Getting off the Chessboard

If you ever talk to Jeff Bezos, don’t ask him about each engineer on his Blue Origin team and the progress each engineer is making. He probably knows about it broadly, but there’s a next to zero chance he knows exactly what his engineers are working on at all points in time. Nor is he soldering panels onto the side of the rocket himself.

There is a reason. He has taken himself off the chessboard.

Stepping away from the chessboard allows him a view of the entire board, the bigger picture. I use this analogy because it’s something I have said before…

In 2020, when the pandemic clouds had darkened the skies for everyone, I said this: Founders need to take a step back. But two years after that tweet, we have now hit a period of re-evaluation.

But why do we need to talk about this? There is a whole new wave of founders who are taking their spot in building high-impact startups. These founders have always done everything themselves. They’ve made their first sale, written the code for their apps and even decided on the menu for the company cafeteria. But as the company scales, there comes a time when they can’t do everything, or else the company becomes single-threaded.

Founders need to hire senior management, sometimes by promoting internally, sometimes bringing in talent from the outside. But I find there is a general unwillingness to let go of decision-making control to other non-founders. In this period of flux, it is very important that founders learn to place themselves in positions of strategy and not tactics. To view a problem fully, there needs to be a little distance.

They need to delegate. Delegating is an art, not science. I can’t say, “Why don’t you delegate sales? Just hire a VP.” Many founders get off to a great start with their early teams. As the business model scales and operations expand, there is a temptation to continue with this set of people who understand the company — its culture, values, and vision.

The initial reluctance to not be able to find the right fit for your executive team is reasonable. I have met founders who have perfectly valid reasons, “We’ve done well with the current set of people so far.” Or “The founding team understands the business. Why hire outsiders when internal people can be trained?” And so on.

All of this is true, and scaling is difficult. But there is a need to hire people, sometimes, who are more experienced than you, in your sector. They understand the nitty-gritty of dealing with difficult clients. Or a CPO knows what kind of customer feedback to ignore, what features to prioritise. Your job becomes more strategic. Setting the agenda for what the company can become. Hiring the people to go be your generals in the war.

I can hear the founders saying, “That’s excellent, Dev. But how do I find that right hire?” It’s a good question. First, different executives will be attracted to your company at different stages in your company’s trajectory. Some will be passionate about the problem you are solving and join early. Some may want to wait until the risk is taken out. Second, leverage your investors and advisors and get that first talent acquisition (TA) head hired.

But you first have to know what you are looking for. So we often introduce new or first-time founders to people in senior positions at other companies. Not from the perspective of hiring them, but just so they can see and learn about the quality level of these people. More often than not, they come back with their minds expanded and a solid sense of world-class talent.

These people who they meet become prototypes of who they need to hire. This changes the way founders think.

Once these senior hires settle into the growth mindset of the company and help it scale, founders gain confidence in seeing the business being moved in the right direction. The conversations post a successful stepping away from the chessboard are very different. “We should have brought in this set of people earlier.” “I cannot remember how I functioned before this.”

Larger, or game-changing initiatives will, of course, require founders to come back and don the “doer” hat — a zero to one initiative, perhaps, navigating the company out of a bad situation, or to get something new started.

Not that all startup founders step away. Some just can’t. They remain involved in every little decision, every little sidestep. And while it may seem like it gives them greater control, this “single-threading” may come in the company’s way of executing fast and reaching its true potential.

Also, keep in mind that hiring senior management does not mean replacing the early employees who stood with you in the difficult times. Early employees are your culture carriers and should absolutely remain and be deployed on the chessboard in a manner that keeps them energised yet performing at the highest levels required by the company.

You have to see this as a game of chess. In order to win, you have to be a player, not a piece.

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