The Adventures of WidgetCo
A totally normally startup with totally average problems
Author’s Note: I serialized the story of Clara and her brave and resilient colleagues at WidgetCo in the poseycorp newsletter and blog because it was the best way to demonstrate that effective communication can sink or save a company. Also because it was fun. Here is the whole WidgetCo drama. Laugh! Cringe! Learn!
Persuading people sucks
“The challenge is not to eliminate conflict but to transform it. It is to change the way we deal with our differences”
― Roger Fisher, Getting to Yes
Welcome to WidgetCo, which makes widgets their customers love. The software company has grown at an enviable pace since Monica and Arun founded it in 2012. They were planning an IPO in 2022, but, well, the market.
The current capital crunch isn’t a huge issue, but the company is facing big questions about generative AI. WidgetCo’s existing products could incorporate generative AI in kind of a bandaid way, or they could re-imagine the whole stack and make something amazing. The question for WidgetCo is this: Should we be first or should we be best?
Clara, who works in product management, is deep in the first vs. best debate.
“No one read my e-mail,” Clara said to Marcus, her friend and ally in product marketing. “I laid out the entire issue with competitive analysis, customer sentiment, current product features, planned upgrades, everything. It was only about eight pages long. But then I got to the meeting and no one had absorbed my doc.”
“TL;DRs exist for a reason my friend,” said Marcus, who never wrote anything longer than three paragraphs.
“You’re a former cheerleader. You like to skim over things.”
Marcus rolled his eyes. “Drum major. Not cheerleader.”
“OK. Uniformed non-athlete on the field at college football games. Whatever. The point is that I showed that we can do both,” Clara said, raising her voice from a whisper to a normal tone, which meant she was worked up. “We can do something now and we can rebuild to create something great. It won’t be as hard as everyone thinks. If the whole company looks deeply at the data, the path forward is self-evident. I just have to get them to study the facts.”
Marcus knew that Clara was super smart but sometimes so blind. “You can’t package information the way YOU want to receive it, Clara. You have to package it the way YOUR AUDIENCE wants to receive it.”
“Fine. Help me dumb it down then.”
“Not dumb. Distill.”
Marcus had learned the hard way in his last job that he must always put his audiences first whenever he communicated. He also thought that Clara’s strategy was sound. He was on board. He suggested they spend lunch doing a Who What What table.
In the first column Marcus listed each member of the management team:
- Jones, the douchey product marketing VP who shouldn’t even be on the management team, but the VCs insisted.
- Justine, the fierce, snobby engineering VP who went to ESIEE in Paris. She never wants to talk to anyone beneath her. And she thinks everyone is beneath her.
- Hector, the CRO, who is impatient and blustery but does have good customer instincts.
- April, the take-no-prisoners CMO with finger tattoos who swears like a sailor. Because she came from the consumer world, April has no patience for any discussions that don’t center on customers or the brand.
- Gary, the jovial, chill CFO, who is on his fourth start up. VPs of Ops, HR and Legal report to Gary, so he makes the company function. No one has even seen him raise his voice.
- Monica, co-founder and CEO. WidgetCo is Monica’s first start up. She is 100% unwilling to make a mistake.
- Arun, co-founder and CTO. WidgetCo is his third start up. No one knows if he’s talented or just lucky. He’d much rather be out on the speaking circuit than taking work meetings.
In the Who What What table’s second column, Clara and Marcus put in what each person hoped for, was afraid of, their biases, their beliefs, their risk tolerance, etc. In the third column they put what they wanted each person to think and feel and do and believe after they’d been persuaded (lobbied?) by Clara and Marcus.
Blog backstory: Dramatis Personae
Here are a few juicy additional details about that team - some of these things Clara and Marcus know, some they don’t. But now you know them!
Jones, the douchey product marketing VP who the VC’s placed at WidgetCo? He desperately wanted to be the Chief Product Officer, but Justine and Monica objected. Jones is pissed, but he still took the job.
Justine, the VP of Engineering, worked with Arun at a previous company. She ignores him 97% of the time. She took the job because she knows she can do whatever she wants at WidgetCo.
Hector, the blustery CRO, is actually a huge supporter of Monica. He loves women leaders because he has two daughters and he’s watched them struggle to lead in the tech industry.
April, the take-no-prisoners CMO, doesn’t really understand enterprise software. She tells everyone that it’s customer outcomes that matter, but that’s partly because she can’t make heads or tails of the stack architecture slides in the sales decks.
Gary, the jovial, chill CFO, who is on his fourth start up, has a pretty serious illness that he’s concealing from everyone. That’s why whatever’s going at WidgetCo never seems like life or death to him.
Monica, the co-founder and CEO, was in the military. So was her dad. And her grandfather. She freaks when things aren’t orderly. She would very much like to murder Arun.
Arun, the co-founder and CTO, may only have one real skill, which is attracting talent and funding. He knows Monica is brilliant. He is at least smart enough to leave her alone. Most of the time.
Clara and Marcus launch their plan
Persuading does take planning!
“The secret to getting ahead is getting started.”
Clara and Marcus are allied in their vision - they can see WidgetCo’s future in generative AI. They just have to convince everyone on the management team.
Clara and Marcus put their audience first by using the Who What What table to understand each member of the management team’s biases and concerns. Now they are ready to take action.
“Before the next strategy meeting we need to prime the pump,” Marcus said.
“And make sure we keep Jones out of the loop for now,” said Clara. “If we get Justine and Hector on board, Jones won’t be able to object, even if he is VP of Product Marketing.”
