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I am interviewing for a well-known company right now, passed the initial phone screening and have been invited to the final round.

My boss is oblivious to this, and since I am effectively second in charge he confides in me. This morning he told me how he has his full trust in me. How I was doing a good job as a project manager etc.

I am now feeling extremely guilty, I feel that I should come clean and tell him what I am getting up to, but at the same time, I know that if he knows the truth, he would look for a replacement immediately and will never trust me the same way again (not good when you are in management!).

I am also worried that if I do get an offer and decide to leave he may feel that I have betrayed him from giving him the impression I am here for the long run. Baring in mind, if I do get an offer, I will take it up.

Do I have reason to be concerned, I am quite anxious about the impact leaving may have on his attitude towards me. Should I tell him? How do I soften the blow if it happens?

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  • Would you feel guilty by bettering yourself at a local college? Nothing wrong with improving your life and your career is a huge part of your life.
    – cbmeeks
    Jan 23 '17 at 20:22
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Should I tell him?

Absolutely not, no. To quote the usual thought in this case: "would your boss tell you if they were thinking of letting you go?" No, they wouldn't. By telling your boss you're thinking of leaving, you put yourself at the very top of people who will be let go - and, depending on your company, you could find yourself walking out the door about two minutes after telling your boss, without another job to go to.

How do I soften the blow if it happens?

Make the transition as easy as possible. Document everything you're doing so your replacement can get up to speed quickly. Depending on culture, offer an extended notice period so there's more time for your boss to sort out the transition (but obviously make sure you've agreed this with your new company first!)

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    One thing I have done when I wa a critical person leaving was document everything they would need to know in one document and hand it in with my resignation.
    – HLGEM
    Jan 23 '17 at 14:29
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I am now feeling extremely guilty

That's normal, but you shouldn't be. When you've been somewhere for a long time or when you've established close relationships, even purely professional ones, with colleagues or managers it can seem like a betrayal that you're leaving. But maintaining an employee-employer relationship is a business transaction like any other and in most cases such transactions end. People moving on to (hopefully) bigger and better things is a normal part of the workplace. As long as you remain professional and haven't acted in bad faith (such as voluntarily promising to stay for X time and then reneging on that promise) you have absolutely no reason to feel guilty over doing what's best for your career.

While I doubt this applies to you, if you are job searching to get away from a toxic workplace or unsustainable workload you might feel particularly guilty when you consider how your leaving can affect your coworkers or manager. That's also a reasonable feeling but it shouldn't affect your decision making process at all. When you reach that level of dysfunction it's just time to move on and high-performers will be the first to jump ship.

Should I tell him?

Of course. When you are handing in your notice, i.e. after accepting an actual, written offer from your new employer and have a reliable start date.

How do I soften the blow if it happens?

By remaining professional and cordial. It's normal for people to move on. If your manager reacts overly emotionally or throws a tantrum then that's on him and there's frankly nothing you can do to prevent that. Resign in person. Give the standard/required notice. Communicate your final day clearly and stand by it. Confirm it in writing after that conversation. Work out your notice period unless your manager makes that impossible. If they are badgering you or otherwise making it impossible or unhealthy to keep working, revisit your final day.

Do I have reason to be concerned, I am quite anxious about the impact leaving may have on his attitude towards me.

If your manager reacts unprofessionally there is very little you can do to salvage things. Agreeing on a (slightly!) longer notice period or being open to them contacting you (within predefined reason!) may prevent irrational resentment and can secure your reference but what will or won't work depends on your manager and just how irrational his reaction is. Avoid making unreasonable promises to remain available and don't even entertain the notion of a counter offer.

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People leave their jobs for various reasons all the time. Yes, leaving is disruptive to those who stay but it's up to them to adjust and adapt, thereby earning their paychecks.

Leaving a job is a business decision and no one should make such a decision into a personal matter let alone read a personal affront into such a decision. You're leaving your manager behind but don't worry, those things go in circles and some day, you'll be in a senior or supervisory position and someone will leave YOU. Just don't take it personally.

From the way you are phrasing your question, you have made a straightforward business matter into a matter of personal interactions whose complexity is horrifying. Don't do that.

Your manager may be upset that you're leaving. If they have a career, your manager most likely did the same to someone else. And they certainly did not torment themselves about it as you are doing. I'll tell you this: if your firm can't survive your departure, then something is seriously wrong with the way the firm is run.

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You should never feel guilty for job searching.

If you are job searching, is for some specific reason, maybe it's a toxic environment, maybe they aren't paying you enough, your career is stagnant etc etc, if everything was ok, there was no reason to search for a new job.

About telling him, I think it actually depends on your relation with your boss.

I know that if he knows the truth, he would look for a replacement immediately and will never trust me the same way again (not good when you are in management!).

This means that you shouldn't tell him! Clearly, he is not interested in fighting for you, so once again you shouldn't feel guilty. and you shouldn't tell him.

For example, last Friday I've told my boss that I was seriously considering leaving leaving the company, I haven't got an interview scheduled and haven't decided yet if I'm going to leave the company or not, but he was approachable and we talked about the problems that made me want to leave the company in the first place. And everything is alright, is not looking for another person to replace me ( I'm the CTO ), he has not changed a bit in relation to me, and I've still have to give him an final answer.

It all comes down to the relation you have with him, in my 11 year of experience, it's the first time I do something like this, the other times, I just went to interviews, and then give the notice after I had a job confirmed.

In your case, I would say not to tell him, and don't feel guilty, you have nothing to feel guilty about.

How do I soften the blow if it happens?

Like Lilienthal said, be professional and cordial, period! If you feel the need to explain why you are leaving, explain it, but don't back down.

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