Investment Flashback - Multitudes | Glenn Gillen
Investment Flashback - Multitudes

Investment Flashback - Multitudes

Feb 07, 2023

Next on my February Funding tour: Multitudes.

I've a friend who runs a VC firm that does a mix of investments directly out of a fund alongside some syndicated deals. Knowing that I have a particular skew towards developer tooling she reached out to me to do some light due dilligence on an investment they were thinking of making and to get my read on the product.

An unflappable confidence

My first intro to Multitudes was less an intro and more of a "here's a copy of the video from the investor presentation they gave to us last week". You know when you watch someone talk about a topic, and you can tell they know their topic? Not because they're overwhelming you with information but rather because they themselves seem unable to be overwhelmed. No question ruffles them, they seem genuinely excited to be able to talk about it, and can keep seamlessly bringing the questions back to to overarching theme.

This was one of those calls.

Lauren just seemed to genuinely love this problem space. It made talking about it seem both easy and exciting. And lets be clear, Multitudes is about helping engineering managers and teams be more productive. It's not on its surface the most exciting of topics.

A problem that resonated

I've oscillated between being an individual contributor and a manager multiple times over my career so I can sympathsize with both sides of the table when it comes to anything in the realm of "performance management". None of this is an issue for anybody when everything is going perfectly. But things are rarely going perfectly, there's always some room for improvement, and so identifying where that is and what enables it is where the tension arises.

As an IC it's that discomfort of working out how to provide constructive feedback to someone else, especially your manager, without the risk that it's received poorly and impacts your working relationship. Often people just don't think it's worth the risk and try to swallow the frustrations and/or eventually leave. Then there's the parts of this area that less about you explicitly taking an action but rather how others are objectively measuring you. Key Performance Indicators, Lines of Code changed, ping pong points won (I assume, it's been a while since I've lived in SF 😉). Now you feel like some overlord is trying to squeeze every last ounce of effort out of you to hit some arbitrary number. It feels gross. It takes the fun out of what you're doing.

As a manager it's not as much fun as ICs often think, especially for those that have been promoted from an IC role into a managerial position within the same company. It becomes pretty lonely very quickly. People you were friends with before are still friendly and social, but it's a bit different now. They're understandably at least 10% more guarded about what they say to you about work because you're part of the machine. You have to do the same because there's things you legally can't share with them, and because you can't be playing favorites with specific employees. There's an uncomfortable balance of staying on message and keeping the official company line which means you can't be your friend and team mates personal work therapist anymore. Meanwhile you've been thrust into a job you've never done before and so you're almost certainly terrible at it. Now you have a dashboard full of metrics reminding you every single day how terrible you are and how unhappy you. You know! You feel it every day.

Non-creepy metrics

Through all of that, it's hard to see how metrics actually help. ICs feel like big brother is scrutinizing their every move, managers feel like they're being reminded every day of how they're failing their team (and in turn being judged by their big brother).

Part of the pitch Lauren gave included a story about an engineer who'd had a bit of a slump. At least others perceived that to be the case. Someone who was previously seen as a high performer and now suddenly wasn't. As a manager, how do you resolve that? Speak to them about it is the obvious and Management 101 answer. It's not always that easy though. I've been on both sides of that conversation and when you're in a slump sometimes you don't even know why. Everything suddenly seems harder than it used to be. You're constantly being interrupted or distracted, and your efforts to fix it don't achieve much. You start the week full of energy and it just seems to dissipate. So when your manager asks "What's wrong? How can I help?" you just... don't know! Now what? Set some specific outcomes and objectives? You've already got work to do, you don't need a reminder of that. You're not an idiot. But the re-formalisation of this suddenly feels an awful lot like you're being put on a performance plan. "Am I going to lose my job? Ugh. This stress probably isn't the help I need to get out of the slump!"

Anyways... back to Lauren's version of this story.

The person in the story had been a high performer. One of the more junior ones, but they'd quickly grown to be a much respected leader in the team. So much so that the other leaders in the team stopped helping, "You're doing great! You got this!", except they didn't got this. All that success had been built on the back of exciting collaboration. Now this high performer had found their own version of being in a lonely place. They didn't have the support network they used to. Those people were still there, and still willing and able to help, they just weren't. Their attention had moved elsewhere. The dynamic had changed, and so did the results, and eventually the morale of the person too.

(Aside: One of the findings in the research conducted for "12: The Elements of Great Managing" was that team members are more frustrated by someone who is capable but lazy than they are someone who is incompetent. That is, if you know someone is able to do the work but doesn't seem to be pulling their weight it will have a larger negative impact on your own mental state than someone who is straight up bad at their job. So the impact of someone who's in a slump like this can cause very real collateral damage to the team as a whole and not just the individual)

How did they work this out? By seeing the communication graph between people. I'd long known this kind of detail was important, I've always tried to make sure people on my team have regular skip-level chats with with any people above me on the org chart. Who you talk to, and who remembers your name, can have an outsized impact on your career development. It shouldn't have surprised me as much as it did to see it at a more team-local level too. And once I did it slapped me in the face so hard, I could see it everywhere now. Juniors who plateaued because their support networks rolled on to supporting the next junior person. Staff/Principal engineers who were frustrated because they now felt like they were on the critical path for providing input on every single thing everyone was wanting to do and the context switching was breaking them. So many of the problems I was witnessing around me seemed like they could be explained by a diagram or two. People with too few lines connecting them to people who could inspire their growth, people with too many lines having to carry too much load, lines that were too fat showing too much volume on specific things.

Improving human outcomes

What really landed for me with Lauren's pitch just how empathetic the whole thing was. This wasn't some "poor productivity is costing the industry seventy squillion dollars a year, we need to work people harder" story. It wasn't a "you need to connect individuals and their commits to the the impact it has on the bottom line" story. It wasn't a "here's how you stack rank your best performers and fire the rest" story. It was a story starting from an assumption that the people you hire really are trying to do their best, but things get in the way. Things you can't always see or notice. But if you could... then you could remove the impediments. It's a story that believes in the best of people and that we just need a little help from time to time, which is one I already believed.

And so instead of just doing the due diligence I asked if there was any room to squeeze into the syndicate. And here we are.

Obviously if you've read this far you definitely need to sign up for Multitudes and start helping your team (or introduce it to every engineering manager you know).

Hi, I'm Glenn! 👋 I've spent most of my career working with or at startups. I'm currently the Director of Product @ Ockam where I'm helping developers build applications and systems that are secure-by-design. It's time we started securely connecting apps, not networks.

Previously I led the Terraform product team @ HashiCorp, where we launched Terraform Cloud and set the stage for a successful IPO. Prior to that I was part of the Startup Team @ AWS, and earlier still an early employee @ Heroku. I've also invested in a couple of dozen early stage startups.