How to Recognize Your Blind Spots Before They Derail Your Career

 

Drivers know to watch for their blind spot when they’re on the road, but there are other blind spots in your life you need to look for–things that can trip you up if you’re not careful. From skill gaps to behavioral issues, areas of personal vulnerability can stop you from reaching your potential, and it’s important to identify and correct them, says Carter Cast, professor of business management for the Kellogg School of Management at Northwestern University and partner with Pritzker Group Venture Capital.

“People who have an inflated sense of skill level are six times more likely to derail in their career than people who have an accurate self-assessment,” says Cast.

Blind spots happen because most of us have a hard time being objective about ourselves, says Cast. “It’s generally painful to recognize a weakness or accept that you’ll never be strong in a particular area,” he says. “What we can do is try to reach minimal level of performance in the area so it doesn’t impede our ability and hurt us.”

Five common areas for blind spots are detailed in Cast’s new book, The Right—and Wrong—Stuff: How Brilliant Careers Are Made and Unmade:

  1. A me-first attitude that leads to poor listening skills
  2. Micromanaging others, hindering your ability to build and lead a team
  3. Being too comfortable with routines and resisting change
  4. Having narrow perspectives on business that undermine your ability to be strategic
  5. Not following through on promises due to poor organization or task management skills

“Chances are high that you have an issue in one of those areas,” says Cast. “It’s nothing to be ashamed of—we all have blind spots. If you can understand them, you can manage around them.

HOW TO FIND YOUR BLIND SPOTS

Early in his career, Cast had a blind spot that nearly derailed him. “I was under a heavy-handed boss who was a micromanager,” he says. “Instead of understanding how he liked to work, I removed myself and tried to create more freedom and distance by not keeping him in the loop. It got to the point where the boss said I was uncommunicative and difficult, and I was kicked off his team.”

If you don’t have a boss who points out your blind spot, you’ll have to be proactive. First, get in the habit of formally or informally asking for feedback, says Cast. “For example, ‘How did I do in the presentation I just gave? What is one thing I could have done better?’” he suggests. “You can give a person the right to be direct by pointing out an area you think you need to improve, such as, ‘I thought that my introduction was too long.’”

Next, try hard to observe other people’s reactions to you. “If you are in a presentation or meeting, are they sitting with their arms crossed?” says Cast. “Are they staring two inches above your eyes? Fidgeting? If so, move faster.”

Finally, seek counsel with a coach. “When I was younger, I never relished the idea of getting a coach,” says Cast. “I was dead wrong. Hiring a formal career coach is smart and useful for asking for advice. They can help you see what you’re blind to.”

CORRECTING YOUR BLIND SPOT

Whether you have a skill gap or a behavioral issue, you need to put corrective action in place by “applying constant, steady pressure to the area,” says Cast.

“Let’s say you are told you’re non-strategic, and you’re not promotable until you become strategic,” he says. “Ask yourself, ‘What does success look like in this area? And what will I need to learn?’ It can be smart to interview people in different departments who are good at those activities.”

Sometimes you can find work-arounds to your blind spots, such as outsourcing the task or simply relinquishing the duty. “You can hire people who are good at what you’re bad at,” says Cast. “Or you can seek help from other people so this area doesn’t stop you from progressing in your career.”

And request help from your boss. “Ask, ‘What will I have done in two years to make you think this is no longer an issue?’” says Cast. “Ask for specific examples of where your blind spot shows up in your work. Also find out which employee in your company models this behavior. Then put corrective plans in place, and keep it front and center so you don’t forget about it.”

Cast has written down his career blinds spots and posts them in the place he puts his belt away at night. “I look at my areas of vulnerability and assess how I did today,” he says. “Did I succumb, or did I work to make sure they didn’t come out to play?”

Travis Kalanick’s ‘Profound Apology’​ Is a Cautionary Lesson for Young Founders

(This is an article David co-authored with our Kellogg colleague Brooke Vuckovic for Entrepreneur Magazine)

The “profound apology” issued by Uber founder and CEO Travis Kalanick that he must “fundamentally change as a leader and grow up,” in response to a video showing him berating a driver that went viral, underscores how the pressures of a high-growth startup can undermine leadership development when and where it’s needed most.

