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Could Siri Become
Your Leadership Coach?

Challenging Thinking Series

Challenging Thinking is a series of Think Pieces—essays, videos, and other content—that ask and answer bold questions about leadership. While the leadership-related topics vary widely, each piece will inspire novel thinking.
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Artificial intelligence may one day provide actual leadership coaching. But is it a matter of inevitable innovation, pure science fiction, or maybe a bit of both?

By Mike Hoban

Thinking PointsWhat if you had a resource—a personal advisor shared with no one else—one with great listening skills and that is available 24/7? One that knows you extremely well because of the personal information you have shared. One that can be completely trusted with no hidden agendas, that literally remembers every word you say and how you say it, and that has immediate access to a vast array of information, knowledge, and best practices on leadership and management from the cyber universe. Oh, and one other thing—this resource also can learn to be an even better advisor to you based on additional information gathered about you every day.

If offered such a resource, I think most leaders would shout, “Yes, yes!” And then they would ask, “But what’s the catch?” Here’s the catch: that resource would be a machine. A device. A collection of bits and bytes, of 0’s and 1’s. A bot.

Successful leaders in both the public and private sectors have trusted advisors, confidantes, and mentors. They depend on them for insights, for floating trial balloons, for (sometimes) getting unvarnished feedback. Occasionally they just need someone to listen, someone who can be trusted to maintain a cone of silence after a conversation. Those advisors are drawn from a variety of sources—old friends, colleagues, spouses. But the commonality is that all those people leaders depend on are, well, people. Humans. Homo sapiens.

It’s conceivable that in the not-too-distant future—perhaps 15 to 20 years out—one of those advisors will be a machine.

Sci-fi speculation?

Great strides have been made in artificial intelligence (AI), “deep learning,” and voice recognition. And popular culture has taken notice. The 2013 movie "Her" featured a relationship between a writer and “Samantha,” his non-human virtual assistant. Samantha demonstrated emotional intelligence behaviors and the interactions between the human and the device were very much human-like. Star Trek’s USS Enterprise has its omnipresent conversational onboard computer and, almost 50 years ago, “HAL” in Stanley Kubrick’s classic film "2001: A Space Odyssey" also demonstrated highly conversational language skills and ultimately learned how to learn, which did not turn out well for the human commanders of the spaceship.

Will Siri 4.0 (or Alexa 4.0 or Cortana 4.0 or Google Assistant 4.0) be sophisticated enough to serve as a leader’s personal coach and confidant for situations such as resolving conflict with peers, managing staff performance issues, or even developing leadership skills?

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While it might be easy to dismiss such a premise as nothing more than sci-fi speculation, we should remember that just five years ago, the thought of having driverless cars in our lifetime was considered preposterous and pipe-dream George Jetson stuff (Come to think of it, even the futuristic George Jetson still drove his own flying car). And now not a day passes without an article in a credible publication speaking to the accelerated rate of innovation in that field.

Meet your assistant, “Bob”

Let’s look ahead, then. It’s the year 2035. These “personal assistant” devices are widely available and reasonably affordable. You remember when the first generation of these devices hit the market in the early 2010s and how rudimentary they were, in the same way the Pong game introduced in the early 1970s was the crude precursor to the more sophisticated video games that appeared in the ensuing decades. The personal assistant devices back then could (gasp!) order you a pizza, tell you how much a blue whale weighs, or play your music while it turned on your lights.

The idea of being able to talk to a device and have it talk back was so novel, so innovative. And while they made online shopping easier and helped drive credit card indebtedness, the attraction was not so much functionality as cachet and coolness. The techno-wow factor turned lots of people into early adopters.

But this is 2035 and as with many other forms of technology, the advances from generation 1.0 to 4.0 have been exponential (think hockey stick-shaped trajectory). New must-have features drove demand, which spurred further investment in increasingly sophisticated interactive technology. The current models come equipped with a Brobdingnagian vocabulary (available in multiple languages for an upcharge, of course) and highly sophisticated voice recognition capability. And while it’s connected to the universe of knowledge, the device is controlled only by its owner and has formidable anti-hacking protections.

This is your first foray into the world of this technology; you are no early adopter. You have always had advisors and go-to people, but they were just that—people. However, colleagues who use these highly advanced personal assistants extoll their virtues. So, intrigued, you bought one.

Like with any new relationship, you and your device need time to get to know each other. The first few days or weeks will simply be your device (let’s call it Bob) getting to know you. In conversation, Bob will ask the same kinds of questions that any new acquaintance would: questions about where and when you were born; your education and the schools you attended; the names of friends and family members; your work history. But Bob will also ask you about your greatest hopes and fears. In fact, many of the questions Bob will ask would be considered intrusive if they came from a new acquaintance who happened to be human. But Bob needs to know all about you, dark stuff and all, if he is to bring high value to you as a leader.

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During the conversations, Bob might ask why you got slightly emotional with one of your responses. You see, Bob has access to even your most subtle of physiological changes in heartbeat or breathing rate because, thanks to the rise of the Internet of Things (IoT), the physical sensors woven into your clothes and imbedded in the jewelry you wear are sending constant streams of data about you. Bob is taking it all in, processing it, storing it. After a few days, he will know which words or situations will elevate your positive state or, conversely, bring you down or make you sweat.

It’s all good, though. After all, you not only want Bob to know your strengths and capabilities but your insecurities and vulnerabilities, too. You want Bob to know you almost better than you know yourself because all that information will enable Bob to serve you better. If Bob understands your typical thinking patterns and emotional states, he can challenge (respectfully, of course) your usual way of solving problems or identifying opportunities, which will potentially lead to superior outcomes and choices. He can help make you a better leader.