“Exactly. So how do we get to Hector and Justine?” Marcus looked worried. Neither he nor Clara could just waltz into Engineering VP Justine’s cube and Hector, the CRO, was always out meeting with customers.
Clara and Marcus knew they needed to master their channels. They had to identify not just the best way to reach Hector and Justine, but the best message to get their attention.
“I’ll Slack Justine just the link to the article I read about what three competitors are planning and tell her I’d like her input,” said Clara. “Then I can float our idea and see if she tears the skin off of my face.”
“Great, and I’ll take the customer data and send Hector a text. I can ask him if he’s hearing/seeing similar things in the field,” said Marcus. “Then I can invite him for a drink. He’s supposed to be back on Thursday.”
“When are we going to Monica?” said Clara. “I think we wait until after we at least soft-sound Hector and Justine, right?”
“Yeah. And I’ll let Gary know what Hector says. The key to Hector is just listening to him. If you can sit with him for long enough you do start to pick up patterns in his customer conversations. Gary will want to hear what the customers are doing.”
“So we have a plan. And we’ll just keep repeating the same thing - ‘We see a way forward that meets both requirements.’ Right?”
“Yup,” said Marcus. “And now I have to go to Jones’s team meeting and pretend to pay rapt attention.”
Blog backstory: Careful navigation
As Clara and Marcus execute their communications plan, there are a few risks. What if Jones finds out? He’s got strong ties to the VCs on the board. What if Arun shows up out of the blue and buttonholes Justine with some new idea he heard at a conference in Basel?
With any communications plan (or any other plan for that matter) there are things we can control and plan for and things we can’t.
Clara and Marcus decided that they’d tell Jones they were just gathering information and that they’d be happy to share it with him when it was ready, but they didn’t want to waste his time with half-formed suggestions. That would mollify his ego and keep him out of their hair while they pursued their plan.
Arun was a wild card, so there wasn’t much point in trying to predict or manage his behavior. They just decided to bet on Justine’s rationality and competitive nature.
Blog backstory: If you listen, you learn
Marcus walked into the small bar he’d never seen before and thought, ‘If there were only one wood-paneled bar with leather club chairs in all of Silicon Valley Hector would find it.’
Hector, WidgetCo’s Chief Revenue Officer, was just walking out of the humidor followed by a bow-tied girl with a cigar on a silver tray. He was holding a scotch on the rocks that clinked as he raised his hand. “Marcus! You don’t smoke do you? If you do, I have some exceptional choices stored here.”
“Uh, no,” said Marcus, wiping his hands on his jeans. Hector, a classic sales guy in the old-school mode, made him feel like he was eight years old, not 28.
Hector put his arm around Marcus and led him to the smoking room, tucked in the back of the bar behind a heavy door. Mercifully there was no one else inside. As he cut and lit his cigar Hector gave Marcus a sardonic look, “So, what are we talking about, out of the office, one on one?”
“We are trying to understand what our customers really do and don’t want with generative AI. We can’t build a product in a vacuum.”
“Ah, I see.” Hector settled in. He had stories to tell.
Two hours and four Coke Zeros later, Marcus summarized. “So it’s safe to say that our customers are afraid of messy copyright lawsuits and killer robots but even more afraid of falling behind?”
“We must help them find the right path, Marcus. We must. Not a competitor, not a giant multinational that doesn’t understand our customers’ businesses. You’re the first person to bring this topic to me. What are we planning on doing?”
Marcus decided to take the leap. He told Hector what he and Clara were planning, and who was and wasn’t on board so far.
Clara and Marcus Make friends with the CMO
Because you don’t want her as an enemy
“Control is the opposite of trust.”
― William Hertling
“I spent about 17 hours with Hector last night, breathing in cigar smoke and hearing what our customers do and don’t want,” Marcus told Clara. “It’s what we expected. Everyone is afraid of messy copyright lawsuits and killer robots but even more afraid of falling behind.”
“How much did you tell Hector?”
“I told him about our plan. I told him we hadn’t brought it to Monica or Arun. Or Jones or Justine.”
“I assume you decided we can trust him,” Clara said, with her eyebrows creasing. She was worried because Hector was a talker, but she knew Marcus wasn’t an idiot. “OK. Let’s go talk to April. I’ve got Justine this afternoon.”
April, WidgetCo’s CMO, wiped a non-existent speck of dust off of her white desk when Clara and Marcus walked in. “What are you two up to?” she said, with equal parts menace and amusement. “Should I ask Emily to join us?”
“Sure,” said Clara, looking at the floor as usual. But she led the meeting and explained (in a non-condescending way) what the stakes were and why they had to move swiftly but carefully to deliver the right generative AI solution in the right way.
Emily, the PR director, took notes. April tapped her fingers on the desk, realizing that these two must not have told Jones, the product marketing VP, what they were doing, which pleased her immensely. April hated Jones. She didn’t understand the architecture diagrams (April came from the consumer side, after all), but she decided to throw in with these two, because it was clear that Clara was no lightweight and because Marcus intimated that Hector was on board. Besides, supporting this plan would have the added benefit of humiliating Jones, who hated any idea that wasn’t his.
“I’m glad we’re preparing to address this massive market need in a responsible, innovative way,” April said to Clara and Marcus as they all stood to end the meeting. “Let me know when you’re ready to polish the story. Emily and I are here to help.”
After Clara and Marcus were out of earshot, April turned to Emily. “I’ll destroy anyone who gets in the way of a clean message on this. We are the ones who build this company’s reputation. We are the ones who have to make this strategy work.”
Emily smiled and nodded as she backed out of April’s office. No one in the universe would ever survive being on HER bad side.
