Ethics: My Newly Assigned Second-in-Command Keeps Undermining Me. What Should I Do?

A Reddit member writes: My colleague and I were both promoted by my boss a few months ago, I was promoted to Head of, and they were promoted to Director (my 2IC). Their role is split between Director and Regional Manager (not ideal). We’d worked together a little before the promotion but not extensively. Since the promotion, there have been occasions where I believe they’ve undermined me.

[For example] They proposed shifting strategy in their region and sent me a short Word document outlining the change. I agreed with the sentiment but asked for a more detailed plan, as it didn’t consider all the risks. They agreed, but a few weeks later, I heard from someone else that they had instructed the team to move forward with the plan anyway.

Now, I’m unsure how to move forward. I’ve lost trust in them. We’ve discussed other initiatives they’ve said they support, but I’m no longer confident they do. Their dual role limits how much they can support me anyway. They are talented, and ideally, I’d like to leverage their ideas–but I don’t have to. To make the best use of their time (and protect mine), my plan is to delegate time-consuming projects I don’t need to handle personally and focus on progressing the broader priorities, as there’s plenty to do.

Minda Zetlin responds:

This is a very awkward situation. You have someone reporting to you whom you did not hire or choose for the role. Which presumably means you can’t fire them at will, either. You mention in the discussion that they’re the top performer in this group, and that they work in the same U.S. office as your boss, while you’re working remotely from the U.K. None of that makes this any easier.

Going ahead with a strategy shift after promising you they’d give you a fuller plan first is a huge red flag. Whether or not they’re actively trying to undermine you, they are refusing to accept your authority. They seem to hope that if they ignore you, you’ll go away. Perhaps they believe your new job should have been theirs instead.

I’ll echo the advice you got from several who commented: You should document every instance of their broken commitments or insubordination. For example, what happens if the new strategy they launched without your approval turns out to be a disaster? Will they be able to claim that you signed off on it? Or is your request for a detailed report and your warning about the possible risks in writing?

This employee has earned your mistrust.

You are very right not to trust this person, which is why documentation is so important. Any solution must start with clearer communication. You mention 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 in which you asked for an update on their new strategy and on the report they promised they’d write? They would have to choose between telling your up front that they were ignoring your instructions or actually lying to you about what they were doing (rather than simply failing to let you know). Or else, they could put off implementation until they had your go-ahead. Any of these would have been better than what actually happened.

Although you can’t yet trust them, both ethically and as a good leader, your first goal should be to create a better relationship with them. They’re a top performer and you say you would like to use their talents. They clearly have the potential to be a huge asset to you as well as to your organization. You must try and turn them from an enemy into an ally.

It’s time to tell your boss.

You say that your 2IC has a good relationship with your boss, but so do you. Alerting your boss to this issue and providing what documentation you can is the first step. Tell your boss know that you want to improve your relationships with this person, and you will need support to do so. Do it right away. You don’t want the boss first hearing about the problem from your subordinate rather than you.

Then, have a friendly and honest conversation with your 2IC. Ideally, it should be an in-person conversation rather than video chat although given the distance, that might not be possible. Either way, let them know that they have to start following your instructions. Tell them you are giving them time-consuming work because you can’t trust them with anything better. But you wish that you could.

Don’t say that they’re intentionally undermining you, even if you feel sure that they are. That gets you into a discussion of their thoughts and motivations, which won’t be helpful. Stick to just the facts: You said this; they did that.

Tell them you’re on their side.

Also let them know that you are on their side and would like to have a good relationship. Ask them about their aspirations and what they would most like to do. Let them know you’ll do your best to help them achieve those goals. Make a specific plan for them to check in with you very regularly about what they’re doing and to make sure communications are completely clear. Get their written agreement to this plan. And then forward a copy to your boss.

What happens next is up to them. If they continue ignoring what you tell them, you’ll have evidence of that in writing. That evidence should be difficult for your 2IC and your boss to ignore. If the problem continues, you’ll be well positioned to initiate or request disciplinary action and/or a transfer away from your area.

But I hope that’s not what happens. I hope that by being honest, friendly, firm, and fair, and letting them know you care about their welfare, you can gain their genuine support. And maybe even turn this enemy into a friend.

Got an ethical dilemma of your own? Send it to Minda at minda@mindazetlin.com. She may address it in a future column.