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I'm leaving my job and I'm wondering if I should address the letter to both the Direct Boss and the Overall Head.

I need to preface by saying that Direct Boss is pretty much an echo of Overall Head. DB is quite cold and formal in their approach but very few decisions are made without the approval of Overall Head. When I give DB my letter, I already know that DB would simply say, "I'll raise this to OH."

OH is younger than DB, and so has better relations with the people in the company. OH is especially nice to me, and always asks me how I am doing, since I have a special role in the company as a consultant with unique benefits. OH can become emotional when provoked (though I have never personally witnessed it) and is very casual, ie. giving instructions directly to junior associates without considering the proper hierarchy of delegation.

I am worried that by resigning only to DB, OH will feel hurt that I did not address a letter to OH, or that I did not raise my issues first. However, if I copy furnish both bosses, DB might feel as if I am stepping over their authority.

Should I stick with protocol and address only to DB? If it is better to furnish both bosses with the letter, how should I go about it formatting-wise as well as process-wise?

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  • +1 This is an excellent example of the downside of an unclear hierarchy.
    – A. I. Breveleri
    Commented Nov 5, 2019 at 17:47
  • @A.I.Breveleri Technically, hierarchies are clear; it's the practices that are messy. It's definitely a disorganized workplace.
    – onthewing
    Commented Nov 5, 2019 at 17:54
  • You could give the letter formally to your boss and send a quick email to OH.
    – Stephan Branczyk
    Commented Nov 5, 2019 at 18:31

3 Answers 3

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I'm leaving my job and I'm wondering if I should address the letter to both the Direct Boss and the Overall Head.

You are overthinking this by a wide margin.

Just resign to your "Direct Boss" and let them handle it from there.

As word gets around, perhaps your Overall Head will want to talk to you about it.

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  • You can also send the formal letter to Direct Boss only, and let Overall Head know via a less formal medium like instant messaging.
    – lambshaanxy
    Commented Feb 6, 2020 at 13:49
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I'm leaving my job and I'm wondering if I should address the letter to both the Direct Boss and the Overall Head.

If it were me I wouldn't... because that's my personal preference. I follow the "chain of command" unless there's an issue that dictates that I break the chain of command.

If you feel that OH would feel sighted by not sending it to them then do so.

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Address it to DB, and include OH as a courtesy if you have any relationship with him.

It comes down to decision theory, choice under uncertainty.

The simple matrix is below:

Prefers inclusion and included equals happy. Prefers inclusion and excluded equals very unhappy. Prefers exclusion and included equals mildly unhappy. Prefers exclusion and excluded equals happy.

The consequences of including OH is that at the very worst, he will be mildly unhappy. But, if you exclude him, and he's likely to be upset, he will be VERY upset.

Logically, you should include him, as the risk is minimal.

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