Coaching With Heart
One of my VP Product coachees raised a topic that comes up often: “I want to become a much better coach for my reports, both around product issues and people management. How do I ask powerful questions to lead my team through that rather than giving the answer?”

This is a hard (and interesting) question because it mixes subject expertise with management styles and essential soft skills. Content critiques alongside motivation and organizational hierarchy.

I like to start by unpacking and understanding our coaching goals. Typically this is about improved delegation: our goal as product leaders should be to delegate as much direct product management work to our teams as possible. There are other things that product leaders need to do — and can’t delegate — so we try to step back from the daily pandemonium and focus on portfolio-level stuff.

And remembering that much of product management is “case method” rather than book learning or template-driven: courses and how-to guides present product as a sequential, logical process where we do A then B then C based on repeatable steps or universal “best practices.” I find that issues and challenges come up in clusters, unexpectedly, without clean delineation or separation. We have to figure out what tool or method or template or framework to apply, then dig into the problem at hand. (So just sending someone off to a workshop or telling them to search for a template isn’t enough to grow product skills.)

Finally, good coaching/mentoring is inherently generous and low-ego. When I notice myself falling into lecture mode or trying to “win” a discussion, I may not be as helpful as I intend. The goal is to move my product team toward self-sufficiency, not to out-PM them. Plenty of other leadership-level work to do.

From there, worth splitting out a few different learning stages:

1. “Since you haven’t done this before…”

There’s a wide range of concepts and tools to master, often tied to product maturity or revenue ramps or team/company size, that few of us get right the first time. For instance, sunsetting (aka end-of-lifing) a product doesn’t happen very frequently so most (junior) product managers have never done it. And EOL is fraught with technical, user-side and political issues (“but our third-largest customer licensed this obscure database connector, and we can’t afford to upset them.”) So our eager young protégé doesn’t know where to start or how to avoid the pitfalls. Conversations might start with…

“Here’s an old EOL plan of mine. It’s not exactly what we need, but a good starting place. Give it a read-through, then let’s talk about what we can borrow or adapt. Don’t worry if it takes a few drafts to get this right.”

“Sruthi went through this a few quarters back. She can give you a head start, share with worked/didn’t work last time. Then you and I can iterate on it until we’re ready to share your plan more widely.”

“Pretend I’m in Sales or Marketing. Tell me how they would describe this as a customer benefit.”

“None of us are fresh on this, sorry. Here are some starter online resources. But you shouldn’t expect this to be a template exercise, so let’s walk through what you discover before you get too far.”

2. “That might be a workable solution, but…”

Much of what we do is pattern-matching, applying hard-won lessons, thinking through a situation from several sides. But new product managers may want to get to the answer quickly or mechanically — sometimes following a stepwise approach to the wrong place. Or they get lost in the data. Or they briefly forget that we fight for our end users, even when another department is pushing short-term thinking. So we need to mix motivational messages with tough feedback; stay upbeat but unambiguous.

“You really captured the technical problem well here. But feels like we’re jumping to one solution without exploring alternatives. Which of our architects or sales engineers might have other ways to slice this?”

“I think that SSO/delegated authority feature is for our largest customers. But most of your interviews and usage data are from mid-market/SMB. What do we know about the few-in-number-but-big-revenue prospects that may need this?”

“I’m not sure how we got from A to B. Walk me through your logic.”

“Looks like this came directly from our BigCorp account team. Let’s back up, talk about why enterprise sales teams might overstate the market demand for a feature.”

“Which customer segments will be excited if we pull blockchain forward on the roadmap? Which might be frustrated that we’re postponing localization and canceling currency symbol options to make room for that?”

Our goal is both to get a good immediate solution and also build critical product thinking skills. Product managers must be able to handle valid critiques, humbly delivered. (Stakeholders and customers will be less humble, often wrong, and off-strategy.)

3. “Really good work. I might have chosen on a different approach, but that’s OK…”

We won’t run out of important work to do, so our team needs things that are (at least) good enough to move the products and business ahead. And this may be the coaching/mentoring moment when we can hand over a whole stream of similar work.

“Great! I think this is ready for early feedback from a few key sales/marketing folks. Let’s role-play some likely responses about wanting delivery two quarters earlier.”

“Next time, I might push the charts and graphs to the back — pull your two key recommendations to the very top — but let’s go with this as it is. If you hear any confusion from Customer Success, that would be a good time to shuffle the sequence.”

“This third party integration plan looks outstanding. There are 5 other integrations waiting in the wings… how would you feel about picking all of those up and becoming our go-to- person in this area?”

4. “The rest of the product team will eventually have to learn this. How about you take 10–15 minutes at Thursday’s PM staff meeting to walk all of us through your approach?”

For the win… one team member has mastered a product skill enough to coach others. To become a broader resource. To take some mentoring off our plates, which are still overflowing.

Finally, product leaders sometimes share concerns that their best people may leave. That skills-building makes PMs even more attractive to recruiters and competitors. Yup. But I hope that we’re in the long game. Companies, jobs, products come and go… growing great product managers and eventually sending them out on their own is (for me) one of life’s great pleasures. It’s fine to be at the back of Carnegie Hall, applauding a virtuoso who we’ve helped get there.

Sound Byte

Coaching/mentoring is a skill we need to develop as (product) leaders. Focusing on constructive criticism and controlling our egos helps us cultivate skill and delegate more. And eventually share some great talent with the world.
['Rich Mironov']
['Coaching', 'Soft Skills', 'Leadership', 'Feedback', 'Mentoring']