Later that afternoon Emily Slacked Clara and Marcus. “Shall I do a media audit of competitors' statements?”
“YES” Marcus replied with about 12 exuberant emojis. “We’d love that!”
Blog backstory: Can my enemy’s enemy become my friend?
Clara and Marcus were glad things had gone well with April, but were both pretty terrified as they prepared to meet with Justine, the imperious VP of Engineering who had pushed their meeting out twice. It was three days after the conversation with April when Justine finally said she had twenty minutes for them.
As they were tweaking their deck, Clara and Marcus debated. “We need more data,” Clara said.
“What we need is less for Justine to pick apart,” said Marcus. “Let’s take out the architecture diagram we created for April. That will just make her mad.”
“And let’s add in the competitive stuff that Emily gave us. That’ll motivate her,” said Clara. It was the first time Marcus had heard Clara consider someone’s emotional reaction to a presentation. He turned his head away as he smiled.
Five minutes before the meeting, Marcus noticed that Clara winced and put her hand on her belly. There were beads of sweat on her forehead.
“Are you OK,” he asked. “Can I get you some water or some tea?”
“No, I’m OK,” she said, straightening her back and taking a deep breath. “Damn the torpedoes, full speed ahead.”
They walked down to Engineering. They both knew that if Justine said no they were sunk.
Clara and Marcus get called on the carpet
Always be ready to sprint!
“Chaos is roving through the system and able to undo, at any point, the best laid plans.”
“Sit,” Justine said, without even looking at Clara and Marcus. “What do you have?”
Clara went through the presentation in ten minutes. Justine pulled the laptop out of Clara’s hands to have a closer look at the customer and competitive slides. “Have you brought this to Monica and Arun?” she asked, raising an eyebrow at Clara and Marcus before she took a sip of her La Colombe cold brew.
“Not yet,” said Marcus. “We wanted to build consensus and get feedback on the proposal before going to our co-CEOs.”
“Ah,” said Justine, as cold, non-committal and Gallic as ever. She chugged the last of her coffee. “I have a code review.”
“Thanks for your time,” Clara and Marcus said in unison as they grabbed their stuff and pretty much bolted out of her office.
After they sat down in the cafe and exhaled, Marcus said to Clara, “Well, she didn’t say we were idiots and throw us out of her office.”
“So we go ahead,” said Clara.
“Exactly,” said Marcus.
That evening and the next day, Justine Slacked a dozen questions to Clara and Marcus, reminding them that fundamental engineering principles must never be compromised. She still didn’t say yes, but she didn’t veto their idea either.
The next morning Hector asked Clara to present her proposal to his sales team. “We’re not ready for this,” she said to Marcus. “Things are moving too fast.”
Right after those words came out of Clara’s mouth, Emily walked in. “Arun said something about generative AI at some conference in the Maldives. It got reported. I’m getting pings from the media and analysts.”
“Oh sh*t,” said Clara, knowing they were in danger of being overtaken by events. “We are running out of time. We have to get to Monica right now.”
Emily Slacked Monica with a 911 and the three of them were in Monica’s office 30 minutes later.
“Arun was apparently trying to de-position a potential competitor,” said Emily, as April rushed in, never wanting to be left out of any drama.
“So strategy by the seat of his pants again?” said Monica. “OK. Emily, work out a benign statement to buy us time.”
“We have been working on a strategy, Monica,” said Marcus. “I’m not sure what we’d want to say externally, but Clara’s got a way to deliver something to the market quickly while we’re in the process of rebuilding our foundation to accommodate the future. I talked to Hector -”
“You met with Hector?” Monica was not happy. “Who else?”
“We talked to Justine too,” said Clara, “because we didn’t want to bring something to you without consensus.”
“Have any of you ever heard of the chain of command?!?” Monica stood up and pounded her desk. “Arun is out there making up strategy and you two are planning something new without even letting me know?”
“We didn’t want -” Clara started to respond but Monica wasn’t having it.
“No justifications, no excuses. You two are presenting at the senior staff meeting in three days and you’ll have the deck to me for review in two. Clear?”
“Yes Monica, we’re sorry that we overstepped,” said Marcus.
“Initiative is great, but stealth is not,” said Monica.
Note: We skipped blog backstory on July 4!
Jones has a temper tantrum
“Any man can make a mistake; only a fool keeps making the same one.”
Two days after their first conversation with Monica, Clara and Marcus sat as still as statues in her office, watching her scroll through their AI strategy deck. Clara feared another all-nighter, but Monica could be a pretty chill CEO. She only wanted two changes - a tighter competitive landscape slide and to cut the slide on pricing. “Let’s just make one decision tomorrow, OK?” Clara nodded.
“And you’ll present?” Monica asked, locking onto Clara’s eyes to assess both her belief in the proposal and her commitment as a now key employee.
“If that’s what you’d like,” Clara whispered. Monica nodded and sent them on their way.
Clara wobbled out of Monica’s office, taking shallow breaths. “Emily will help,” said Marcus. “Let’s Slack her now.”
Twenty minutes later Emily from PR walked into the break room where Clara was still trying to slow her heart beat. “What are we, the Three Musketeers now?”
“Well, you need a clear story to tell externally and we need help getting that story sold internally, so I think we have a pretty great alignment,” said Marcus. “Coffee?”
“Red Bull,” said Emily. “Lemme see the deck. And breathe, Clara. We can get you through this.”
Emily told Clara to deliver a simple soundbite for each slide. That night Clara memorized them and then spent the rest of the night on the Q&A she and Emily outlined. The next afternoon, Clara stood and delivered. She did a tight five minute TL;DR on the industry landscape and her recommendation. Her decision request was urgent and clear.