In his apology, posted on the Uber site, Kalanick admitted, “This is the first time I’ve been willing to admit that I need leadership help and I intend to get it.” For Kalanick, who has also faced criticism for the culture at his company after sexual harassment allegations went public in a blog by a former employee, this is a crucial admission. The serial entrepreneur, who founded file sharing startup Red Swoosh in his early 20s and Uber in his early 30s, shows the importance of entrepreneurs developing holistically — vertically into self-awareness and self-management, as well as horizontally across the skills needed to run a business.

Kalanick’s statement that, “My job as your leader is to lead…and that starts with behaving in a way that makes us all proud,” is also a cautionary tale for entrepreneurs who don’t put sufficient emphasis on personal and leadership development.

As our work with young entrepreneurs shows, capturing the investors’ interest takes more than just a great idea or even good results. Founders who exhibit self-awareness, leadership ability and agility, and who can grow along with their company, will be more likely to go the distance. The intensity and pace of launching and scaling a high-growth startup are so great, young founders, in particular, must pay attention to the amplifying effects of speed on their leadership. Entrepreneurs who develop holistically establish the foundation for building the necessary confidence to manage complex relationships, competing priorities, and fast-paced decisions.

While it’s common for young entrepreneurs to have mentors, many of whom are experienced entrepreneurs and investors, much of the feedback from these sources is focused on the functional elements of business-building (product development, marketing, design, finance etc.). What’s far less common is thoughtful guidance on how these founders successfully evolve into leaders — and how their “executive DNA” may positively or negatively impact the success of their early ventures.

No matter how good the idea or convincing the business model, a startup rises and falls on the leader’s capacity to develop and grow alongside the business. There are three dimensions of awareness that deepen a young founders EQ.

Awareness One: Strengths, Weaknesses and Derailers

Without self-awareness of one’s strengths and weaknesses, it becomes difficult if not impossible to build a team with complementary skills and expertise. To gain this awareness, young founders need to reflect on the key strengths essential to the team and to the success of the business. They also should know when to rely on others’ strengths and perspectives.

The temptation among many organizations, including startups, is for leaders to gravitate toward those who are “same as me.” But as research has found, homogeneity can stifle creativity and hold back the organization. A team that is diverse in terms of gender, race and ethnicity, as well as experience, thinking styles, and background is better equipped to tackle problems and bring to bear insights that create breakthrough innovations. One cannot do this without a high degree of self-awareness.

Awareness Two: Orientation to Conflict

Without understanding their orientation to conflict, founders will struggle to manage difficult or disappointing conversations. Key reflections here are how they manage interpersonal conflict with others, and how they manage operational conflicts among competing priorities and commitments.

For founding leaders of startups, there’s no avoiding bad news, disappointing results, tough feedback, and making hard decisions that leave others unhappy. A “softer” version of conflict comes into play internally as the young founder struggles with when and how to say no. The leader who learns the art of a “positive no” is more apt to maintain a laser focus on priorities in the business and in their personal productivity. They will also avoid the classic trap of becoming over-committed and yielding anemic results across the board; unable to prioritize and delegate authority to others, particularly as the company grows.

Awareness Three: Your Values and Purpose

Though last on this list, knowing one’s values is perhaps the most important awareness founders must have, as their personal values establish their startup’s culture. Key questions here are what do you stand for, and why does this venture exist?

Much like the process of product development, developing one’s identity as a leader is an iterative, others-focused process that involves trial and error. However, the leader’s identity and toolkit are often developed at warp speed as their business begins to scale. Without a clear sense of one’s values and purpose, founders are less likely to project the optimism and confidence demanded of them, and are more likely to become over-invested in their image, less open to learning, and less clear about their goals.

In the corporate world, leaders typically gain these three dimensions of awareness as they build a sense of self over time, through training, experience, and classic management relationships. But high-growth startups are a “heat inducing laboratory” in which young founders are thrust into high-stakes leadership roles quickly, and sometimes prematurely, as the business scales and the team grows. This makes foundational coaching and interpersonal development more important early on, even before a startup is launched.  In this respect, founder-leader fit is a close second to product-market fit.

For many young founders, the first taste of executive leadership accompanies the excitement and pressure of a startup launch. For those who grow both horizontally across business functions and vertically in leadership maturity and skill, success may be more likely, and certainly more satisfying. Chances are, they’ll never have to apologize publicly for a lack of leadership maturity as Kalanick just did.

The 4-Step Guide to Refining Your Innovation Process

You may not have unlimited time to brainstorm, but you can do more to ensure that it’s on your side.

