Something that stood out to me in Chapter 8 of The Founder’s Dilemmas was how much a company’s hiring needs can change as it grows. When a business is first getting started, it makes sense to hire people who can do a little bit of everything. There usually is not enough money or work to have a person dedicated to every individual role, so having generalists who are willing to jump in wherever they are needed can be extremely valuable. As the company grows, though, those same hiring decisions may not work as well.
I think this is one of the harder parts of being a founder because it means constantly reassessing the team you have. Someone who was exactly what the company needed in the beginning may not necessarily be the person who is best suited for the company five years later. Wasserman (2012) discusses the trade-off between hiring people with more experience and hiring people who may have more flexibility to grow with the company. Experienced employees can bring knowledge and stability, but they can also be more expensive and may have a harder time adjusting to a less structured startup environment. On the other hand, someone with less experience may be more adaptable and willing to take on different responsibilities, but they may require more training and support.
This made me think about how different hiring can look depending on the stage of a company. Early on, a founder might need someone who is comfortable figuring things out as they go and doing whatever needs to be done. As the company becomes more established, it may need people with much more specialized knowledge. A person who was able to handle marketing, customer service, and operations in the early days may eventually be overwhelmed when the company has hundreds of customers and a much larger team. At that point, having someone who specializes in each area may become more valuable than having one person who can do a little of everything.
Another part of the chapter that I found interesting was the idea of hiring people you already know. I can understand why founders would do this. If you already trust someone, hiring them can feel much less risky than bringing in a complete stranger. You may already know how they work, what their strengths are, and whether you get along with them. For a new business where there are already so many unknowns, having someone familiar around can feel like one less risk.
At the same time, hiring friends or family can create problems when the business has to make difficult decisions. It is much harder to have a tough performance conversation or let someone go when that person is also someone you have a personal relationship with. There can also be an expectation that the person should get special treatment because of the relationship. I think that could become especially difficult if the company grows and other employees start noticing that personal relationships are influencing business decisions.
This made me think about how I would want to approach hiring in my own business. I know I would want people I trust around me, but I also would not want personal relationships to become the main reason someone gets a position. I would rather build a team based on what the business actually needs and be willing to change that team as the business grows. That does not mean I would never hire someone I already know, but I would want there to be a clear reason that person is the right fit for the position beyond the fact that I trust them.
I also think this connects to the importance of thinking about future roles when hiring. If I am building a business, I do not want to only think about what I need today. I would want to have an idea of what the organization could look like as it grows. The people I hire in the beginning may eventually move into different positions, take on more responsibility, or specialize in an area that fits their strengths. At the same time, there may be situations where I need to bring in someone from outside because the company has reached a point where the skills we have are no longer enough.
That is probably what makes hiring such a difficult founder dilemma. There is no single type of employee who will always be the right choice. The needs of the company are going to change, and the founder has to be willing to recognize those changes instead of holding onto the original team structure just because it worked before.
To me, the biggest takeaway from this chapter is that hiring is not something a founder can figure out once and then forget about. The right team for a startup today may not be the right team for the company five or ten years from now. Founders have to be willing to recognize when the business has outgrown a certain role, structure, or even way of hiring. I think building a strong company means not only finding good people, but also making sure the team continues to fit what the business needs as it evolves.
Reference
Wasserman, N. (2012). The founder’s dilemmas: Anticipating and avoiding the pitfalls that can sink a startup. Princeton University Press.