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How to Assert Yourself on Expectations to your Subordinate?

I have agreed with my intern to a remote working arrangement with lots of freedom as he started university.
I also helped him quite a lot in his personal statement to apply to a Master's program.

After asking him to revise his personal statement and plan out the subsequent tasks, he sent me this email:

Thank you for all of your feedback.
I have made adjustments to my personal statement accordingly.
It would be tremendously helpful if you could help me to take one last look!

Also, apologise for the delay on updating video analysis.
I was quite caught up with school coursework and personal statements.
I will be continuing my analysis this week.
Thank you for understanding.

Generally, he's very respectful and gets tasks done.
This is why I got him to work with me again because we work well together.

As such, I was quite surprised to receive this email.
In a way, it's very honest but he indirectly (actually quite directly) communicated that his personal statement is more important than our project.
And then he asked me to help him with his personal statement again.

I believe that this application is very important to him.
So he may have been carried away.

This could potentially be detrimental for me in terms of social exchange and also in terms of leadership influence in getting things done through him.

However, I was thinking asserting the importance of the tasks directly would not be ideal though as it may promote an employee mask.
He will feel the need of keeping up an appearance.

The root cause is probably that he needs to

  • Communicate expectations well
  • Manage his time well and not stretch himself thin

As such, I'm thinking about a response like

Yeah, I know this personal statement is important to you.
Why not you take some time to focus on getting this done first?
Feel free to let me know if you need to take time off for whatever personal reason.

We can always reconvene at a better time as I would prefer you not to spread yourself thin.

It's also best if you can let me know in advance when you will be busy.
Although I understand that workload can come unexpectedly at times.

I feel that this promotes transparency, and, at the same time, comes across as a caring leader.

Task-wise, he will not hinder the progress of the project.

What do you think?
Thank you for your time in any case.

An important question I'd have is:

Is it paid internship?

If there is money involved, then it's more cold exchange and he has no call in playing power moves.

If it's unpaid, then it's more about mentorship and exchanges of favors.

You're more aware of the relationship.
If he's done great work, then I'd take a look at that personal statement.

As it stands, your reply seems cold and answer to some small power moves with even more games -ignoring his request rather than addressing it-.
I'd address it more openly.

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Thanks a lot for the advice Lucio.
I really appreciate it.

The context is a bit long so skip ahead to value exchange if lack of time.

More Context about our Working Relationship if You Have Time

It is a paid internship.
He tracks the tasks and time, and I pay him according to the hours that he clocked.
I'm rethinking if this is a good decision.

Previously, he worked full-time for me for a few months and was very focused during the summer.
He enjoyed the internship, working with me and the previous project.
And he wanted to continue with a part-time internship.
I was sceptical then because it will cause competing priorities: internship, schoolwork and applications.
He might not be able to focus so I told him to start school first and reach out to me if he think he can cope.
He didn't reach out to me as I guessed.

Fast forward, a year later, we caught up, and he says he's interested again in a part-time arrangement.
Finding out his interests and background in social science and technology (he wants to do social data science), it's aligned with the project interests and my personal interests.
As such, I decided to give that a go.

Working with him has been generally good so far.
I spent time getting him up to speed on how to find and analyse videos.
"Great work" could be giving the wrong impression.
He produced good work and is getting better.

The issue is that he probably didn't foresee how much time applications would take and how schoolwork could get busier over time.
Now, I'm thinking about how to navigate this.

He was very fair in how he asked for compensation.
He told me that he wanted to get started on the work first and then we can discuss the pay based on what I think is fair.
Regarding the pay, this was the nature of the discussion:

Thanks for the chat and the clarification on the tasks.
I have attached the timesheet for hours worked.
My latest hourly rate was $X amount working as a research assistant, but as the nature of this internship is quite different from a research assistant; also you helped me alot in many ways, I think the final hourly rate should be decided by you.

Also please let me know if you have any questions regarding the timesheet. Thank you.

Letting me decide on the pay came across to me as he valued a fair exchange.

Summary of Value Exchange

What I get out of working with him:

  • He produces relatively good work.
    I fine-tune the work but he saves more time than if I do everything from scratch.
  • Sometimes he brings about a good perspective.
    For example, he lived in the US so he understood the cultural aspect of African Americans better.

What he gets out of working with me:

  • In the previous internship, I taught him tangible skills like email marketing, Facebook/Instagram ads, LinkedIn cold reach-out.
  • In this internship, I got him up to speed on social analysis and what to look out for.
  • Personal favours like a personal statement, letters of recommendation, career advice, books (product management), etc.
    I also shared with him the general principles behind writing more persuasively so that's a step further.

