Chee Chew joined the CTO & Product Guilds on 7/17 for a special session where he shared his leadership philosophy, organizational insights, and more. Chee is the Chief Product Officer at Twilio. Previously, he was VP Consumer Engagement at Amazon (team of 3,500), VP Engineering at Google (built Hangouts). Earlier in his career, he coded the Windows 95 UI.

1. Becoming an Executive

One of the most challenging transitions is to shift from becoming a manager of ICs, to manager of managers.

As an IC or frontline manager, you are in the position of weighing in on specific solutions, architecture, etc. It’s a trap!

What happened: IC and a manager came to Chee to resolve a technical issue, and there was a debate about the best path forward. Chee broke the tie and even suggested a superior solution. He loved it. Next week, the same thing. The week after that, the same. The week after that, his manager quit; “You undermined me, Chee.”

On managing managers: One member transition from managing ICs to managing managers asked “if I know the right answer, how do I give that feedback without undermining the manager?” Chee’s response was two-fold:

(1) The simplest technique is asking a question; a plainly-stated hypothetical.

(2) “If you want to learn how to influence someone, you need to learn how to ask the right question. It’s human nature to tell. They will only learn when you ask.”

2. Avoiding Shock Absorbers in Communication

As you have more layers of management, one interesting thing happens: you have shock absorbers in organizational communication. This applies to communication flowing from the top down, and bottom up. Positive feedback gets watered down… and critical frontline issues get positioned as minor issues.

Enter Vegas Lunches. These are skip meeting lunches with guaranteed confidentiality (“What happens in Vegas…”) Chee is extraordinarily candid and open, and will speak on any topic. This encourages candor from the IC/frontline manager, so Chee can truly understand what’s happening on the front lines.

One thing you will have to constantly fight: ”Oh, that’s not important enough to bother the Chief Product Officer with.” Well, it is important enough. If you can prevent a bad decision with 5-10 minutes of effort, it will save you hours of effort down the road.

3. Radical Transparency

Chee is a huge proponent of radical transparency through open meetings and open project reviews. Almost every (non 1-1, non-customer) meeting that Chee is a part of is public and open to the company. Some meetings have as many as 70 people, with as many as 30-40 people just passively listening via Zoom. All meetings are recorded and published across the org, so that people in other timezones can understand what was decided… and more importantly, why. Everyone is allowed to join and weigh in with concerns. (That said, there have to be clear rules of engagement to avoid meetings getting bogged down.) Donut also has a “lottery” feature that lets people opt into a lottery program for meeting execs, either 1:1 or in groups—if you’re trying to encourage that connectivity in your orgs.

4. Recognizing Team Members

Chee is an enormous believer in spot bonuses (regardless of $ amount) to recognize great work and build culture. He has done it on teams small and large, and thinks that it is single handedly one of the most important tools in reinforcing culture and telling the organization what good work looks like. If you’re interested in implementing this into your org, be sure to check out Bonusly (part of FirstMark family)

5. How Chee spends his time at Twilio scale:

  • 25% of time is one-on-one (and in fact with anyone who asks)
  • 25-30% are project reviews
  • Balance on cross-functional meetings (exec team, e.g.)
  • 5-10% maker time, topics

Pro Tips

Pro tip #1: If employees learn that you give employees a salary bump to retain them… you’re telling everyone that is your comp philosophy. And all of a sudden more people will threaten to quit. Broader takeaway: whatever your policies are, you need to be so confident in it that you’re comfortable with the entire org knowing the policy.

Pro tip #2: on finding a mentor, you need someone who can mentor you. Perhaps they approach the world like you do, or can coach someone like you. Everyone says, “hey, who’s a good mentor…” and then immediately starts focusing on accomplished people.