What do you say to your boss to try and break him out of Analysis Paralysis?

Hey guys, so I have a recurring frustration with my MD. 

It feels like his response to anything and everything is to build a new model from scratch and/or to reorganize our existing model. The problem is that for the MASSIVE amount of iterations and from-scratch modeling exercises we do - we make absolutely no fucking progress. Nothing is ever "done" or "good enough". It's always "Hmmmm, okay this is helpful". And then the next day he'll say "Hey Brian, you know what would be helpful..." and it's typically just him asking me to reorganize our financial model or build a new bespoke, ad-hoc analysis for him that looks at the financials in a different way. This cycle literally just never fucking ends. We never make actual forward progress, we just iterate in circles again and again. 

This is by far the most frustrating person I've ever had to work with in my career and it's starting to make my life hell because I am very Type-A and practical and like to think that I can "get shit done" when left to my own devices. But I can't make progress on ANYTHING with this guy because he never fucking stops changing his mind about how a slide should look, how a model should look, etc. There have been several times we have simply bled a client to death and they've just walked away from us because our "digging in" process simply never ended and they signed an EL with someone else who is actually willing to get going. 

There's a deal we have been looking at since April. I counted 10+ different models in our Model folder. I'm not talking 10 iterations of the same model, I mean 10 completely fucking different models that each have 10-20 different iterations per version. We have made over 100 models, ad-hoc analyses, variance analyses, comparing model-to-model analyses, etc. Today, we started building a new one FROM SCRATCH because he changed his mind AGAIN on how he thinks the model should read and which line items we need to once again "get smart" and "dig in on". I'm at the point where I don't even know what the fuck we are trying to accomplish. I have no idea how to move this forward because I have submitted so many different models that the other junior MDs and VPs have no problem with, but he just looks at them and goes "Mmmm nice, very helpful." then a day later wants to completely redo it. 

Does anyone have any advice for managing upwards and pushing back in situations like this? How the hell can I hold this guy to a concrete set of marching orders so I'm not just pursuing endless mental masturbation tasks for him all day that get us nowhere? 

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A) I feel you, because we've all dealt with someone like this and it blows.

B) You need to continuously hold him accountable. Never just say "yes okay" and walk away when given stupid marching orders. Ask why. Not in a snarky way, just questions like "hey so help me understand - what specific question are we trying to answer with this?", "what is the end-point for this that we are trying to work backwards from", "can we sit down and come up with a concrete list of specific, answerable questions that we need to answer in order to feel good about our projections?" Stuff like that. Hopefully he isn't also an asshole and will humor you. 

 

Unfortunately bankers have been trained to reward this behavior and never shake the habit as they get older. I've dealt with a similar situation where any conversation or detail provided would result in my boss asking 5 follow up questions which would require more research/delays. I started responding with "does the answer to this change our decision?" Has helped cut out 90% of the back and forth.

"I don't know how to explain to you that you should care about other people."
 

Have you tried talking this through with the mid-level people above you?  May be harder for you to stick your neck out personally alone to push back.  But this has to be frustrating for them as well (unless they've just given up on ever checking any of these analyses anymore), so I'd imagine better if the pushback came from the Director or VP.  It's really what they should be managing.

 

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