How to Actually Grow in Your Organization

Part 1: Digging a leadership reputation hole 😬

Greetings, friends. I hope you’re enjoying your weekend.

It’s been quite a busy few weeks transitioning from summer to fall. Typical stuff: preparing for back to school, making meme-filled videos of what we did all summer.

Reforgers and fellow engineers often ask me, “Why does it feel easier to get a promotion to leadership by switching jobs?” Well, I’ve felt this pain acutely so I can really sympathize. I eventually succeeded in getting promoted in place, but in Part one here, we’ll cover all the ways in which I made it harder on myself than it needed to be.

You got this.

Making A First Impression

When I arrived at ezCater, there were ten engineers, product market fit, money & momentum. The task before us was to add as much fuel into the rocket ship as possible and scale in every dimension, without blowing our selves up.

I came in fresh off my time at HubSpot with that sheen of “credibility” glowing on my skin, having been through a well-known IPO. I’d seen and participated in doing this successfully, but I hadn’t lead though this. No problem, as the surgeons say “See one, Do One, Teach One” right?

I joined ezCater because I saw they were poised for this hypergrowth. They’d been focussed on making the business work and not doing anything that wasn’t directly aligned to that outcome. As a result the engineering organization was fairly “minimally viable”. In the same way that the stack was simply Ruby on Rails with a single Postgres DB, the org didn’t have much in the way of structure or process. Would it scale? Maybe not, but they hadn’t made many mistakes yet, either. I viewed it as an opportunity to skillfully cherry-pick the elements of scale that HubSpot had done right but tailor them to the ezCater environment, all while confidently saying YAGNI to stuff we didn’t need yet.

I attacked the problem with a lot of youthful vigor—slinging code here, giving people their first review in 4 years there. I brought a bunch of energy in a friendly and relaxed demeanor. I worked my butt off, but there were a lot of jokes and not a lot of “business cat seriousness.” We went fast. We scaled. We were doubling every year on every metric, which meant 20 engineers, then 40, then 80. Soon, we became an org looking at what we needed to do for that next doubling to 160.

When you’re stuck between a rock and kind of an OK place.

On getting branded as “The Kid,” or a reputation Cul de Sac.

As this went along, I ended up with a reputation I would describe as "The Kid." This wasn’t all bad. In practice, this meant people tended to describe me like so: "Jeff is a powerful do-er, a catalyst, a dreamer, a bit of a loose cannon who can make big bets and win. He can manage if he must, but he doesn’t care about the people side." 

There are a lot of admirable qualities in the description, but when the org is looking to go from 80 to 160, is that the kind of profile you want leading an org of that size with a 10-20M dollar budget? Not everyone was sure about that.

Also, it was excruciating to hear this. I DO care deeply about the people on my team. I have made mistakes, but I love coaching, career guidance and putting my people first. But I had no visible wins in the people & management column. I hadn’t contributed to things like career ladders, I was happy to avoid the middle of the hiring funnel and I was consistently being the voice of “maybe we don’t need that process.” Why? I’m not against elements of structured people management, but I hate waste. If somebody else takes the ball on those areas, I want them to own it, and I’ll do something else. We had people who liked that part, so I was delighted to tackle the abundant alternative priorities. Unfortunately, this ended up with a list of achievements with everything on the business side and nothing on the people side, which translated into “Jeff doesn’t particularly care about people.”

So now I was 3-4 years in, at an impasse. I wanted to keep growing with the organization and learn how to solve problems with the leverage of a Director or VP, but the org wasn’t convinced that it was a good idea. At times, it felt like I would need to change organizations to find someplace to start fresh without my baggage.

Time to be your own Goldblum.

Intra-org growth comes with its unique challenges.

I had arrived as “The Kid” and I’d been very effective in that role, but I’d actually learned and grown a ton. But many people didn’t see that. This underscores a vital lesson: First impressions are lasting. Particularly if you don’t do anything to change them. As you climb the corporate ladder, colleagues might still perceive you based on their initial interactions. It's essential to be proactive in communicating your evolution, highlighting your learning curve, and showcasing your expanded skill set.

