Dear Ex-Bigco New to Smallco

We are excited to have you here! We put a lot of emphasis in our interviewing for what people bring to the table in taking us to the next level. Your experiences while at a BigCo are a large part of that. Again, we are really excited to have you here!

However. However, we have also found a decent number of Ex-BigCo people arrive here super excited to start making immediate organizational change, in a way that is non-productive and so when they try, turns out demotivating both for them and all the great people who have got us here. This document is my suggested path to avoiding that. Which is 3 things:

• Go read Camille Fournier’s Other People’s Problems, and internalize its lesson — take one problem to focus on, ensure you understand all stakeholders, fully deliver a solution, get the learnings and organizational credibility that comes from that, then onto the next. (A caveat to that is start small; credibility is a snowball you need to have iterated success on to drive iteratively bigger things).
• In the meantime, try really hard in shared channels to avoid mentioning how you think your last company’s solution was much more sensible than ours and is just inevitable here. Even if you think you are just doing this as an interesting comparison.
• Rather, focus on understanding our culture that has made us successful in our business, and gain the intuition for why it works, and why it should be challenged to change for our success ahead.

Now, coming from someone with a senior title who has been here a good amount of time, this likely sound negative and demotivating after you just took a massive career risk. The flip side of it is Camille is not only a friend but was my manager for my last 18 months at a prior role at a fintech, which I joined after 10 years at a BigCo, and Camille wrote the OPP article 4 months after I left citing incompatible culture, so I am pretty sure I was on her mind. I especially know that as on my first day here, she had these coffee mugs sent to my new desk…

I.e. I speak from personal experience here.

Now the thing is, new ideas and new people’s passion are important, not only wanted, but needed to succeed at the next level of scale. Camille herself championed and has publicly praised my Amazon 6 pager lift that I introduced to the fintech. But in hindsight, continuously making analogies grated on people who had been there longer. And I was not even making statements that Amazon’s way was better; I was just being comparative — even that grated. And I was just 1 ex-Amazonian in an org of 800; there are certain BigCo’s with much higher ratios both there and here, where you find they repeat the same analogies (“a monorepo will solve all our problems because they did at G/F”…). And with my experience here I can tell you each repeated “have you thought about X which worked so well at my last company” grates more than the last.

Why does it grate so much? I think there are 3 major reasons:

It’s an Implicit Critique — Even just by virtue of bringing it up, there is a subtext that the status quo here is inadequate and the Bigco’s solution was likely better. That’s a great conversation in a 1:1 where it’s easy then to have an understanding conversation of tradeoffs, but not a really easy conversation to have in a group setting where you are challenging them in lacking the insight you bring.

Not understanding the cost/benefit requirements of change — There are libraries of books written about the difficulties of organizational change management. Every change to an organization sucks some amount of oxygen from the room for other changes to happen — at a certain point too much change is churn and the organization will reject it. Thus an organization needs to be thoughtful about making the highest leverage changes at any point in time. So when newcomers point out a problem pointing to a solution that clearly worked at their last company but seems like it will require a lot of work to implement, they usually lack context to being able to further answer “why this is the important thing our business needs us to come together to solve now”

Not understanding the culture and the business ahead of a critique of its processes — Most organizational processes are path defined based on a company’s challenges and the culture that is needed to empower the right people to overcome those challenges. So if you come in criticizing processes, you are also criticizing culture. And this is a problem because the right culture for one set of business problems is not the right for all. I have become a big fan of Simon Wardley’s Pioneers/Settlers/Town-Planners analogy for individuals’ preferred organizational behavior, particularly the idea that each “steals from” the last. What I have observed is that “stealing” often takes the form of forming alliances with others of the same type, that then “push out” the earlier type’s behavioral preferences, and so eventually ends up pushing out all people of the type. Now depending on the needs of the business (particularly the focus on execution needed to not fall apart as the number of stakeholders radically grows), that cultural change may be the right thing. But it’s as easy to be too early as too late here — go early and you lose the bottom-up discovery and creativity needed to build great products. So you need to make your argument for change bottom-up based on localized need at this particular time, as opposed to assuming a top-down, org wide solution.

So in conclusion: We are happy you are here! We need to change to grow! Newcomers with less normalized deviance and a lot of passion will be a big part of that! But it can easily go awry for the individual and the company, so watch and learn, seek to understand, pick your battles, and put personal skin in the game in resolving them!