Overcoming The Awkward Ask: How to Get What You Want At Work

by | Apr 30, 2020 | Culture + Team

Whether it’s a raise, a promotion, help on a project, or that $20 your colleague owes you (but never mentions), most of us have had to deal with the ‘Awkward Ask’ at work. 

For some people asking for things is simple regardless of the situation. These are the people who will tell you things like, ‘just ask’ or ‘all you need to do is speak up’. For other types of people, it’s easier said than done.

There may be genuine concerns of ridicule, backlash, retaliation, or manipulation; and there may also be (less discussed but just as genuine) personal fears. These personal fears generally involve the emotional discomfort of asking for what you want, need, or was promised to you – aka the ‘Awkward Asks’.

Now listen, if you’re dealing with a strong negative culture at work – one that includes a lack of trust, transparency, collaboration with your fellow team members, or ridicule – we urge you to reconsider your place of employment. Concerns of retaliation or manipulation by the people you’re supposed to be able to count on to get your job done are pretty serious issues that shouldn’t be taken lightly. 

However, if you find yourself hesitating to ask for the resources, recognition, or recompensation you deserve because it’s…well…just plain awkward, we’ve got some helpful template solutions for you below.

Solutions For Broken Promises, Brush-Offs, and Inconvenient Requests

At the start of Q3 your boss needed help creating the marketing plan for next year. You were employed as a Project Coordinator but your marketing skills caught your superior’s eye so he asked for your help.

While working on the project together he mentioned he thinks you should be promoted to Marketing Manager. It’s a better title and will include a pay increase. You’re stoked! But that was then. Now, Q3 and Q4 have come and gone, a new year is here, and still no title change or pay raise. He seems to have forgotten about it altogether.

Whether the promise is from your leader (e.g. a pay raise, a bonus, a promotion, time off, the OK to attend a conference or purchase a course) or your colleague (e.g. agreeing to help with a project, stick to a deadline, or pay you back for the lunch you bought them) communication is key. Here are a few tactics you can use.

Solution #1: Act Swiftly

As soon as possible/appropriate after the promise is made, send your boss a written acknowledgment and a request for more concrete details. It can be as simple as:

Thank you for giving me the green light to purchase ‘X Course’. I’m looking forward to using the information I learn to improve ‘These Areas’ of my current role. The cost of the course is ‘X Dollars’. Who should I speak to about the purchase process and use of the company credit card?

Notice the request to use the company card. If putting an expense on your own credit or debit card and waiting for reimbursement isn’t feasible or would be a huge inconvenience, this helps to stave off another awkward ask (more on this below). 

If it’s monetary payback from a colleague, ask what mobile payment provider they prefer to use. Not if they use one, but which one they’d prefer you use to request payment. 

Solution #2: Send a Helpful Reminder

What if you didn’t act immediately and time has passed? First, unless you have irrefutable evidence to believe otherwise, always assume the good. Perhaps it’s an honest mistake, a simple ‘CEO’ (Case of Extreme Overwhelm) blip or plain ol’ forgetfulness. Your coworker or boss may have a lot on their plate and their promise to you slipped their mind. If this is true, ignore your jitters, dismiss your bitters, and send a straight-to-the-point reminder. Something like:

I enjoyed the opportunity to work on the X Marketing Project with you in Q3 and am looking forward to discussing the promotion and pay increase you mentioned then. Can we set up some time this week or next to discuss so I’m clear on all of the details?  

For your colleague:

Thanks so much for agreeing to help me work on X Project. I’d like to meet before Thursday of this week to put together an action plan. What days/times work best for you? 

It’s now officially on their radar.

Solution #3: Be Direct

OK, you sent an initial acknowledgment or reminder email and still…nothin’. Or, you’ve been getting the, ‘we’ll discuss it later’ brush off. Now, it’s time to be direct. If you were promised something, you’re not out of line for asking the other person to follow through.

