BLUF: The former manager of my team, now a team member, fills in as my #2 when I'm out on vacation. He's a High S and will do just about anything anyone asks. My directs often disregard my wishes and involve him to help cover for them when I'm out. How do I address this? With the direct, with the #2, with both?
Example: I was out sick a few weeks ago and received an email from a peer-manager (not my #2) stating that my employees were pretty much going romper room - feet up in the cubicles, not working, listenting to music, etc. in my absence. I have one employee in particular that likes to take certain "liberties" with her leaving time when I'm not around. She had left over an hour early that day.
I'm scheduled to be out again soon on a day when she had requested to take a half day of vacation time in the afternoon, and work from home in the morning. We discussed her work from home need, only for me to find out that she really does not intend on working from home, she just doesn't have the vacation time balance to take the full day. Of course, I told her that she would need to come in to the office and work that time. My gut tells me that she will NOT come in this day because she's knows I won't be in the office, but will attempt to have my #2 cover for her if I do catch wind of it. I've asked other peer-manager to look in to validate my suspicion. I hope I'm wrong, but 99.9% certain I will not be.
Who do I need to address in this situation, how, and with what feedback?
FYI - this is a recurring situation with my #2 - others take advantage of him because he cannot say no. This is just one example. He's my #2 based on knowledge, not leadership ability, and that may be part of the answer I get from my MT friends...
Thanks in advance!

I think you answered your own question
"He's my #2 based on knowledge, not leadership ability" says it all to me. This person is clearly not ready to step into your role (and be effective), so why is he your #2?
Who would be the obvious choice to take your position if you got an offer elsewhere that was too good to pass up? Your professional reputation depends on developing your people and making them ready for promotion. If your #2 is coachable and he's willing to develop, you have a good path. If he's not the guy for the job, start developing some others and see who rises to the top.
Finally, where is the breakdown in setting & maintaining standards within your group? If others in your group think it's play time when you're out, there's some work to be done there.
Steve
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Thanks, Steve. I agree
Thanks, Steve. I agree with you that I need to rethink my choice of #2. I inherited him, but it is time for a change. Being the former manager of the group, many of my directs (his former directs) remain loyal to him. Change has been difficult because he often does not support it, so while the team outwardly accepts to my face, any chance they get, they undermine me.
I'm not talking about Draconian law here either….basics, like show up to work on time, put in 8 hours, be professional, etc. I mean, really basic. The old manager (#2) was so laissez-faire about everything, that I walked into a situation where it was basically lawless. So, as I can see it, the breakdown is that I'm now "the bad guy" because I set and have some expectations. Despite the fact that what I'm asking for is completely reasonable and very much the norm, everything I'm doing is perceived as bad because they could do whatever they wanted before.
I have a clear #2 replacement ready to go, and this just makes me see now that it's time to make the change.
How long have you been their manager?
It might be worth taking a look at the cast about being a new manager. One of the rules stated is don't do anything in the first 90 days.
Then roll-out O3s for a couple of months. Then feedback. Start with lots of positive even if there's a lot of "negative" going on. I'm pretty sure you can find one.
My personal story, while i may not have an inherited group nor a big team, my rollout of the Trinity is very long. Maybe around 1.5-2x the suggested timeframe that Mark gave. The primary reason is i'm a very task-focused person (High C High D) and developing that relationship was very difficult for me. And once i got that relationship, giving them feedback, eventually, about the negative things became so much easier. Plus, they see the value of it, they accept it, because they know you care and not simply attacking them.
AYLIM14 makes a good point
I hadn't considered the length of time in your current role. I assumed (and we know what that does...) that you had been in the position for a while. I have to agree that rolling out the trinity is a better approach, and will likely get better long-term results. You may still have to replace the #2 and better relationships with the entire team will probably make the change easier for them to accept.
Steve
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