Negotiating The ASK: 3 steps to get them to invest (in you)

Negotiating The ASK: 3 steps to get them to invest (in you)

By Sam Trattles

We get asked all of the time about tips for negotiation - particularly how to get your boss to invest in the Women Rising program for you. We spoke to Sam Trattles, CEO and Negotiation Strategist at Other Side of the Table and asked for her best tips. She shared her 3-step negotiation process for getting funding for the Women Rising program, or any other ask that you have.

To help you confidently step into a negotiation, let’s walk through our 3-step process to prepare to make the ASK…


Approach this phase with a positive mindset, envision a scenario where the person you’re going to negotiate with is going to say yes to everything you ask for. As you step through the process keep this top of mind, so you don’t think for them, and you don’t be a nay-sayer before you even step into the conversation.
With your fresh mindset, ponder your request solely from your perspective. Get clear on:

  • the reasons you explored the opportunity to join this program.
  • what’s driven you to identify this program as the best use of your time, money and effort.
  • how this program fits into your development plan.
  • and, why doing this program at this time makes sense.

Next, let’s assess the emotional connection between your involvement in the program and your job satisfaction. Consider how you feel about the company you work for recognising the impact this program can have on your abilities to do your job with confidence, and your overall happiness at work. And what it would feel like if they didn’t, because it’s likely that’s what you’re really negotiating here.

Take all these thoughts and feelings into account as you aim to get laser focused on: what you want, its personal significance, and the strategic alignment with your organisation’s expectations outlined in your job description and your KPIs/OKRs. This will pave the way for how you'll articulate the compelling business case you’ll be negotiating.


Once you’re clear on your request, it’s time to unpack the best way to say it so your boss, and the business, will ‘hear it’ as you step into the negotiation.

Try and think like your boss, what do you think is the first thing they’ll say when you put this idea forward for consideration? People are creatures of habit, so depending on how long you’ve worked with them, you’ll have a good sense of how they’ll react.

With this top of mind, you can craft your message in a way that’ll make it a ‘heck yeah’, or at least a, ‘let’s explore this further’ for them.

To help you negotiate with confidence, you should get clear on these elements to contextualise your request:

1. Know your company’s policy on training budgets and programs - this will anchor your request within established guidelines.

2. Back it up with data points that support your request. Consult sources like The Voice of Women at Work Report 2023 and similar research to substantiate the value of the proposed investment.

3. Share success stories from program alumni (in and outside your company) highlighting the tangible impact of the program.

4. Align it with your development plan and how it contributes to achieving your KPIs/OKRs so it’s a seamless request.

5. Emphasise personal value by articulating how this investment will make you feel valued as a key team member and outline the potential impact of lacking support.

Ahead of creating a summary of your request, it’s important to determine where you’ll start this conversation. If your boss likes to process things, you may want to send a summary via email first, OR if they’ll respond better by raising it in your regular catch up add it to the agenda, OR you may find it better to discuss it while you’re on a walk and talk. Again, it comes down to your knowledge of what typically works well for your boss.


With all this clarity, it’s time to distil your request into a concise and impactful summary that you’ll share when you make the ASK.

There’s so much you could share, however, this can be overwhelming for you and confusing for the person you’re making the request to. To avoid this, get tight on 3 points:

1. What’s your request?
Clearly outline the opportunity you’re seeking support for, underlining that your well-researched approach streamlines the path for approval.

2. Why does it make sense?
Highlight the key supporting points or evidence that should make it a ‘heck yeah’ proposition for the business to seriously consider this opportunity, as it clearly aligns with the organisational objectives.

3. What contribution do you want?
Outline the level of support you want from the business – whether to fully fund the program, a percentage contribution to the fees, time to complete the program during work hours, or something else.
Ensure you’re confident your request is fair and reasonable, and explore why you think they will think the same, and if not, why not? reshaping your summary if necessary.

You don’t have to have all the answers, this is a collaborative 'we' discussion – meaning it’s an opportunity for the business to demonstrate how much you are valued. It’s also an opportunity for a broader discussion with your boss, emphasising why investing in your growth is beneficial for the team and the business.

Note, in the current challenging business landscape you should be prepared for potential pushback. If this happens, seek clarity on whether it's a 'no for now', a flat 'no', or a ‘no to this opportunity’ and understand the reasons why, and what next.

Stay engaged in the process, collaborating closely with your boss to find a way forward that ensures you’ve been heard, you feel valued, and you’re clear on the next steps in the conversation.

Armed with these insights, it's time to take the plunge and make the ASK.

No matter how it goes, be proud of yourself for putting yourself first and initiating the negotiation. Remember, we don’t always get everything we ask for, but if we don’t ask, we don’t get!

Afterwards, take time to reflect on the experience – shine a light on your successes and embrace the lessons learned. Celebrate what went well and note what you learnt that will help you know what to do differently in your next negotiation.

By integrating this reflective practice, you’ll find your voice to make The ASKs more often, with confidence.

If you’re ready to put your negotiation skills into practice and ask your boss for funding for the Women Rising program, you can learn more here.

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