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Negotiating Work Conditions

For some context I got offered a role as an Executive Assistant but at the same time I want to finish High School so I'm attempting to Negotiate for a win=win situation where both parties benefit. Any feedback is appreciated!


Hi ______

I would love to work in_____

I believe I can add value and be a great asset to your company.

I'd love to further discuss the offer and how we can cooperate for a flexible schedule. As within six months, I'll be fully available to work full time.



I try to frame the situation as something positive and try to add the WIIFM by showcasing my potential value to the company as they value me as an employee but at the same time are looking for one urgently so they may not accept this...BUT hopefully all goes well. I also use "only" to minimize the impact

BD, man, congratulations!

That's awesome to score an opportunity like that in high school :D.

Generally speaking, we have an easier time persuading over the phone or on a video chat than through static words on a page that convey no tonality or body language.

Over the phone or on a video chat, if they don't like what you're saying, it'll be far easier for you to continue negotiating for win-win until you both reach a satisfactory agreement.

But, continuing to negotiate over email can feel very high-effort and potentially cause them to lose interest as they feel forced to repeatedly check their inbox for you over the span of a few days (especially if they're busy people with other priorities).

A better strategy here might be to schedule a quick meeting or phone chat where you discuss this with them further.

I'd appreciate it if you could share what you might say to them to schedule a quick conversation. If you're open to it, that could help us give you more feedback and strategies here in the forum.

selffriend has reacted to this post.

Hey Ali,

for some further context:

I went for an interview today with 2 head of directors but the one I’ll be an assistant to is the one I haven’t built that much rapport with meanwhile the other director really wants me onboard and has bragged to other director about me, However the Issue lies in the full time job as it isn’t exactly part time,I’m trying to get an education because of parents ->Just to make them happy I guess because I do value family.I also want to make this opportunity work out...

After the meeting/interview,I felt highly distressed due to my parents disapproval as they view finishing High school success in that way.Depsite my attempts to convince them it has come to avail.My only chance is through proving that it’s a worthwhile offer and pay to take.Hence I have tried calling them once to convince them in advance for a flexiable schedule.

When they call back I’ll tell how it goes...But they have showed great investment in me even potentially buying me a new laptop and giving access to their work email.


What I might say:

I think I’ll primarily talk about how I can add value to the company and how I can be a worthwhile investment and try to create a win-win situation through a flexible schedule allowing me to finish high school meanwhile getting the job part time but even that is hard in it of itself.I’m open for suggestions 🙂


Alright, cool, that helps :).


As we sometimes like to say around here, "Allies empower and enemies disempower."

The director you'll be an assistant to doesn't sound like an enemy, but it would give you more power to recruit him as an ally by building up some more rapport. There are some good networking strategies I can recommend that you can use for that.

Ultimately, in my opinion, you'll want to check out Power University. It has strategies on how to turn him into a mentor for the best possible outcome if you do eventually start working with him.


A part of being a high-power assertive is being willing to have tough discussions. Including those difficult conversations with family.

Hopefully, your parents are recommending you finish high school because they understand the importance of a high school diploma. That diploma on your resume can give you more negotiating power in the job market than a GED. It's not about how good this opportunity is that you have, it's about covering any possible downsides in order to maximize your life success.

That said, hopefully, your parents aren't urging you to stick to high school only out of ego. As parents, it's not popular to have a kid that didn't finish high school and they might not feel too good about that when talking to other parents who have kids that did. And, I say only out of ego because "ego" can factor into everything for them when one builds part of their identity on being a "good" father or a "good" mother.

From the outside looking in, based on the information you've provided, I want to lean on the positive side. If you were able to get an opportunity like this in high school, then I don't think you should downplay your value as if this is the best opportunity you'll ever get in your entire life. If you have good parents who have good reasons for wanting you to finish high school, chances are it's because they see your potential and know you're capable of achieving even more with that diploma backing you. That's why I urge you to have those difficult conversations: to figure out what your parent's reasons are so you can factor them into your decision-making.