“This plan dovetails beautifully with what our customers want,” said Hector, always affable when things were going his way. “And it has the added advantage of being differentiated from our competitors. I want to start training the sales team now.”
“While I can’t speak to platform issues, I do very much want us to make the right move. We don’t have to ship first, we have to ship the best,” said April, the fierce CMO.
“I can’t believe this!” said Jones, the product marketing VP and Marcus’s boss. “This plan is too complex, it will take too long, it’s more than our customers would understand, more than they know to ask for. We have to just bolt on a simple LLM model right now!” He slammed his hands on the table and glared at Monica and Hector across the table.
“Spoken like the sloppy child that you are, Jones,” said Justine, whose veins were filled with ice water. “We don’t just throw things over the wall to look cool to our friends at other companies. We make considered decisions.”
“Speed is never tidy, Justine,” said Jones, clenching his fist. “But what would you know about producing anything fast? Like ever? Besides,” he said, scanning the room to look for an ally, “Why are we even entertaining a proposal from Clara? Isn’t she the most junior person on the product team?”
Gary, the thoroughly grown up CFO/COO, sat impassively next to Monica, who was also inscrutable. Justine wasn’t having it with Jones’s objections. “Have you looked at your own resume, Jones? You were doing demand gen three years ago. You’ve never written a line of code in your life and you think we should listen to you? Do you still think YOU should be our Chief Product Officer?”
“Well at least I have a bold idea. We’ll lose if we don’t jump into the market right now.”
“You just want to smack our customers in the face with something so they don’t notice that what you hit them with is crap,” said Justine. “Clara’s plan is an elegant evolution. I am on board.”
Jones was about to retort but Justine stood to walk out of the room. “I have no more time for this. Monica, you’re the CEO. This is up to you.”
“Whatever we do, we need a consistent message,” said April. “He may be our co-founder, but Arun’s comments last week were awkward. He can’t just make up product strategy over cocktails can he?”
“Why does messaging matter, April?” said Jones, who seemed to think that offense was the best defense. “You’re probably already using ChatGPT to write all of your content.”
It was at that moment that April decided she’d do literally anything to see Jones fail. Clara, who was still standing, clutched the edges of the conference room table. She had no idea that this was what went down at e-team meetings.
Jones kept sputtering, “Besides, this meeting is a waste of time. Nothing can get decided without Arun here. He’s really running the company.”
“And that is quite enough from you, Jones,” said Gary, calmly, but with menace.
Monica, who was boiling with rage, managed her emotions before she spoke. “Jones, your objections are noted. The rest of us are aligned. We are going forward with Clara’s plan. I’ll speak to Arun. Clara, please coordinate with Justine on a schedule. Marcus can work with April and Emily on messaging. Hector, we will have something for your team ASAP. Thanks everyone for your time.”
Monica and Gary left first. Hector clapped Clara on the shoulder before he walked out. April stood and folded her arms across her chest, staring at Jones until he left the room.
“Well done, my girl,” said April to a visibly shell–shocked Clara.
“Emily really helped a lot,” said Clara. “I’m so grateful.”
Clara debriefed Marcus and Emily in the break room after the meeting. “It was insane. Jones is a menace. But everyone else is on board.”
“Tell me something I don’t know,” said Marcus. “But I am glad we know where we are going.”
“Great,” said Emily. “Now let’s get to work!”
Blog backstory: Conversations are had
After the disastrous (at least in his mind) e-team meeting, Jones asked Marcus to build a couple of new slides.
“I need something like a Magic Quadrant for our sector,” said Jones. “But we can't use the Garntner one cuz I didn’t pay for the subscription this year. So make your own. I also need the latest quotes from academics on LLMs.”
“What are these slides for Jones?” Marcus asked.
“I don’t have to f***ing justify myself to you,” Jones spat out. “You work for ME. Do it. NOW.”
Marcus waited to roll his eyes until after he was out of Jones’s office. WidgetCo was great, but did that outweigh being under this guy’s thumb?
‘This is a question for another day,’ Marcus told himself as he sat down to Slack Clara and Emily on a private channel. ‘I think we might have a problem. I have no idea what Jones is up to. Should we tell April or Monica?’
Emily wrote back before Clara had even finished reading the message: ‘I’ll tell April there may be a situation brewing. But we don’t have enough facts to go to Monica yet.’
As Emily walked by Monica’s office on the way to April’s, she heard Monica on the phone. “We have a problem.”
Meanwhile, Clara stopped by Justine’s office for a planning meeting. Justine waved her in even though she was finishing a call. “Don’t be a narcissist Arun. This company can be way bigger than your ego if you’ll let it.”
Clara knew better than to ask Justine about that call. She just popped open her laptop and they started reviewing Clara’s draft PRD.
Cleaning up after the angry toddler
If you can’t make it, break it
“When anger rises, think of the consequences.”
Jones left the e-team sputtering profanities under his breath. After yelling at Marcus, he stomped back to his office, grabbed his keys and ran down the stairs and out to the parking lot, where he hopped into his silver BMW M8. He was going to the city to drink expensive whiskey. While accelerating to 95 mph on 280 North he formed a plan. “Whassup dude,” Jones yelled into his phone over the wind, because of course he had his top down. “How are things at Great Oak Capital?”
“Awesome as ever dude,” said the VC who had insisted that WidgetCo hire Jones as product marketing VP when his firm made the investment. “What’s going on? Testing the aerodynamics of your sweet ride?”
