Dances with HiPPOs

Daniel Tunkelang
3 min readSep 4, 2019

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Decision making, especially at technology companies, is supposed to be data-driven. Unfortunately, even in this wondrous age of science, decisions often depends on what Avinash Kaushik and Ronny Kohavi call the Highest Paid Person’s Opinion, or HiPPO.

How should a data-driven developer deal with the HiPPO in the room?

Having worked across the organizational stacks of various companies, I’ve learned a few survival skills for dancing with HiPPOs.

Make opportunity analysis a required part of the development process.

Opportunity analysis is a best practice for all development work. The size of the opportunity that a project addresses is an upper bound for the project’s impact. If the maximum potential impact is low, the project had better be a quick, low-risk win to be worth doing at all.

Unfortunately, there never seems to be time to include opportunity analysis on the development schedule. Developers are busy and HiPPOs want results, so implementation is prioritized over analysis. As a result, developers are always busy coding, but much of that code has little or no positive impact.

The solution is simple: make opportunity analysis a required part of the development process. Making opportunity analysis a requirement takes away the discretion of HiPPOs and developers to just dive into implementation. Opportunity analysis does add time to every project. But that time quickly pays for itself by short-circuiting low-impact projects and reducing waste.

Insist on clear metrics targets before any development work starts.

In Lewis Carroll’s Alice in Wonderland, there is an exchange between Alice and the Cheshire Cat that every software developer should memorize:

Alice: Would you tell me, please, which way I ought to go from here?
The Cheshire Cat: That depends a good deal on where you want to get to.
Alice: I don’t much care where.
The Cheshire Cat: Then it doesn’t much matter which way you go.
Alice: …So long as I get somewhere.
The Cheshire Cat: Oh, you’re sure to do that, if only you walk long enough.

If a project doesn’t have a clear metrics target, then there is no principled way to evaluate the project’s success. You should not start developing until you have a clear definition of success. Otherwise, as the Cheshire Cat tells us, it doesn’t much matter what you do — you’ll get somewhere, if only you code long enough. But you are unlikely to produce a meaningful impact.

Encourage HiPPOs to prioritize problems rather than solutions.

Data tells us how well a solution addresses a particular problem. Data can also tell us about the prevalence of a problem. But data, at least on its own, cannot tell us how important a problem is to the business. That’s what HiPPOs are for: they are paid the big bucks to decide what’s important.

But that means prioritizing problems, not dictating solutions. Prioritizing problems tells developers which metrics matter to the business. In particular, it helps developers manage trade-offs among competing metrics. But HiPPOs should let developers determine the best solutions to those problems. The last thing a developer wants — or needs — is to be micromanaged by a HiPPO. That generally leads to suboptimal solutions and grumpy, unproductive developers.

Finally, try to be a bit empathetic.

Finally, while it’s frustrating to deal with HiPPOs who don’t seem as data-driven as you are, try to be bit empathetic. HiPPOs make high-stakes decisions and often bet their careers on those decisions. They share your goals, but they often lack your knowledge and tools to address those goals.

Help them see how data can help them achieve their goals more effectively and efficiently, and HiPPOs will become your favorite dance partners.

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Daniel Tunkelang
Daniel Tunkelang

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