How to scale your engineering team the modern agile way / Part 1

Nils Weber
Haiilo
Published in
5 min readDec 28, 2021

Insights from a servant leading VP of Engineering — a multi-part series

You‘ve probably been there too: you have founded that company based on some revolutionary and successful (business) idea which is built upon or consists of a software product. To start off it’s either you doing the job or that co-founding CTO you have managed to get on board, maybe with a handful of coder friends supporting the young company with their skills.
If things go well you’re going to recruit more engineering people, preferably from your personal or professional network first. And slowly but surely you’ll eventually find yourself in a product business driven by tech with a dozen or so developers, maybe even counting up to 20 already — but where to take it from here? How to decide what people to hire? What roles to introduce? Or to put it more broadly: how to scale up your tech organization into something that remains fit and future-proof?

Because only in those rare cases you will already have exactly those structures and tech stacks in place that you are going to need in order for your engineering team to scale up in an agile and healthy way without losing too much performance and motivation alongside. You know, these new kids on the block approaches like PaaS, BaaS or Everything-as-code that somewhat guarantee you that you will be able to react to any kind of change fast indefinitely. But make no mistake: nearly every piece of code will eventually reach its limits, both in the sense of maintainability but also with respect to its ability to handle the ever changing requirements set upon it. Also, let us never forget that the grand Fowler himself has always been more an advocate for a monolith first (micro-service second) approach.

Generally, the more successful in a short amount of time your product has become in its earlier stages, the more likely you will know the struggle between staying competitive, satisfying high customer demand and staying fresh and up-to-date with respect to your technological base.
So naturally you will seek out to grow your tech organization alongside your success, servicing your product roadmap by effectively creating customer value frequently and fast. But at the same time your key players in tech rightfully point at the growing amount of technical debt and the decreasing attractiveness of your stacks, a state which can render you quite unattractive as a serious tech employer mid- to long-term.

So, how to approach it?

Grow your people

1. Empowerment

Coach and enable your teams and hold them accountable

First off you cannot possibly do it all by yourself, can you?

So, while it seems trivial and the term empowerment itself is a bit overused, it is actually one of the most crucial aspects of sustainably scaling your team. With the help of coaches, e.g. Agile Coaches or generally colleagues who are very inclined to reason about the dynamics of growing companies, it is important to show people the amount of power and influence they have on the whole endeavor. I personally find Stephen Covey’s Circle of Influence (sometimes also called Circle of Concern) to often times get people into pondering about behaviors like being reactive versus proactive, being forward looking and generally positive instead of generally introversive and pessimistic about things.

Whatever you do or are trying to do, the key aspect about your mission to empower and uplift people is to really mean it and to really go the extra mile yourself and never stop embracing the benefits everyone gets in the long run. Even if that means to drive on a bumpier road for quite a while and taking one or two wrong exists here and there. Everyone that really is and feels themselves empowered to create reasonable impact on various levels eventually makes the difference for keeping the momentum and remaining that successful company you already are.

And to be very clear on that: empowering people and teams to take decisions on their own can and will be overwhelming for some. Every single individual and every single team needs to be closely watched and accompanied on that journey. So prepare yourself with new kinds of requirements knocking on your door while you are letting go of those parts of your work that are now being owned by others. Again, if you’re looking for a set of tools or a framework I can highly recommend checking out 7 Levels of Delegation which was popularized by Jurgen Appelo. This very accessible method greatly supports you and your team to reason about the various levels of maturity and seniority they are at and can cope with.

The power of delegation (image licensed from designer491 at iStock)

“Cope with” because what you will want to have achieved is empowered key-players in your organization that have a deep sense of responsibility for the parts they own and can be held accountable for the results they come up with at all times — not everyone is able and willing to follow that invitation right from the start. Again: stay close to those who are new and inexperienced for it can and will be psychologically challenging!

Having said that, something that cannot and should not be underestimated is the fact that while others enlarge their sphere of impact and influence, yours eventually might get smaller and smaller; at least if that promotion to becoming the next group CTO is not exactly just around the corner. I will however go into more details on that in the next parts of this series.

Lastly, at some point in time while people are already doing their cool stuff proactively and totally feeling empowered, they will have assumed de facto new roles, meaning they are wearing new or additional hats. So, what’s also more than advisable at roughly this point is to formalize those roles to both give people clearer pictures of what is being expected from them and start introducing official types of leadership. Depending on the levels of hierarchy and structure that is being present in your organization already, people will most certainly start asking for comprehensible career opportunities alongside adequate forms of compensation. Again, more details will be outlined in an upcoming part of this series.

This article is part 1 of a multi-part series. Please hang tight for the insights about leadership, independence and perspective. I will edit this article and include the according links as they flow in.

Thanks for reading.

Part 2 — Leadership
Part 3 — Independence and Scalability

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Nils Weber
Haiilo
Writer for

aficionado of things great and small, pretty and ugly, fancy and shmancy. an urbanoholic turned countryside, thinker, tinkerer, father, kickass dude.