“We need to strategize. Things are going off the rails at WidgetCo. Come meet me in the city. We are drinking and planning.”
“See you at the Battery in an hour.”
After he tossed his car keys to the Battery’s long-suffering valet (who recognized both Jones’s arch smirk and the totally extra car), Jones found a quiet corner and started drawing up a list of customers who’d back him. ‘Hector is out of touch, he doesn’t know what our customers really want,’ he muttered. ‘If no one else can face this competitive threat and this huge opportunity we’re on the verge of missing, I will!’
That evening, Jones and his VC buddy formulated a plan and drank five rounds to Jones’s genius.
Two weeks later, on a seemingly placid Tuesday afternoon, Emily got a text from a reporter. “Your guy Jones just presented your new LLM product at AI Next. He’s got you competing directly with Zilthru. He says you’ll ship in weeks. What other details can you give me? The deck was pretty light.”
At the same time, Hector got a call from a very big customer. “Hector, we were thinking of doing a beta with Zilthru but I just saw Jones at AI Next. Why haven’t you shared these plans with my team? Who is getting access to your new build before we do? You don’t want to relegate me to second tier do you?”
Hector dissembled with the customer while typing the world’s fastest Slack message to Monica. Fifteen minutes later Hector, April, and Emily were on GVC with Monica.
“Does anyone know what happened?” asked Monica, as calmly as she could.
“I got the link to Jones’s presentation. It just went up,” said Emily. “There are also several Tweet threads. Zilthru is now dissing us because Jones dissed them. Analysts are asking questions. A couple of blogs have already been written. It’s a definite situation.”
Hector reported on his customer conversations. “So far, I’ve been able to mollify them without making commitments, Monica. But I have to ask. Did you know about this? Did any of us?”
“No, Jones has gone rogue. We are in crisis mode now.”
“And he’s given airtime to a competitor no one had ever heard of: Zilthru. WTF,” said brand-conscious April, rolling her eyes. “Emily and I will put together a press statement. You can then share it with a note to customers, Hector.”
“We can’t publicly throw Jones under the bus,” said Monica.
“I know,” said April. “We can’t look like we don’t have a plan. We are on it.”
After Emily and April left, Hector and Monica started reaching out to customers together. Meanwhile, Arun, WidgetCo’s perpetually absent CTO and co-founder, texted them to say he was getting on a plane from Ibiza. “I’ll help sort things with customers. I have some deep relationships - you two can deploy me however you need.”
Monica and Hector looked at each other after reading his text, their eyes mirroring worry. They were both glad to have the extra help, but they also knew that Arun was as capable of freelance strategizing as Jones. Would Arun help or hurt them?
Monica and Hector sent Jones a cease and desist email, cc’ing Arun, but not the board. Monica tasked our product management and marketing heroes Clara and Marcus with building a strategy deck that would gracefully evolve from Jones’ bulls**t to the correct strategy that the company had already agreed. Clara gulped. “On it,” she typed.
When the press statement was ready thirty minutes later, Emily hopped onto a GVC with Hector’s sales team. “Look guys, answering angry customer questions is pretty similar to answering nasty questions from reporters. Just acknowledge that you heard them and then pivot to what you want to say. Acknowledge - pivot - message. Got it? OK, let’s practice.”
After she finished with the sales team, Emily walked into April’s office. “I wish our company were big enough to have a sales-enablement team, but I think the guys have what they need. I’ll go check on Clara and Marcus. They can help me come up with a Tweet to put a damper on Zilthru.”
“And have them take care of Cthulhu while you’re at it!” April said, feeling very clever.
“Ha. On it!” said Emily as she hustled out of April’s office, opening her third Red Bull of the day.
Blog backstory: Put that baby in a corner
April walked down to Justine’s office overflowing with smug delight. She knew exactly what would happen when she told her what Jones had said at AI Next. It was even more delicious than she expected.
“Here’s what Jones announced as our company strategy this morning,” April said as she threw a printout of the architecture slide onto Justine’s desk. “My team’s cleaning up, but he put your team on the hook for a lot.”
In about four seconds Justine was on her feet. “Putain de merde,” she growled. “I can’t believe this guy.” And then, at an alarming volume, Justine shouted out of her office door, “Conference room. NOW.”
April heard laptops slam shut, chairs squeak and many sets of hurried footsteps. Justine looked back over her shoulder as she walked into her conference room.
“You can tell Monica, Hector, and everyone else that my team has no higher priority than Clara’s strategy.”
After she organized her engineering team to build “the right thing, the right way and as freaking fast as possible,” she texted Arun. “We are in it. When will you be here?”
Monica manages the monkeys
Heavy hangs the head
“We can’t save everyone. The kindest cut wins.”
— Umbrella Academy
Jones didn’t sit when Monica called him into her office. Without saying a word, Monica pulled up his unsanctioned AI Next talk on her screen. She met his eyes and waited. “I’m the only one who sees what has to be done,” Jones sputtered, his voice cracking. Monica said nothing. He doubled down. “I’m the product marketing VP. This is my job! We are going to lose in the marketplace if we don’t announce an AI strategy right now. I saw the opportunity and took it. You should be thanking me!”
Monica smoothed a non-existent wrinkle out of her shirt cuff before speaking. “Jones, if you want to make unilateral decisions, go found your own company, get your own funding, and recruit your own team. Then you can do whatever you’d like.”
Jones could’t formulate a suitable response, so he just sputtered again and fled, out of Monica’s office and the building. He hopped into his car, turned over the ignition to let his engine’s fierce power soothe him. ‘We’ll see how they all do without me,’ he said to himself as he peeled out of the parking lot at 80 mph.
