Imagine you’re Lex, an ambitious 31-year old software engineer with some good managerial experience. You’ve just been offered the role of Head of Engineering for a hot young series A start-up, reporting directly to the CEO, Meg.
Naturally, you’re super pumped: this role puts you in the senior leadership position you’ve been wanting. Based on Meg’s description of how she sees the role, you’re feeling you’ll be very empowered.
Two years go by and all is well. In fact, things have been going great: the company has grown at 60% per year, raised a series B, and is now closing in on a huge Series C. So, it comes as a massive shock when Meg tells you that, as part of the Series C, she’ll be recruiting an external CTO — and you’ll be reporting to them! This feels like a real kick in the teeth. Your first reaction is to hand in your resignation.
But instead, you take time to cool down. Then you schedule a meeting with Meg to ask her for her reasons. It turns out she has a lot, and while you don’t fully agree with all of them, you have to admit some of them seem pretty valid.
As she points out, managing the cross-functional work your team supports has become nearly a full-time job. You agree that, as a result, you haven’t had the time to coach and train your team leads as much as you’d have liked. It’s also true that you’re not getting much coaching (since Meg isn’t an engineer), and that you’re struggling to manage such a large team.
But still, you’re pretty pissed off. Reporting to the CEO was one of the main attractions of the job, and you could easily get a job as a CTO yourself now. So why not quit, go to a new company, and end up with a bigger title and more money? Sounds like a reasonable move, right?
Of course, losing you is clearly not in Meg’s best interests. You have deep knowledge of the systems as well as invaluable relationships with the team. So how did we get to a place where what seems like the best course of action for you is in direct conflict with what’s best for the company?
Or, to ask the question differently, what would it have taken for you to react to this news by saying “Great — I can’t wait!” instead?
Layering is inevitable
I’ll come back to this question in a moment. But first, let’s look at the situation from Meg’s perspective. She has always been clear that she intends to build a multi-billion dollar company and that she’ll need a world-class executive team to do it, especially execs who have already been through the scaling process at another company. She would have loved to bring on that world-class team at Series A, but that wasn’t realistic — she couldn’t afford them at that time, and they wouldn’t have been interested anyway.
The truth is, she didn’t really need their high-level skills at the outset. The people you need to build your company early on are more hands-on. Hopefully they’re great at what they do, but it’s likely the company will grow faster than they can grow their skillset…which means at some point, you’ll probably need to bring in a new management layer of more experienced executives. In short, the situation that Meg faces now is almost inevitable.
So, this is just an unfortunate necessity, and there’s nothing to be done about it… right?
Wrong.
Meg always knew she’d need to bring in more seasoned execs at some point, and she knew that meant layering some of her existing execs. She thought that was fine…but now she’s discovering just how much they resist it.
It doesn’t have to hurt
Meg had the opportunity (and, I would argue, the obligation) to do something about this inevitable scenario long ago. By not raising this possibility when she hired you, she allowed you to believe you would be in the role, reporting directly to her, forever.
But what would have happened if you and Meg had explored this scenario early in the hiring process? She could have shared her aspiration to build an enduring, world-class company and attract the very best people to help. She could have explained her philosophy that everyone — including herself — should be prepared to step aside and be “layered” if someone else could clearly be a more effective leader going forward. Would that have helped?
And what would have happened if she had shared her belief that successful companies grow exponentially, but most people only grow linearly? If she’d committed to supporting you with ample feedback and clarified that nothing would make her happier than having you prove her theory wrong?
What if she’d committed to you that, if “layering day” ever came, she would involve you in the recruiting process and only hire someone that you could work well with and learn a huge amount from? And if she’d asked you to genuinely consider all of that before accepting the role?
What would have happened?
It’s all in the preparation
Well, you might have withdrawn your application…but that would seem petty. You’re self-confident. You pride yourself on your growth mindset. So in the end, perhaps you might have said this to her:
“I get it. It’s a good philosophy. I think I can still grow a lot, but let’s see what happens. And promise me that you’ll always be straight with me in terms of how I’m doing and scaling.”
There’s no guarantee that “layering day” wouldn’t have come anyway, but I reckon both you and Meg would feel very different about it.
So, for all you Founders & CEOS out there, remember to follow these 4 steps whenever you’re hiring an exec who may need to be layered in the future:
- Raise the issue early in the recruiting process. Explain your philosophy and see how your candidate feels about it. Be sure to listen as well as speak.
- Clarify that you’re completely open to them going “all the way” but that you want to be very clear that it’s not guaranteed.
- State your commitment to supporting their development in any way you can and to involve them in the hiring process if layering day ever comes.
- Finally, remind them that this scenario is a “high-class problem” — one that only arises if the company is outrageously successful…so first, everyone needs to get to work!
