Combining Business & Product Mindsets

Christian Strunk and Alex Dapunt host the Product Bakery podcast. In this episode, I joined them to talk about how Product Leaders work with executives, as well as the topic of negotiating and managing stakeholders and incoming requests. 

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Podcast Minutes/Table of Content

  • 0:28 – Intro
  • 5:45 – Organisational misalignment
  • 6:45 – Product vs project management
  • 7:45 – Product management becoming the bottleneck
  • 10:15 – Working with a founder CEO
  • 13:00 – PMs are anthropologists
  • 17:05 – State of Product Management vs. Product Design
  • 22:15 – Prioritizing & negotiating with stakeholders (e.g. Sales Team)
  • 30:05 – Working with stakeholders who have no product background
  • 33:40 – Working as a PM with a boss who has no product background
  • 39:20 – What keeps Rich awake at night
  • 42:45 – Deeply understanding customers & values
  • 48:30 – Three tips for everyone who recently started a Product Lead role

What are the biggest challenges for companies and product leaders?

Rich: Product management is loosely defined, and we ended up owning the problem of making a product successful, even though almost all the inputs and all the staff and all of the resources are not in our control. Right? We have all the responsibility and none of the authority. To some extent, a lot of what I see is organizational breakage or misalignment, where classically the sales team is being incented to sell something that’s different from what the engineering and product teams are building. Salespeople do what you pay them to do, not what you want them to do and so if the compensation plan and the way we reward and promote salespeople are misaligned, then nothing else in the company is going to go well. Right. The other sort of core things I see a lot of is, that I see product teams where the folks they’re working for don’t actually understand the distinction between product and program or project management.

So to the extent that we give people a label, what we really want them to do is make sure we ship stuff on time and to stand over the development team with a whip or pizza or whatever it is that is going to make them work faster.

That’s a critical job. That’s an essential job. Someone should be doing it. But the product role is really all about making sure that we’re sequencing the work in a way that delivers the most value and motivating our development teams as best as we can. So we get good work out of them. But the leverage we have, the advantage we have, the value we deliver is that we’re doing the more important things first because if we do the less important things first, we still get a lot of work done but it just doesn’t matter.

The third thing I see a lot is product teams that are dramatically understaffed versus their engineering counterparts. Almost on all of these assignments or consulting gigs, I’ll get an org chart and I’ll count the people.

There’s a broad category – I call them makers. That’s developers, designers, dev ops, or cloud ops, tech writers, test automation engineers – all the folks who actually do work to create the thing that we’re going to call the technology pieces of the product. Then I count them up and I get a ratio from them to the product team, product managers. When that’s above, let’s say nine or 10. Let’s let’s imagine it’s 30, which means we have one product manager matched against three whole development teams. I know the product managers are failing no matter how good they are. I can’t pull an entire car behind me. I’m not strong enough and big enough if we have four product managers and 60 people on the developer and the maker side. I know they’re not serving well, no matter how experienced or smart they are. So often this is trying to figure out what’s missing.

Since I was an engineer, I can remind us that every system has a bottleneck and when we fix that bottleneck, the system has a new bottleneck. Because every system has a bottleneck. When product management is the bottleneck and when there are not enough product managers, then everybody else is scrambling to figure out what’s important. Everybody else is scrambling to do their own segmentation and pricing and packaging, to have developers on their own, going out to figure out what users want to have, designers not clear on what the goal of the interface is. When I see that the ratio of makers to two product managers exceeds nine or 10, I know that everyone else is having to do their own bits of product work and they’re not trained for it. They’re not experts at it and it’s not why they hired them.

What is the biggest issue you usually tackle when you get started as a coach and consultant?

Answer: One of the big ones is when the CEO is also the founder and is pretty sure that he or she knows all the answers and is not interested in any feedback from the market.

It may have worked when it was eight people or 12 people. And the thing that’s really difficult about that is there’s this, survivorship bias or selection bias, which is the 96% of the companies that are utterly failed because their founders CPO didn’t have a clue aren’t in this situation. It’s the ones where they, got it right enough, but we really want to have more expertise, more tools, more analysis, more thought, more strategy. It’s really hard to go back to a founder CEO and say: You need help in these areas. You’re busy. You have a lot of other jobs. You’re not doing it that well. We could make more money, if you would relax some of your control. That’s a very hard sell and notice it actually has nothing to do with an individual product manager on the team. If I were the head of product or the VP of product, and I had nine folks on my team, all nine of them are failing for the same reason. None of those nine can convince the CEO to back off. So that’s an executive level of leadership challenge for whoever’s running the product team to find some thoughtful, humane, polite, acceptable way to help the CEO founder. Redirect energy without getting fired and without upsetting everybody.

Noticed that’s as much about people skills and EQ and understanding your audiences — Myers-Briggs whatever — as it is about knowing how to write a user story.

How can product leadership improve this relationship?

Answer: The best outcome here is that there is a product leader and that, that product leader deeply understands that this is a core issue and that they have a lot of good tools and skills because generally the first one or two or three things you try may not work.

There’s persistence and there’s a real depth here. I think in a lot of ways, product managers are anthropologists. We’re students of human behaviour. We have to really understand how the different parts of the company are motivated, how they’re rewarded, what they care about.

That’s about looking deeply into the people, as opposed to thinking that showing a spreadsheet with 11 columns and weightings is going to prove that my strategy is better than your strategy. That actually works on the engineering side but it doesn’t at all work in the executive suite or on the marketing sales side.

So if you’re a product leader, and a lot of my coaching is around this, you as a product leader have to know, psychoanalyze and really understand what’s driving the different players in the company and you have to package up the right answer in a way that they can hear that they can accept.

There’s a lot of coalition building. Sometimes I can get sales on my side if marketing’s not quite there and sometimes I can get marketing on my side if the professional services team isn’t getting me to the right place. I’m happier when in the weekly executive staff meeting I don’t make the proposal that I wanted to make, but somebody else on the executive staff, maybe three people on that staff bring forward the idea that is the right one. I don’t care who sells it. It’s not about me and my ego. So often there’s a lot of shuttle diplomacy here where I pitch or sell or convince or discuss with every single member of the executive team one-on-one. So that when we get to the big meeting, there’s no drama and everybody is there. In some ways, those are selling skills rather than product skills. But I don’t think you can be a product leader if you’re not outthinking the rest of the executive team. So we can get to the best answer.

Some executive teams run on facts and some of them run on recency bias and some of them run on whatever the CEO said this morning or thought of in the shower. As the product leader, in fact, you are product managing the executive team. In the same way that individual product managers are managing products. I have to figure out my audience. I have to figure out my message. I have to figure out how we’re going to get to the place where we ship more stuff and make more money and have happier customers. It’s important that we, as an executive team, get to a good answer and make our customers love us more.

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