How to get buy-in from stakeholders with competing priorities

The recruiting platform I wrote about in October is live and being used across the company. I figured launch was the end of the resourcing fight. Turns out I have to keep winning that fight every planning cycle.

Engineering capacity here is shared. The same developers who could improve the recruiting platform could be building operations tools, customer-facing software, or the systems our field crews use. Each of those has a leader making a real case for it. Winning the argument is hard because nothing on the table is a bad idea.

A few things have been working for me.

Starting from what they're measured on

My old approach was to build the strongest case for the product itself. Better screening, faster scheduling. All true, and it landed flat, because nobody deciding on resources gets measured on interview volume. Finance leadership thinks in cost and return. Operations thinks about whether their teams can handle another change. The executives think about growth.

Now I figure out what each decision-maker is already trying to accomplish this year and build the proposal backward from there. With finance I barely talk about the platform. I talk about what a rep produces in annual revenue, what an empty seat costs us, and how recruiting capacity turns into headcount. Once the proposal is written in their numbers, saying yes gets a lot easier for them.

Naming the tradeoff myself

When I win a resourcing decision, someone else's project waits. If I pretend that away, the argument just happens later, in a meeting I'm not in.

So I put the tradeoff on the table before anyone asks. If we spend the next cycle on recruiting improvements, this other work waits, here's roughly what the waiting costs, and here's why I still think recruiting should win right now. They were going to run that math anyway. Running it out loud, in front of them, has bought me a lot of trust.

Sometimes I run the math and end up dropping my own ask. That stings, but the next yes comes easier because of it.

Involving people while the idea is still rough

The advice that's helped me most here is a couple years old. Lenny's newsletter ran a guest post on getting buy-in, and the line that stuck with me was that a great idea is worth very little if you can't execute it, and execution runs through the people affected. So involve them while the thing is still rough.

I used to polish a proposal before showing anyone, since a finished case felt more persuasive. I had that backwards. Show someone a finished plan and they poke holes in it. A rough plan gets a different reaction. People start suggesting fixes, and once their fixes are in there, part of the plan is theirs, and they'll defend it in rooms I never see.

Rehearsing the hard questions

A newer habit: before a resourcing conversation I'll give ChatGPT the proposal and the audience and have it play the skeptical CFO or the overloaded ops leader. Most of the objections it generates are generic. Usually one or two are ones I hadn't prepared for, and walking in with an answer ready for the hardest question changes the tone of the whole meeting.

Same thing I already do with PRDs. I still have to actually know my stakeholders, but a cheap rehearsal beats walking in cold.

I still lose some of these. That's fine, or at least it's fine when I lose on the merits, in front of decision-makers who understood exactly what I was asking for and why. The relationships survive the no, too. That matters, because next quarter I'll be back in the same room.