How Socially Oblivious People Interact (Avoid These Mistakes!)

by | Business / Work / Career

Got a new coaching client who booked a call for business networking coaching, yet asked all sorts of questions surrounding his goal to reach a 100 million net worth.

It was a good case study as far as why social skills are so important for life effectiveness and success (he made quite a few mistakes that made it difficult for me to want to continue working with him and I’d imagine those same avoidable errors could cost him high-quality mentors on his journey if he’s not careful to learn from them.

How This Coaching Client Lost Me As A Mentor

Let’s start with his introduction:

Power-unaware introduction: the “unofficial authority”

He makes a few mistakes here including saying “really appreciate it” instead of “thank you” (which would have made his judge role more in the green).

But, he did a great job of following my instructions to send an email before booking a call on my coaching calendar. And, I appreciated his respect for my boundaries on that.

So, I accept his coaching request.

(Sneaky) negotiation attempt 1: pay upfront, then “take” any added time

Then, he says this:

I charge by the minute because oftentimes a client will try to pay upfront, then go over our set time limit, and then try to avoid paying for any added time.

Plus, the covert judge power move of trying to judge credit-award my compliance rather than actually make it up to me with real value makes his request less appealing.

So, two days pass without my response (as I think about how I want to go about it) and he decides to book the call on my coaching calendar without going the PayPal route.

Now, we’re good to go.

Negotiation attempt 2: review their pricing, then slash it in half

After we completed our first session, he sent me a follow-up “thank you” email:

The added gratitude this time around makes me feel more like I’d want to work with him again.

The problem is that after we finished our session, I noticed that the coaching platform took a fairly large cut, leaving me with an amount that felt unfair for the time and effort I invested into the coaching.

So, I increased my pricing. And, he noticed, which is what led him to request a “special price”.

But, the issues with his request here are:

  • He didn’t give a reason for the request: which would’ve made his ask far more persuasive
  • He doesn’t have any social capital to ask for anything: which also would’ve made his ask more persuasive
  • He doesn’t limit my losses as a seller / signal future value-giving potential: which would’ve been a more collaborative frame and also (positively) boosted my chances of compliance

So, I ignore his request.

His risk: “ignoring the SCM (and social exchange) to chase more support”

Then, he sends two more emails back-to-back, while opening and reopening the email thread multiple times:

His emails are in the interest of correcting his initial message and providing me with more information (which helps me give better recommendations), so I let it go.

But, it’s an approach that puts him much lower in power because it feels neurotic and invests so much more social effort than the other party (me).

His hope is that I won’t care about the stereotype content model (SCM) and whether or not he’s high/low-power and that the increased communication will increase his chances of getting better advice, more support, and more investment from my side as well.

But, the SCM and social exchange are crucial to understand because even if that were the case here, that’s not how the world works (which is why I recommended Power University to him on our coaching call, but he wasn’t interested).

Either way, I send him my coaching follow-up email with the resources that I recommend:

That last line was to draw boundaries on giving any more investing advice (something that I’m not an expert in and don’t feel qualified to give yet), but also to give him some encouragement on his ambitious goal because he seemed on the fence about his own dream.

And, as someone who practices an extreme growth mindset, I wanted to share my positive views on his goal in the hopes that it might be even more value-giving than anything “informational” I have to teach (sometimes all we need to hear is that we can do it, especially when we’re at our lowest point — which he wasn’t, but it still had the potential to be hugely value-giving based on where he seemed to be in his self-doubt).

He then proceeded to send me 11 emails back-to-back starting with his ideas, then changing his mind about his ideas, then apologizing for changing his mind again.

If you can zoom in, you’ll see the first sentences of each email he’s sending. And, my notes are my interpretations of his emails.

Each one he sends becomes increasingly more value-taking because he’s:

  • Causing numerous email notifications across all my devices
  • Repeatedly bumping his emails to the top of my inbox (which makes me feel like I’m being “forced” to respond now)
  • Sharing useless information that he later changes his mind about so he can share more useless information

It looks like the behavior of someone who doesn’t respect my time or inbox, probably won’t go far in life, and has the communication habits of a value-taker.

So, I address it (with a similar message that Lucio sent me once when I made a very similar and potentially equally value-taking mistake with him):

Negotiation attempt 3: acknowledge their pricing, but lower the time (by a lot)

He apologizes, which already makes me feel much better about working with him (a great first step).

This time though, he doesn’t seek to cut my price in half, he only looks to cut the time of our session down. Not a big deal.

And, he gives a reason for his request this time, which is also better.

Unfortunately, there is still the issue of being uncompensated for any added time he takes up (because of the PayPal route) and, judging from his previous behavior, he has no qualms about taking up more of my time than is allowed/fair.

Also, the short amount of time he was requesting wasn’t worth making space for in my calendar.

So, I deny his request.

A mistake on my part, I was unclear in my communication before that he actually needs to book the time slot on my Calendly to get the availability.