Meanwhile, Emily in PR had her hands full, walking back both Jones’s made-up presentation on their AI strategy and Arun’s vague speculative comments about WidgetCo and AI. Marcus stopped by to check on her. “How’s it going?”
“Just rinse and repeat, Marcus. Smiling, speedily responding with the same damn words over and over again. Fulfilling my job description!”
“Anything I can do?”
“Get me another Red Bull?”
About two hours after Jones left, Hector and Gary walked into Monica’s office. “We have a problem,” Gary said.
“You mean besides our customers wanting to buy Jones’ fake product?”
“On that, I know the new customer deck is underway,” Hector said. “Emily did a great job coaching the sales team on handling customer calls. And I hear Justine is making Clara’s plan our top priority. So as long as Arun doesn’t derail us, it seems like we’re on the right track.”
Hector was nervous talking. Monica could tell he was avoiding something.
Gary said, “It’s about Gordon, the newest hire in sales . . .”
Hector cut in to blurt out, “He took our prospects from Chevron to the Gold Club.”
Monica took a deep breath, reminding herself internally that she signed up for this insane job.
“Did he get out of a time machine from 1972 before starting here?” Monica spat out before she got a hold of herself.
Neither Hector nor Gary knew how to respond to that one. Monica put up her hand. “OK. Three things. You two meet with HR and decide whether you’re going to rehab or exit Gordon for taking customers to a strip club. Second, Hector, make it clear to your entire team that this is unacceptable behavior. In writing. Third, Gary, let’s re-run our ethics and professional practices course. For everyone, not just sales. And make sure we’re covered with legal.”
“Got it boss,” Hector said. Gary gave Monica an encouraging smile and a thumbs up as they walked out of the room.
Monica sat back in her chair, closed her eyes and wondered if she should just move to Jackson Hole and be a ski bum for the rest of her life. Then she sat up straight, took a sip of water, arranged her face into the perfect picture of confidence and reassurance and got on her fourth customer video call of the day.
Aug 15 blog backstory: No one gets a rest
Because there was no one else to do it, Clara, Marcus and Emily appointed themselves to build a solid customer (and analyst and press and board) deck about WidgetCo’s new product direction. They were more or less living on pizza, ramen, Red Bull, and chocolate.
April showed up at their deck review meeting with good news. “Gary knows we need another pair of hands to focus on sales enablement.”
Marcus put his head down on the table. “Thank heavens. We are dying here. Sales people are so needy.”
“And if we don’t meet their needs we won’t sell any product,” said April. But then she read the room and changed tack. “I’m sure you’re doing great. The work you do on this deck will be repeatable across all of our audiences so it’s worth it.” She sat down. “Let’s see where you are.”
“Here are the critical slides, April,” said Clara. “I’ll walk you through what’s new and why we’ve changed it.”
Marcus and Emily smiled at each other behind Clara’s back - Clara was learning how to speak up and drive! They were both so proud.
April pushed back her chair and said, “This is looking really strong. I want a clever positioning statement, so I’ll stew on it. And Emily, when this is final, we need to rationalize our brand approach and create guidelines.”
“And hire help?” said Emily with a weak smile.
Teamwork makes the dream work
“Don't be ashamed of needing help. You have a duty to fulfill just like a soldier on the wall of battle.”
— Marcus Aurelius
Four days after the debacle of Jones freelancing on WidgetCo’s AI strategy at an industry conference, Monica and Hector were feeling better. They’d held 32 customer meetings to pivot away from Jones’ deck. They presented Clara, Marcus, and Emily’s beautifully simple and compelling strategy deck. April had threaded the needle on their positioning message, Justine’s team was on fire. They were both so relieved to have a good story to tell. “Monica, I really appreciate your commitment. It takes a ton of discipline to tell the same story over and over again with the same energy to everyone,” said Hector. He was grateful for Monica’s maturity and grace. He’d become an even more committed Monica partisan.
“We can’t leave our customers in an information vacuum. We did what we had to do! I’m glad we were able to get to everyone, and to be able to do it together” said Monica, exhausted but relieved that she was leading the company properly through its first major crisis.
Just as she reached for her iced coffee, there was a gentle knock at the door. It was Arun, who asked, in an uncharacteristically respectful and non-intrusive way, “Is this a good time?”
“Sure,” Monica said. “Hector and I are just taking a breather.” Arun was tan but otherwise, there was no evidence that he’d been clubbing nonstop in Ibiza for 30 days.
Before Arun sat down, Hector got a text. “Oh no,” he said. “Chevron’s going with Zilthru. I’m going to see if I can rescue the relationship, but if I can’t, I’ll ping Gary. This’ll impact our number this quarter.”
“I know their CTO,” Arun said. “If it’s helpful . . .”
“Let me call my line of business contact first and see where I get,” said Hector. “But thanks!”
After Hector left, Arun said to Monica, “So you’ve been in it.”
“Uh yeah. We all are. All hands on deck. Justine’s hair is on fire, like I’ve never seen before.” She stopped to give Arun, her irresponsible, egotistical, absent co-founder a skeptical look. “Why are you being so chill?”
“I think I’m finally learning that leadership really is service. Just tell me what you and WidgetCo need and I’ll do it,” said Arun, with more sincerity than Monica had seen before. “Oh. And I’m done with improvising in public on company strategy. I’m sorry about that.”
“Well, that’s a relief,” said Monica. She saw the olive branch Arun was offering and she was SO grabbing it. “The next chapter of WidgetCo is about to begin. I’ll address strategy, customer success, and culture in the next all hands. Want to join me?”