(This post originally appeared in Inc. Magazine and Kellogg Insight)

Time: you can kill it, call it, serve it, save it, make it, or get it to fly. But one thing entrepreneurs should not do with it, per David Schonthal, is leave it in a liquid state. Constraint, properly harnessed, can be one of the most powerful forces behind ingenuity. And no constraint is more powerful than time.

There are a lot of ways to deploy time successfully. Whether you are deciding to speed up or slow down processes, impose deadlines, or set aside time for reflection, the key is to be conscious of how much time you have and realistic about how you plan to allot that time.

Schonthal, a clinical associate professor of innovation and entrepreneurship at the Kellogg School and a portfolio director at IDEO, offers four key suggestions for how innovators can use time to their advantage.

Change Up Your Brainstorming Sessions

The first step of any creative process–generating ideas–can also be the most painful. Cue the mental image of your team members sitting listlessly around a conference table, ostensibly brainstorming but actually inventing new ways to doodle in the margins of their legal pads.

The best way to kick-start the idea-generation process may be to mix things up.

When brainstorming more creative solutions, one approach–backed up by Kellogg research–is to push yourself to brainstorm beyond your normal limits. Once you hit the wall, the thinking goes, you may still have a lot of very good ideas that have not made it out yet.

Schonthal swears by a process that is a bit more counterintuitive: hit it and quit it. Give your team a very short period of time–no more than 10-15 minutes–to get as many ideas as possible related to a specific prompt out on the table. Then work from there.

“People usually enter brainstorms with the wrong objectives and expectations in mind, so it’s no surprise they are dismayed with the results.”

“When you take a resource and constrain it, it forces people to do more with less, and oftentimes they come up with unexpectedly creative solutions,” Schonthal says. “So when you constrain time, it’s great for the process of being generative. People are always surprised by how much they are able to accomplish in three to four minutes. Just getting things out from the inside doesn’t take a lot.”

An important distinction Schonthal makes, however, is that he believes the best use of brainstorming is to set a general direction or vector for design, not that it will yield the

“final” billion-dollar idea right there and then.

“People usually enter brainstorms with the wrong objectives and expectations in mind,” Schonthal says, “so it’s no surprise they are dismayed with the results.”

Launch to Learn

Once your team has identified a concept to pursue, it is tempting to devote a lot of time to refining it before showing it to others. But that may not be the most effective course of action, Schonthal says.

“Something that’s been developed within a week–why not toss it out into the world and see what happens to it?” he asks. “Take the minimum viable version and get real reactions from real people.”

“Some of the earliest examples of Twitter and Airbnb products, they were literally just sketches,” Schonthal says. “But they were good enough concepts to put in front of people for reactions. Yes, there’s the danger of falling on your face, but you don’t want to spend $50 million making the same mistake that you could have made much sooner for less money.”

But will enough face-plants make potential customers wary of your creations? Not necessarily, as long as you are up-front about the fact that you are showing them products in beta.

“You can let them know, ‘Look, this is a work in progress. I just want to see your reaction to it,'” Schonthal points out.

“Consumers have become much more comfortable with looking at stuff long before it’s ready. Look at Google. They slap the word ‘beta’ right there on the masthead, so you know that you’re taking a risk in trying something that’s maybe a little bit ahead of its time.”

Iterate Often and Quickly

If you are launching in beta, you are accepting the fact that you will need to iterate–protoyping, testing, analyzing, and refining your product.

“People often don’t build time in for the iterative process,” he says. “They just assume that things will go well. They look at iteration as a very linear progression: you start at this stage, and you go to this stage. But the reality is, it’s totally messy.”

To allow for that messiness, Schonthal advises, factor in time for lots and lots of iteration cycles–but move through those cycles as quickly as possible.

He points to the experience of student entrepreneurs he oversees in Kellogg’s Zell Fellows Program, a selective venture accelerator. Initially, it takes the students three weeks to move through the first iteration cycle. The next cycle takes two weeks. By the end of the course, each iteration cycle takes less than a week, because the students have learned what “good enough” is.

That’s a crucial lesson, given how quickly things move in today’s product-development world.

“Innovation is faster today than it’s ever been,” says Schonthal. “What can be accomplished in a unit of time is completely different now than what it was when I started ten years ago. Innovation is going to be faster next year than it is today. It’s probably going to continue to go down, down, down, down.”

Take Time to Reflect

But structuring time for invention does not always mean speeding up processes. One of the most important steps in the design process–synthesis–entails deliberately pausing to reflect on what has been observed. And it is a step that is often overlooked.

