Earlier quoted context omitted.
> You said, "Counteroffers are poison for both the employee and the company." That's a very strong position you're taking. My opinion is that counteroffers are poison, generally because some employers or employees have unrealistic views on what loyalty means, and it always turns out badly for the employee. > This is true, but inapplicable to the decision of whether to take a counteroffer. If the employer, management,…
> However, it's fairly common (especially for new managers) for them to think of employees looking for other jobs as a personal affront, and will make your life miserable. Why would someone who takes my looking for other jobs as a personal affront make a counteroffer?
Maybe he needs to close a deal with an external customer, and he doesn't have enough time to train up another person to take care of your job responsibilities, and he really needs to close that round of funding.
Maybe his hiring pipeline is dry, either because your skills are hard to find, or maybe because candidates picked up on his managerial faults.
Maybe he needs time to vet external consultants to take over your job, and needs you to stick around to train them, stick around longer than 2 weeks or however long you gave notice for.
All these situations are the worst. He thinks he needs you, but doesn't really want you around. That way you stick around in an environment where management doesn't like you, and whenever there is a viable alternative, they'll dump you for the alternative.
Edit: Another reason why the situation is bad is because management will never let on why exactly they're trying to retain you. They'll string you along until they figure that you're not longer indispensable, and then cut you lose. And you have no idea whether or not that's what he's actually thinking, or "I am an adult and I can respect the logical choices that this guy is going to make to better his career."