So, I restated it here, but realized after sending it that the miscommunication was actually entirely my fault. And, not acknowledging that (by taking full responsibility) felt unfair to him, so that’s something I learned from and have been keeping an eye on to avoid for the future.

Negotiation attempt 4: seek completely free value

A completely fair request in this case, in my opinion.

After the message I sent above, he says this:

Overall, not a horrible message, in my opinion.

I’m happy to give advice over email for small questions, no need to nickel and dime anybody.

Plus, he mentions it would be very helpful, which is a way of acknowledging the value that I’d be giving. So, he avoids debt-erasing to be more fair to me, my time, and any value that I have to give (which is good).

The areas that I see for improvement in his message are:

  • He sends three questions: which makes it seem coaching call-worthy
  • He frames his questions as problems: which implies that they need real (potentially detailed/well-though-out) solutions, not “hints” or “tips”
  • He asks an open-ended question: which would require more of my time and effort to answer
  • He goes back to judge credit awarding again: which would deny me of any real value in exchange for anything I give

So, better, might’ve been if he had said:

Hey Ali,

Thanks for all your messages! (Exclamation point implies excitement, and that positive mood is inherently more value-giving)

I’m not expecting you to invest too much time into this, only a few tips would be really helpful. (Good, gives the receiver the freedom to limit how much time and effort they invest into their response)

I watched all the videos, read the entire review, and even did a test from Dr. Demartini to identify the top values that I’m driven by, and the one that stood out is “communication and psychology”. (Communicates: “I did the homework you gave me — I’m an action-taker implementing everything you’re teaching me and more”)

Everything you shared was very insightful (gives more emotional value), I’m only looking for more clarity on how to come up with a career or business that’s aligned with my top values. Are there any quick tips you can share on how to go about that (“quick” implies low-investment, great to preserve the receiver’s time and energy)?

If you think this deserves a coaching call, that’s cool too, just let me know, it’s completely up to you 🙂 (gives the receiver an “out” and strategically puts the power back on their side).

Kind regards,


Then, save the other two questions for another time such as a follow-up coaching call or a day when you have more social capital to spend.

Negotiation attempt 5: sneakily push for free value

Before I can even respond to his email above, he follows up with an ask for a coaching call (a good move, in my opinion, given how much he was asking for and how little social capital he has by now):

So, I confirm the call, adding in a few techniques as well to increase the chances of him fully following through:

This may not have seemed necessary given that he proposed the call, so it’s implied that he was already pretty much sold on it and there wasn’t much more “selling” needed.

But, it felt necessary given that I felt like I was dealing with a value-taker. So, I took this approach based on a hunch that it would help increase the chance of full compliance.

And yet, it seems like this approach of framing the homework answers as necessary for a productive discussion might have backfired.

It was his idea to move forward with the coaching call. So, it seemed like it was already implied that we could cover any questions he has (homework or otherwise) over that coaching call.

But, he interpreted the homework answers as being necessary before a coaching call and used that as an opportunity to backtrack to ask for free advice again:

Whether or not he interpreted my message incorrectly on purpose to avoid paying for my advice is anyone’s guess. From the value-taking he’s done so far, it felt that way (at the time), but I don’t believe in jumping to conclusions.

And, as I said before, I was never against the idea of giving away a free tip or hint anyway.

So, I did.

Poor social strategy: trying to use an undeserved exception-seeking frame

He thanks me for the free advice, then comes back seeking a different type of coaching.

I’m always open to making an exception for someone who’s shown they deserve it, but with his behavior so far and lack of social capital, it felt unfair for my time and boundaries.

So, I deny his request:

Poor social strategy: shows indecisiveness as a pattern of behavior

Initially, right after our coaching call, he said that he wanted to be a thought leader using communication and psychology.

Then, he changed his mind a few times and, now, after receiving my email above, he says this:

A complete switch to real estate.

This continued indecisiveness runs the risk of coming across as low-quality. It can be perceived by others as a lack of self-awareness about one’s own wants, desires, and motivations in life.

And, it made me feel that we’re not a fit to work with each other. I can help you get what you want, but there’s that initial first step of knowing what you want. And, there are other coaches out there who are better equipped to help with that self-discovery than I am.

So, in total, this email thread is 35 emails long. And, only 8 of those emails are mine.

In the end, this exchange felt like it was taking more than it was giving, so I moved on.

Poor social strategy: negative frames lead to negative outcomes

Four days later, after sending his last email (the one above), he sends me a new email in a completely new thread:

More than the communication mistakes here is the timing. It would’ve been better to wait at least a week given the decline our previous email thread was taking.

But, such is the case when dealing with the socially oblivious. They often have no idea how social dynamics and power dynamics work, including the basic laws of the social exchange and, sometimes, basic communication (such as actually typing out a subject line).


Many of the mistakes made by this person were very much avoidable.

And, while it helps to have good social skills for better social navigation in situations like these, power skills are also very important to keeping a good mentor.

About The Author

About The Author