I firmly believe three things for a scaling startup:

1. It always pays to promote an existing team member into the Head of Engineering (HoE) role, where there’s a strong internal bet
2. The management of that promotion can drastically increase their chance of success
3. They will need some external coaching, no matter how experienced a manager/engineer they are, or how good you think you are

Full disclosure - Re #3, I offer said coaching and make no apology for this somewhat self-serving stance. I offer it because I’ve experienced the challenges first hand and know how hard but rewarding this shift can be, both for the individual and organisation.

It always pays to promote someone into the role, where there’s a strong internal bet

“we need a pair of safe hands in that role, someone who’s worked at that level before”.

I hear this a lot. Let me save you the surprise:

• Very very few Engineering Leaders have gone through the 5-to-50-engineer team growth stage. You will spend months fruitlessly trying to find the unicorn that can revert to coding when needed + scale teams + act as a seasoned executive when needed.
• No one has gone through this growth stage for your company, and though some patterns rhyme, it is different and unavoidably chaotic every time.
• Leadership consistency, commitment and cultural fit trump expertise and experience at this stage. You can always coach or consult support to help pre-empt any typical scaling hurdles.

With a promoted HoE, what you have is someone you know and trust, whose forward growth is now tightly aligned to your organisation’s success. If they’re a strong bet (see next section) they’re worth a shot.

Conversely (cue some quiet introspective honesty on your part), even if good HoE’s were common, you’ve probably never hired a HoE before and you probably won’t know how to do it effectively. This is no slant on your intelligence, it is an extremely nuanced and difficult thing to do well.

The most common pattern I see is the hire of seasoned Directors with big names on the CV (the default proxy measure for ‘quality’), who subsequently try to mature the tech organisation early to reach the structured and stable setup they’re accustomed to. This is like building a brick house on a moving platform, best case creating a little unnecessary churn / friction and worst case killing velocity / flexibility when the org needs it most.

What makes a strong internal bet?

#1 Is a committed cultural fit

First and foremost, this is someone who is one-off-founder bought into the mission. They aren’t leaping at the prospect of a higher pay check, they turn up to socials and they are loving life at the org. This person is only a little training off being a bar raiser interviewer / cultural fit interviewer.

You have a strong direct relationship with them and enjoy spending time in their company, you’re about to spend a lot more time talking to them.

#2 Is an ambitious manager by choice

Technologists are thrown into management / leadership positions all the time. They do pretty well running engineering in a low-maintenance early stage environment. These leaders tend not to scale well into the high-maintenance setup that follows.

You need someone who is a manager first, technologist second, who wants to be a the management-oriented VP one day. They are a strong independent line manager and have proactively demonstrated their own bar at a team level, be it through interviewing / performance review etc.

#3 Is a ‘people’s champion’

The vast majority of engineers in the org would support their promotion to HoE. It is in no small part the sincere buy-in of the team that will turn them into a highly effective group leader.

#4 Has terms that align with your expectations

You will no doubt expect a certain amount of commitment (time / investment in growth etc). They too will likely have their own terms for taking the role, which aren’t necessarily surfaced by default. It’s important to probe their terms and ensure they match what you’re willing or able to offer. E.g. “I’m contactable/uncontactable at weekends when I’m with my Children” might be a hard blocker either way.

How you can better manage this, to set them up for success

Go all-in

What you put in, you get out. You are investing in a long term, pivotal organisation leader who can make/break org success. Show and communicate commitment to them and they will commit to you. One way I’ve seen companies handle is explicitly is to name people as “Part of the founding team”, not a founder but also not just an employee. That could e.g. mean a strong share allocation if they hold their role >1 year. This can take many other shapes, e.g. Inclusion in all leadership meetings, introduction to the board etc etc

Skip the ‘interim’ title, unless they want it

Interim is often used to cover bases for a trial position. My personal opinion is that a half-committed stance half-bakes the cake (as it were..). The only person this might matter to is the individual themselves, maybe they want the title just to lift team expectations in the first instance, making it explicit to everyone that it’s a trial, offering up a gentler step back if it doesn’t work out. That’s their choice, it really should be no skin off the company’s back.

Get the whole Leadership Team behind them

It takes a village to raise a Head of Engineering. More seriously though, a major growth area is going to be working effectively with cross-domain leaders at a more executive level. How the hell are they meant to glean this without constructive, supportive feedback from those leaders. Expect it of the others: - ”As a commercial leader, I love it when you share X transparently” - “From a marketing perspective, the team would love to hear more about Y”

Stakeholders can mentor just by being more explicit with their requirements. If they’re seasoned executives, they should be able to coach / feedback on the new Head’s pitch/comms/behaviour in meetings.

Set the tone with the wider Organisation

Everyone knows this person has never been a Head of Engineering, they haven’t magically developed all necessary skills overnight, this is no secret. Why not set the tone gently with the org - “We are going to invest in X, turn them into an incredible leader. That’ll take time but its an investment we’re willing to make and if anyone can support this person with feedback, please do!”. This should be something to celebrate.

Be explicit and direct with your ramp up on expectations, and your feedback

The most straight forward, but again often missed, requirement. What do you expect them to be able to handle by when? When are the check-ins and what are you looking for. How are things going, are they on track? This individual will need a little more managerial than the average exec.

Push them to seek the support they need

(Here it comes, the self-serving portion…)

Chances are they’ve got to where they are today without a need for external coaching. To an engineer it can feel like a clunky, old-fashioned and frankly inefficient or even awkward way of learning. I’ve been there and I was resistant, I needed to be encouraged/dragged into it before I’d accept help. The next section covers why I think it’s a must and how to go about it.

The difference coaching can make

I was put into a startup Director position with little-to-no support, and I’ve worked with many individuals in a similar position. One pattern repeats pretty consistently, Managers tend to become ‘Super Managers’ rather than Directors, without the proper guidance.

Simply put, a ‘Super Manager’ is someone who continues to manage rather than direct, which can be highly effective for a Senior Manager role but does not scale past a couple of teams. This table lays out some key differences I’ve observed in certain circumstances:

It is very common for Managers to fall into the Super Manager trap without guidance, with good reason. It is the natural path of least resistance, with quick and early wins and familiar behaviours that the Managers knows and understands. Directing meanwhile introduces behaviours that are new, difficult, non-obvious and can challenge an individuals very sense of value/impact.

This leap needs to happen over time and it needs prompting. That comes best from someone who has been there and gets it - the nuance, the pressure, the stakeholders, the discomforts, the imposter syndrome, the learning curve etc etc.