Harness the HiPPO (or get flattened)

Last week, I came across the acronym - HiPPO - or Highest Paid Person’s Opinion.? Hmm.? At first, I wanted to split hairs about it being the top organizational person’s opinion.? Or TOPO.? Maybe, Most Senior Person’s Opinion.? MoSPO.? No ring to that one.? So, ok.? HiPPO.? It’s catchy and encapsulates all the hairs I am trying to split.?

A lot of you can relate to this situation. HiPPOs fill the room, are hard to wrangle, and are sometimes quick to anger. The worst thing about a HiPPO is that they usually don’t stay in a particular lane. The HiPPO is an expert at everything. This behavior, on its own, is challenging, but the worst part is that a HiPPO models lane-busting, which is disruptive in complex delivery management.?

It’s not lost on me that I was frequently that person in the room—a HiPPO. My own experience led to my reform. I am a reformed HiPPO.?

Years ago, we didn't have unique roles, and it wasn’t uncommon for me to be an architect, project manager, and analyst, all on the same project. Fortunately, delivery budgeting has improved, and now we plan for the right talent and expertise.??

HiPPOs come from many places: sales, operations, VC, engineering, product, etc. For this discussion, let’s agree that HiPPOs serve in top organizational positions.? They achieved their role due to a demonstrated history of doing a great job.? A successful HiPPO should have a vested interest in highly visible enterprise deliveries. As a team, we should respect the HiPPO.?

As a result of playing so many different roles, HiPPOs may have many views. It took me some time to internalize the saying, “No one likes a know-it-all.” I am a slow learner.? Over time, I recognized that I was more likely to be heard if I stayed in my lane and spoke expertly about my domain.??

As my roles narrowed to product ownership or engineering, I realized that despite my vast (wink) expertise, sometimes I needed to stop talking (an ambitious goal).? This epiphany was never more apparent than when I ran an engineering team.? While my intentions may have seemed motivated by fairness, courtesy, and deference, it was also about protecting my lane.?

An engineer's critical responsibility is estimating a delivery timeline without sacrificing code quality, resiliency, and security. I’ve been in situations where product owners argued for “faster” options that were also technically irresponsible. And our teams are under pressure to deliver faster, faster, faster. Perception of speed sometimes comes with additional manual processes, poorly factored code, and, most likely, tech debt.

As an engineering leader, advocating for realistic and achievable timelines is a priority. My teams need to demonstrate predictable outcomes to build trust throughout an organization. Getting estimates wrong creates chaos in a company.??

I mentioned that I have opinions on many topics, including (but not limited to) product features, user experience, and compliance. But in this example, I run engineering.? My most crucial voice and highest value to the company is to speak for engineering.? I have to trust my peers in their roles so that they will trust me in my role.? It is essential for us to stick to our expertise so that our recommendations are not clouded by a cacophony of other opinions.?

As leaders, we must intentionally recognize and celebrate the expertise across our teams. Doing this will create efficiency and momentum so that we are not subjected to unnecessary debates between teams. Of course, allowing for energetic discussions about strategy, features, and technology is essential. But, in the end, we may have to “disagree and commit.” I expect respect in my lane, therefore I need to give it to my partners in theirs. Fighting every battle is exhausting and unnecessary.

Unfortunately, without the proper feedback framework, HiPPOs will cross all the lanes and even stop the traffic entirely.? How do you harness a HiPPO so that they can collaborate productively and use their weight to keep the project going in the right direction?

HiPPOs are notorious for demanding last-minute or out-of-scope requirements. Because of their position, HiPPOs expect the team to comply with these changes. As I said above, it’s critical to respect HiPPOs. They are in the role for a good reason and often have market or client insights necessary for the project. But, the organization should leverage a process that ensures that the HiPPO isn’t simply a disruptive force.?

My negotiation style with the HiPPO is to provide detailed information about the current planning and approach - and remind them that a reliable process dictates that any acceptance of new features will be part of a trade.? Working with the HiPPO, we review the current prioritization and determine what feature(s) can be removed from the cycle to insert their request. Most importantly, I am always fully committed to the communicated delivery timeline and the agreed upon requirements; otherwise, the HiPPO will think that all schedules and estimations are flexible.? Reminding a HiPPO to trust the team and the plan isn’t an easy task.? But it’s better than allowing a HiPPO to run wild.??

Ultimately, all of these clever words and acronyms are talking about stakeholders. I rely on a delivery framework that includes frequent stakeholder check-ins because stakeholder management and participation are vital to successful project delivery. I include team representatives so that the stakeholders become familiar with their expertise. I aim to show the stakeholder that the company's talent reflects their expectations and can be counted on to represent the HiPPO throughout the project.?

Bringing stakeholders in too late tends to backfire by putting team members in a defensive position instead of allowing them to advocate for the project. Regularly engaging stakeholders ensures they are part of the problem-solving process and navigate the project's challenges throughout its timeline.

I’ve seen three outcomes using the strategy I’ve described: 1) the HiPPO becomes an active and timely collaborator; 2) the HiPPO recognizes the complexity of the project and also knows that they don’t have time to contribute fully and begins to trust the team; and 3) the HiPPO does whatever they want.? And we, as a team, deal with it.?

Lastly, as I noted earlier, I’ve been a HiPPO.? My management style is about developing and trusting the talented people around me. As a CTO, I remind my teammates that their expertise - in engineering, UX, Product Ownership, whatever - is their most important value to a delivery. Yes, I wrestle with my teams.? But my goal is not to win or prove something.? We aim to agree on the smartest and most practical approach.? As a result of their expertise and dedication, I can communicate transparently with my client, my boss, or investors.

Whatever animal you're dealing with, proceed with caution. Good animal stewardship starts with ongoing care and feeding.? If you ignore them, they won’t be inclined to be domesticated, and you’ll find yourself as prey.?