Aug 29 blog backstory: Just when you think it’s safe
In the middle of another no good, terrible, very bad day with Jones, Marcus took himself out for a walk to clear his head. There was a gravel path by the bay marshes not too far from the office. He listened to his feet crunch and talked to himself.
‘You’re the most positive person here! But you’ve got the worst boss in the whole company. Why!!!???”
He looked at the sky. Blue as always. No answer there. He kept walking. ‘Is this just the price of working in the tech industry? Is it the company, is it working in product marketing? Is it me?’ He stopped and said aloud, “No, it’s him.”
Marcus turned around to walk back to the office, humming his uncle’s favorite old Clash song to himself. ‘Should I stay or should I go now?’
Walking back to his cube, refreshed from the vitamin D of being outdoors but still unclear on his career path, Marcus overheard Jones on the phone. “We need an emergency board meeting. It’s time for a change at the top.”
‘Oh s**t,’ Marcus thought. He sat down as stealthily as he could. He didn’t want Jones to know he’d been heard. He Slacked Clara, who met him in the lobby immediately. They left the building, looking over their shoulders.
“Who do you think he was talking to?” Clara asked. “What do you think he wants to do?”
“I’d guess his VC buddy who’s on the board,” said Marcus. “And nothing good.”
Blog backstory: Let’s just tell one story
Monica and April were out for a walking one:one, but Monica was moving so fast that April could barely keep up. “I’m sorry,” Monica said. “I have a lot of negative energy to expel.”
“How could you not after Jones’s shenanigans?” said April, “We need to clarify things in the market ASAP.”
“Totes. Get me a speaking platform, now. A big one.”
“With pleasure,” said April, with a satisfied smirk. Another nail in Jones’s reputational coffin.
Twenty minutes later Clara and Emily rounded up Marcus. “We have to turn that customer deck we just finished into something flashier, and we have to do it, like, today.”
“Yup,” said Emily. “All it took was one text and we got Monica on as the closing keynote speaker on the first day at Safe AI.”
“We’ll have to distill the description of our data vetting and provenance automations down into accessible language and we’ll have to add a few strong use case examples,“ said Clara. “This is our chance to inspire. Marcus, do we have any customers who are ready to talk?”
“Look at you using distillation in a sentence like it’s a good thing,” said Marcus. “And yes, I’ve got two customers who want to show off how they’re NOT scraping the entire internet to feed their models, so we’re good.”
Twenty-four highly-caffeinated hours later, Emily, Clara, and Marcus watched as April polished the deck and added some tangy soundbites to Monica’s talk track.
“I’ll start on the Q&A,” said Emily to Clara and Marcus. “After we are all happy with it, I've got to get it through legal. We don’t get a do-over on this opportunity, so it has to be perfect.”
“Oh it will be,” said April, standing and clapping. “You guys have done amazing work. Yay team. And especially yay you, Clara. This was all your idea, wasn’t it?”
Clara was too flustered to answer. She stared at the table and mumbled, “We all made great contributions.”
After April and Emily left, Marcus turned to Clara. “It was your idea. You proposed the new company direction. You did that.”
“Well, no one even read my email until you fixed it for me, so . . .”
“We are lucky to be on the same team,” said Marcus with a big smile.
WidgetCo puts a stake in the ground
Tell the right story
“It’s good to be the king, especially if you’re a woman.”
— Tom Petty (modified by me)
“Tomorrow I’ll be delivering the closing keynote at Safe AI,” Monica said at a hastily-called company All Hands. “The speech isn’t yet 100% finished, so I can’t share it now, but we will be laying out a comprehensive new vision for generative AI that has trusted, owned data as its foundation. We’ll be having a watch party at the office tomorrow at 4 p.m. Next Wednesday we’ll hold a full-day offsite. We’ll do a plenary session in the morning on our objectives, strategy, and timeline and then each team will do their own two-hour deep-dive session. After that, we will all go out for a much-needed celebration.
“It’s a crazy time in our industry, which means we have to work harder than ever for our customers, who depend on us to steer them in the right direction. Each one of you has a vital role to play.”
“What about the product direction that Jones presented at AI Next?” said the sales guy who Monica noted had apparently not been fired for the Gold Club incident.
“We’re clarifying and augmenting,” said Monica. “We have a robust, responsible plan. In tomorrow’s keynote, we will lay out all of the details and set a clear path forward.” She searched the room for Jones. Was that him lurking by a pillar in the back of the room?
“And what about Arun’s comments a couple of weeks ago?” said a junior engineer who looked a little indignant.
“Let me address that,” said Arun, who so far hadn’t said a word at the All Hands. “I made a mistake. Monica and Justine and the whole team have been hard at work on our AI strategy and I was too out of touch to know what was going on. I should not have said anything in public. It won’t happen again.”
“We’ve reached agreement on our strategy. We are now all rowing in the same direction,” said Monica, nodding and smiling at Arun, who nodded and smiled back. “Now 10,000% of our focus has to be on making each one of our customers successful.”
The next afternoon, Monica got huge applause at the end of her keynote.
Emily called Clara and Marcus as soon as she got into her car. “It was a smash,” she said. “The customer stories got whoops. Analysts were swarming me asking to come in for briefings, I even had a few clueless VCs give me business cards. At least six reporters wanted time with Monica, but I only let them have five minutes each. Oh, I have to go, another one is calling me now.”
Monica called Clara just a few minutes later. “Clara, things have been so crazy, I don’t know if I have said it clearly enough. I want you to know that I know the source of our new strategy. I am so grateful that you brought the right idea to us in the right way at the right time. You changed the future of WidgetCo.”
