Why Is It Easier Getting a Job From Somene You Know Reddit
Dig into Nick Caldwell's resume, and you'll see leadership posts at an enviable listing of startup staples — Reddit, Looker, and now Twitter. But less typical these days is the xv-year stint he put in at Microsoft beforehand. His tenure at the company culminated every bit a founding member and eventual GM for Power BI, one of the company's biggest success stories. It was just afterward accumulating this deep bedrock of experience that he took on his get-go startup office at Reddit, where he led the engineering team through hypergrowth, scaling from 35 engineers to 150.
He and then joined Looker every bit a product and engineering exec, steering the teams through the company'south $two.half-dozen billion acquisition past Google. This brings u.s.a. to his latest role — every bit the VP of Applied science for Twitter, spearheading an org that's 700 engineers potent.
Information technology'due south a remarkable rise with stops at some of the most interesting and innovative companies effectually. Merely what perhaps most sticks out about his career journey is that Caldwell has institute success at companies with vastly dissimilar cultures, from Microsoft's buttoned-up enterprise to Reddit's fast pace. "Each place I've worked has radically different cultures, which I didn't appreciate at the time considering information technology's difficult to understand the culture while you're in information technology," he says.
Part of the joy I've had over the class of my career is learning that there are a lot of different ways to ship software and get things done.
In our exclusive interview with Caldwell, he pulls on threads from each stop in his career journey at companies with different cultures, scales and functions and he opens up nearly the biggest leadership lessons that stick with him. He makes the case that Microsoft'southward operational practices should get more than of Silicon Valley's spotlight — including the company's approach to org design and its improved operation management organisation. He gets vulnerable nigh ane of the harshest (yet warranted) pieces of feedback he ever received, and how a home run at Microsoft prompted him to leave the company and attempt his hand at startups. Caldwell too dives into his functional expertise, with his vision for how product and engineering science tin can squad upwards instead of tussle and the system he leaned on for architecting Looker'south engineering science roadmap.
It's an incredibly wide-reaching fix of frameworks and although Caldwell'due south breadstuff and butter is engineering science leadership, at that place's plenty to sink your teeth into for managers all over the org nautical chart. Caldwell is a adept speaker and writer, and he'due south got a knack for distilling complicated topics or thorny impasses into crystal-clear lessons. Let's dive in.
LESSON #1: TAKE RESPONSIBILITY FOR WHAT HAPPENS Side by side & GET OFF THE Floor.
Caldwell points to ii of his old managers at Microsoft for some of his primeval and most pivotal leadership lessons. "When I was very early on in my career, I was a brash, headstrong engineer. I was complaining to my manager at the time, Ravi Shahani, most how crappy the PM team was," recalls Caldwell. "I was like, 'These guys don't know what they're doing, they're making me build all this stuff and none of it's going to work.' I was just going off on him."
What came next was a (somewhat painful) wake-upwards telephone call. "He said, 'Nick, you're an amazing engineer, but you're just a shitty leader.' I was similar, 'Ouch!'" says Caldwell. But Shahani imparted a critical piece of advice. "He said, 'Leaders take responsibility for what happens next. So are you going to sit in my office complaining almost this, or are you going to exercise something to change it?' And that was an incredibly of import turning indicate in my career — it was the moment I decided I was going to do more than but exist a grunt engineer," he says.
His adjacent motion? "I immediately left his office and went to the product's GM to say, 'Hey, we need to change this in the production strategy — give me a adventure to prove information technology to you," he says.
Another leadership lesson came a few years later when Caldwell had climbed from IC engineer to engineering managing director, and somewhen engineering managing director. "James Phillips was my GM at the fourth dimension, and he taught me a lot nearly the difference betwixt being a manager and a director," says Caldwell.
"Up until this point in my career, I loved line-level engineering science management. I carried that through to my role as a director, even though I had like 30 people reporting to me. I did all the things that you would from someone with a much smaller team — I got to know everyone individually, and worked hard to motivate and inspire people on a one-to-one basis. I was having trouble scaling all of the things that are great about beingness an EM," says Caldwell.
To close the gap, Phillips gave him a mantra that Caldwell at present passes along to other folks making the director-to-director transition. "1 day James said, 'Nick, you lot have to learn how to get off the floor.' What he meant by that was if yous call up nearly the engineering science team as a warehouse product, you've got your line managers and then you've got your directors. The directors have to be off the flooring, overseeing multiple lines," he says.
Phillips took an additional step to hammer home his bespeak. "He made me stop sitting with the teams straight to strength me to get a scrap of removal from the day-to-day. It did teach me how to delegate more effectively," says Caldwell.
When y'all get off the floor, you tin see systematically how your teams are working together and better spot the bottlenecks from that vantage point.
LESSON #2: ACTUALLY, You SHOULD Transport YOUR ORG CHART.