“I can’t think of very many organizations that create a very clear project objective for reflection,” Schonthal says. “Usually it’s ‘Go, go, go, go, go! What’s the next step? What’s the next step?’ Well, sometimes the best next step is taking a look back at what’s happened already.”

It is natural–even expected–to realize during the synthesis process that the problem you have set out to solve with your product may not be quite the problem your product solves. That may seem like less than great news, but there is an upside: taking time to reflect makes course correction possible.

“Trying to rush synthesis is the kiss of death,” he says. “Unexpected insights necessitate reflection. They’re never on the surface. If they’re on the surface, they’re obvious to everybody, and they’re probably not all that innovative.”

 

Here’s What Can Happen When You Don’t Check Your Ego at the Door

(Originally published by David in Fortune Insiders)

A mistake that is not only foolish in the moment, but that can have long-term negative impact is letting difficult decisions linger. Maybe you’re procrastinating on dealing with a “people issue,” such as needing to let someone go for the good of the organization. Or, perhaps you’re reluctant to admit that your current business strategy or product just isn’t working out and you need to start over. If you agonize over informing stakeholders of a problem that has come to your attention, issues like these will only get worse.

Many of us tend to avoid the hard things — the decisions and actions that may make others unhappy or prove to be unpopular. As humans, we don’t like to be the bearer of bad news and disappoint people.

With difficult decisions, though, the longer you procrastinate in taking action, the worse things can become. For example, firing someone can be painful, and having empathy for the person to be terminated may delay your decision. But the longer the person stays in a job that, for whatever reason, is no longer a good fit, the worse it is for the rest of the organization. In my own experience, I can recall situations in which people needed to be let go, but we dragged our feet on making the decision because it was hard (not because the choice wasn’t clear). By the time we acted, what had started as a manageable problem had mushroomed into a major organizational issue.

When it becomes clear that a product or strategy isn’t working, the thought of disappointing stakeholders can be so overwhelming that you put off the decision to change direction or go back to the drawing board. That reticence may be tied up in not wanting to disappoint others, including customers and investors. But often, there is a deeper reason — ego. You’ve invested so much time, money, and energy into a particular strategy or product, that now you’re disinclined to admit that you were wrong. In this instance, your reticence to make the decision is all about your need to be right.

In startups, the ego issue is further inflated because of the glamour associated with entrepreneurship; you may tell yourself that the only way to bask in that glow is to be right. With this thinking, “humble pie” becomes very unappetizing. True entrepreneurial leadership, though, requires having the maturity to know that things don’t work out all the time. Moreover, telling investors about a problem as soon as it hits your radar may actually net a positive , even if the news is disappointing initially.

With startups and other early-stage companies, experienced investors expect problems and setbacks. Even more important, savvy investors have ideas, connections, and other resources that can help solve problems. But if you wait too long to tell your supporters, there may be nothing they can do.

There is another decision that should never be delayed: when there is an ethical problem. The longer a breach of ethics goes unaddressed, the worse the problem becomes — a potentially fatal mistake for the company, its brand and reputation, and its longevity. For example, Theranos is facing federal, civil, and criminal investigations after serious questions were raised about the validity of its testing products that were said to require only a few drops of blood. Theranos CEO Elizabeth Holmes has been banned from operating a laboratory for at least two years, and the company continues to face difficulties, including an investor lawsuit.

In contrast, consider the actions of Johnson & Johnson and its McNeil Consumer Products subsidiary when several people died in 1982 after taking Tylenol that, unbeknownst to anyone, had been contaminated with cyanide. The swiftness of the company’s response and the transparency of its actions allowed it to recover consumers’ trust and preserve the valuable brand. It’s hard not to wonder what would have happened had Theranos followed J&J’s lead and disclosed the reported problems with its blood tests as soon as they surfaced.

For startups and early-stage companies, the road forward is often bumpy and unpredictable. But being unable or unwilling to make tough decisions quickly will only compound problems, and lead you to regret a foolish mistake.

How to Nurture Your Superstar Employees

This piece is based on insights from Carter and originally published in Kellogg Insight

Most organizations have employees who are solid performers; fewer organizations are astute—or lucky—enough to have superstars.

So how can you ensure that your organization gets the most out of those superstars?

