Lessons, Learning and Leadership

Every business leader needs a lieutenant. A wingman or wingwoman who they turn to for advice, a much-needed reality check, and most importantly, help pushing forward the ideas and priorities they have established for their organization.

Lieutenants are those rare individuals who can translate vision into execution. Who are able to think ten steps ahead, but still comfortable in the operational details. They are some of the most important people in any organization, yet you don't hear as much about them. There thousands of CEO profiles out there, magazines dedicated to the C-suite, and advice up the wazoo about how to attain that coveted CEO role. What about the number twos and the leaders behind the leaders who are so critical to the growth of companies, many of whom choose not to be CEOs?

That is the impetus behind this new Q&A series which I call Lieutenants - Lessons, Learning and Leadership (L4 for short because I shorten everything). This series is designed to highlight lieutenants from across industries. To hear their story, in their words on their path, perspective, what they love about their role, the leaders they support, and the habits and tools that make them so effective.

What better lieutenant to kick off this series than one of my most trusted lieutenants at Appirio, Glenn Weinstein. Glenn is now Chief Customer Officer at Twilio where he looks after all post-sales services, making sure Twilio re-earns its customers' business every single day. With one of the highest Net Expansion Rates in the SaaS industry, Glenn and the team are doing something right!

Glenn credits his training and early career as an officer in the U.S. Navy as a big part of who he is and his ability to effectively straddle the line between visionary and tactician. In this interview, he highlights how he keeps himself organized, the importance of being able to pull your own data, and why he's a team-first kind of leader.

What is one word that describes your personal leadership style?

Collaborative.

What are two or three characteristics of a great lieutenant?

You have to help translate the brand vision of your leader or the company into a set of actionable steps so people know what to do when the meeting is over.

You also need the ability to disagree and commit. You have to be willing to speak your mind before a decision is made, and then once the decision is made, even if you disagreed, be willing to get behind it. Then it's about harnessing other people in the process to do the same thing.

It's your job to encourage everyone to give input freely and aggressively when it's time for input, and to corral everybody to back up the decision.

A good lieutenant makes sure people have the data they need to make the right decisions, but is also able to make those decisions. They need the capability to be the leader when necessary. You have to be a little bit of a chameleon and know when to start acting more like the visionary and not get so bogged down all the time.

What work habits do you have that you think make you more effective?

There's a fine balance between being online 24-hours-a-day and protecting your ability to prioritize. In general, I try to respond to stuff that can have a quick response immediately. I get it off my plate and leave the bigger stuff for when I have bigger blocks of time. I've seen this with other great leaders. They don't let hundreds of emails pile up. They just answer real quick, surprisingly quick. Sometimes, the CEO of a company answers you much quicker than an SVP. There's some sort of multiplication that happens with email. If it's not particularly urgent, but it's super easy to answer, then just answer it. Keep your plate as clean as possible

Also, be a reader. It's nice if you have a write-it-down culture like what we have at Twilio where you have a written paper on the topic before the meeting. Then you can come into meetings having done your homework. You can skip all the pleasantries and start asking the hard questions in the first few minutes of the meeting instead of spending the first 20 minutes hashing over slides and only leaving 10 minutes for the real discussion.

Do the pre-reading, do the research, come in with the hard questions already teed up.

How do you give yourself room to prep when you're in back-to-back meetings?

Well, having a write-it-down, do-your-homework culture can help. You also have to carve out reading time in your calendar. You shouldn't have a calendar that's scheduled with 16 consecutive 30-minute meetings. You need that prep time carved out.

What tips would you give to someone who's not super organized?

First, my inbox is my to-do list. Everybody has their own email style, but if I've done it, then it leaves my inbox. If I still have to do it, then it stays in my inbox.

I also use Google Docs now for every meeting, and I always take notes. I used to carry around a little black notebook everywhere. Now, instead, I fire up a new Google Doc. If it's a recurring meeting, I just keep adding my notes at the top. I re-read the last couple of meetings before I have a one-on-one with somebody so I can ask how something is going. It shows you are paying attention.

Finally, it also helps to be able to pull your own data, because if you're waiting on other people it's just too slow. The world moves too fast.

If you can pull your own data, it's like having a super power.

You've heard me say that companies have 3 dials they can turn - customers, team and financials. While leaders will say they try to balance the three, I believe you can only optimize for one. Which type of leader are you? Financials-first, customer-first, or team-first?

I'm definitely team first. If you're someone newer to the workforce, you might think financials come first, but in the long-run, especially in leadership roles, you know you have to take care of your team. If you do, they'll take care of your customers which, in turn, will take care of your financials.

Your CEO at Twilio, Jeff Lawson, has built an incredible company. What drew you to him, what do you admire about him as his lieutenant?

There are many admirable traits to Jeff. First, he is 100% a people person. He has a certain sincerity in the way he talks to Twilions (what we call ourselves here at Twilio) that is unshakable and people feel it.

People know that Twilio will always do the right thing, because if it ever gets to Jeff, he will make the right call.

Jeff is also a gather-the-data kind of a CEO, and he rewards good lieutenant behavior because he doesn't make snap decisions. He'll have five or six people around a table and go around asking, "What do you think?" to each one of them. Then he walks away and makes the call.

Do you ever aspire to be a CEO, or do you love the lieutenant role?

That's a hard one. I'm not sure what my final answer is on this yet, but I don't think you have to be a CEO to feel fulfilled in your career, or to feel like you made a huge contribution. Not everybody aspires to be the CEO. Being a CEO requires a very unique skill set that takes you pretty far away from the operational details, which I like. So I don't know if I'd be happy as a CEO. I might just be a frustrated operator. Being on the first-level executive team that reports to the CEO that's, probably, my optimal role.

Being a CEO matches a certain personality type. You have to be so visionary and so optimistic that you almost have to not pay too much attention to the details or you'll get too conservative. I'm glad that we have that type in this world, but I'm not sure that's me.

In one sentence can you describe what you would like your professional legacy to be?

He helped build great technology organizations.