On organizational dynamics - jumping the chain of command
Going above your boss should be done with care and reserved for important things.
The chain of command is where you get your authority as a manager. It’s the formal authority that you’ve been granted by your company to execute towards its desired outcomes.
Yet, many inexperienced managers completely disregard it whenever they disagree with their boss. They chain jump - going above their boss to get their problem solved instead of working within the confines of the authority structure.
In smaller organizations, this is actually fine - it’s baked into the authority and decision structure, and the relatively small size enables the chain to be more of a network. However, as the organization grows, this structure start to fail and causes a cascade of issues. Hierarchy becomes more important to ensure the company continues remaining effective.
Chain jumping creates a lot of organizational dysfunction - companies simply can’t operate effectively if every decision is being second-guessed. At lower levels, this may result in minor mistakes or wasted time, but at higher levels jumping the chain could cause catastrophic alignment issues.
What you’re actually doing when you jump the chain
When you jump the chain upwards, you’re indicating that a complete breakdown of trust has occurred in your relationship with whoever you are bypassing. If you’re in a half-decently run company, this is a bad thing.
It’s strongly frowned upon by every leader I have ever talked to and only the most patient of bosses will tolerate it.
It’s considered the nuclear option for a reason - either you’re absolutely 100% right and in full alignment with your boss’ boss, or you’re out of a job because you’ve dismantled your relationship with your boss with a single action.
How do you successfully jump the chain?
For you to chain jump successfully, a lot of factors have to be true:
The issue has to be critical to your boss’ boss.
The issue has to not have been visible to your boss’ boss.
The issue has to be in complete disagreement with your boss and your boss’s boss.
The issue has to be so egregiously violative that it breaks the trust between your boss and your boss’s boss.
Outside of unethical or illegal actions, a loss of integrity, company-ending risks, whistleblower scenarios - very, very few items will meet this criteria. If you jump the chain without all four - you run a massive risk for very little organizational benefit.
The issue has to be critical to your boss’ boss.
Your boss’ boss is dealing with a set of problems you aren’t even aware of. They have tradeoffs, risks, and decisions that they manage. They’ve entrusted a segment of their problems for your boss to handle on their behalf.
If you bring up an issue that’s irrelevant to them in the grand scheme of what they are dealing with, then you’ve turned something they’ve otherwise been able to ignore into, at best, an annoyance they have to deal with. It’s not likely they’ll view it as something even worth investing their time in, if not for the fact you brought it up to them.
They have higher leverage activities, and are likely to view you bringing up things as a waste of their time if it’s not critical to them.
The issue has to not have been visible to your boss’ boss.
It may or may not be a surprise - but your boss and your boss’ boss communicate with each other.
It’s quite possible that your boss’s boss already knows about the issue exists and otherwise trusts your boss will handle it. If they had a strong opinion, they likely would have aligned with your boss already.
It has to come as a surprise - something that your boss was actively hiding or that wasn’t visible to your boss’ boss.
The issue has to be in complete disagreement with your boss and your boss’s boss.
Your boss and your boss’s boss are probably in closer alignment than you can see. If you disagree with your boss’ strategy, but that strategy was already aligned with your boss’ boss, you’re basically telling your boss’ boss you disagree with them, too.
Whatever issue you chain jump has to ensure that there is ultimately a misalignment you are bringing attention to. Otherwise, you’re the misaligned person in the chain, not your boss, and you should introspect on that.
The issue has to be so egregiously violative that it breaks the trust between your boss and your boss’s boss.
Your boss is your boss for a reason - your boss’ boss authorized them to have authority on their behalf. This doesn’t mean they always agree. Sometimes your boss will approach a problem with a different perspective and solution than your boss’ boss will.
Even if your boss’s boss disagrees with your boss, your boss’ boss may happily give them the autonomy to try it a different way.
The issue you chain jump for has to be egregiously violative, not just a disagreement or something with less than ideal outcomes.
Otherwise, trust comes into play and your boss’ boss may trust that your boss will achieve the desired outcomes, even if done differently or with less perfection than you may personally desire.
How do you best frame your chain jump?
You’re going to need a lot of tact in the delivery.
If you go in heavy ranting against your boss, you’ve lost - you’ll be perceived as irrationally biased, and you’ll immediately torpedo any trust in yourself.
If you go in arguing passionately against a decision, you’ve lost - you’ll be perceived as a single-issue or overly emotional person and your future concerns won’t be taken seriously.