My Thoughts on Replying While Setting Up a Call

As it stands, your reply seems cold and answer to some small power moves with even more games -ignoring his request rather than addressing it-.
I'd address it more openly.

Thanks for the advice regarding how my reply is not ideal.

I see how it's gamey because it doesn't address his request and what's wrong with the dynamic.

Now, I'm thinking of writing along the lines of

Probably you didn't mean it this way.

When you say "apologise for the delay" and "thank you for your understanding" with regards to the video analysis, it comes across as putting our work as a relatively low priority without asking for my input.

I'm very happy to help with checking your personal statement.
At the same time, it's important for me to have a fair relationship.

If your other workload is getting too heavy, please let me know so we can set the right expectations.
It's also okay to take some time off the project.

Let's have a call to talk this through.

Thank you to anyone for your time in any case even for just reading.

Much better.

I wouldn't personally say "probably you didn't mean it this way" as that's inferring his motivation.

I'd greet him warmly, then transition with "quick feedback".

But that's also about personal preferences.

Matthew Whitewood has reacted to this post.
Matthew Whitewood
Community, new content and Confidence University now available here.

Thanks Lucio.

I am on the same page.
I'll switch to a warm greeting followed by quick feedback.

I have probably used this phrase too much:

"probably you didn't mean it this way"

I thought that it's power protecting for negative feedback.
But now I see how it can be guessing intentions/motivations.

Thanks a lot for your help Lucio.

I think I still have work to do on assertive communication.
I have a tendency to try to resolve conflict in indirect ways.
When assertiveness is the fastest and healthiest way to do so.

The response from my intern was generally good:

thanks a lot for your feedback on my second draft of the personal statement.

I also want to appreciate for your professional manner in expressing your concern and expectation on the video analysis. While it is true that my workload is getting heavy towards the end of the year, I believe I can do a much better job in balancing different tasks. I will take this warning very seriously. We can have a call to talk more on this should you like.

In truth, assertive communication is sort of like a "warning" but that was negative connotations like threats.
It also conveys a more authoritarian relationship between me and him in a not so good way.

As such, I am planning out a warm response.
And I will help him more with the personal statement.

I am thinking of responding with

Thank you very much for seeing my perspective on this.
We can view this as a work/personal relationship where either of us can raise issues.
I very much would like to hear your perspectives on work or other matters as well.

Things seem to go well from here! Thanks Lucio.
Feel free to leave any further thoughts, and thank you for your time and advice in any case.

Lucio Buffalmano has reacted to this post.
Lucio Buffalmano

I called my intern today.

First, he thanked me for teaching him why "thank you for your understanding" is not very good to use.
Then, he said that pointing this mistake out will help him avoid this mistake in professional situations.
This partially framed the mentor-mentee relationship.

Then, he discussed the video analysis next.
He knew that this is what I want.
Then, he said that he should follow my expectations on the analysis.
Technically, this is part of the cold exchange: money for work.
But the money was not mentioned in the discussion so it's not focal.

Finally, he asked me for advice on the personal statement.
Now it's a bit hard for me to say "no" because of the reciprocity effect and mentor-mentee framing.
So I opened up the statement on email and pointed out one paragraph.

Then, he said again

I may not have the level of experience to craft this.
(...)
This is really helpful.

This further frames the mentor-mentee relationship.

Then, he starts asking about investing.
I was a bit afraid here so I said

I'm not an expert here and don't want to steer you in the wrong direction. (which is true)
But I can certainly share my approach.
Although you should definitely read up on your own.

Then, I went back to the frame of how I learnt social skills from analysing videos which help in writing essays:

How I got good at writing is thinking and practice.
And I've been doing that for real-life situations and social situations on videos.
Let's continue working together, and our writing will improve naturally.

I have to see whether this works.
We both benefit when he focuses on social skills so it's theoretically win-win.

Objectively, he's adding value so all good in my opinion.
Thanks to Lucio for helping me with the situation.

Lucio Buffalmano has reacted to this post.
Lucio Buffalmano

Rock on Matthew, handled it really well.

It shows what a big difference it makes to approach people and situations well and with an honest, eagle-like approach.

You could have easily gone down the path of making this a series of games, as most people would have. Instead, you handled it straight and honestly and now you have a much better (working) relationship, plus much higher odds of markedly better results.

Matthew Whitewood has reacted to this post.
Matthew Whitewood
Community, new content and Confidence University now available here.
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