While the cultural practices of FAANG companies have permeated nearly every company in Silicon Valley — from early-phase startups to industry juggernauts — Microsoft's operating principles haven't captured the zeitgeist. That's a missed opportunity, says Caldwell. "Google'southward direction practices and Netflix'southward culture deck are held on a high pedestal. Just my honest assessment is that they stake in comparison to the effectiveness of Microsoft's organizational design," he says. "Any other identify I've worked relative to Microsoft has been less effective at forming business concern units and understanding how to motion people and resources to whatever the almost urgent problems are. It doesn't get talked nigh much publicly, but it'southward Microsoft's cultural superpower."
Here'south how he breaks downwardly the company's product-based org structure. "Windows, Deject, Gaming or Office are all generally speaking multi-billion dollar businesses with even larger partner networks. So with that framing in heed, the visitor needs to organize its resources and people to address each disparate business organisation's needs. Each business unit is run by a VP, which then breaks downwards into product families, and within those product families are production units, and this trickles further down into engineering teams and feature teams," says Caldwell.
The word "reorg" may elicit groans from enough of folks, but Caldwell points to this process as one of Microsoft'south most powerful tools for rigorous prioritization. "Microsoft on a very regular cadency changes the org chart, whether it's where people sit down, which products are owned by a particular PM, et cetera," he says.
Merely it'due south not just the org (and reorg) blueprint that sets the tone here — an air-tight comms strategy is key. "You lot tin look that every quarter or every other quarter there will be some sort of reorg announced by your executive. It's communicated very conspicuously and backed up by explaining what the business organization strategy is — whether that'south moving people to shore up investment in a particular area. There's a regular cadence of pruning and shaping the org chart to match any the goals are that we're trying to striking," says Caldwell.
"Don't ship your org nautical chart" is a common maxim. Merely this is incorrect — you should be aircraft your org chart to make sure it maps to whatever production or objective the business is trying to attain.
LESSON #three: CODE Tin'T SOLVE EVERYTHING.
While Caldwell'due south primarily been an engineering science leader, he's likewise taken on product leadership — including merging the ii as Looker's Primary Product and Engineering Officer. Information technology brings him a unique perspective on how these two orgs tin avoid the frequently at-odds, "frenemies" relationship.
"I started in engineering and really had no clue what product people were supposed to be doing — I thought that lawmaking solved everything. Plain, we can't transport anything without code in our line of business organisation, simply I over-weighted information technology considering I didn't understand everything that went into getting the software out the door and into the customer's hands," says Caldwell.
Here's how he now delineates between the two. "Product'southward task is to consider a broad variety of inputs — customers, market strategy, going across organizational boundaries — and synthesize that into a winning strategy. Then they influence everyone from engineering, product marketing managers, become-to-marketplace to hold with that strategy," he says.
He'southward got a greater appreciation for the many potholes along the way. "The challenge here is that each of these different groups has completely dissimilar motivations. PMMs recall very differently than engineers, who think very differently than designers, and they're incentivized in unlike ways," says Caldwell. "They take different rubrics for how they judge their success, and product people have to sit down in the eye of all that and effigy out a way to corral it all towards whatever your product's goal might be. It's a maddening, multi-dimensional, never-catastrophe chess game."
On the technology front, Caldwell finds that the biggest trap is leaving engineers out of the decision-making phase. "Engineers are often asked to go work on things without explaining why they matter to the business. Like, 'Become build this feature.' Or they're asked to proceed legacy code alive without agreement why or how it contributes," he says.
Many companies call up of engineers in a mode that'south like, "Lock them in the basement, throw a pizza down there every in one case in a while, and hope that lawmaking comes out." But every minute you spend explaining the "why" to an engineer is a minute well-spent.
Here's his recipe for a happy marriage between product and eng orgs: "The best output is when engineers can trust that the PMs have a great understanding of the market and how the eng work ladders up to the customer. Meanwhile, the PMs look outward and endeavour to collect and synthesize all the data. Their skillset has to be balancing data and intuition to come upward with the right roadmap — and then explicate that in a way that resonates across multiple functions," says Caldwell.
It relies on a relentless focus on the customer. "When I joined Looker, information technology was a very engineering-focused production, and I remember there was a saying on the engineering team that said, 'The engineer has the pen.' That meant that the engineers on the squad had the all-time understanding of what needed to be built," he says. "I changed that mental attitude pretty speedily toward, 'The customer has the pen.'"
LESSON #4: WEIGH THE PROS AND CONS OF INTRAPRENEURSHIP AND ENTREPRENEURSHIP.
Despite working for such a large enterprise company during his time at Microsoft, Caldwell got a taste of edifice from nix to ane, although he admits it's not quite the same as a true startup. "Whatsoever large company is going to accept a challenge with nil to i projects in general. Considering annihilation you build could impact existing business lines," he says.
