Product Management Masterclass #8 : Diego San Miguel

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1. Tell us a bit about yourself!

My name is Diego San Miguel and I’ve been doing product management for the last 7-years, working with Techstars backed startups and more recently, creating economic opportunities at the world’s work marketplace, Upwork.

2. In one word or one sentence, how would you describe your product management style?

Moonshot. I always aim to have the biggest impact.

3. How did you get into product management?

I started my career in business managing a helicopter operations company. It was a great job, and I got to train as a pilot, but it didn’t give me the opportunity to build which is something I’m incredibly passionate about. It made sense to move in a direction that allowed me to do that.

4. What are one or two things you typically do during the first hour of your day that lead to a productive day?

Most days I do a little bit of puttering before getting in the zone and checking current progress versus my OKR tracker. Then, I’ll typically check in with my teams to see how I can help move the needle.

5. How would you explain Product Management to a 5-year-old?

I have a 4-year old and he’s way more interested in Ninjago than in what I’m doing, but I’d probably tell them Product Management is about building things (i.e. LEGO) that people can use or kids can play with. It’s about taking an idea, and turning it into something you can touch.

6. What’s one of your biggest challenges in product management today?


7. What are some of the qualities of great product managers?

You need to be resourceful, and you need to be creative. You won’t survive for long without either and they kind of go hand-in-hand.


8. What has made you successful in your role?

I don’t stop learning, and I don’t back down from a challenge/opportunity.

9. How do you decide what (or what to not) to build? To buy?

Going back to the moonshot analogy, I aim for where we can have the most impact and frequently run A/B tests to confirm a hypothesis early on so that engineering resources get put on what works.

10. How can PMs stay ahead of user requirements or make sure they’re aware of them early?

Partner with user research. If you’re on a small team, talk to customers. Talk to your competitors’ customers. Make sure you understand your customers.

11. How would you prioritize your resources when you have two important things to do but can’t do them both?

Always bet on impact.


12. One of your highest paying customers demands a feature from you that isn’t on your roadmap…what do you do?

I’d understand the value and weigh it against what else we’re working on. Who else would this feature provide value to?


13. What qualities make a good product? Any tips and tricks for our readers for building a better product?

Understand the problem. Don’t ship a product, ship a solution and iterate on that solution until it is the best possible solution on the market.


14. How do you know if a product is well-designed?

Use test data to understand how users are interacting with your product. Collect qualitative data to understand what is working and what is not.

15. How do you make sure/ know you have a solid roadmap?

Collaborate. Ensure your roadmap aligns with your team, your colleagues, and overall business direction. Focus on the value you bring to the table.

16. What aspects of product management do you find the most exciting? The least?

That build up and anticipation to launching a product is a wonderful feeling. Seeing positive reactions that reaffirm what your building is even greater, but I’d be lying if I said there wasn’t a lot of pre-launch paperwork!

17.Tell me about how you interact with customers/users?

I’m on LinkedIn every day, and I try to get on the phone (or Zoom) with customers every week. It keeps me grounded.

18. Talk about how you overcame product failures/challenges or poor feedback.

It’s always an opportunity to learn. When I first started in product management, I launched a product that had zero impact. A couple of months ago, I launched that same idea with a new spin, and we’ve seen great results.

19. What is one best practice you’ve adopted/applied in the last few months that had a positive impact on your role? How has it helped you?

I’m always learning and adopting new techniques, but the most important thing you’ll learn over time is how to gauge impact and where it is important to place resources. You’ll never stop improving in that.

20. What are some common mistakes you see product teams making?

I see product teams make assumptions all the time. They don’t talk to customers, they just file them away as a persona somewhere. They’re not customer-focused.

21. Any closing thoughts/things you’d like to add?

Keep going. Keep learning. You’re going to have failures, you’re going to have weekend crunch time, but you’re going to have fun and the work is extremely rewarding.

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