There is an episode in the West Wing (“Separation of Powers”) where Josh Lyman, top legislative negotiator for the president, is “benched” because of personal problems. In his stead, a woman named Angela Blake is sent in to negotiate.  Josh is deflated, and angry. He feels like this is his role being taken away; he barely holds it together when he hears the news.

Negotiations go poorly.  Josh is frustrated, as is the rest of the staff.  However, when the president asks Josh his opinion of how Blake is doing, Josh says, “You gotta trust the person in the room.”

I think about that moment a lot, because it’s true – you do have to trust the person in the room. You have to trust that the salesperson is doing her best to close the deal, that your boss is doing his best to advocate for you, that product management is doing their best to prioritize features accurately.  And all of this happens when you’re not in the room.

This is where a lot of people get crazy.  Take the salesperson example – sure you might send the salesperson in to close the deal on their own, but if they don’t close it, then suddenly the sales manager is all over them asking if they did this, or did that, and can they get another meeting, and try this other strategy.  Or how many times has someone’s manager committed to trying to get them a raise or promotion, only to come back empty-handed; the employee often feels betrayed, or let down, or feels as if the manager had a lot of things to negotiate and his or her salary fell off the list at some point.

So the key is to find an organization, and a leadership team that you can trust in the room.  And the leadership has to trickle down to everyone – because the product management example above isn’t about a manager of yours going to do something, it’s about a peer organization trying to get things done. To me, that’s probably one of my top few yardsticks for assessing how I feel about an organization – do I trust these people in a room without me?

The key is also to remember that sometimes you are the person in the room.  You are the one negotiating and speaking for someone else.  And as such, you carry a burden of doing your best for them – of being worthy of their letting go of the opportunity to advocate for themselves, as they are not the person in the room.

A few weeks ago I caught up with a former colleague who, like me, finds himself in a leadership role at a startup.  His role is different from mine, but we find ourselves in some similar situations.  For example, we have both had the experience of off-handedly suggesting something and having it executed, almost accidentally. We both marvel at how much decision-making gets done in a startup, and what we get to contribute to.

And then he was explaining to me how there will come a time at his startup when his specific role in the company will need to be formalized and its scope determined.  He took the job with a few conditions, one being that he get to be part of that conversation when it occurred.

“You want to be in the room for those conversations,” I said.

“Exactly.  I get to be in the room.”