Recently, I have been thinking about the role of the executive in a scaling startup.
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 and The Hard Thing About Hard Things.
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, the people that got you to where you are today, 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.
By the time the problems are apparent outside your team, it will be nearly too late.
When these problems first arise, you need to put together a plan. If you missed the early signs and the challenges are visible outside your team, you need to act immediately.
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 window to mentor, 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, and this is why it is hard. It feels disloyal to the people that have been loyal to your company and have helped to build it along 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 whom your boss or the board hire 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 employees at startups 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 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 your 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.
Reid Hoffman talks about these ideas in his book The Alliance. I think Netflix has done well being explicit around the Tour of Duty in their culture. I do think Netflix is a bit too employer-focused in its attitude towards these ideas. This approach works for them because they favor hiring experienced developers and do not invest much in training their employees relative to other companies. That is another definitive decision of their culture.
I advocate for a more balanced and sustainable approach for companies, one that encourages employee development and business realities. Startups that are willing to hire at all levels of experience and support employee growth can hire and retain better. Even those companies face challenges at their scaling inflection points when company leadership changes by 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 and 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 have replaced to assume the role once again. If the position opens up in the future, the person may now have the skills to step back into it.