Here's how information technology played out for Caldwell: "I was on the team that built Microsoft'south Power BI product. In the early days when nosotros were talking about building a new data visualization tool, we had to become and articulate that idea with multiple teams that would exist impacted to even get moving on the concept," he says. Later on clearing the initial concept, it wasn't exactly off to the races. "It'southward not a i-and-done moment to overcome inertia. You have to make time in your schedule and product roadmap to continuously clear ideas with other teams," says Caldwell.
Despite the hurdles, Power BI eventually became a massive success for the visitor — which led to an impasse for Caldwell. "Microsoft does a phenomenal job of structuring a career — there are clear career ladders and they permit for a ton of employee mobility so yous go exposure to a wide diversity of unlike opportunities. I was working on tongue, machine learning, search, gaming — all sorts of different things. They make it a very like shooting fish in a barrel place to spend your whole career there," he says.
If you but work in 1 place for a long time, it becomes your earth. The execs at the company become your heroes. You get wedded to the tech stack. Your agreement of the marketplace is influenced by the products around yous. You first to live in a bubble.
Caldwell realized he had been overweighting the wrong things. "I had been billowy effectually to all of these different intrapreneurial projects inside Microsoft. I was always focused on the downside of joining a startup. Similar, 'Hey, if this thing doesn't piece of work out, at least I'll notwithstanding be at Microsoft with my safe, cushy job.' Only I'd never securely considered the upside of joining a startup if we build a hit multi-billion dollar business," he says.
Here'due south what caused the shift in his mindset: "Power BI ended upwardly being colossally successful for Microsoft, just information technology wasn't earth-shattering for me personally. If I had done this as a true entrepreneur, information technology would have been a phenomenal victory. I realized I was self-limiting past only living within that one ecosystem, which had been very comforting for so long. That's what caused me to offset souring on intrapreneurship and focus more on true entrepreneurship," he says. It's a turning point that led to his side by side move, taking the leap into the startup scene and joining Reddit as its VP of Engineering.
LESSON #v: Apply Functioning REVIEWS TO CAPTURE LONG-TAIL EVOLUTION, NOT A Unmarried MOMENT IN TIME.
Reflecting dorsum on his tenure at Microsoft, Caldwell saw plenty of other changes beyond consequent reorgs — including the dismantling of one infamous system. "Microsoft used to have a really atrocious stack-ranked performance review system, which they got rid of 7-8 years ago. They replaced it with what I've come to believe is the simplest, virtually straightforward, and equitable performance review system I've seen since. I've tried to reproduce it in every place that I've worked," he says.
In the new-and-improved system, you brainstorm by outlining OKRs and personal development goals for the year, alongside input from your manager. Every other month, you have a check-in with your managing director on progress and then far, plus a formal review at the half dozen-month mark that's not tied to compensation, with a final review at the stop of the yr that can result in boosted bonus compensation for high performers.
Hither's why Caldwell believes information technology works so well: "Considering those regular check-ins are happening every other month, you've got a trajectory that's collected over time. Information technology's not just reviewing a long list of goals every 12 months or checking in on OKRs at one point in fourth dimension — information technology's actually getting an cess of your momentum with a lot of boosted signals," he says.
On the compensation front, managers have the discretion to spend boosted budget on their top performers, with a deep level of oversight from HR. "When you make your budget recommendations as a manager, they roll upwards to the director and eventually the VP. 60 minutes overlays their checks on superlative of this, so promotions are beingness distributed evenly and diverse employees are not being disregarded," says Caldwell. "Or if you've got a new manager with a unlike assessment of your functioning, 60 minutes tin weigh in with the historical data of your bi-monthly and bi-annual cheque-ins trajectory."
His advice for startup leaders every bit they craft their own performance review processes? Consider how you tin can implement a regular drumbeat of feedback, rather than a one-and-done arroyo. And don't forget to layer on checks and balances so no 1's overlooked.
LESSON #6: FOR A WINNING MINDSET, Go along A CLOSE EYE ON COMPETITORS.
Caldwell points to another force of Microsoft that he believes folks often overlook. "Microsoft was relentless in terms of understanding its competitors in the market. When I talk to early founders (or fifty-fifty some experienced founders), I call up they overweight technical cleverness or a product idea without fully agreement what'southward come up before or how other competitors are situated in the market," says Caldwell.
"Microsoft had entire teams of people doing zip but understanding competition and crafting the right strategy to come out on top. That level of investment is non necessarily feasible at a startup, but the more you tin sympathize the mural, the more effective you're going to be."
I frequently hear communication from folks in the startup community that you take to ability through and ignore your competition. But you need to sympathize how your competitors are positioning themselves then you can cleave out your own niche.
