When the 'ass' is in charge
Managing upward to a 'donkey' with wisdom (and sanity)
You’re in a meeting and your boss is talking. It’s not that they’re wrong… it’s that they’re missing the point entirely. Again. You glance at your colleagues. Everyone’s wearing the same polite grimace.
In the world of organisational politics the Donkey doesn’t lead with insight and integrity, they ascend through persistence, proximity and surface-level performance. With low political skill and high self-interest, they often reach management roles by appearing reliable, yet their decisions lack strategic depth. What looks like decisiveness is often confusion in disguise: instructions are delivered with confidence but contradict each other, priorities shift without explanation, and accountability is diffuse. The result is a veneer of control masking a reactive, short-sighted approach.
Donkeys don’t seek to destabilise, but their leadership is shaped by personal convenience, not collective clarity, and the impact is felt in every direction.
So what’s the formula for reporting into these people?
Upward management, Donkey edition: What works (and what really doesn’t)
Work with what’s stable, not what’s ideal
Donkeys resist change and rarely respond well to direct challenge. The same traits that now limit their leadership are the ones that helped them rise so transformation is unlikely. Instead of pushing for what won’t land, work within their comfort zone to stay effective and maintain momentum. If they crave control, offer visibility. If they avoid challenge, frame feedback as choice, not confrontation.
Align your language to their goals
Even if their motivations aren’t always aligned with the organisation, finding common ground in what they want to be seen achieving is a great way to get them on board with your ideas. Frame your initiatives in terms of reputational benefit, ease, or risk mitigation. Position yourself as someone who helps them look good without compromising your values.
Speak their language: “This will save time” or “This will land well with senior leadership” carries more weight than “This is the right thing to do.”
Be graceful, less is more
Donkeys often don’t know they’re being unhelpful. Instead of correcting, redirect subtly.
“Would you be open to…?”
“What would it look like if we…?”
Pitfalls to avoid
Don’t try to “fix” them. You’ll exhaust yourself.
Don’t join the cynics’ chorus or risk being seen as two-faced.
Don’t martyr yourself with quiet resentment, it won’t nudge the donkey toward the outcomes that you need.
Protect your work
Document everything. Full stop.
Avoid relying on verbal agreements.
Build alliances elsewhere, especially with Owls who can quietly validate your credibility and offer air cover.
Reframing agency: find the learning edge
Working under a Donkey boss refines your leadership the hard way. It teaches tactical patience, subtle influence, and how to lead upward without losing your integrity. Use this to become the leader you wish you had.