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Alex Shootman of Workfront: “Comfort Your Employees”

Comfort Your Employees — Stuff was pretty crazy a year ago — nothing any of us had ever seen. We had daily business continuity meetings and then I did a video at the end of each day letting folks know what we had discussed. We were very transparent about the business and shared details about our financial situation, our […]

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Comfort Your Employees — Stuff was pretty crazy a year ago — nothing any of us had ever seen. We had daily business continuity meetings and then I did a video at the end of each day letting folks know what we had discussed. We were very transparent about the business and shared details about our financial situation, our projections and what we were doing to keep the company and employees safe. I also ended every communication with a link to an application that allowed anyone to book time directly on my calendar.

Take Care of Your Customers — Our customers wanted to know they could count on us. Some also needed help continuing to use our software even though they were having expense problems. We held frequent meetings with our Customer Advisory Board, communicated to our customers about our financial health, and made payment adjustments for some customers who were in significant distress.


As part of our series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times”, we had the pleasure of interviewing Alex Shootman.

Alex leads Workfront, an Adobe company, and has over 30 years of experience leading SaaS-based technology companies. Prior to joining Workfront, Alex was President of Apptio, where he was responsible for the company’s integrated sales and services functions globally. Prior to Apptio, Alex was the President of Eloqua, where he was responsible for leading the organization’s global sales, customer success, and field operations teams. Alex was integral in leading Eloqua’s category creation as an enterprise SaaS company, and in 2012 was a member of the team that helped bring Eloqua to a successful public offering, subsequently being acquired by Oracle. Shootman has also held executive-level positions with Vignette, TeleTech, BMC Software and IBM.


Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I got into the technology industry quite by accident. My original plan was to fly jets for the US Navy, but several weeks before I was due to join, I blew out my knee playing basketball and that disqualified me from flying jets.

So with a few weeks to go before college graduation, and needing to find an alternative career-route, I attended a job fair. While waiting for an interview with Coca-Cola I engaged in a conversation with someone who turned out to be from IBM. He asked me to move forward with some conversations and that was the start of a three-decade-long career in technology.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

I started as a sales person at IBM. Early on I spent months trying to get into an account called Adams Oil, which was owned by Bud Adams who at the time was the owner of the US Football team called the Houston Oilers. I finally secured a meeting with Bob McGlaun who was the head of IT. We walked into the computer room and I had a cup of coffee in my hand. I set it on top of an IBM printer not knowing that when the printer ran out of paper it opened automatically. Well, you guessed it, coffee went all over the rest of the computers. I was pretty shaken and embarrassed that I did not know the printer would do that. Bob walked me into his office and said, “Alex, I don’t care how much you know — I need to know how much you care.

And that sentiment has been welded onto my brain ever since.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I have to give you two; because one gave me ‘the’ break and the other changed my leadership style. Darroll Buytenhuys put me in a bigger job by a factor of ten than I’d ever had. The risk he took on me and the confidence he demonstrated changed the trajectory of my career. And Lynn Rousseau has been my coach for over fifteen years. She is the person who guided me to leading with my heart and my head — not just my head.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

We were founded in 2001 on the vision for a software package that would allow companies to better manage dynamic, collaborative work across the enterprise. Twenty years later we remain committed to the notion that human dignity is fulfilled by work, that people want to be proud of their work, and Workfront exists to help people and companies do their best work. In addition, we want to show the world that an enterprise SaaS company can do the right thing and win.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

I originally shared this experience in my book, Done Right.

In the spring of 2003 I was leading the sales team at BMC Software in Houston as we approached our March 31st fiscal year-end. Typically, almost 40 percent of what we sold during the entire year was closed in the last quarter. And we’d expect to close almost 80 percent of that in the last two weeks of the month. But with eleven days to go, the market vanished thanks to geopolitics. The American-led coalition’s invasion of Iraq began on March 20th, prompting every major company and prospective client to shut down decision-making. Our final quarter and fiscal year fell off the table. We missed our numbers and our earnings guidance. Bitter disappointment doesn’t come close to describing how I felt. But on the morning of April 1st, I found a handwritten note on my desk from my mentor and one of the company’s vice presidents, Joseph “Chip” Nemesi. Chip wrote:

“I stopped by this morning, but you were in the gym. Since you looked like you had just watched your puppy get run over last night, I wanted to check in on you this a.m. However, knowing you as well as I do, I know you have moved on to a new year and are walking with confidence and enthusiasm this morning. Your team will expect you to be mad and lack some confidence and conviction after a rough close, and as usual I know you will surprise them, and they will draw strength from your example.”

