Allen Bernard - April 01, 2019

Jim DuBois on optimism and persistence as force multipliers

Jim DuBois
Former CIO

In the final part of our four-part series (part 1, 2, 3) dissecting former Microsoft CIO Jim DuBois' book on IT leadership, Six-Word Lessons to Think Like a Modern-Day CIO, and how it relates to digital transformation, we look into how optimism and persistence are critical qualities for any successful IT endeavor as companies embrace digital transformation.


Thanks for taking the time to speak with us today. In chapter nine of your book, Six-Word Lessons to Think Like a Modern-Day CIO, you talk about optimism and perseverance being force multipliers. Given that optimism and perseverance are qualities that transcend technology, I was wondering what connection they have to leading IT today?

These qualities are even more important today given the digital transformations that are happening now and the pace of change. If you're persistent and keep learning and don't give up, you're more likely to succeed, which feeds your ability to be optimistic. And your ability to be optimistic gives you some ability to be persistent. Together, they build off each other. They've been keys to my own ability to achieve what I have.

It does go back to the vision stuff that we were talking about last time. When you're trying to get teams rallied towards a big vision, you need to have some inspiration to go with that. People don't want to follow a leader who isn't optimistic, and they don't want to follow a leader that's going to give up.


Most everybody likes to be around positive people who are also realistic. You don't want to be around someone who's just wearing rose-colored glasses, sitting in the middle of a house fire saying, "Everything's fine," right?

If you're not being realistic and people can see that, then you're going to lose trust. Optimism isn't just having a bright picture of the future. It's also having a positive attitude about the things that you run into. As I say in the book, using one of Winston Churchill's quotes, "Optimists are the ones that are looking for an opportunity in every difficulty, as opposed to looking for difficulty in every opportunity."


That sounds like a Benjamin Franklin quote.

It does. Maybe he stole it from Benjamin Franklin. But there are a lot of people that will, from a risk management perspective, look for the difficulty in every opportunity as opposed to the other way around. It makes a big difference in how you approach it.

It's fine to manage risks well but are you looking for the opportunities? Are you looking for what you learned in something that didn't go perfectly? When someone says something critical, do you assume that they're trying to undermine you or do you assume that they're trying to help you do better? It makes a big difference that you're assuming positive intent in how you interact with people.


Do these qualities need to permeate an organization's hierarchy? Let's take a leader vs. a manager. A managers' role is to see that processes are followed; they're tactical in nature. Their job is to continually demand better of their teams, even when performance is high. Do they need these qualities to succeed?A leader could be the manager, but they don't have to be.

A leader can be anyone that is inspiring the team to do more. There's part of the manager's job description that includes that, but the best managers are the ones that are developing leaders, so they're not the only one playing a leadership role.

This is because things are changing so quickly. Compared to history, where a leader could paint a vision and expect that vision to hold true for a long time and reinforce the vision but not have to think about how to change it. Today, things are going so fast that the visions need to be put out there far enough that people can be working towards them but recognizing that we're going to learn a lot more in a shorter amount of time and likely change those visions. Leadership becomes even more important to make sure that everybody is clear on what the vision is, but also clear as we learn more and the vision changes.

The job of management is to remove obstacles that are in the way. As teams work faster, there is more friction. Optimism and persistence are tools in the management toolbox they can use to get things to move faster towards the vision. Having an optimistic attitude where you're looking at everything that people do with positive intent, then you're less likely to have the friction that could slow you down. You're less likely to have misunderstandings, because you're seeking that clarification, as opposed to trying to fight against ideas.


So optimism is the proverbial glass is half-full attitude, right? What about persistence? Is that self-explanatory?

A big part of it is self-explanatory. That's the continuing to strive toward the vision part, to not give up. I've found environments where you're trying to change quickly; there's something that we call "change fatigue" in the teams where it just feels like everything's changing too fast.

Having some persistence and optimism within the team helps to overcome change fatigue: "We're making progress. We are getting in there. We can't give up now.


"What's the difference between persistence and being stubborn?

That's a good question because it is a fine line. I would say that the ability to learn is going to counteract being stubborn. Where persistence is going to keep you moving forward. If you learn something new, you're going to adapt but keep moving forward. You're still able to change. Stubborn, to me, is when you're not open to change.

If you're open to change, if you see the new things but know what you are doing is still a higher priority, then you need to keep pushing forward, but articulate it as, "Yes, that's a good idea. But it's not as important as what we're doing right now. Let's do that next." Stubborn would be, "No, this is the plan, we're not going to change it. We're going to keep going." You're not hearing that there's something else that might be better.


Do you have examples of that from your professional life?

I've got examples of both. In the early days at Microsoft, I was on the MSN team [MSN, short for the Microsoft Network, is Microsoft's version of AOL and Yahoo!'s homepages] when they did the 2.0 launch. And they were confident that they had the right content and everything to make it good. But we were trying to explain to them that the way they were building it was going to be slow and it wasn't going to perform. And they didn't want to hear it because they thought that they had the right approach. And it ended up being a disaster, and it took months to recover.


What is it about optimism and persistence that removes friction and keeps teams focused? Because if you just take a well-designed business process, that would also remove friction, correct?

It's a good question. I don't know if I've got a great answer there. It's been more my experience in seeing it work as opposed to drilling into the psychology of it. If you add optimism and persistence to the team executing the process, when they run into issues, optimism is going to help you find new opportunities faster.

It's going to help eliminate some of the miscommunication that happens within teams or between teams without that optimism. Communication's never perfect. When people hear something, if it doesn't sound like their picture of how things should work, they start making assumptions. If their assumptions are not optimistic, if they are on the negative side, then they're going to start filling in an ulterior motive. If you have an optimistic view, if you always assume positive intent, it cuts off all the friction that would have been created from the negative assumptions.


Can this be learned or are these qualities innate?

Yes. People that have had a bunch of negative experiences in their life are going to have a harder time learning it, but it can be learned. You need to be open and recognize where people have had difficult experiences and help them see that you value what they've learned from that.


How do you teach it? Do you send them to optimism training or something? Or is it just by example?

It is harder to do as a training class. It's more like the things we talked about when you're trying to instill culture, where you have to explain to people what you're looking for and then, as leaders, you have to be able to model that. And all the incentives and rewards and recognition models must tie in to support it.


Okay. So last question: How would you, as the leader of your team or how did you, as leader of your team, instill these values?

We made it a value in our team that we would assume positive intent. It's hard to tell people to be optimistic, but you can say, "If you see anything that doesn't seem right, assume that the person had a positive intent and ask them, as opposed to assuming that they had some nefarious purpose.


"People really had that negative a view of their colleagues’ intentions?

The old Microsoft culture was so competitive between people and teams, people often would assume, "Well, they're just trying to make themselves look good," or, "They're just trying to make me look bad," or, "They're just trying to get something for their team," as opposed to if they had the best intents for the company.

Bill [Gates] purposefully instilled that competitive culture, the "smartest person wins" culture. He has since, in an interview he did last year, talked about how he wished that he would have understood earlier in his life that intelligence wasn't everything and that they hadn't instilled that type of culture.

[Steve] Ballmer's on record as saying that he was afraid to change the culture that Bill had put in place. So that perpetuated that culture. Satya came into the CEO role having told the board already that he felt what Microsoft needed was to change the culture and had the full support to do that, including Bill, who still on the board.


»Read next, on Emerge:

  • Five cloud computing predictions for 2019
  • Forrester’s “Transformation is Pragmatic” report: What to expect in 2019
  • Five cybersecurity predictions for 2019

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