High-potential performers (or Hi-Pos) stand out due to their associative thinking skills—which help solve problems and drive innovation—their strong emotional awareness, and their incredible perseverance, according to Carter Cast, a clinical professor of innovation and entrepreneurship at the Kellogg School and former CEO of Walmart.com.

When your team lands a superstar-in-the-making, nurturing these traits is critical if you want that superstar to flourish. And tailoring a career plan gives high-flyers challenge enough to stick around.

“With high-potential high performers, it’s important to put your arm around them and say, ‘I think you have a lot of potential, and one of my key jobs is helping you reach your potential. I will get satisfaction out of helping you do that,’” says Cast.

Encourage Associative Thinking

One of the calling cards of valuable employees is the ability to innovate. But not everyone is automatically inclined to blue-sky thinking. Encouraging associative thinking—making connections between seemingly disparate ideas—can spur high-potential employees to become more creative and innovation-minded.

“Learning agility may be the most important trait of them all,” Cast says. “You are curious. You’re open to new experiences. You read a lot. You question things. You don’t take no for an answer—if something just doesn’t seem right, you go ahead and investigate it yourself. That trait drives creativity and leads to innovation.”

When Cast was at the CEO of Walmart.com, he had an interesting exercise to get his high-potential employees thinking creatively: a little bit of show-and-tell.

“As a leader, I can provide direction, clarity, and resources, and I can try to figure out what motivates an employee and then try to appeal to their motives.”

At Monday morning senior leadership meetings, the first twenty minutes were devoted to a simple question: What did you see over the weekend that struck you? Employees then shared any new trends, think-pieces, objects, or experiences that had captured their attention. “We had people bring up clothes, devices, articles, advertisements, circulars, you name it,” Cast says.

Next, they had to explain how these new trends or observations might positively affect the organization.

“People loved this open session because it was all about experience and application. You observe, capture, and try to parlay into what the company can do differently: If you saw this, what’s the application? If yes, then what?”

Cast advocates a healthy dose of career self-reflection for all employees, and those with high potential are no exception. Encourage them to consider: “What can impede your progress? What about you—we all have these things, because we’re humans—could hurt you? Where do you have weaknesses that could derail you? If you don’t want to come clean with me, at least come clean with yourself—talk to your friends, mentors, and colleagues to get a better understanding.”

Cast also suggests that employees look beyond their own intuition for skill gaps and other blind spots by utilizing 360 feedback. Putting a mirror up in front of people can help them recognize weaknesses, triggers, and gaps that may be impeding self-regulation and performance.

“Not putting your foot in your mouth, not butting in, not having flashes of anger, not receding into your shell when you’re challenged—basically, learning to modulate your behavior—allows you to present yourself more effectively, which can help you to be more effective with other people,” Cast says.

Remember, as well, the importance of developing an emotional awareness about others. High-potential employees need to learn how to really listen. “The basic principle is: seek to understand before being understood,” Cast says, “which can be hard for hard-charging Hi-Pos who are driven to complete their agendas.”

He reminds Hi-Pos to ask their own employees and colleagues how they can help. “Do you understand what goals and objectives they’re trying to accomplish? Do you understand what they need from you? If you help them, they’re more likely to reciprocate.”

Another way to cultivate that awareness of others is to make sure Hi-Pos actively engage across the organization.

“At Walmart, we encouraged our associates to get out from behind their desks, go out to stores, observe and learn,” Cast says. “We said, ‘you should shadow employees who handle customer checkout. You should shadow employees in electronics to see how they handle tough questions about how to install a home entertainment system. You should sit in the product return center to see firsthand how confusing the process is for customers to return an item they bought online to a store.’”

“Encourage them to go through an actual user scenario where they’re trying to buy something or conduct a task. It’s a really good way to get inside the experience of the consumer to see what they go through.”

Motivate, Motivate, Motivate

Employees with the grit and perseverance to keep answering the bell after getting knocked down will go far. But toughness is difficult to instill in people. It is most often a complicated, very individual drive.

“As a leader, I can provide direction, clarity, and resources, and I can try to figure out what motivates an employee and then try to appeal to their motives,” Cast says. “But ultimately they have to find a way to tap into what drives them. In the case of high-potential performers, they’re usually highly motivated and it’s more about tapping into it and directing it.”

Still, there is plenty that leaders can do to stoke employee motivation. For one, recognition can go a long way.

