Dealing with HiPPOs - Product Management Best Practise

Nov 4, 2022 

John J. Schaub

If you've been working in Product Management for any length of time you've almost certainly watched the train wreck that occurs when your finally crafted and well considered roadmap, feature or marketing plan crashes into a HiPPO. For those that don't know HiPPO, meaning ‘Highest Paid Person's Opinion’, is a polite term for bosses and senior leaders we've all had that are far too confident that their outsized salary combined with their 'gut feel' or 'decades of experience' trump data, carefully conducted user research and basic common sense. These folks march in 90% of the way through the process and promptly insist on massive scope, direction and goal changes making everyone work far harder than they should have to often resulting in an outcome that is measurably worse then if the HiPPO had not been involved at all. In my career I've seen this drama unfold from every vantage point including a few times as the HiPPO so I thought I'd share a few things I've learned along the way. 

Before getting into the actual tactics you will use to deal with these folks let's spend a few seconds figuring out why they are doing what they are doing. The approach you are going to take will vary depending on the exact type of HiPPO you are dealing with. Looking back at my experience the HiPPO almost always falls into one of four subtypes based around their level of experience, their position in the wider organisation and the status of the org as a whole:

Jr. HiPPOs - Are new leaders typically but not always middle of the pack in the organisation who feel the need to prove their value to those in the higher ranks. Jr.HiPPOs are the easiest subtype to spot, they have typically been in their role less than six months and they are very visible in every meeting they attend. Jr.HiPPOs are probably going to be pretty easy to deal with in that they should calm down in a few months and you really just need to wait them out.

Sr. HiPPOs - The Sr. HiPPO knows stuff, a lot of stuff. The problem with Sr. HiPPOs is that some of the stuff they know is no longer accurate but because they’ve been doing HiPPO work for so long they really aren’t sure which pieces of their knowledge are still applicable. Sr. HiPPOs are both pretty easy to deal with and extraordinarily dangerous depending on how you set things up. If you’ve done your job right and set up the conversation correctly there is a 90%+ chance you can end the encounter with the Sr. HiPPO saying something to the effect of ‘cool I didn’t know that’ or ‘huh learn something new every day’ and wandering away. On the other hand if you haven't done your job right and the Sr. HiPPO is actually correct, and because of their deep expertise there is a very real chance they are, you’re about to learn why they’re the HiPPO. As an aside, Sr. HiPPOs can be tamed and make great mentors and you should do your best to befriend them.

Peter Principle HiPPOs - The Peter principle is a management concept that states essentially that people get promoted until they hit the level at which they are no longer competent. The concept itself is questionable in that it is very normal to struggle when taking on a new role and the situation is not necessarily permanent but with Peter Principle HiPPOs it probably is. These folks have hit their personal ceiling and rather than put the time and effort in to grow they instead try to make sure everyone knows just how smart they are. You can think of Peter Principle HiPPOs as Jr.HiPPOs that never really figured out leadership but managed to hang on anyway. Peter Principle HiPPOs are going to be hard to deal with.

Outsider HiPPOs - You're most likely to run into this type during massive org level changes when new leadership has stepped in and is in the process of cleaning house. These HiPPOs are bringing an entirely new culture and approach to Product Development to your org and are likely to question the very basic approach you are taking. As an example a small FinTech company that historically operates via a move fast and break shit ethos being bought by a large bank will result in a lot of very interesting meetings as different projects get reviewed by a new executive team. There are no options to deal with these folks that don’t involve change on your part. The reality is if the way things are being done at your org are changing in a big way you can either change with them or change orgs. The idea of holding onto the old culture is an absolute fool’s path. As an aside moments of tremendous change are a very easy way to grab a promotion if you can demonstrate to new leadership that you are open to learning the new way of doing things (you should be, even if you end up hating it at least you’ll know why) and that you have deep knowledge of the existing org.   