Chip went on to write that he knew I’d never let “two or three accounts, a war, and an IT slump” affect my confidence or ability to lead. I’ve kept his note for fifteen years. It was a well-timed kick in the behind. Chip wrote things I did not yet feel. He described a course of action I had not yet imagined. With Chip’s encouragement, I walked in the footsteps of the stranger he introduced me to. What did I learn from the experience? Through whatever successes, highs, and lows I’ve experienced since, I know that on the other side of failure is another chance to win again.

Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?

I’ll give you an academic answer and a personal answer. I sit on the board of True Search, which is the fastest growing executive search firm in North America. True has a division called Synthesis that was founded by Inbal Arieli. The purpose of Synthesis is to identify an executive’s strengths and weaknesses to give a better understanding of leadership style and potential. One of the main things they’ve come to understand is the importance of resilience, a growth mindset and inner motivation in the success of a leader; particularly in difficult circumstances.

From a personal perspective I think your ability to sustain depends upon the reason you are leading. If you are leading for yourself, it can be easy to give in. But if you are leading out of a sense of duty and/or obligation, then you cannot give in because you are putting other people at risk by giving up.

What would you say is the most critical role of a leader during challenging times?

The first thing to realize is that, according to António R. Damásio, “We are not thinking machines that feel, we are feeling machines that think” and for better or worse, the team draws their emotions from the emotions of the leaders in the organization. Leaders have to understand that they are the emotional regulators and they must first regulate their own emotions and then demonstrate that regulation as a way to moderate the emotions of the entire team.

The second thing to understand is that you have to develop a way to see the truth but not for worse than it is. You have to speak reality to the company, but not communicate that the current reality means there may be a worse situation to come, or that the company may not get out of the current situation.

When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?

I just finished reading The Splendid and the Vile by Erik Larson, it is an intimate chronicle of Winston Churchill and London during the Blitz. Towards the end of the book there is the following passage, “On one of Churchill’s full-moon weekends at Ditchley, Diana Cooper, wife of Information Minister Duff Cooper, told Churchill that the best thing he had done was to give people courage. He did not agree. ‘I never gave them courage,’ he said. ‘I was able to focus theirs.’

Don’t put it on your shoulders to inspire your team. Your team already has the raw materials for inspiration, motivation, courage and passion inside of them — you need to be the instrument that allows them to find what they already possess. You need to connect them to their own ability to be inspired, resilient and centered.

What is the best way to communicate difficult news to one’s team and customers?

This is similar to the point in a previous question. See the truth, but not for worse than it is. Be factual about exactly what is occurring, what you know and don’t know, and the immediate steps you are taking in the moment. Ambiguity and inaction are the enemy in a difficult situation. Objective reality and forward momentum create a sense of purpose and hope in the team. When in doubt, do something!

How can a leader make plans when the future is so unpredictable?

Dwight Eisenhower famously said, “Plans are worthless, but planning is everything.” For me the key to an effective plan is a small set of key initiatives and milestones in which you need to answer the following questions: what’s going to be done? Who owns it? When will this be done? What does “done” look like?

And from there everything runs on the concept of the Best Next Action or BNA. At heart, a BNA is a simple question or pair of questions with a bias towards action. To get to your BNA you should ask the following questions: what are we going to do next? What’s the one thing we’re going to do within the next two weeks that will take us closer to a milestone? By taking this approach you’re not inviting answers with multiple possibilities. You want to hear about the one action that matters most right now. Here is a personal example of the BNA concept:

When one of my kids turns fourteen, their challenge is to climb one of Colorado’s “fourteeners” a mountain 14,000 feet high or more. When my son Sam turned fourteen, we spent seven hours climbing a peak called Mount Quandary. At 12,000 feet, Sam sat down in a heap and said he couldn’t go on. “Okay, well, let’s just try to reach the cairn over there,” I said, pointing to one of the many small stacks of rocks serving as a marker along the trail. Sam carried on.