“Wow, uh, well, it was just a proposal,” said Clara, too overwhelmed to know what to say. “Everyone added so much.”
“Of course. That’s what we do. But the kernel came from you. I’d love to sit down with you next week and talk about your role at the company and what you’d like to do.”
“I’d love that,” said Clara, feeling a little dizzy.
Monica hung up feeling proud of and grateful for her whole team at WidgetCo, but about four seconds later, her happy bubble burst. Jones was calling.
“We’ve called an emergency board meeting,” he said. “Tomorrow morning at 10. To discuss the makeup of the executive leadership team. Your attendance is, of course, mandatory.”
Blog backstory: Stealth mode
Monica hung up after Jones’s call and took a breath. She knew just which board member supported Jones’s emergency board meeting request. She also knew not to let him know that she knew anything.
She texted Arun and Gary. “We need to meet tonight. Not at the office.”
And then, for the remaining thirty minutes of her drive, she decided to let herself celebrate her triumphant keynote. She put on her favorite playlist, rolled down the windows and sang at the top of her lungs all the way down 280.
WidgetCo is what’s next
Oh happy day (for almost everyone)
Monica walked into the conference room fifteen minutes before the emergency board meeting was scheduled to start to find Jones in her seat at the head of the table, and Peter, his VC buddy on the board, seated to his right, fiddling with his phone. Without even raising an eyebrow, Monica took a seat in the middle of the table. Arun and Gary came in and sat on either side of her, both looking graciously impassive. They stood to welcome each board member that arrived, shaking hands, clapping shoulders.
“We called this meeting to discuss an urgent problem with WidgetCo’s current leadership,” said Peter, as soon as everyone was settled. Jones, his chin jutting, could hardly contain his excitement. “We believe that Monica must be replaced as CEO immediately. And that Jones must become Chief Product Officer. These steps are essential to securing WidgetCo’s future.” Peter called a vote.
But the only person who raised his hand in favor of Peter’s motion was Peter himself. (Jones was not a board member. He couldn’t vote.)
Gary nodded to the other two board members in the room. “Actually,” said one, “we believe the problem resides with Jones. Monica has the board’s full faith and trust as WidgetCo’s CEO. Her strategy has gotten exceptional feedback.”
“I don’t know why we are even having this meeting,” said another.
“There is a reason,” said Arun. “It’s time for me to officially step back. Monica will be sole CEO of WidgetCo. I will resign from my Co-CEO position and just have a board seat. I’d like to vote on this now.”
Every hand in the room except Peter’s and Jones’s went up.
Peter bolted the second the meeting was over. After Monica, Gary and Arun said goodbye to the board members, Jones, who was waiting in the hall, stomped up to the three of them and said, “You can’t fire me. I quit!”
“Really,” Arun laughed. “That’s really how you’re going to say it?”
“HR will get in touch with you, but you’re welcome to clear out your desk now,” said Gary. “And I’ll take your badge.”
Two weeks later, all is well at WidgetCo. Not calm. Everyone is insanely busy. But all is well.
Monica and Justine have bonded. They are both running at full speed to stay ahead of the inevitable emerging competitors. “It’s nice to be part of your team, Monica,” said Justine after a marathon strategy review. Monica was surprised. Those were the kindest words Justine had ever said out loud to anyone at WidgetCo. “Same, Justine,” she replied. “Same.”
Monica met with April. “Take that ferocity and build us a multi-market, multi-audience, multi-channel strategy. Come back in two weeks and wow me. Oh - and we need Emily in our senior team meetings. Will you let her know?”
April walked into Emily’s office with a huge smile on her face. “You know that mythical seat at the table? You have it now. Heaven knows you’ve earned it. Congratulations!”
Hector and April got Monica to approve two people for a sales enablement team. Emily was so happy she nearly cried when she heard the news. Gary’s last act before he officially went on long term health leave was to suggest a possible Chief Product Officer to Monica. “I think he’s brilliant and humble, which is just what we need, but what matters most is whether you and Justine feel the same way.”
“Gary, I am going to miss you every day. I’m not sure what I’ll do without you,” said Monica.
“You’ll do amazing things Monica,” he said, in full paternal mode. “You’ve managed to steer us through the chaos. You can handle anything WidgetCo has to face.”
“You’re the new chief Monica cheerleader and supporter,” Gary said to Hector when he came to say goodbye.
“On it my friend,” said Hector. “It will be my pleasure.”
At the end of a demanding but happy Thursday, Marcus came to Clara’s desk. “You had your meeting with Monica today, didn’t you? How did it go?”
“Good. She wants me to meet with the potential CPO candidates. And she wants to make me a senior director. And I, I, I still can’t believe it.” Clara looked up and noticed that Marcus looked less happy than usual. “What’s up with you?”
“I’ve decided to leave,” he said. “The experience with Jones really showed me how one bad person can derail a whole company. I know we’re on the right track now, but I started looking for a new gig when things were really bad and I got an amazing offer.”
“Oh,” said Clara, looking down. She felt hollow inside.
“No one knows yet. But I wanted to ask you two things.”
“Would you be a reference for me? They need peer references for a background check.”
“And, uh,” Marcus looked down for a second before he looked up and met Clara’s eyes. “Now that we won’t be working together anymore, maybe we can have dinner sometime?” He paused. “Not as friends.”
“Oh,” said Clara, as she grokked the look in Marcus’s eyes. “M - may - maybe.”
She smiled a little half smile and then, too embarrassed to maintain eye contact, Clara turned to her monitor and went back to work on her PRD.