I think you have a pretty good chance of achieving both school and the opportunity. It feels like the questions you should ask are:

  • "What made you decide to take an interest in me?"
  • "What do you think separates me from most candidates?"

My intuition is telling me that there's something off about this entire negotiation.

They're willing to give a high schooler a position as an executive assistant. OK, got that. That means you bring some good value to the table.

But, you're also saying that they're looking to fill this position urgently. So, they're likely urgently looking for someone to fill this position. And, with all of the options out there, they're so invested in getting you that this negotiation is still ongoing.

I keep thinking back to a sales role-play I watched by The Futur where the prospect said something along the lines of "you charge too much, XYZ doesn't charge that much" and the freelancer (Chris Do) said, "OK, so why aren't you working with XYZ?" Clearly, there was something that set that particular freelancer apart. Some value that the freelancer brought to the table that XYZ didn't. And, he was able to uncover what exactly that was to reframe for win-win and get the contract.

This looks like a similar situation. Instead of, "XYZ doesn't charge that much" it's, "This other candidate isn't limited to only working part-time." So, why are they still invested in you? What do you have that it seems the others don't?

If you can figure that out, you can learn what it is they're looking forward to most in working with you and use that as the grounds for your win-win frame.

Other questions you can ask are:

  • "What else can we do to make this work?" (they're already invested, this gets them more engaged in the process)

And, a script that Charlie Houpert recommends to his coaching clients who are applying for jobs:

  • "So, obviously I'd love to get this job. But, when you're thinking down the line, whether you hire me, whether you hire someone else, how will you know a year from now whether or not you made the right choice? What will that person had to have done to have been an excellent hire?"

I'm open to feedback on this situation and my comments from anyone reading this as well. This is a bit of a tricky situation and one I'm unfamiliar with providing feedback on.

Matthew Whitewood, Transitioned and selffriend have reacted to this post.
Matthew WhitewoodTransitionedselffriend

Thanks for the feedback Ali if It's not too late


I didn't get the job.

What happened:

I essentially called them to discuss my results with no avail but I think I might be able to use this connection to perhaps obtain a internship as he(one of the directors) sent an invite in LinkedIn(I think of it as a sign of goodwill/or that I will provide future value as he strongly believes in my potential. During the interview, I got to know one of directors by connecting with his story and  thus building strong rapport and I think in that we built a strong emotional connections and he even vouched for me during the interview with the other director. He even drove me to the site for the meeting (30-45 min drive) which is when I built a strong rapport.

What I Learnt:

I think I also could have gave a small concession as a sign of goodwill when he picked me up. For context they needed me urgently which meant that I had to leave school. I think I could have used Best Alternative To Offer better and negotiated to an internship and work for free and prove my value to them to get a job(aka offloading huge value with no losses).Thus win-win. It essentially resulted in a lose-lose since I didn't get the job and they didn't get an employee, I do feel a tinge of regret and hoped it was a win-win, but hey I think I'll take this experience as a golden nugget for later.



@aliscarlett ,Sorry for the late reply and thanks for the  feedback as it was a unfair exchange. I will to reflect on this experience and  hope to grow even further to repay value. I think it was ignorant and a bit selfish on my part to not reply back  as it's WIIFM failure in a nutshell.

In the end I decided to stay in High School and finish my academics partly due to my parents and started my journey of growth to "Empowering myself in pursuit of the peak to soar above like eagles" would be my mission statement right now.



Lucio Buffalmano has reacted to this post.
Lucio Buffalmano

Awesome to hear back from you, BrightDemon.

And, thank you for receiving my feedback well man, it feels great to know we're on positive standing.

BTW, please forget about the whole repaying thing, we're all good :).

Lucio Buffalmano and BrightDemon have reacted to this post.
Lucio BuffalmanoBrightDemon