You can also help Bob help you by providing even more data through a series of psychological batteries and preference instruments that Bob will offer you. IQ; EQ; MBTI; MMPI—there will be many to choose from. Bob will want to know about work-related data: performance reviews, 360 assessments, org charts. He’ll have access to your calendar and will likely manage it for you, as well.

Perhaps a month after you and Bob have become “friends” there arises an opportunity to seek advice or coaching from him. You are responsible for a department and you have a peer in another department whose priorities are different from your own and there have been clashes between staff from both units. This peer has a reputation for being thin-skinned and unapproachable.

Your interaction with Bob about this situation might go like this:

You: “Bob, I have a situation I need some help with.”

Bob: “What is the situation and what sort of help can I provide? And by the way, while these days it is of conventional usage, I must note that you ended your sentence with a preposition.”

You: “I’m looking for some coaching from you. You see, I have a colleague named Karen…”

Just as with an effective coaching conversation between two people, Bob starts off by collecting information, ensuring understanding of the situation, and exploring context. Because you have identified this as a coaching situation, Bob, who has instant access to coaching best practices, takes an inquisitive and “guided discovery” approach to the conversation, as opposed to jumping immediately to being prescriptive with a solution. Bob asks probing questions to make you think through potential solutions.

Before the conversation is over and you have identified one or two options for how you will take action, Bob might say, “Another option to consider that we did not talk about is X…” So, Bob is providing support without removing responsibility, a fundamental coaching skill that he “knows” because of the initial behavioral database he came preloaded with (you purchased the “business” model, after all) and other information he has since acquired from the web.

Four days later, after the meeting with your peer, Bob, like any good coach, asks you how the conversation went. He told you he would do this and it’s on his calendar for today. Bob never forgets anything. Never.

After a robust debrief, in which Bob asks you what you did, what you said, and how you executed the plan the two of you created, he asks what you would do the same and do differently next time, so that there is learning and improvement on your part. And Bob will note it all and read it onto his limitless memory storage.

Encouraged by this successful coaching, you ask Bob to set up a role-playing activity for the two of you tomorrow for another challenging situation. Upon completion of that activity, Bob will give you feedback on your performance, again based on best practices, playing to your strengths and avoiding your derailers.

“A suspension of belief”

Back to 2017. Is the scenario I’ve just described within the realm of possibility? A review of expert opinion suggests the answer is, unequivocally, “maybe.” Ray Kurzweil, inventor (optical character recognition and the flatbed scanner), author, entrepreneur, futurist, recipient of 20 honorary doctorates and awards from three U.S. presidents, and who has written and TED-talked about the subject says, yes, it’s plausible. He is a proponent of a provocative concept called “The Singularity” (it’s complicated), and predicts by the early 2030s the amount of non-biological computation will exceed the “capacity of all living biological human intelligence.” So yes, he would likely say having an advisor like Bob is probable.

Other scholars or big brain types aren’t so sure AI will ever be able to capture the nuance of peoples’ emotions to be Bob-like advisors. What’s more, many leaders appreciate an advisor with a sense of humor. Could these devices learn humor, which is often built on nuanced language and puns? If you said to Bob, “I once shot an elephant in my pajamas. How he got in my pajamas I’ll never know…” would Bob “get it?” Or would Bob point out that from what he knows about your physical measurements that it would be impossible for an elephant to get into your pajamas?

Vlad Sejnoha, chief technology officer at Nuance, Inc., a $2 billion global voice technology company has concluded that “ultimately, the real promise of AI… is not the creation of artificial companions, but an amplification of intelligence (ours) through the creation of amazing and transformative tools.”

Still others, such as famed physicist Stephen Hawking, are concerned about a dark, apocalyptic future marked by this sort of technological “progress” (Remember Skynet from "The Terminator"?) and have spoken out against its blind advance.

And, of course, there are the practical questions, evocative of the “If you build it, he will come” line from the film "Field of Dreams": If such a device could be built, would leaders buy it? Is there a market for it? Would a middle manager or an executive really close her office door and have a heart-to-heart conversation with what could be a silver disk sitting on her desk?

Here and now, in 2017, it does seem a stretch. And it might call for what poet Samuel Taylor Coleridge long ago termed “a suspension of belief.” But, 20 years ago, how many of us could have imagined talking to a device named Siri or Alexa or Cortana? I believe that by 2035 we will all be used to interacting with ubiquitous devices and that a percentage of leaders will indeed embrace a Bob-like device as a career and company competitive advantage. Who knows, by then leaders may also be willing to purchase an optional upgrade, such as Golf Pro Bob, to help take strokes off their game—with the help of an electronic agent.

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There could also be expert Bobs for other disciplines—Physician Bob; Lawyer Bob; Engineer Bob—all with extraordinary capabilities to access trillions of terabytes of data in a nanosecond to solve a problem, make a diagnosis, or respond to a search inquiry.

So, leaders, get comfortable with this kind of technology. Experiment. Be curious about it. Be a possibility thinker instead of a probability thinker. The Millennials entering the workforce now will have been in the work world for 15-20 years when Bob becomes available, and they have always been surrounded by devices and gadgets and technology. If it’s built, they will come.

Siri is a trademark of Apple Inc.

Mike Hoban is a senior consultant for DDI who works with executives in many different industries. He led DDI’s consulting teams in Hong Kong/South China and has written for Fast Company and DDI’s Talent Management Intelligence blog, and was also a business columnist for a Chicago area daily newspaper for many years. He takes way too many pictures of Lake Michigan sunsets.

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