When you look for more leadership responsibility in your organization, some people may remember you as a developer or team lead and may not know how much you've learned and grown. It's crucial to keep this in mind when communicating your role and responsibilities.

Marketing remembers you as the coder who fixed that bug. When did you tell them you are now a manager and leader?

In retrospect, a small amount of image management would’ve gone a long way. It’s very uncomfortable for most engineers, but Define yourself or be defined by other's first impressions of you.

Has this happened to you? I want to hear about it.

How does one go from being the Pilot to the Admiral?

Perception is personal branding. At different points, you’ll find opportunities to switch things up. But man, it’s not always an intuitive process.

There’s a recurring theme in my career. At PatientsLikeMe, I had a specific...maverick persona. So much so they actually called me Mav. (Yes, you’re allowed to cringe.) That’s a helpful character for accomplishing a lot, but nobody thought they should put this fighter pilot in engineering leadership. This identity inadvertently pigeonholed me past its sell-by date, making it challenging for others to see me in a leadership role.

The Power of New Contexts

So the goal is to talk about growing in place, but let’s briefly detour into the alternative and why it can be so attractive to try to make a diagonal move (switching organization and getting promoted in the same move), because unfortunately it really works.

Switching to HubSpot was fascinating. I blustered my way into a role with some management responsibilities and, because I’d started as a manager, nobody ever questioned that management made sense for me. I introduced myself to the org as a Tech Lead, and thus, I was always a manager in their eyes.

It was actually crazier than that. The real way that I introduced myself to the org was by writing emails to all@hubspot about the ongoing critical situations with the code I inherited (it was a crazy time). So my introduction was anything but celebratory, but this only served to make me come across as more competent. This Jeff guy is “the leader in charge of something significant.” This was dramatically different than a hotshot fighter pilot, and I had effectively kicked that reputation.

The most fantastic instance of this context switch came when I left ezCater and became an Executive in Residence at Reforge. Yes, I was VPE at a unicorn, but I was still Jeff, and in many ways, ezCater had been my first rodeo. Then I arrive at Reforge and I’m interviewing the likes of Nick Caldwell, who was VP at Twitter or Head of Engineering Heidi Williams at Grammarly, and suddenly people are very interested to what I have to say.

Talk about the power of the right context. The program said I was an expert executive, and I’m up there with other talented executives, and people paid good money, so they wanted to believe I knew what I was talking about! Being labeled an "expert executive" changed how people received my insights, emphasizing the significance of positioning and branding.

So the reason that a diagonal move can be so effective in gaining authority is that you get to throw off your old baggage and make a new first impression with an entirely new context. How do we replicate some of that in place?

A List of Mistakes

We’ll more “things to do” in Part 2, but let’s wrap this part up with a catalog of “ways in which I made things harder on myself”.

Oversharing

Bring you whole self to work they said! People love knowing about the “whole you” they said! Well… I’m sorry to say that’s not always a great idea. Look, I’m weird and I love the weird things that people get up to, but the business is not your friends & family. People can not help but make judgments about you. These judgments will be deeply biased and maybe unfair, but they exist. If your boss only drinks Fresca and only eats Fruit Loops, you’re going to have questions. As a leader, you’re asking people to trust their careers and livelihood to you and it’s just fundamentally more comfortable to put your career in the hands of somebody fairly “normal”.

There isn’t any particular thing I wish I hadn’t shared, but I have an extreme drive to “not be boring” and on any number of occasions I emphasized the weird / haphazard / risky things I’ve done instead of the rational / normal things because those made for more interesting stories. Would I change this? Yes. Not all the way, but I can tell you that when I have 30 min with a VC to raise money for Prefab I’m not leaning all the way into the weird.

Impatience

The 3 virtues of a computer programmer according to Larry Wall are “Laziness, Impatience and Hubris”. I’ve always enjoyed this and I’ll write more about this at some point, but my impatience has been the most double-edged sword of them all.

My impatience is what drives me to ship and I couldn’t do without it. It’s what makes me a catalyst and an agent for change.

