what you’re asking for and why. Don’t try to wing the conversation – that never works.

Year end review:

This is the meeting where you discuss what you’ve done, usually a self-assessment that you do for your manager. This is before they submit this info for raise and promotion consideration. This is before the company decides how they’re going to award raises and bonuses for the year. Here you’ll again bring a document that outlines the goals you had agreed to in the first meeting and how you’ve performed since then. You can also add on where you see this going over the next year. Having this document, and the lead up over the past few month opens up the door for you to easily negotiate that raise you want.

And then, cue the celebration!

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