Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik)

1. Journal for Self-Reflection

When experiencing negative thoughts, write them down to explore their origins, identify irrationalities to let go of, and clarify what’s within your control to address.

2. Find Fun in Work

Figure out how to have fun in your job, even during difficult times, to avoid operating from scarcity and open your mind to more opportunities.

3. Be Strategic: Why & Champion

To be seen as strategic, articulate a compelling and simple “why” behind decisions and directions, and champion difficult changes that are best for the company’s long-term interest.

4. Prioritize Decision Making

Avoid analysis paralysis by making decisions quickly, even with 70% certainty, because you learn more after committing and can iterate on the remaining unknowns.

5. Foster Learning Culture

When making decisions, clearly state hypotheses and assumptions, and reward learning from outcomes (even “bad” ones) rather than just the outcome itself, to encourage risk-taking.

6. Manage Energy, Not Time

Architect your day to maximize energy by doing simple things like eating lunch and scheduling difficult tasks during your peak energy times, avoiding your worst times of day.

7. Summarize for Strategic Clarity

In meetings, summarize what people are saying and what it means for direction, then check for agreement; this synthesizes discussions, makes people feel heard, and is perceived as strategic.

8. Work with Difficult People

Believe you can work with anyone by understanding what drives them and then motivating them by aligning their desires with what you need for company success.

9. Give Feedback with Care

Convey genuine care and desire for their success explicitly, be direct about the feedback, provide specific examples, and brainstorm solutions together.

10. Receive Feedback Effectively

Allow yourself to feel negative emotions without reacting immediately, then approach the feedback with curiosity, asking “where is this coming from?” to decide if action is needed.

11. Everyone Teaches, Everyone Learns

Remind yourself that everyone has something to teach and something to learn, which helps in interactions and combats imposter syndrome by recognizing your own value.

12. Learn from Challenges

In difficult situations, actively look for what you can learn and what positive outcomes you can gain, even when facing significant hurdles.

13. Gratitude for Difficult People

Instead of anger, approach difficult personalities with gratitude by asking what you can learn from them, whether it’s their communication style or visionary ideas.

14. Be a Company Historian

Understand past decisions, product launches (successful or not), and the reasons behind them to learn from mistakes, inform future decisions, and address organizational baggage.

15. Make Ideas One Click Better

Take existing ideas and focus on making them slightly better, especially from an outside-in customer problem perspective, to generate big, impactful ideas over time.

16. Tactics for Summarization

To summarize effectively, use phrases like “Let me pause here and try to capture what has been said,” then ask a question. Alternatively, use a whiteboard or Zoom chat for lower-stakes summarization.

17. Operate in Founder Mode

As a leader, deeply understand the business details, ask detailed questions, and collect information to decide where to make significant course corrections for the organization.

18. Guide Team Strategy

When correcting team strategy, get involved early by asking them to present their thinking, then ask questions and make suggestions to improve it, rather than rewriting it.

19. Seed Assumptions, Discuss

When offering a perspective, share it as a hypothesis or observation (e.g., “I heard this feedback, and this is what it made me think… what do you think?”) to encourage discussion rather than shutting it down.

20. Research Motivations

To understand what drives difficult personalities, talk to others who have successfully worked with them (subordinates, peers) to build empathy and insight into their wants.

21. Leverage Founder Power

As a CPO, recognize the founder’s power and use it as a resource to push initiatives that are best for the company by making them an ally in getting things done.

22. Understand Founder’s Objective

When a founder has an idea you don’t agree with, deeply understand why they are pushing it and their ultimate objective, then propose alternative options if their mechanism is wrong.

23. Pick Your Battles Wisely

As a product leader, decide which battles are worth fighting with a founder, focusing on what will truly make or break the company and what is most important.

24. Tailor Feedback to Goals

Before giving feedback, ask the person about their career aspirations to tailor the feedback to what truly matters for their growth and increase their receptiveness.

25. Frame Feedback as Perception

When giving feedback, frame it as “this is how you’re being perceived” rather than “you are doing X,” which gives the person the benefit of the doubt and opens a discussion about changing perception.

26. Prioritize Feedback

When receiving abundant feedback, anchor on what is best for the company and what it needs from you/your team right now, focusing on “must-haves” over “nice-to-haves.”

27. Bring Humor to Meetings

Start meetings on a light note with humor to elevate your own mood and add levity to the situation for other people, which is important as a leader.

28. Clarify Ambiguity Skill

Understand that the core skill for product managers is consistently driving clarity in ambiguous situations, rather than just mastering specific tools or processes.

29. Break into PM (Internal)

Build credibility in a product-adjacent role within a company, then raise your hand, interact with the product team, take on related projects, and build relationships with product leaders.

30. Sell Before You Build

Before building a product, understand how it will be sold and who will sell it, to ensure adoption and avoid building something that goes unused due to lack of sales readiness.

31. AI for Research Summaries

Leverage AI tools like Dovetail to summarize user research calls, tag insights, and quickly retrieve context and transcripts for specific topics, unlocking valuable information.