I spend much of my time with product leaders – folks who manage teams of product managers – including at a recent series of workshops. These discussions are substantially different than my conversations with line product managers (aka individual contributors).
As Directors or VPs of Product, we expect a lot of the product managers who work for us: understanding their markets and customer segments; motivating development teams; helping drive sales; defending roadmaps from daily random interrupts; making hard choices among many worthy improvements. We count on them to ship great products that meet customer needs and financial goals. But there are some problems that individual product managers typically can’t solve for themselves.
At the next organizational level up, product leaders create the conditions for product managers to succeed. We need to build strong relationships with Engineering and Marketing/Sales; craft sensibly lightweight processes; and help cut through the inevitable company politics. We need to push our product managers to take strong action and defend them when they do. We need to keep executives focused on markets, value and problems to be solved.
Here are five issues that keep coming up:
 Working with founders or business owners who “help too much.” Our product managers receive a daily barrage of good ideas and product requests, especially from founders (at startups) or business unit/sales executives (at big companies). These requests may make sense individually, but are impossible in the aggregate.
Part of our job as product leaders is to negotiate ways for our team to push back in the best interest of their products. And not to get fired. While still listening for truly great new ideas.
 Finding, hiring, training and mentoring product managers. Even ignoring the arguments about experience versus attitude, hiring and growing great product teams is hard work. Our folks need a rare blend of hard and soft skills; market empathy and technical vision; application detail and financial big picture. These are hard to demonstrate in the interview cycle, and costly to get wrong. Two-day training sessions, online academies and pay-to-play certifications don’t capture the complexity of real products, real markets or real organizations.
So as product leaders, we need to craft individual mentoring/training plans for every new hire. These might mix pairing Junior PMs with their Seniors; Myers-Briggs communication workshops; whole-product-team reviews of each others’ strategies; sales ride-alongs and tech support listen-alongs; design thinking classes; and tons of face-to-face meetings with actual users. Make a plan.
 Building trust and understanding among stakeholders. Often, our VP-level peers in Sales, Marketing, Engineering and Support have limited view of what product managers do. (Sales: “put what I need into the roadmap.” Engineering: “write down what customers say in the form of user stories.” Marketing: “do customer briefings and staff trade shows.”)
We have to get out ahead of the confusion: draw role boundaries; give what-do-product-managers-do presentations at other departments’ staff meetings; push for decisions on strategy and evidence; evangelize the idea of curated products; unclutter roadmaps; relentlessly sell the subtle value of product management. Persuade others that having a strong product team is a net positive for the company.
 Managing product portfolios. If you have many products or a few large products with many development teams, there are a near-infinite number of ways to divide up the product work. By market segment? Technical architecture? Revenue? SKUs? Personas? Lots of theories, no general solution. And company size/maturity has a huge impact. Yet we’re called on to decide.
There’s also the sticky problem of assigning development teams across established versus emerging products. Given limited resources, how do we carve up the engineering pie, and how often do we revisit the allocation?
 Innovating in large organizations. Very hard to do, whether we call ourselves change agents or intrapreneurs or lean startup enterprise practitioners. Big companies, big budget processes and impatient shareholders create their own momentum.
I’ve seen that market logic (by itself) isn’t sufficient: we need to build coalitions; work budget magic; and find important customers to champion good ideas from the outside.
These are meaty issues with complex, situation-dependent answers. No magic bullets, no universal templates, no one-size-fits-all. In recent workshops, we’ve pooled approaches and shared personal strategies. From the outside, our conversations may have sounded more like marriage counseling than WSJF analytics.
Time after time, product leaders tell me that such peer discussions have a calming effect: we talk about hard problems, which are not unique to any one organization. There’s some comfort knowing that others are wrestling with the same organizational challenges. We can recognize issues as pervasive, give them names, and depersonalize them a little.
Watch for a series of follow-on posts on each of these tough topics. And let me know if you’re a product leader who’d like to join a working session.