So now you have an understanding of the subtypes but how do you deal with them? The best defence is to simply keep the HiPPO away from your project and regardless of the subtype of HiPPO you are faced with, the first line of defence is a solid reputation for making good decisions. With most of the archetypes you’ll have earned this reputation over your career and can pretty easily ride on it. The challenging archetype is the Outsider who will have absolutely no idea who you are or how closely they should be diving into your work. In these cases it is important to over demonstrate that you know what you are doing in a way that will give them confidence and hopefully stop them from diving in on your project. For example do not just send a meeting invite with the subject line ‘Prioritised Roadmap Discussion’ take the time to put a few pages in the meeting invite detailing what options were considered, what decision making process was used and why you rejected any obvious alternatives. Then be prepared to speak to the content in the meeting if you are questioned by someone that didn’t prepare or some HiPPO that wandered by. If during the meeting the HiPPO says something to the effect of ‘What about XYZ?’ and your answer is ‘We considered that but rejected it for A, B and C reason’ while you quickly flip to the spreadsheet showing all the gory details of a robust analysis you chance of HiPPO attack have not just been reduced in that meeting but will permanently be reduced for the rest of your career. A reputation for being thorough and careful will keep HiPPOs of all sorts far away while the contrary will act like bait for HiPPOs. People don't like it but the reality is most executives are vastly time constrained and will absolutely decide which projects they need to deep dive on based solely on the earned reputation of the people running those projects and the impact of the project.

The next best practice is to make sure you've clearly and concisely shared the details with key stakeholders ahead of time. Do not under any circumstances fall into the trap of avoiding sending info to an executive because they are the type to ask questions I can absolutely guarantee that the questions will still come but you'll end up answering them in front of an audience with no time to prepare where if you'd dropped an email two weeks earlier you'd have all the time in the world to think it through. One of the major errors jr. staff make is to assume that meetings are where decisions are made and treat them as such by bringing the relevant discussion items to the meeting. The fact is that any important decision should be made before a meeting through smaller conversations and the meeting exists only for people to publicly endorse the decision (or better yet send an email to everyone explaining the decision and free up an hour). Regardless under no circumstance should you bring new information to a large group of people as doing so is very likely going to result in the HiPPO offering their input and the group going along with it. Experienced leaders will often find a way to not give an opinion but even very experienced people  can fall into the trap of stating an opinion when information is dropped in their lap unexpectedly. These opinions have a way of taking on way more weight then they should so do yourself and everyone else a favour and make sure everyone gets the info ahead of time and has the necessary time to consider.

So you’ve done all the groundwork, you can prove the work and you are still sitting in a meeting or worse an email thread with someone spouting frankly bizarre opinions at you, now what? At this point you have a couple of options:

First you need to consider the fact that they might be right. Sometimes that VP who last pushed code to production over a decade ago knows some deep esoteric detail that really matters, possibly because the code in question was cludged together by them personally. The key task is to figure out why they are on about without it completely derailing your project. In this case the magic words are 'lets take that offline?'. From there, get in a room or on a call and figure out why they think what they think and be prepared for the possibility that they are correct. 

If you are absolutely certain they are incorrect again the goal is to disengage and figure out why the disagreement exists. In my experience these sort of intractable disagreements between HiPPOs and Product tend to boil down to some fundamental misunderstanding of the market by one side or the other. These misunderstandings can probably be discovered by making very explicit the assumptions both sides are operating under. When you arrive at the assumption that is either disagreed upon or isn’t shared you will likely have solved the problem. If you want to shortcircuit the problem do a quick brainstorm on where the HiPPOs experience differs from the current problem space and you will have a short list of assumptions to confirm. 

Finally if you arrive at a point where the HiPPO simply disagrees with the decision you are making you need to figure out who the actual decision maker is. If it is the HiPPO you are going to have to go along with their opinion. If it is you then you owe it to yourself to make the decision and push through. Being wrong is one thing and is likely survivable but being wrong because you went along with something you knew to be the wrong call won't feel good at all.

Hopefully this gives you some useful insights as always if you have questions do not hesitate to reach out.