Don’t start your direct ask with an apology. Apologizing is for when you’ve done something wrong or offensive. Feeling uncomfortable asking for something you’ve already asked for is fine. It’s just your body’s way of telling you you’re stepping outside of your comfort zone. Acknowledge those feelings then move forward.

If you’ve received no response after a few days to a week, you might resend your original request and say: 

Just in case you’ve had a lot going on and my previous message got overlooked, I wanted to bring the promotion discussion back to your attention.

If you’ve received the brush off:

I know you mentioned we’d discuss my pay raise later, I’m really looking forward to it. So I don’t continue to bother you unnecessarily, can you give me a date and time I can put in my calendar for us to meet about this?

(for good measure you can also include this pièce de résistance):

I appreciate that you’re the type of leader who notices their team’s efforts and rewards them accordingly. It makes me happy to work at this company and for someone like you. 

Why compliment someone who’s taking their sweet time getting back to you? Because it utilizes the principles of ‘Consistency’ and ‘Cognitive Dissonance’ to help you get what you want.
People don’t just act according to their own beliefs but also the beliefs they want others to have of them. When you compliment someone on how you want them to act, even if they aren’t behaving that way in the moment, they generally play up those positive behaviors to continue being seen by others in that light.

Solution #4: The ‘Compliment Sandwich’ Decline 

Occasionally someone will make a direct request, like ask you to donate to their favorite charity or buy baked goods for their child’s fundraiser, that you’d prefer not to do. If that’s the case, try declining their request with a compliment sandwich:

What a wonderful thing you’re doing, raising money on behalf of ‘X Organization’; I admire your kindness and generosity. 

  • I’m not in a position to give at the moment… 
  • This isn’t an opportunity I can participate in at this time…
  • I’m currently invested in other areas…

…however, good luck with your efforts and thank you for understanding. 

Just because you’re asked to do something personal for a colleague doesn’t mean you’re obligated to do it.

Solution #5: Counteroffer

Then there’s the inconvenient ask. It may be your boss asking for your help on a non-work related task or the department director asking you to charge a large expense to your personal credit card.

If these are things you can’t or would prefer not to do because you have too much on your plate, or not enough of an available balance on your card, try providing a counteroffer. For example:

I’d love to assist you with the design for your family’s annual holiday card, however, I have four projects with tight deadlines I’m working on. Would it be helpful if I sent you the contact info for a couple of my design colleagues or links to freelance design sites?

There’s also the “what other options are available” counteroffer:

Thank you for getting back to me regarding booking my travel and accommodations for the conference. Is there a company credit card I can use instead of my personal one?


Being that this is such a large expense, can I receive the reimbursement now to cover the cost before putting this on my personal credit card?  

Wrapping It Up…

To get what you want at work when faced with an ‘Awkward Ask’:

  1. Act Swiftly
  2. Send a Helpful Reminder
  3. Be Direct
  4. Use “The Compliment Sandwich” Decline
  5. Include a Counteroffer

We understand these solutions don’t remove the sense of dread that accompanies an awkward ask. But they do provide language templates that should make it easier to address a variety of ‘Awkward Ask’ situations.

To help alleviate the emotional unease experiment with workarounds. One may be having someone else literally hitting the ‘send’ button for you on a message you’ve crafted.

As counterintuitive as it may seem, taking action immediately instead of putting off addressing an issue can be another helpful tool in reducing your anxiety around the ask itself.

And finally, talking yourself through the worst possible outcomes can also be beneficial.

In non-threatening situations, most of our worry actually comes from our imagination. We tell ourselves how bad the outcome will be in an attempt to protect our egos from embarrassment and rejection. But when we play out the worst-case scenario – which is generally just responding ‘no’ to our Awkward Ask or denying our request – we begin to see the reality isn’t as scary as our subconscious has made it out to be.

You may never feel 100% confident asking for what you want, but the more you do it (and survive the process) the easier it will become.

Want to get better at communicating? Check out our Whyzze Business Solutions Leadership or Team Events and request a Whyzze Communication Workshop.


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