This Week #0: Advice on growth, product, and leadership

Thank you for taking a chance on this newsletter. As you may have noticed it’s been relatively dormant for the past few months 😬

It’s time to change that — with a little experiment.

Thanks to some of my previous writing (and tweeting), I get a lot of great inbound questions centering around driving growth, building product, and broad leadership skills. The advice I’ve shared seems to resonate with folks (while also selfishly helping me crystalize my own thinking) so I’m going to lean into this. Instead of answering these questions privately, or just on Twitter where they quickly disappear, I’m going to share the advice here in this newsletter. Think of this as an advice column for growth, product, and leadership. I’ll aim to do this every one to two weeks, and depending on the interest, tackle three to five questions each round. On occasion I may have guest contributors, or dive deep into topics. It’s an experiment. If it ends up being valuable, I’ll continue. If not, I’ll stop.

CALL TO ACTION: If you are having a hard time with anything at work (or even trying to just optimize something) related to growth, product, org, management, communication, or leadership — simply reply to this email and let me know. I’ll pick a few questions, keep it anonymous, and share some candid suggestions in an upcoming newsletter. I don’t expect to have all of the answers, but I do hope to make things a little bit better for you.

To kick things off — a few recent questions I received about management, product, and business…

Q: Do you have any advice for how to “manage up”?

Managing up, a.k.a managing your manager, is an essential skill at every level (even CEO). It enables you do your best work, while getting the recognition you deserve. A few behaviors and tactics that have helped me over the years:

  1. Over-communicate: Consistently share what you plan to do, what you’re doing, and what you did. It’s nearly impossible to over-communicate. I started sending a weekly “State of Me” email to my boss, with (1) things they can help me with, (2) my current priorities, and (3) things on my mind. It worked wonders.

  2. Set expectations: When taking on work, set realistic expectations around time, resources needed, and quality. Your performance will be judged based on how it compared to your manager’s expectations. Be ambitious, but also be realistic.

  3. Share the trade-offs: When asked to make changes to a plan, be transparent about the trade-offs. Don’t assume they know what you know. What will suffer? What will benefit? What do you recommend? Partner with your manager to make the best decision.

  4. Prioritize and communicate: When asked to take on additional work, particularly last minutes, prioritize it amongst your existing priorities and share your updated priorities with your manager. Ask them if they disagree — adjust if so.

  5. Do great work: The better you do -> the more your manager will trust you -> the more freedom and influence you will have. If you feel micro-managed, and others around you don’t, it’s likely because you aren’t performing well. Do great work and life will get better.

Q: As a PM, when the team is humming along, what should I do when I have extra time?

Work your way up this stack, finding ways to refine and optimize each step:

Execution —> Strategy —> Vision


  • Does everyone know what they’ll be doing next?

  • Are there any blockers slowing down the team, now or approaching?

  • Are there any processes that could be improved?

  • Are you on track to hit your goals? What are 3 things you could do to increase those odds?


  • Do you have a clear plan for how your team will achieve its mission?

  • Is the strategy easy to understand and find? If you ask anyone on your team what your strategy is, would they be able to explain it?

  • If you had to be more bold, what would you change?


  • Is it clear to you what long-term success for your team and product concretely looks like? Is there a North Star for your team?

  • Is this also clear to your team?

  • Does achieving your vision matter? Remind people why.

And last, a few things you can always do more of:

  • Communicate: Is there any additional communication you can do, within your team and to key stakeholders?

  • Listen: What challenges is your team having that you haven’t yet recognized?

  • Have fun

Q: How can I differentiate my product/business from potential competitors, in the eyes of our customers?

With so much noise and competition it’s crucial that your offering stands out. Customers need a reason to choose you over the nearly identical competition. What makes you different and better? This is where differentiation comes in. Here’s twenty ways you can differentiate your product or business:

  1. Lowest price (Walmart, Amazon)

  2. Highest quality (Whole Foods, Ritz)

  3. Most convenient (Uber/Lyft, 7/11)

  4. Best product experience (Apple, Zoom, Instagram)

  5. Best customer service (Zappos, Nordstrom, AMEX)

  6. Best solution to a problem (Google, Superhuman)

  7. Limited supply (Supreme)

  8. Unique supply (Netflix, Disney, Airbnb, Hipcamp)

  9. Most personalized (Stitch Fix, Five Guys)

  10. Most delightful (FaceApp, TikTok)

  11. Most trusted (DuckDuckGo, Yubikey)

  12. Most flexible (Salesforce)

  13. Celebrity endorsed (Air Jordans, George Forman Grill)

  14. Good for the world (Patagonia, Beyond Meat)

  15. Good to employees (Southwest, Costco)

  16. Good for you (Lush, Fitbit)

  17. Most local (Colombiana Beer, Waterstones)

  18. Tribe (Harley Davidson, Soulcycle, Crossfit)

  19. Status (Louis Vuitton, Rolex, PBR)

  20. Story (Bob’s Red Mill, Airstream)

Some of the best companies are a combinations of these:

  • Trader Joe (1 + 2 + 5 + 8)

  • IKEA (1 + 3)

  • Tesla (4 + 5 + 6 + 7 + 10)

  • Costco (1 + 2 + 3 + 5)

  • Coke (3 + 8 + 20)

Alternatively, you can decide not to differentiate significantly and just win by scaling faster: Uber vs. Lyft, DoorDash vs. Uber Eats, Rocket Internet

Have a question you’d like advice on? Simply reply to this email. I promise I won’t bite.


Lenny 👋