But my impatience can also steal defeat from the jaws of my victories. Here’s how this plays out. We’re thinking about a problem. I propose something novel, that is perhaps a bit radical. “Here’s how we should re-design the org”. It turns out it’s a good idea, it’s the right idea. It’s also a big change for just about everyone. Normal humans need some time to process this, think through the ramifications. But I’ve done the napkin math and there are more positives than negatives and I’m ready to go. We start down the path of making the change, I check this off as “catalyst reaction achieved” and move on to the next most important thing. People are implementing this, adding some “riders” to the bill and making some decisions I don’t think quite make sense, I re-engage and do some pushing, but the wheels are in motion and it’s too tough to change. Now people get the impression I’m the one against the change! My impatience to do the next thing has somehow turned this “win” for me into a story where I’m the stick in the mud that doesn’t want to change.

Inessential Accuracy

I’m an engineer and engineers like accuracy. If we aren’t accurate in our speech, our programs don’t run right and we can’t understand what is truly happening in our systems.

But it turns out there is a time for accuracy.

When you communicate technical details to the rest of the organization they are going to restate things to verify that they understand. Here’s a tip: it often doesn’t matter if they really understand. They need to know the bits they need to know. Sometimes accuracy is critical. If they think your new system will do X but it won’t, you’ve got to correct that. But I have often done myself an enormous disservice by being too accurate.
One of my biggest wins was building a machine learning system that predicted the estimated revenue we would get from a customer in their first year, based on the first few days of data. This was a big deal for the company, but it was also my first machine learning project. It really worked, but I didn’t know how to convey that it worked. It was complex, probabilistic stuff.

What I said: “It looks good, but I don’t have the math background to describe this. I’m looking at this using R^2, RSME, MAPE and other methods and here’s a spreadsheet.“

What I should’ve said: “Right now we assume every user is worth the same amount. This is always better than that.”

Unwillingness to Signup For Goals

Engineers have a huge achilles heel around goals. We expect accountability.

Here’s the thing, goals means something different to everyone. Goals are a way to convey strategic direction and priority. Goals are a way to encourage effort. Goals are sometimes a commitment to achieve a specific result, but (spoiler) the rest of the organization is regularly agreeing to and missing goals all the time.

I hamstrung myself on numerous occasions by not committing to a goal. Most memorable was my work building out an application for the catering driver to help with ezCater deliveries. It was a bit of a baby of mine. By instinct and rational analysis I think it’s a great idea. I built the vision and sold it and everyone is on board. The CEO says “The goal here should be 40% of customers adopting it by end of year”. But I think that’s very aggressive. We’ve got a heterogenous driver population with very different incentives than normal drives. I’ve modeled it out and in that time period 25% would be truly impressive (and would be an enormous win).

So what do I do? Well, I speak my truth and try to outline the challenges. I show the math and the modeling. What should I have done? “Yep boss! That’s real challenging, but I can’t wait to get there”.

Instead, in another astonishing reversal I managed to give the impression that I was a “non-believer” in this new project. This project needed momentum and optimism and I was supposed to be the champion. Lesson learned, sometimes just “say yes”.

Wrap Up

All right, summary time. Growing and taking on more leadership responsibility often happens as a result of diagonal moves, because we’re able to reset the context in which we are seen and build a new impression of ourselves.

If we want to grow within our organization we need to replicate these context resets, but it’s not easy because a number of “things that got us here won’t get us there”.

Some specific blunders of mine were:

1. Sharing your whole self works for building bonds and psychological safety with your reports. Running that same playbook for your organizational persona doesn’t necessarily engender confidence & trust.

2. Impatience drove me to ship and deliver for years. But leadership projects are slower and impatience can frustrate and alienate the people you need to enact change.

3. Accuracy was key to your success as an engineer, but you have to accept that the message is going to get muddled at larger scale and think strategically about how / when to correct it. Trying to ensure perfect accuracy can lose your audience in minutiae.

4. Missing the different meanings / usages of “goals” at the organizational level. Sometimes words change meaning at different scales and if you don’t understand that you don’t look ready for leadership.

That’s all for Part 1, I hope you enjoyed a list of some “things not to do”.