How do you challenge the system you work within, without undermining the people responsible for it—or becoming the person who has to fix everything?
We often talk about managing up as though it’s a skill in keeping our managers informed, understanding their priorities or influencing their decisions.
Those things matter. But I think there’s another, more difficult form of managing up.
It’s the ability to help your manager see something about the organisation that they may already suspect, but haven’t yet found a way to confront.
And to do so constructively, without making it personal.
I’ve been reflecting on this, about the responsibilities we have, not just to do our jobs well, but to challenge the conditions under which we’re expected to do them.
When individual performance isn’t the problem
One of the easiest mistakes organisations make is to interpret structural problems as individual behaviours.
Someone struggles to make progress, so perhaps they need to become more pragmatic.
Someone works beyond their role, so perhaps they need better boundaries.
Someone raises recurring concerns, so perhaps they need to accept that things won’t always be perfect.
Sometimes those interpretations are entirely reasonable.
But sometimes they miss the point.
What if people are being pragmatic precisely because the organisation hasn’t provided the structures they need?
What if they’re working beyond their responsibilities because decisions aren’t being made, ownership is unclear or essential capabilities are missing?
And what if the person raising concerns isn’t seeking perfection, but simply asking for the basic controls that make delivery possible?
There is a fundamental difference between improving how an individual responds to a problem and actually addressing the problem.
That distinction is where constructive managing up begins.
Moving the conversation from frustration to evidence
It’s easy to complain about organisational dysfunction. Most of us have done it, usually with colleagues who already agree with us.
The more difficult task is to explain the dysfunction in terms that management can act upon.
Instead of saying governance isn’t working, ask what happens when a risk is escalated.
Instead of saying decisions take too long, identify who has the authority to make them and whether that authority is being exercised.
Instead of saying colleagues are overstretched, examine the responsibilities they’ve absorbed and the functions that should properly own them.
The point isn’t to assemble a prosecution case against management.
It’s to make the system visible.
In my own experience, I have found that specific examples are far more persuasive than broad criticism. A business case produced without a subsequent decision. A reporting requirement with no clear purpose. A project that has a manager but no agreed route for resolving issues beyond their authority.
Individually, these can appear to be administrative inconveniences.
Collectively, they can reveal something more significant: an organisation relying on individuals to compensate for weaknesses in its operating arrangements.
Once that becomes visible, the conversation changes.
We can stop asking why an individual isn’t delivering and start asking whether we’ve created the conditions in which delivery is reasonably possible.
The paradox of being useful
This is where things become uncomfortable.
I have spent much of my career stepping into gaps. If something needs doing and I have the knowledge or experience to help, my instinct is to contribute.
I don’t think that’s inherently a bad thing.
In complex organisations, particularly during periods of change, waiting for every responsibility to be perfectly allocated can mean important work simply doesn’t happen.
Sometimes the consequences of stopping are far greater than the inconvenience of stepping outside a job description.
But there is a paradox.
The more effectively capable people compensate for organisational weaknesses, the easier it becomes for the organisation to tolerate those weaknesses.
Progress continues. Meetings happen. Problems are investigated. Information reaches decision-makers.
From a distance, the system can look as though it’s working.
But progress achieved through exceptional individual effort is not the same as sustainable organisational capability.
The answer, I believe, isn’t necessarily to stop helping.
It’s to make the intervention visible.
To explain what you’re doing, why you’re doing it, which responsibility is missing and what would need to happen for the work to transfer to its proper owner.
That distinction matters enormously.
Supporting decisions without taking them
There’s another boundary I think is important.
Having the experience to recognise what needs doing does not automatically give you the authority to decide it should happen.
In my own work, I may bring people together, investigate problems, connect evidence, develop options or help colleagues understand an unfamiliar area.
But executive accountability must remain with those who hold it. When I had it, I knew the accountability to act was mine. But when I don’t, it’s vital to let those that do, lead.
That is not an excuse to be passive.
Quite the opposite.
Good managing up means helping decision-makers understand what they are being asked to decide, why it matters and what the consequences of delay might be.
It means being prepared to say that the information is incomplete, that a proposed arrangement is unlikely to work, or that the organisation is accepting a risk it has not properly considered.
And sometimes it means asking the deceptively simple question:
Who is actually responsible for deciding this?
The purpose is to strengthen the exercise of authority, not to circumvent it.
Trust makes challenge possible
None of this works particularly well without trust.
A manager who feels ambushed or personally criticised is unlikely to engage constructively. Equally, an employee who feels unable to speak openly will often retreat into compliance or quiet frustration.
I have been fortunate to work with managers who are prepared to hear uncomfortable observations and challenge me in return.
That creates room for a different kind of conversation.
One where I can acknowledge that my own behaviour may contribute to the situation. That I sometimes take on more than my role requires. That I enjoy solving difficult problems, and that my willingness to help can itself create unintended dependencies.
Acknowledging those things doesn’t invalidate the structural concerns.
It makes the discussion more honest.
It also helps move the conversation away from personalities.
I’m less interested in whether someone is doing a good or bad job than whether the arrangements around them allow them to succeed.
A manager can be committed and capable but poorly supported by the system in which they operate.
That possibility deserves as much attention as individual performance.
Managing up should lead somewhere
There is, however, a danger in having these conversations.
They can feel productive without producing anything.
Everyone agrees that communication could be better, ownership should be clearer and governance needs improving.
Then the meeting ends, everyone returns to their overflowing workload, and nothing changes.
Constructive challenge needs to move beyond shared understanding.
Not necessarily towards a wholesale redesign of the organisation, but towards a small number of practical commitments.
What do we need to make clearer? What can we stop doing? Which decisions need an owner? What should happen when a project reports a problem it cannot resolve?
And perhaps most importantly, who will take responsibility for making the improvement happen?
I have come to believe that modest, dependable controls are more valuable than elaborate processes that nobody consistently follows.
A reporting mechanism that produces a decision is useful.
A beautifully formatted report that disappears into a governance meeting is not.
Building something that works without you
For me, the ultimate test of managing up is not whether management agrees with my assessment.
It’s whether the organisation becomes more capable as a result.
That means sharing knowledge rather than retaining it. Coaching colleagues rather than making myself indispensable. Documenting decisions and processes so that someone else can take the work forward.
It also means being genuinely willing to step aside.
If the right people and arrangements are put in place, I should be able to hand over what I’ve developed and move on. The aim is not to create a permanent dependency on my involvement.
There’s an important leadership principle here.
A successful intervention should reduce the organisation’s need for the person making it.
If the work can only continue because one individual understands how everything fits together, then however impressive their contribution, the organisation still has a problem.
A different measure of managing up
I don’t think managing up should be about winning arguments, getting your own way or persuading senior people that you’re right.
At its best, it’s about improving the quality of organisational decisions.
Sometimes that requires making uncomfortable connections, challenging accepted explanations or pointing out that the organisation’s expectations exceed the capability it has put in place.
Sometimes it requires continuing to help despite those weaknesses, because the consequences of walking away would be irresponsible.
And sometimes it requires recognising that you cannot, and should not, solve every problem you can see.
The balance is difficult.
But perhaps the most useful principle is this:
Take responsibility for the contribution you can make. Make visible the responsibilities that remain unmet. And never confuse keeping something moving with having fixed the system that makes it work.
Because the real measure of managing up isn’t whether your manager starts seeing things your way.
It’s whether, together, you create the conditions for people to succeed without having to compensate for the same problems over and over again.