Cast and a colleague were in a shop in Bentonville, Arkansas and found a dusty red razorback statue at a five and dime store. “The guy gave us two bucks to get it out of the place,” Cast jokes. “We brought it back to our office in California, where the Internet division was headquartered, and we created a Red Razorback Award. Every quarter, the person that went above and beyond, or had a really good idea that improved the customer experience, got the Red Razorback.

“This ugly thing was actually coveted! I saw in resumes years later, where people wrote, ‘Red Razorback Award winner, Q2, 2006.’”

As you might expect, it is also crucial to make high potentials feel like they are improving their skills and working on projects with value.

Just don’t assume you know what counts as “self-improvement” or what motivates employees. You have to ask them. Here is a place where some leaders go wrong: they lay out a development plan without input from the employee. Cast once had an employee whom he was grooming to become a general manager. But it turns out, that employee was not looking to become a CEO. He wanted to become a CMO—the best retail and e-commerce marketer in the United States.

“I had the wrong assumption,” Cast says. “He wanted to be a functional expert. So we stopped and I said, ‘Let’s look at your skillset in marketing and where you think you have gaps, and let’s start talking about how we can fill those gaps.’”

“Treat different people differently,” Cast stresses. “Seek to understand their motives and what they’re trying to accomplish. With super high-potential people, I worked to create tailored programs to develop them, giving them unique experiences and access to resources in order to accelerate their growth.”

Cast opens these developmental conversations by asking high potentials where their passion lies—what they want to be doing in five to seven years—rather than starting with their current position. He then has them work backwards into their current position to create the through line.

“I always lead with their passion of interests and motives,” Cast says, “and then secondly, have them define areas where they have effortless ability or strong talents. So I like to start with passion and talents. Then, together, we can move on to how to apply it through projects, assignments, and other developmental activities. But I’ve found it’s key to ask them! Take nothing for granted and let them lead the conversation.”

Follow Through

You have invested in your superstars’ success. You’ve increased their learning agility and strengthened their emotional awareness. You have helped them to find their own passion and collaborated on a plan to keep them engaged and progressing. What could possibly go wrong? Well, a lot—if you leave the plan to chance.

Whatever you do, “don’t overcommit upfront and offer something you can’t deliver on,” says Cast. “Find a couple things you can do to help them, and then a couple more. If you talk a good game and don’t follow through with a cadence of assistance, it could be very detrimental, because you’ve set their expectations. It takes high potentials about five minutes after they don’t feel challenged to leave.”

Of course, superstars may leave a company anyway. But the chances are much better that they will stick around to realize their potential if they see that they are valued. “One, they’re going to be excited about the challenges, and two, they’re going to feel this affiliation towards you and towards the company for investing in them,” Cast says.

He likes to tell a story about one particular high-potential employee under his wing.

“I said, ‘You’re not going to leave here, because the opportunities we’re going to give you are going to be so phenomenal that you’re just not going to think of leaving.’ He laughed and said, ‘We’ll see.’ Seven years later, when I left the company, he was still working there.”

Calling an Audible

Carter and I were sharing embarrassing stories of our own well-intended presentations gone awry and we decided to write a quick blog about it.

Great quarterbacks in football tend to have a handful of attributes in common, not the least of which are a mastery of the playbook, the ability to read defenses and an on-the-spot ability to improvise based on what they see. (Just watch Peyton Manning make constant play adjustments as he barks orders on the line of scrimmage)

Like quarterbacks, good business leaders (be they entrepreneurs or otherwise) tend to possess similar improvisational qualities. They too have an ability to read their audiences and throw out the playbook and improvise based on what they see going on around them.

It’s this last point that we want to focus on – the ability to read your audience and “call an audible” if you don’t like how your message is being received. In some cases mastery of the playbook and reading an audience can be in direct opposition to each other. Mastery can sometimes become reliance on the playbook, and this can cause problems. Or mastery can lead to overconfidence, resulting in a lack of flexibility in adapting your message to the circumstances you’re facing.

Here are examples from each of us:

David’s recent experience:

This past month I gave a presentation to a group of executives. They were interested in a topic that I’ve spoken on a number of times, and my material on this subject was… if I may say so… pretty damn good.

I had delivered this presentation dozens of times and it had never once failed me.

Things started off decently, but it wasn’t long before I could see that I was losing the audience. I hadn’t adapted my material for their specific interests or vantage point at all, it was a tough time of day to talk to them (after lunch), and I could tell that the one-directional way in which I was delivering the content was not engaging them at all.

