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The Art of the Ask

Updated: May 1

"I want something.” – Graham, age 3 

My son, Graham, has spent most of his life as a semi-professional negotiator (he isn’t paid directly, but he did negotiate an exceptional relocation and benefits package).

He’s particularly gifted at identifying the timing, recipient, and delivery of his requests to maximize outcomes. Want a toy? Ask mom when she has a fully loaded grocery cart and your little sister’s already crying. Want a complete rundown of snack offerings? Ask dad 10 minutes before bedtime, incorporating foot stomps and tears.

For those who haven’t inherited this innate talent — or whose requests have graduated from toys and snacks to earning more money — you may wonder … can the timing and/or delivery method of asking for a raise actually impact its outcome?

In short: yes. 

But before we delve into the nuances of this point, it’s important to state that, while there’s certainly value in considering your timing and delivery method — know thyself.

  • Need to write it all down and send an email? Great! Do it! 

  • Gotta get it off your chest to stop sleepless nights? Well, there’s no time like the present!

If it’s the difference between advocating for yourself or not, stick with what’s comfortable. But if you have the mental capacity and are looking to improve your outcomes, here are a few observations from my experience with raise requests that might help. 

How to Ask for a Raise — and Increase Your Odds of Getting It


People often ask: Is it better to put my raise request into writing, or should I always ask for a raise in person? My experience (and what I’ve witnessed working with dozens of others through this situation) is as follows:

Written works better if… 

  1. You’re relying on another party to convey your message and tone and want to avoid the proverbial game of Telephone.

  2. You’re not comfortable, or practiced, with regular negotiations and are nervous about the initial discussion. 

  3. You aren’t deeply informed about the benchmarks or able to quickly evaluate an offer.

Verbal works well if… 

  1. You’re talking directly with the decision maker(s). 

  2. You’re comfortable with negotiations and advocating for yourself. 

  3. You have a good understanding of the benchmarks.

  4. You’ve practiced your delivery and rebuttals. 

In practice, I often find that raise negotiations require at least some verbal interaction, but they can be complemented by written summarizations/key points to ensure that your message is being heard and delivered effectively. 


As for when to ask for a raise, the answer lies within a riddle wrapped in a mystery inside an enigma. That’s probably a bit of an overstatement, but the answer is most closely related to the fluidity of the process, your achievements (i.e. leverage), and how far you’re willing to go.

Let’s break that down… 

  1. The process: To negotiate effectively, you need to understand the process (or sometimes lack thereof) within your company. Otherwise, you may find that your efforts are stymied (intentionally or unintentionally) by procedural issues. E.g. “I’d love to give you a raise but the budget is set, the ratings have been calibrated, blah blah blah.”  So it’s in your best interest to understand the process before you get to negotiations. A good time to get a feel for this is during the onboarding process. Ask if you can expect an annual review, which, by the way, is an excellent time to ask for a raise. You can even ask directly: Is there a preferred salary increase protocol in place, or how and when are raises and promotions typically handled? Save your future self stress and mental fatigue by entering into the job with clarity.  If it hasn’t been discussed on the front end, it’s never too late to inquire with your manager and demonstrate an active interest in the process. 

  2. Your achievements and contributions (i.e. leverage): Taken on more work and responsibilities? Recently closed a big deal or achieved a major milestone? We all (managers included) have a tendency towards recency bias, so don’t let your leverage diminish over time and strike while the iron is hot.  Not only will your recent accomplishments shine a positive light on why you should receive a raise, but they serve as a natural kick-off point for the conversation. For example, “I’m excited about the opportunity to contribute more value to the team. Given my new responsibilities, I’d like to discuss what an appropriate salary is for the role.”    

  3. Your line in the sand: If you're ready to walk away if your asks aren’t met, then you’ve got a powerful leverage point and the ability to cut through protocol. Put simply: Timing and mode of delivery don’t matter as much if you’re ready to walk.  It’s especially important that you play this card if, and only if, you’re willing to walk away from your current position. Otherwise, you may find yourself being forced to reject offers you’d be willing to take or losing internal credibility if you decide to concede. 

Though it varies from company to company, in general, raises can be expected annually. That said, I’ve worked with clients who have asked for a raise with success twice a year or even quarterly depending upon the industry and dynamics.


As for how much of a salary increase you should ask for? I’d love to provide a very specific % range, but, alas, it isn’t quite that clear. I’ve seen that 10-12% increases are achievable, but there have been many outliers on both high and low ends. 

What I do know is that if you’ve done your research and have a confident understanding of internal (other peers, new job postings, etc.) and external (online resources, postings, network, etc.) salaries in line with your role and experience level, then you should anchor around hitting that number… because why shouldn’t you? 

Remember that you are your best — and really, your only — advocate for increasing your earnings. It’s a daydream (albeit a tempting one) to imagine that if you work hard, a raise will come to you. In almost all cases, you’ll need to be proactive and start the conversation. 

If you need help developing a strategy for your raise request, reach out. I can help guide you through evaluating the landscape, uncovering your value, practicing verbal negotiations, and delivering the ask most likely to succeed.

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