Talent Development Centre

Asking a Favour From Your Boss: A Contractor’s guide.

Asking a Favour From Your Boss: A Contractor's guide.

Brianne Risley By Brianne Risley,
Director, Delivery Strategy & Development at Eagle

A question I am often asked is “What is the best way to approach my boss to ask for something important?”

As an independent contractor, it can be daunting asking your leader for something you need. This is particularly true today when most workers do not want to ‘upset the applecart’ during a precarious time for companies in the market.

You may be looking to address one of the following big topics affecting your work-life:

  • Work hour concessions during the pandemic
  • Accommodations for a return-to-the-office work plan
  • A recommendation/reference for a new project
  • New project work, or a transfer to another department

In this article, I will give you an easy way to frame a conversation where you have an important ‘ask’ in a way that it will work for any audience – your client, family, friends, anyone.

The Format:

The message is best delivered in person (voice-to-voice) first, with a follow-up via email in a work setting. The verbal delivery helps the listener understand the tone of your message and helps convey the sincerity and importance of the ‘ask’. The written follow-up is like any business proposal – it helps to ensure follow-up.

The Opener:

This will be a gracious expression of a heartfelt thank-you, and appreciation for the current state of affairs. Your focus is to establish a sense of gratitude, and convey your positive energy – both as a team player, and a core contributor to your organization. You will also take the time to list out your personal key, results-based achievements. When listing your achievements, try to include as much detail as possible including facts, figures, earnings, time-saved, users helped, recommendations, etc.

The past few months with a reduced staff have been hard work, but have been motivating for me. Thank-you for retaining and supporting our team members. We’ve worked well together to deliver significant achievements on the project, and on a personal level I’ve really been able to excel in the following areas: 

  • 15 integrations completed resulting in a 20% reduction of admin time
  • Completed 3 remote workshops, and trained team members on how to achieve good meeting facilitation results via Zoom Meetings.
  • A business user had this to say about my customer service ________.

The Ask:

A common mistake people make when asking for something is not stating how it benefits the employer on a business level, and themselves on a personal level. In my view, you can’t ask for more of something while still offering the same work results or benefits.

State what you want, and then explain how that change will save you time/money/piece of mind that you will reinvest in other areas to get a return. Make sure there is a carrot to motivate the decision maker to side with you.

Next month, I will continue the complex integration work on this project to make both us and the project stakeholders happy. That said, there is an important impediment that I need your help and support with. I would like to shift my work hours from 9am – 5:30pm to 7:30am – 3pm in the month of September to help balance my remote work schedule with my children’s re-entry into the classroom.

  • The early-morning hours will allow me to clear off after-hours work orders before my colleagues start, thereby promoting faster ticket response times. (employer benefit)
  • On a personal level, this would give me piece of mind that I am able to handle any school-related issues well outside of my core working hours and avoid unnecessary distractions. (Personal benefit + employer benefit)

The Closer:

Finish with a quick recap of the ‘ask’, and invite the chance to answer questions.

  • I like being a top contributor to this team, and I enjoy doing it for an organization that values customer satisfaction and work-life balance.
  • I welcome the chance to discuss this with you further. What questions can I answer?
  • Thank you for the continued support, and I look forward to discussing how we can be even more successful moving forward.

As the ‘hired gun’ on a project team, consultants are paid to be self-sufficient and low-maintenance. If you find yourself needing something big from your leader, let this framework give you the tools you need to get it.

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