How to Be an Effective “Outsider” CEO

Editor’s Note: The following article is based on a recent episode of OpenView’s BUILD podcast. You can listen to the full episode featuring Alex Shootman, CEO of Workfront here.

One of Alex Shootman’s best moves when he first joined Workfront as CEO was completely unconscious.

During his first 100 days after taking the reins at Workfront in 2016, Shootman took part in a three-hour product review session that ran over lunch. The crew ordered some pizza and after eating his portion, Shootman picked up his plate and walked around the table. “I asked, ‘Are you done with your plate?’ and I put some plates in the trash. I didn’t think about it.”

Others apparently did. Head of Engineering Steve ZoBell called Shootman aside. At first, Shootman thought he made some kind of faux pas. But Zobel said that cleaning up everyone’s pizza sent a message about what a mensch Shootman was and how the action reflected what Shootman thought of the company.

What’s notable about that story is that Shootman doesn’t generally seem to do anything unconsciously. His process of moving from outsider CEO to trusted CEO was literally scripted. Here are the steps he took and how it played out:

1. Get a lay of the land

Outsider CEOs like Shootman are on the rise. A recent analysis from PwC strategy consulting business Stategy& found that 22 percent of CEOs hired in a planned succession between 2012 and 2016 at the world’s largest companies were outsiders. That’s nearly double the rate from 2004 to 2007 and disruption is a primary reason.

That wasn’t the case for Workfront. Founded in 2001 as AtTask, by 2016 Workfront had established itself in the work management solution category, raised an E-round and had 3,000 customers when Shootman replaced another outsider CEO, Eric Morgan.

Shootman, who had formerly been the president of Apptio and Eloqua before that, started by looking at what he called the “as-is situation.” He looked at eight aspects of the company, including its financial situation, the budgeting process and how the company generated revenue and made forecasts.

“I wanted to go through products, what are the titles, the pricing, the performance, the roadmap. I wanted to understand the customer base,” he said. Shootman learned these things by arranging interviews with various people at the company.

2. Meticulously plan your first 100-day schedule

Shootman scripted his first 100 days as CEO, looking at everything from travel to meetings with analysts. “It was important that I not get trapped at headquarters in the first 100 days, but make sure that I had been in customer offices,” he said.

3. Solicit help from other CEOs and executives

Before writing his plan, Shootman canvassed a dozen CEOs he knew. “I asked, ‘What should I pay attention to?’ And from all of that I kind of amalgamated this, you know, kind of home grown startup plan.”

Like a screenwriter eager to punch up a script, Shootman sent that inchoate plan to investors and Workfront’s board.

4. Write an introductory letter to your team

Shootman didn’t just write out a plan, he wrote a letter as well and presented it to his team about two weeks before his first day. The letter said “I am wide open to learning a lot of things, to getting input, and advice, and opinions. But I have 10 items that are non-negotiable.” The items included “culture eats strategy” and “the customer signs the paycheck.”

“The response to that was predictable,” Shootman said. “It was a scramble both to prove that they were doing that and a scramble to get educated on what I meant.”

5. Make a big entrance.

Board member Susan Carstensen was the interim CEO prior to Shootman. On the day he arrived, Cartensen was MIA and founder/chairman Scott Johnson introduced him instead. “It was an intentional decision between Susan and myself to basically say Susan doesn’t exist anymore,’” he said. “Obviously that took a humble ego on Susan’s part.”

6. Change the names of the conference rooms

One of the first things that Shootman did as CEO was change the name of every conference room in the company to be named after a customer.  “It made people mad because they’re like, ‘We’re on the second floor, our conference rooms are named after rock songs. And we’re on the third floor and they’re named after places.’” Shootman’s response? “Well, you don’t get to choose that because every time you go in a meeting, I want you to think about a customer.”

7. Enlist your most trusted employees as advisors

Another of Shootman’s unorthodox methods was to pick 27 company veterans and divide them into three teams. Each team picked one of three plausible directions for the company to go in and spent six weeks honing their argument. The teams spent a day making their cases to the senior team. Shootman said he did this to hear voices that would keep him from making a bad decision. “It also created some authority within the company because we were speaking with the voice of 27 people that they respected,” he said.

8. Make yourself accessible to the board

Shootman approached everyone on the board and asked them how they’d like to communicate. “For the first two or three months for the ones that wanted a scheduled call, it was on my calendar,” he said. “For the ones that just said, ‘Call me on your way to work,’  I just called them on the way to work.”

Shootman wound up being an effective CEO. But looking back, he said he might do things a little differently. “I think that my biggest mistakes have been in trying to do too much too fast,” he said. “I was trying to go 100 miles per hour on everything. Next time I’d slow it down.”

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