You miss the point. View it from another perspective: you have at least one employee that loves what she is doing RIGHT NOW. Do you see an issue in this?

is there something about this position where your company will suffer if people do not progress? Nobody wants a team with perpetual juniors.

Please do yourself a favour. You cannot ever think what the other person wants. I think she is totally engaged. She is getting what she wants out of the job. She may have hobbies elsewhere.why push it?

Don't push the Peter Principle on your employee's. If they are happy and effective in the positions they are in, and want to remain in that position, you should encourage that too.

"I just want her to feel engaged, challenged, and fulfilled so that she wants to stay with the company for years to come" -- She told you she was happy where she was. Do you think she's lying? This type of activity should only be offered at most once per year by you. At the same time, you should make it clear to her that you are always very happy to assist her at any time if she wants to do career planning. She'll come to you when she's ready.

Keep in mid that this person has probably had multiple bosses with differences and personalities not fully known by others. You may genuinely want unvarnished candor to the point of her being as blunt as it takes to let you know exactly how she sees things. With previous bosses, it would have been political suicide to try to be diplomatic in only communicating about one nuisance. You may be one of the few bosses she's met who wants full candor, and in other cases it was hard to really know before it was too late.

Nothing wrong with wanting to continue doing what you are doing, but it's beneficial to consider the future. It's quite possible, due to new technologies, changing economies, or any number of other possibilities, that her job may not exist in the future for her to continue doing.

"We've done this several times now. I do not want to force anything on her." This seems to be contradictory. She keeps refusing, and you don't accept that as an answer. How is that not forcing when the only allowed outcome is compliance?

If by tech company you many IT, I would share your concerns. It is very important to re-invent yourself and evolve, or your skills end up end-of-life along with the products that once provided a very good living.

This sounds like the workplace equivalent of trying to force people into heaven...

After 10 years in a particular role, I was finally "promoted", which only increased the BS I had to put up with, without changing any of the rest of what I did. I got to a point where we ran some numbers one Saturday, and emailed my resignation Monday morning. I've been much happier since then, even though I now work as much or more than I did before.

Does she also expect her salary to stay constant?

@RemcoGerlich Salary must never stay constant, even if you stay in the same position. Inflation applies to everyone.

I mean apart from inflation correction. Where I live it is customary for employees to increase in wage scale every year unless performance was bad (up to some limit); that makes managers more likely to press for career improvement to go with that extra pay.

What's your definition of career advancement? My dad has been in the position to "advance" his career and moved in a more managing position. He utterly failed because of 0 people skills. It was no advancement for him. Luckily people recognized his qualities and he advanced his career in another way, becoming the "rock-star" SPSS guy. Doing in a day what 10 other "specialists" couldn't do in a week. This was also recognized so much that he ended up with better pay then his direct manager. (try that these days). So what kind of career advancement do you offer?

Here's a very relevant question from your employee's perspective: "How can I communicate my preference to stay where I am now in my career path, and not move “up”?"

@Thomas Carlisle people tend to greatly exaggerate and overestimate the short-livedness of the core knowledge behind IT.

"I just want her to feel engaged, challenged, and fulfilled so that she wants to stay with the company for years to come." - other than being happy in her current role, what leads you to believe that she isn't engaged, challenged, and fulfilled or that she doesn't want to stay with the company for years to come? You may be looking for a problem that simply isn't there.

I'd have kept it but would have needed to preserve 3 comments total for it.