At each trail marker, we stopped, took a break, and set reaching the next trail marker as our next goal. At 700 feet short of the summit, Sam said, “Dad, I’m done.” The air was thin, and he was tired. “Sam,” I said, “just look behind you see how far you’ve come. All you’ve got left is 700 feet.” So, he picked himself up and reached the top. No one can ever take away the satisfaction on his face when he looked down from the summit of Mount Quandary.

What’s the moral of this story? We broke down what seemed to be an impossible goal into best next actions. And we celebrated successful momentum at each milestone. Sam now has a story of extraordinary achievement that tells him he can accomplish far more than he imagined possible. In fact the following year he challenged me to summiting two 14ers in one day.

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

My very first boss told me, “Alex you are never as good as you think you are or as bad as you think you are.” His point was that if things are going well, don’t act like you have it all figured out and when things are difficult, don’t give in.

For me, what helps during difficult times is that I have been through difficult times and I know that they end. Maybe the best way to express this is “History doesn’t repeat itself but it often rhymes,” as Mark Twain is reputed to have said. I have found no evidence that he did say this, but it is too good a line not to use. So while the difficult time we are in today might have unique characteristics, it will end and we will come out the other side. The important thing is to learn a new lesson during each difficult time.

Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?

  1. Leaders are invisible
  2. Communication is opaque and incomplete
  3. The organization has no heart
  4. No one articulates the way out

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

As CEO, there are a small number of things that only I can own and communicate the vision of the company, establish and reinforce the culture of the company, hire the right people to work directly for me, and make sure the company has the financial resources necessary to succeed. I have to do these things in good times and in tough times. So, for me there is not a new thing to do in a difficult economy. Perhaps the most important thing is to not forget the fundamentals when things are difficult.

Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.

  1. Don’t Run Out of Money — In the March/April timeframe last year when COVID hit we went from quarterly, to weekly to daily cash projections. We ran significant downside scenarios and made a half-dozen decisions to ramp our cash on hand.
  2. Comfort Your Employees — Stuff was pretty crazy a year ago — nothing any of us had ever seen. We had daily business continuity meetings and then I did a video at the end of each day letting folks know what we had discussed. We were very transparent about the business and shared details about our financial situation, our projections and what we were doing to keep the company and employees safe. I also ended every communication with a link to an application that allowed anyone to book time directly on my calendar.
  3. Take Care of Your Customers — Our customers wanted to know they could count on us. Some also needed help continuing to use our software even though they were having expense problems. We held frequent meetings with our Customer Advisory Board, communicated to our customers about our financial health, and made payment adjustments for some customers who were in significant distress.
  4. Increase Visibility for Investors — We were a private company when the pandemic hit. But this would be the same if you are a public company. We brought our investors into the details and kept them there. We normally have a quarterly investor call but we started having bi-weekly calls with our investors to keep them apprised of our progress.
  5. Go On Offense — Ask yourselves how you can win in the environment you find yourselves in. We did just this after the first two weeks of ‘lockdown.’ We make work management software for large enterprises and customers were relying on us to pivot to remote work. So we went on offense, looking at how we could quickly adapt and enhance our product to meet the rapidly changing work needs of our customers. We had invested more in our Slack integration than our Teams integration. And even though we’d been a Zoom customer for years we did not have a Zoom integration. We immediately enhanced our Teams integration and built a Zoom integration. And we brought to market a brand new product for interactive scenario planning.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Maybe happiness is overrated, freedom, too. Maybe the only way to get anywhere worth being is to pick up the heaviest thing you can carry. And carry it” — Prodigal Son by Gregg Hurwitz

How can our readers further follow your work?

On Twitter @shootman

LinkedIn https://www.linkedin.com/in/alexshootman/

Thank you so much for sharing these important insights. We wish you continued success and good health!


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