16 Powerful Insights From Alex Shootman’s Interview w/ Gordon Whitehead

February 1, 2017 Marcus Varner

Last December, Workfront’s CEO Alex Shootman sat down to chat with Gordon Whitehead as part of his “Leadership 24/7” podcast about his approaches to leadership and helping employees reach their full potential. The following 16 quotes are some of the most eye-opening insights Shootman shared during the conversation. You can listen to the full conversation here.


 

On Motivating People

1. “Don’t think that you are burdening somebody with something, but realize that most of the time you are inviting them into a great adventure that they want to participate in.”

2. “[People] want to help. What they really want to do is the thing they love, which is usually their chosen profession; they want to do something noble. So if you can give them the opportunity to do something noble in the thing that they love, you won’t have to work on motivation because they’re going to work on it themselves.”

On Focusing on People

3. “The simplest things that we’re taught early in our careers end up becoming the most important things later in our careers. It’s things like making sure that you hire good people. When you first hear that early in your career, it’s such common sense that you almost dismiss it. Or things like, ‘Character in leadership is going to matter’. And you think, ‘Of course, it’s going to matter’. But after a while, you realize that, if you spend time and energy on those simplest of things that you heard early in your career, it will create the greatest rewards.”

4. “I think the toughest thing for a salesperson is to not become a number. You’re told you’re a number and so how do you not become a number? What I’ve always found is that if you’re willing to invest in those parts of the sales team that aren’t just about the number, you start to realize that making the number is a trailing indicator of doing all the right things, as opposed to a leading indicator. Once you realize that, then you can step out in faith and say, ‘No, I am going to invest in the people because investing in the people and investing in leadership will eventually get me to extraordinary sales results.’”

5. “Human beings are very interesting creatures because we think in a flawed way. We think of past, present, and future. By that I mean something happened in the past and we think about what just happened. The way humans should think is past, future, present. Let me learn from the past, let me envision what I want to happen in the future, and then decide what I can work on today to make sure that the future happens.”

On Developing People

6. “The first thing I’m looking for is the manager who says, ‘What am I going to do for my folks today?’ If there’s an employee who really needs something developed in them—and they’re going to derail their career if you don’t develop that in them—that’s something that you could do for them today. It might be a very difficult task for them; it might not be something that they like to go through. But you’re still willing to do it for them.”

7. “All people lead out of a basic worldview that either people are good or they're bad. If you think people are bad, then you think your job is to control them and prod them into doing the things that you think need to be done. If you think people are generally good, then you’re going to spend your time figuring out if you have clarity of vision, if you’ve set appropriate boundaries and expectations, if you’re investing in them so that they can be successful.”

8. “The biggest mistake that young leaders make is, they think their people need to like them. You’ve got to start with, if your people respect you, then they will do the things necessary for them to be successful. And when they are successful, then they’ll be satisfied and motivated.”

On Hiring Well

9. “I’m never going to hire a sales leader that says he’s never missed a number, or she’s never missed a number. Because they’re going to miss a number someday and I don’t want to clean up their tears when they miss a number for the first time. I want them to have been through that before they get to me!”

On Leading By Example

10. “What gets measured happens. As a leader, what you are interested in, everybody else will be fascinated by.”

11. “Culture is the external manifestation of the shared values of a group of people. If I think about you individually, I actually don’t know what your personal values are. I can only see what your behavior is. Your behaviors are the external manifestation of your personal values. There’s only one way that we as leaders can change the values of the organization, and that’s by making believable, observable sacrifices.”

On Building Trust

12. “It’s the leader’s responsibility to do a self-assessment to say, ‘How am I doing on integrity, intent, capability, and results?’ Because if I’m not doing well on any of those, then I can’t be offended if my organization doesn’t trust me. If you’re a brand-new leader going into an organization, you have no results yet in that organization. You need to understand that your people don’t yet trust you.”

On Soliciting Input

13. “When you stop asking questions, and you start thinking that you know the answers, that’s usually when you get blindsided.”

14. “The team’s input is not a vote; you don’t get a vote, but you get input. So we talk about debate periods and decision periods. We’ve got a decision we need to make in the next 90 days. The first 60 days is going to be a debate period, where I’m willing to listen to all the debates possible. But then after that, the debate period is going to end and I’m going to cut that off and make a decision.”

On Spreading the Vision to the Organization

15. “A really critical skill that middle management needs to learn is what I would call ‘translating the message’. Senior management creates very broad, horizontal communications. ‘We’re going to be a great company. We’ll be a billion dollars in five years. Let’s create excellent customer service.’ Only middle management can translate the message. If they do it, they will be hugely successful. If they don’t do it, teams are just going to flail.”

On the Need to Be Self-Aware

16. “I think that we’re leading at our best if we understand at a pretty visceral level why we’re leading. The one thing that I would advise any leader to do is, look in the mirror and ask yourself, ‘Why do I want to lead?’ After you give the first answer, ask yourself, ‘Why do I want to lead?’ again. And then after you give the second answer, ask yourself, ‘Why do I want to lead?’ Whatever your answer is after the third time that you ask is going to be the wellspring from which you lead. By the way, not all the reasons are noble. When you really break it down, you might find some pretty un-noble reasons why you want to be a leader, but you better really figure that out.”

 


 

To listen to Shootman and Whitehead’s full conversation, click here.

About the Author

Marcus Varner

Marcus is a content strategist and producer who loves helping brands craft content that improves customers' lives, builds brand credibility, and demands to be shared. For the last 10 years, Marcus has worked in every type of content—from writing to video production to design—and is currently a senior content marketing manager at Workfront, where he oversees all corporate- and awareness-level level content. When he's not producing content, he's consuming it, in the form of books, movies, and podcasts.

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