Where are we going and why are we in this handbasket? (Part 2)

*I'm not the OP. This entire tale was originally posted in r/talesfromtechsupport by u/lawtechie. Due to length I have split this post into two parts. [First part](https://old.reddit.com/r/BestofRedditorUpdates/comments/11nn2l2/where_are_we_going_and_why_are_we_in_this/)*

[Part 3](https://old.reddit.com/r/talesfromtechsupport/comments/atty9u/where_are_we_going_and_why_are_we_in_this/) posted on Feb 23, 2019

Ian:"Don't tell me how to do my job"

Ian pulls into the strip mall, shoves the car into Park and starts stomping towards a chain sandwich shop. He's like the sullen teenager I never wanted. Nowadays, I'd direct him to Hot Topic and let him wallow in his feelings.

Even though I'm in the advice business and know that unsolicited advice has negative marginal value, I think Ian needs an intervention.

I follow him into the sandwich shop. While we're waiting to order and get our sandwiches, I try to talk some sense into Ian.

Me:"Look. I know you're annoyed with me, but we have a lot of tasks to complete to get this engagement completed. I want to prevent the client from hating us by the time we have to deliver"

Ian:"All you do is talk to the customer and write reports. I'll do the real work"

I realize that I've never started a fist-fight in the order line at a Subway. Ian and I may have a new experience today.

Me (adopting my the therapist voice I learned when I was on a helpdesk):"Ian, the work we have to do is in the Statement Of Work as well as the project plan. There is an application pentest, but no host pentest. Client isn't paying for one. What do you want to do?"

Ian, looking at me with a strange intensity:"I want to make it rain shells. That'll show them"

I'm looking at the menu board in the hopes that the right answer to Ian is written there. Instead there are a selection of sandwiches. I make myself say "Italian Sub" to the order-taker.

While waiting for our order, I try again with Ian.

me:"Ian, put aside that they're not paying for a pentest. What value does a pentest have for them?"

Ian:"It will make them more secure once they're scared"

me:"Ian, a pentest is for mature shops to say that all the ground floor doors are made of steel and locked except for that wooden one 'round back. These guys are missing walls and don't know it. They'll think if they fix the one path you came in, they're good. We need to get them good enough to where a pentest will actually be of value"

Ian:"Are you saying pentesting is useless?"

I'm losing my temper.

me:"For this client, at this time, yes. "

Ian:"You're saying that because you. just. can't. hack"

That's it.

Ian's order comes up. He grabs his sandwich and walks out the door towards the rental car.

I don't have my sandwich yet. I step out the door and yell at him across the parking lot:

"USE BURP, YOU ASSHOLE!"

I seem to have the attention of everyone in and near the sandwich shop. I think they're less scandalized by my language wondering what kind of insult it was. Ian gets in the car and drives off. I get my sandwich and a bottle of soda and walk the half mile back to INSCO's offices.

I sit outside and eat half my sandwich in silence. If I get him kicked off the project, it's going to look bad for me- I'll be rushing the deliverable and it'll look like I can't manage projects. If Ian breaks something, it will be clear that I can't manage projects.

I do need someone to interview INSCO's development team. Ian claims to know the frameworks that they're using. Maybe flattery will work.

I enter the building, find the kitchen and put the rest of my sandwich in the fridge. Ian's staring into the blue glow of his laptop.

I take a quick stroll and notice that INSCO's not too bad with the security culture. Staff lock their screens when they get up. They've got locking shredder bins and reminders to be careful with sensitive data on posters. I bump into Betsy.

Betsy:"Hey, how's it going? Is everything as terrible as it looks?"

me:"We've identified some issues around your architecture, but everything's fixable. It's just convincing y'all that you can and should. It's like an intervention. We'll all read our letters about how much we care, there will be arguments and tears and you'll get on a better path while cheesy music plays"

Betsy seems scandalized for a second.

Betsy:"I love that show, but not for good reasons"

me:"WHERE ARE MY BABIES? Yeah, me too. It's to make you feel better- I might not like my life, but at least I'm not drinking mouthwash"

Betsy covers her mouth and laughs. I sense a presence behind me.

It's Ian.

me:"Betsy- I don't want to take up your time. Just wanted to give you an update and let you know where we are in the process. "

I turn to Ian. He's less hostile than the last time I saw him.

me:"Ian, let's see what we have left to do today and we can split up tasks"

I start guiding him back to the conference room. He's strangely compliant. If he's going to start yelling at me, I'd prefer a closed room to the cube farm where people are talking to customers.

Back in the conference room, I close the door.

Ian:"How do you do that?"

me:"Do what?"

Ian:"Talk to her"

Uh-oh.

me:"I'm letting her know that we're finding issues and that they're not insurmountable, which is good news to her. She knew there were problems, which is why we're here. What we all want is that the report will be concerning, but not shocking"

Ian:"But how do you talk to her like that?"

No, Ian. No.

me:"Ian, we can talk about that when we're done for the day. I'd like you to help me with something technical- can you figure out how to break up the customer facing, card processing and commission tracking databases? Without breaking too many things? If you can write that up, I'll talk to you about more successful interactions with people"

Ian:"Ok."