Who Gains? A Guide to Better Understanding Motivations

Let’s try a thought experiment. If I gave you the opportunity to cure cancer, but it would cause you to be broke for the rest of your life, would you take the offer? Depending on the person, I’m sure many would and many wouldn’t.

Now let’s take this scenario one step further: if you found out that by curing cancer, you would make me a billionaire. Would you still take the offer? Even if you still would, you would likely at least question my motivations for pushing you to take the offer.

I’d like to offer a framework for how to evaluate such a request if you were on the receiving end, inspired by the crime detective show, Numb3rs. As with most crime detective shows, the detectives look for both evidence and motive. In particular, one scene stayed in my memory over the years:

One of the FBI agents, Colby, was suspected of being a double agent. He was then detained and interrogated by his supervisor, Don:

Real life is clearly not a crime detective story (or at least I would hope not!), but by asking “who gains?”, hence understanding motivations, it can provide you great insight into people’s behaviors.

A few years ago, a startup I worked at conducted a survey. One of the questions was:

For context, the company built solutions for financial institutions. Two-thirds of the engineers voted for (1) pushing the deadline back, while two-thirds of the account managers voted for (2) working later hours. In the discussion, both sides came up with reasonable explanations for their responses: engineers claimed that working longer hours would increase the chance of bugs and reduce software quality, while account managers claimed that clients always come first.

Who Gains?

While both sides are speaking the truth, they’re also conveniently leaving out some key information. Pushing the deadline back requires the account managers to put in extra work talking to the clients, while (in a healthy environment) the engineers would be shielded from those difficult conversations. If the conversation does go awry, the account managers are the ones on the frontlines.

Conversely, working later hours require engineers to put in extra work and risk burnout, while the account managers can continue on with business as usual. It also reduces software quality and increases likelihood of bugs, which ultimately come back to haunt the engineers who have to fix them — usually on short notice, too. While both sides came up with seemingly reasonable arguments (“we’re optimizing for the customer” and “we’re optimizing for software quality”), it still fundamentally came down to the same question: “who gains?”

People in maker roles (e.g. engineers, designers, and data scientists) often get requests from business, product, and marketing, some of which may require them to go the extra mile. Similar to the thought experiment above, it is typically framed in a grandiose way: “This is exactly what the users need!” or “This will literally boost our revenue by 50%!”

That said, it is imperative to develop your own critical thinking to truly understand the full context of the requests. “Who gains?” is an easy reminder to assess the situation: if you were to agree to the request, who stands to benefit the most? Who stands to lose the most? Then, use that as an input into your decision-making process for responding to the request. I have seen countless instances where engineering teams work around the clock over months to one person’s benefit when that work was not at all aligned with the company strategy nor impactful to the business. Don’t fall into that path — you may end up being broke for the rest of your life, making the other person a billionaire, and yet still not cure cancer.

On the other hand, as a leader, there will be times when you have to make difficult requests of your employees. Have empathy for those you’re about to put a burden onto: they are the ones who have to put in the work to make things happen, yet you are the one who typically stands to gain the most. Be extremely transparent with the full context of the ask. Sometimes I just flat-out tell my team, “this is a top-down ask from the CTO — if we don’t do it my neck is on the line.” I have also seen cases where the development team was so burnt out they refused to take any incoming request from sales, missing key opportunities to close a contract against a competitor. This is also a reminder of the importance of building trust during regular times, so that those who have to make that extra effort (i.e. sacrifice their financial well-being for the rest of their lives) will trust that they are truly doing it for the greater good (i.e. cure cancer). This applies even if it’s clear you’re the one who stands to benefit the most (i.e. become a billionaire), because they trust that you will have their backs no matter what.

For more musings on tech culture, organization building, and management, follow me on Twitter @kenk616.

Product-minded Engineering Leader. Organization & Cultural Builder. Traveler. Martial Artist (Muay Thai & Pekiti Tirsia Kali).

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