A practical tool for moving a structure-averse partner: propose a pilot with a learning goal instead of asking for an exception.
Exceptions make some leaders deeply uncomfortable, and if you work with one, you already know the feeling of watching a sensible idea bounce off a reflexive no. I got a genuinely useful tool for this from a new team member, a veteran Product Manager who recently joined us from a string of consumer-product roles and has a sharp read on how to move people.
The setup: one of our senior partners dislikes structural asymmetry. The standard ratio of product managers to designers to engineers is something he’d rather hold constant, and any request to break it tends to read as special pleading. For a while I was bringing him exceptions as exceptions, which is to say ‘can we please make this one different,’ and getting nowhere.
The PM’s reframe was to stop asking for an exception and start proposing a pilot.
Stop asking for an exception and start proposing a pilot. Same change on the surface, a completely different conversation underneath.
A pilot has a learning goal. It says: here’s a hypothesis about why this team needs a different shape, here’s what we expect to learn, here’s how we’ll know if it worked, and here’s when we’ll revisit it. That gives a structure-minded person something to say yes to, because you’re not asking them to abandon the model, you’re asking them to test it. It also gave my own manager a much better case to carry upward, because a time-boxed pilot with a clear learning goal is an easy thing to defend, and ‘an exception because Leonardo asked’ is not.
The broader tool here, which I’ve started using well beyond this one situation, is to figure out what the person you’re persuading is actually protecting, and frame your ask in those terms. He’s protecting consistency and a clean operating model, and a pilot respects both while still getting me the thing I wanted. Two other small moves from our new PM pair with this nicely: write the ask as a from/to, current state on one side and the future state on the other with concrete examples, and be explicit about which few things genuinely matter to you, because a leader who treats everything as a hill to die on doesn’t get help choosing the right hill.
The teachable part
When someone reflexively says no to exceptions, find what they’re protecting and reframe your ask as a pilot with a learning goal. A test is easier to approve than an exception.