It'southward a mindset that's stuck with Caldwell many years after he left Microsoft. "My fashion of running product and engineering comes from my time at Microsoft — I like to win. If you drop into whatsoever organization that I'm running, you'll run into that we spend every quarter doing an assessment of our strategy and the competition. What game are we playing, who are we playing confronting, and what does winning expect like?" he says.
Here's what that looks like in practice: "What are the tactical things that we are going to do to become closer to victory, and how can nosotros measure success? Once we've agreed upon all of that, the next question is if we take the correct organizational alignment, not just beyond applied science and product, just all functions of the company, to achieve our goal," says Caldwell.
LESSON #7: STICK TO THREE-MONTH ROADMAPS.
When Caldwell joined Looker in 2018, the visitor had been humming along afterward emerging from stealth five years earlier (for a ton of details on what happened in between, you've got to dive into the Review article with co-founders Lloyd Tabb and Ben Porterfield). "I was very explicitly brought on to ready upwards an R&D cadence because the team hadn't really been operating with a clear roadmap. Very quickly I determined that we needed to add together some understanding of what a roadmap is, what value it has, and build some systems for developing and maintaining that roadmap," he says.
He outlines how he got started. "The framing I used was that nosotros're going to start from the peak-down exec layer. I outline the strategic mural as I see it, and describe in one folio some of the opportunities that I call back are ahead of us. For Looker, that might've been addressing some of the technical debt, moving toward a programmer platform, a few other things — but keeping it at a super high-level framing," says Caldwell.
Next, he brings in folks further downwardly the org chart. "Then, over a ii or three-week period, I asked the teams to come up upward with ideas and strategies that contribute towards that high-level set of goals (or button back against them). This would get a prepare of strategy memos which outlined how we're going to win," he says.
He and then returned to his Microsoft roots, with a rigorous focus on aligning the org nautical chart to lucifer upwardly with the strategy. "Exercise we have the right setup and the right resource? Do nosotros have the key leaders in identify to meet each of these objectives? It's giving folks an opportunity to move to the areas that they are most passionate about. Or for projects that were a piddling more controversial, similar changing out our visualization tech stack, do nosotros need to await exterior for folks that are passionate about that bet?" says Caldwell.
The strategy memos were then converted into roadmaps, filled in with specific items that volition assistance achieve the overall goal — and Caldwell'south got a strict time frame for his roadmaps. "I like to run teams that have predictability. Annihilation further downward than three months, it'southward harder to accurately predict what'southward achievable and I desire to ensure we've got a articulate picture of what nosotros'll evangelize to the client within a quarter," he says.
Then the clock starts, with a weekly cadence for tracking progress towards those goals. "I sat with all of the drivers beyond each of these bets once a week, and we looked at progress towards every single item on the roadmap," he says. His tip? You may eventually move to a bi-weekly check-in — merely start with more than frequent meetings as the team gets used to the roadmap framework. "At the end of the quarter, you retro, you lot optimize, and yous do information technology again like clockwork," says Caldwell.
LESSON #8: BRING OTHERS Forth WITH YOU AS You lot CLIMB.
Caldwell was at Reddit for just about two years, but his human relationship with the company's co-founder Alexis Ohanian left an indelible mark. "When I joined Reddit and met Alexis for the kickoff time at one of the board meetings, he told me, 'Nick, I'm here for yous. I'm going to back up your career," says Caldwell.
Looking dorsum, he admits he wrote the interaction off at outset. "We had literally just met, so I idea, 'Aye, everyone says that.' Merely Alexis has been a phenomenally supportive person, non merely for my career at Reddit but later on in encouraging me to become an investor. I'chiliad now a fairly well-established angel investor. He helped with my referral to the Principal Product and Engineering Officeholder function at Looker. He helped with my recommendations for public board roles," he says (Caldwell sits on the board for True Search and HubSpot). "He has, in every way, shape, or form kept an eye out for me in means that cause me to often inquire myself why." (We got a take a chance to interview Ohanian for The Review back when he was still at the company, and it's chock-full of wisdom well worth returning to.)
It'south a selfless spirit Caldwell tries to embody in his ain tech career. "What I've taken abroad from Alexis is that you need to detect ways to lift others every bit you climb. Whether it'south through my involvement in the nonprofit DevColor, or the educational blogs and videos that I do, to find ways to bring other folks along with me and look out for the side by side person," he says.
This article is a lightly-edited summary of Nick Caldwell'south advent on our new podcast, "In Depth." If you oasis't listened to our show notwithstanding, be certain to bank check it out here .
Comprehend image by Getty Images / laremenko.
Source: https://review.firstround.com/get-off-the-floor-and-other-career-advice-from-microsoft-looker-reddit-and-twitter
0 Response to "Why Is It Easier Getting a Job From Somene You Know Reddit"
Mag-post ng isang Komento