Succession for Scale
The final chapter!
AVE MVNDE (“Hello World” in Latin)
We’ve made it! This issue contains the final chapter of It Depends! But of course, we’re not done yet! In the following few issues, I’ll be answering questions I’ve received during the last year. If you want to ask me a question, it’s not too late! Please send it to contact@itdependsbook.net.
About this week’s chapter
Senior technology leaders often find themselves typecast over time. You excel in a role, and recruiters approach you for opportunities that mirror what you're already doing. They target companies at a similar size or stage, assuming your success in one environment translates perfectly to another. After fielding several of these calls, a pattern emerges. You become known for a particular kind of leadership.
This pattern defined my career trajectory. At Adobe, I progressed from engineering manager to director, transforming a small team into a multi-office organization of fifty professionals. This experience led to Spotify, where I managed a similarly-sized team and scaled it significantly across multiple regions. Later, as CTO at Avvo, my mandate was to expand the engineering team by 50%.
Through these experiences, I developed a specific reputation: I became the person companies sought when they needed to grow their engineering organization thoughtfully, typically post-Series B or C funding, when the challenge was scaling without sacrificing the culture and approach that had fueled their initial success. I'm not the candidate recruiters call for early-stage startups or massive enterprises; I'm the one they contact when a company needs to build mature systems and processes while preserving its essential identity.
This often means stepping into a role previously held by a founding CTO, someone who built something remarkable but struggles with the next phase of organizational scaling. My responsibility is to continue their foundational work while evolving the organization for its future. When that founding CTO possesses self-awareness, they find a new position within the company that allows them to continue contributing their valuable experience.
I've been fortunate to work with several CTOs who stepped back strategically, creating space to learn and grow before returning to leadership. One subsequently accepted a CTO role at a peer company, leading a larger organization than they could have managed previously. Another eventually reclaimed the CTO position at the company he co-founded, now equipped with the skills to lead a much larger organization. Unfortunately, these leaders struggle more often to find their place after transitioning out of their original role.
These experiences inspired this chapter. I hope to build frameworks that foster more positive transition stories and fewer painful departures. The goal is creating organizational structures where technical leaders can evolve alongside their companies, rather than becoming casualties of their own success.
This is Chapter 36 of "It Depends."
Succession for Scale
Originally published on November 29, 2020
Recently, I have been thinking about how the role of the executive in a scaling startup evolves.
As a senior leader in a growing company, you need to be scaling faster than the organization. You grow by scaling yourself and the leaders in your team more quickly than the business. This fact is well known and is covered excellently in such books as Zero to One by Peter Theil and Blake Masters, and The Hard Thing About Hard Things by Ben Horowitz.
Even if you are aware of this fundamental requirement, it is still challenging to recognize when you are starting to fall behind on that scaling. The people on your team who got you to where you are today and who are working as hard as ever should be doing better than they are. You may start seeing the signs: teams falling behind, tensions between groups or functions, team leaders beginning to struggle with their work and increasing responsibilities.
You might not know what these scaling problems look like because you haven’t seen them before. Maybe you do recognize them, but your loyalty to your team lets them go on longer than they should. You can get away with that for a while.
Eventually, your boss (the CEO, the board) or your peers start to recognize the growing gaps in your organization between where you are and where you should be. In a company with a good culture, they will let you know. In a company with a less open culture, your peers may notice but not feel like it is their place to say.
It will be nearly too late when the problems are apparent outside your team.
When these problems first arise, you need to put together a plan. You must act immediately if you missed the early signs and the challenges are visible outside your team.
You need to bring in new talent who can help close that gap. It will take time to do that. If you choose to re-double your efforts to mentor the existing folks, you will only fall further behind. Either you missed your mentorship window, your leaders need more mentorship than you can provide, or they are not yet ready to take on the new responsibilities in their role, even with mentorship.
Replacing people who have historically done well in their roles can seem cruel, which is why it is hard. It feels disloyal to the people who have been loyal to your company and helped build it with you. It is not their fault.
If you don’t make those hard choices, though, they will be made for you by the person your boss or the board hires to replace you.
It doesn’t have to be this way.
We have an assumption that in a growing company, people will remain in the roles they have had, and newer employees will come in below them. This assumption is one of the exciting incentives of joining a startup. It can be a career accelerator. Indeed, there are many stories of early startup employees remaining in their senior leadership roles through rapid growth and past the point of going public. Very few people are capable of this kind of speedy personal development, however.
Instead, we should be explicit about this challenge of growing a company. We should build a culture that acknowledges and celebrates this fundamental fact. Let people you hire know that you will support their growth, but be honest that if the company is scaling faster than they are, they may need to help hire the person who will help with the next phase in their role.
Reid Hoffman talks about these ideas in his book The Alliance. He discusses creating a “Tour of Duty,” a compact of set length between the employer and employee that does not make expectations beyond that time.
I advocate for a more balanced and sustainable approach for companies that encourages employee development and business realities. Startups willing to hire at all experience levels and support employee growth can hire and retain better. Even those companies face challenges at their scaling inflection points when company leadership changes to the new business reality’s necessities.
Suppose your company builds the concept of succession for scale into its culture. In that case, hiring your successor should be expressed as an opportunity for further mentorship and growth, not as a demotion or failure. Celebrate it as a rite of passage. Challenge the leaders in your team (and give them the tools) to recognize when this time has come and praise their self-awareness.
Build succession for scale into your compensation structure and leadership career pathing. Ensure that the newly hired leaders train the people they replaced to assume the role again in the future. When the position opens again, the person may now have the skills to step back into it.
The Latest Podcast
Since this is the book's last chapter, I decided to share the podcast and newsletter about it in subsequent weeks. In the podcast, I discuss more of my experience and cover a bit more background than I could fit into this issue, so it is worth listening to even after reading the newsletter.
You can download the episode from Apple Podcasts, Spotify, YouTube, directly via the RSS Feed, or wherever you listen to podcasts (see pod.link for a more extensive list).
About this newsletter
What makes this newsletter unique is that every two weeks, I share a chapter from my book It Depends: Writing on Technology Leadership 2012-2022, which Unit Circle Press released in March of last year. These chapters are not sequential; each is a standalone piece. In addition, a podcast serializes the audiobook in order, released alternate weeks from this newsletter.
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