The best way to approach it is to remain factual, remain open to being wrong. Frame it as raising awareness or getting context, not a disagreement or misalignment. Be prepared with data, evidence, and details. Be honest with what you know and don’t know - acknowledge you may not have the full picture - because you may not.
Ensure your boss and your boss’ boss know either way that you’re going to execute whatever decision is made to the best of your ability.
Try to give your boss an out - “it’s possible they’ve already considered this” is a lot better than “they aren’t aware of it at all”. This is especially important if you end up being wrong - it’ll ensure that your boss knows you didn’t also question their competency and help preserve the relationship.
Always ensure you tell your boss first and after. Give them the opportunity to address your concerns, and then provide them a specific update afterwards as to what you discussed and with who so they can understand the context - this can go a long way in ensuring that even if there’s a disagreement, you’re still preserving trust.
What happens after chain jumping?
So, let’s suppose you jump the chain. You meet your your boss’ boss and give them the details of your disagreement with your boss (their report). You explain the who, what, when, where, and why. You present the entire scenario and why you think your boss is wrong.
Your boss’ boss thanks you for bringing it to their attention and ends the meeting.
What happens after?
Well, the first thing your boss’ boss is going to do is reach out to your boss and give them all of the details.
If your item didn’t meet the criteria of the above, the only directive to your boss’s boss would be “let me know if there’s messaging you want me to reinforce”. That’s it. Your boss and your boss’s boss are fully aligned, and you just torpedo’d your most important relationship at the company.
If you brought up an issue that met one or two of the criteria above. In that case, your boss and your boss’ boss may have a sidebar. They may discuss the situation, see if that decision needs to be re-considered in light of the strong feelings. Maybe, maybe not.
In any case, there’s an alignment - either a reinforcing of the current position, or an adjustment. In a best case scenario, you may get your way - maybe your involvement was enough to tip the scale. However, the end result is still the same - you just destroyed your relationship with your boss.
If you bring up an issue that meets ALL of the criteria, above, it might work differently.
There might be a serious discussion, other leadership might be called in to discuss the situation. I’ve even seen outside personnel pulled in to conduct investigations. In these cases, your best case scenario is your boss gets replaced with someone else.
However, in many cases, a realignment might occur - you might get your way, but the chain of command remains the same.
Why you should be judicious on jumping the chain
There’s quite a few reasons why you should not jump the chain:
You’re usually at an information disadvantage
You can usually solve your problem by just talking to your boss
When you win, you probably still lose
You’re usually at an information disadvantage
You boss and your boss’ boss are privy to information and context you don’t (and probably shouldn’t) have. They evaluate decisions based on factors outside of your visibility and scope which may influence and outweigh the specific tradeoffs you can factor.
Unless you know the specific criteria your boss’ boss is evaluating their decisions on, you may actually be arguing based on tradeoffs they don’t even care about.
I’ve had reports jump the chain to argue about decisions I’ve made based on an increased cost when the directive from my boss was “I don’t care how much you spend to get this done.” It’s not a good look for the chain jumper when they didn’t even bother to get the context of the decisions being made.
You can usually solve your problem by just talking to your boss
If you’re worried about a decision or problem, in most cases you can just ask your boss about it. In many cases, they’ll give you additional context that makes you go “oh wow, yeah, that totally makes sense”. In the situations they can’t, they may tell you outright “this is privileged information I can’t provide” in which case - accept it and move on.
Sometimes, you can provide additional information that makes them change their mind. Even if they don’t, you can get acknowledgement they’ve considered whatever you’re worried about. This is a much better outcome - you collaborate with your boss on achieving a better outcome vs. bypassing them.
The way you ask is important - you don’t want to come across as demanding justification for their decisions. Frame it as attempting to learn, improve, and understand context. When you do get an answer, be appreciative.
Even when you win, you probably still lose
Even if you jump the chain and get your way, you’ve now soured your relationship with your boss. Unless they’re an incredibly patient person (which, most are not), you’ve essentially shown yourself to be untrustworthy within the context of the authority structure - not the best if you’re trying to advance in the organization.
Final thoughts
Think carefully about when to jump the chain. Reserve it for the most serious, important, company impacting concerns. If you ever chain jump for frivolous reasons, or without full context, or do it poorly, all it does is make the company lose trust in you - particularly in situations where a simple conversation with your boss would’ve solved the problem. Make sure it’s worth it, and that you exhaust all of the other options first.