 Having read the situation, I had two choices:

  1. Stick to my material and my script and hope that eventually they would join me on my wavelength
  2. Stop what I was doing and change the game plan on the fly with some unrehearsed Q&A, stories or other conversational ideas in an attempt to reengage them

I wish that I could tell you I went with choice B, but I didn’t. I proceeded forward with more-or-less my original plan and probably brought about one-third of the audience along with me while other two-thirds silently stared at their smartphones.

If I were to have a do-over, I clearly would have done it differently. I would have stopped the presentation the moment I saw it going sideways, acknowledged it and asked for the audience to offer-up some stories/examples of their own, or even to share some contrary opinions – just to get a real conversation going. If I were particularly bold, I might even try to throw in some kind of an exercise to get them interacting.

Carter’s recent experience:

Actually I have two: one where I just chugged along (poorly) without making any adjustments, and one where things were going so badly that I did call an audible. In the first example, only a week ago, I delivered what I generally consider to be my best lecture, my signature move. Oh the pearl that were dripping from my lips! Bang! Pow! Zowee! How do you like me now?! There was only one problem: midway through delivering my magic, I noticed that people were giving me this certain “I’m digesting my Thanksgiving meal” look, eyes glazed over, arms crossed over bellies. It was like they were being held hostage to a Kenny G song.

What did I do? Like a person sinking in quick-sand, I thrashed about harder, increasing my decibel level and gesturing about wildly, like I was swatting at a bee. It didn’t work. A student came up to me after the lecture and said, “Professor Cast, that’s a long time to hold our attention in the middle of the afternoon.”

Here’s my second experience. Last fall I was at the Allen Center, delivering a lecture to a group of eMBA students who had just taken their final class exam and were ready to graduate. I’d decided to talk about Joseph Campbell and The Hero Journey. Good stuff, right? What’s not to like about the dragon-slaying message of The Hero Journey to a group of students about ready to walk out into the working world, armed with MBAs?

 Well, in this case I was worried from the get-go. These eMBA students had been celebrating the completion of their curriculum with a glass of wine and they were in a festive mood. I wondered if it was the right time and place to deliver a lecture. Nevertheless, I gamely started. But about eight minutes into my one hour lecture, I noticed that people were swiping through their smartphones, getting up to find more wine, even talking quietly to one another. So I did two things. I first politely asked one fellow in the front row to please remove his feet from the desk and put them back on the ground and then I turned off the projector and said, “This isn’t working. What do you guys want to talk about, if anything?” We ended up having a really good free-form conversation about career management and career direction…

These experiences got us thinking about past presentations, customer meetings, investor interactions and other important “playbook” moments. Funny enough, we both realized that some of our most effective and successful sessions were ones where we allowed ourselves to make unscripted, on-the-fly changes.

No question that these types of “audibles” come with inherent risk, and moving off script can be scary – especially when you’ve rehearsed a lot and feel like you have a really sound playbook. Yet there are few (any?) scripted plays that are more effective than having a genuine connection with the individual or group you’re speaking with, even if it comes at the expense of polish.

Oh well, we live and learn. We both feel like we can’t train for these moments. We just have to stay aware of our surroundings and remain flexible…just like a good quarterback.

“Proprioception”

Carter here.

In the spirit of SNL’s Deep Thoughts by Jack Handy, I’d like to share an interesting word I just ran across—“proprioception.” Literally, it means an awareness of the position of one’s own body. Figuratively, it can beg an examination of some worthwhile questions such as: “Am I self-aware right now? Am I well-oriented to the situational context in which I find myself? Am I in touch with what I’m projecting to others?” The word makes me think of being both the participant & observer simultaneously—having a healthy detachment from the moment, as I’m experiencing the moment. (This is stuff the Buddhists and Stoics advise us to do to maintain our equanimity.) Huh?—earth to Carter—what does this have to do with entrepreneurship? Here’s just one example of its application…In my venture capital job, on quite a few occasions, I’m at the receiving end of a pitch where entrepreneurs deliver a Phil Spector Wall-of-Sound monolog, not allowing me the opportunity to ask questions about their venture and explore ideas with them. Pitching is a dance and they don’t include me as their partner. In other words, the entrepreneur wants so badly to deliver their value proposition message and communicate why I should invest, that they lose their sense of proprioception.

Isn’t that a great word?

P.S. Note the Resources+ Tools section, which we’ve loaded up and will discuss more in days to come…