My newly appointed second in command continues to undermine me. What should I do?
By Minda Zetlin | Published: 2025-11-01 09:47:00 | Source: Inc.com
A Reddit member writes: My colleague and I were promoted by my boss a few months ago, promoted to President, and promoted to Manager (my 2IC). Their role is split between Director and Regional Manager (not ideal). We worked together a bit before the promotion but not extensively. Since the upgrade, there have been occasions where I think so They undermined me.
(For example) They proposed a strategy change in their area and sent me a short Word document outlining the change. I agreed with the opinion but asked for a more detailed plan, as it did not take into account all the risks. They agreed, but a few weeks later, I heard from someone else that they had instructed the team to go ahead with the plan anyway.
Now, I’m not sure how to move forward. I lost confidence in them. We discussed other initiatives they said they support, but I’m no longer confident they do. Their dual role limits the extent to which they can support me anyway. They are talented, and ideally, I would benefit from their ideas – but I don’t have to. In order to make the most of their time (and protect my time), my plan is to delegate time-consuming projects that I don’t need to handle personally and focus on progress on broader priorities, since there’s too much to do.
Minda Zeitlin answers:
This is a very embarrassing situation. You have someone reporting to you and you have not hired or selected them for this role. Which means you can’t fire them at will either. You mentioned in the discussion that they are the top performers in this group, and that they work in the same office as your boss in the US, while you work remotely from the UK. None of this makes it any easier.
Going ahead with a strategy change after they promised you they would give you a complete plan first is a huge red flag. Whether they are trying to undermine you or not, they refuse to accept your authority. They seem to hope that if they ignore you, you will go away. Maybe they think your new job should have been theirs instead.
I’ll repeat the advice I’ve received from many of those who have commented: You should document every instance of them violating their obligations or disobeying them. For example, what happens if a new strategy they launched without your approval turns out to be a disaster? Will they be able to claim that you signed it? Or is your request for a detailed report and warning of potential risks in writing?
This employee has earned your distrust.
You are right not to trust this person, which is why documentation is so important. Any solution must start with clearer communication. You mentioned that you have regular one-on-one meetings, but not how often. For example, what if you had a weekly or even daily check-in asking for an update on their new strategy and the report they promised to write? They will have to choose between telling you up front that they are ignoring your instructions or actually lying to you about what they were doing (rather than simply failing to tell you). Otherwise, they can delay implementation until they get the green light from you. Any of these things would have been better than what actually happened.
Even though you can’t trust them yet, either morally or as a good leader, your first goal should be to create a better relationship with them. They are high performers and you say you would like to use their talents. They clearly have the potential to be a great asset to you and your organization as well. You must try to turn them from enemy to ally.
It’s time to tell your boss.
You say your 2IC has a good relationship with your boss, but so do you. Alerting your manager about this issue and providing whatever documentation you can is the first step. Tell your manager that you want to improve your relationship with this person, and that you will need support to do so. Do it right away. You don’t want your boss to first hear about the problem from your subordinate and not from you.
Then have a friendly and honest conversation with your 2IC. Ideally, it should be a personal conversation rather than video chat although this may not be possible due to the distance. Either way, let them know they need to start following your instructions. Tell them you’re giving them time-consuming work because you can’t trust them with anything better. But you wish you could.
Don’t say they’re intentionally undermining you, even if you’re sure they are. This leads you to discuss their thoughts and motivations, which will not be helpful. Just stick to the facts: I said this; They did it.
Tell them you are on their side.
Also let them know that you stand by them and want to have a good relationship. Ask them about their aspirations and what they would like to do most. Let them know that you will do your best to help them achieve these goals. Make a specific plan for them to check in with you very regularly about what they are doing and to make sure communications are crystal clear. Get their written approval for this plan. Then send a copy to your boss.
What happens next is up to them. If they continue to ignore what you tell them, you will have proof of this in writing. It must be difficult for 2IC and your boss to ignore this evidence. If the problem persists, you will be in a good position to initiate or request disciplinary action and/or transfer away from your district.
But I hope that’s not what happens. I hope that by being honest, friendly, firm and fair, and letting them know you have their best interest at heart, you can get their genuine support. Perhaps he will turn this enemy into a friend.
Do you have an ethical dilemma of your own? Send it to Minda at Minda@mindazetlin.com. She can address it in a future column.
The opinions expressed by Inc.com columnists here are their own, not those of Inc.com.
(tags for translation) Ethics
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