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A while back, a manager requested my advice about moving a stalled initiative forward. She had sat down with her boss several times to discuss this, but nothing seemed to come from these meetings. After sharing with me her previous conversations on this, I noticed a trend and asked, “Have you ever asked your boss for help?”

She paused and then slowly responded, “No, I haven’t.” So, I went on to suggest that the next time she discusses this initiative with her boss that she begin by asking, “Nancy, I could use your help on something. May I discuss it with you?”

After her boss says, “Yes,” she is to thank her first, then describe her plan for moving the initiative forward and specifically telling her boss how she can help by asking, “Nancy, can you help me by doing . . .?”

Many times, as this manager did, we just expect bosses to suggest their help when we explain a situation. We might also be uncomfortable delegating upward, appearing inadequate or possibly receiving a rejection.

In this situation, the manager successfully moved the initiative forward by following this approach, but the point is this: bosses like to feel helpful too – they’re human. Of course, asking the right way helps. Bosses are more likely to help if we ask in a way that ties their help to us. This personifies our request. For instance, asking, “Can you help me by doing . . .” is much better than just asking, “Can you help?”

So, the next time a project stalls, an effort becomes difficult or a roadblock appears, ask your boss for help. Not only might you solve the problem at hand, but you might build a stronger relationship with your boss.

Even though writing down the problem can help us solve it, it’s also a form of defining the problem. Thus, we will tend to define problems according to a nomenclature that we typically use. Since problems don’t care how we define them, our problem-solving approach problem will tend to be clunky and segregated rather than smooth and integrated.

For example, below is a schematic. On the left is a typical functional perspective of business. On the right how a problem has no regard for those functional boundaries.

While obvious, we easily forget. For instance, if we define a problem as, “We need to generate more sales,” we will automatically tend to view it initially as a Sales & Marketing problem. In actuality though, many aspects such as pricing, delivery, servicing, management and technology could exist.

Therefore, in solving problems, it’s best that we assume the solution is an integrated rather than a segregated one. In other words, rather than ask something such as:

• Is this part of the problem?
• Does the problem affect this?

We should ask whether we can prove without a doubt that:

• This isn’t a part of the problem?
• The problem doesn’t affect this?

Thus, returning to the above example, rather than start from the premise that it’s a sales and marketing problem and then see if any other area is affected, start from the assumption it’s a business-wide, integrated problem and eliminate areas as we conclusively prove that they aren’t involved.

By assuming the problem is bigger and more integrated than we initially perceive it, we expand our field of potential solutions and success. Moreover, since we aren’t omniscient, it’s often better to assume the problem is more involved than it initially seems.

The article, “The Modern Matchmakers,” from the February 11, 2012 edition of The Economist contained two major business lessons that I’ve discussed earlier regarding the solving of people-related problems:

1. What people think they want isn’t necessarily what they will choose
2. When faced with too much choice, people have less energy to think about them

For example, the article cites the work of Eli Finkel of Northwestern University on speed-dating in which he found that “people’s stated preference at the beginning of the process do not match the characters of the individuals they actually like.” Furthermore, “that when faced with abundant choice, people pay less attention to characteristics that require thinking and conversation to evaluate . . . and more to matters physical.” In short, just as Sheena Iyengar of Columbia University and Mark Lepper of Stanford concluded that too much choice is demotivating,” Finkel found it can dull thinking processes.

As I had also done in an earlier post on online dating, we can translate these themes to our business efforts by asking three questions:

1. How much freedom does someone want?
2. What does someone really want; what will he really do or decide?
3. How much (and what kind of) thinking will someone require from a leader?

These further translate into more tactical questions for managers and executives such as:

1. How much flexibility or process must I give someone?
2. What differences do I see between what he wants and what he actually does?
3. What kind of decisions do I give her to make and what (or when) do I decide for her?

Complicating this further is the fact that the answers will vary for each employee, requiring deeper and more interpersonal skills from managers and leaders. Are your managers up for the challenge?

Previous post on online dating:  What the Failures of Online Dating Can Teach Us

YinYang, as expressed by the Taijitu symbol, has helped me solve many problems. The two major components represent the two major opposing forces in any event. The smaller part of each in the other represents the interplay between the two.

I have extracted five principles from YinYang that have helped me. In short, optimal solutions will:

1. Have opposing forces (i.e. ideas, emotions, things) at work
2. Not choose one force over the other
3. Balance and integrate the two forces
4. Have one force as dominant and the other supportive
5. Vary by situation

For example, let’s consider the problem of how much to water a plant. Two forces exist, dryness and wetness (#1). If we choose dryness over wetness by never watering the plant, it will die. If we choose wetness over dryness by constantly watering the plant, the plant will die (#2). Thus, we need to integrate the two and find the right balance between watering and drying (#3). In this balance, the plant’s soil will be mainly dry or wet (#4). This balance varies by plant (#5, i.e. cacti versus willows).

In business, we often view these as tradeoffs such as processes versus flexibility, positive versus negative reinforcements, best practices versus differentiation, focus versus situational awareness, change versus resistance, profits versus investments, and glass half-full versus half-empty. However, tradeoffs encourage the temptation to choose one over the other; it’s really about integrating the two (#4).

Many times, it’s difficult to identify the opposing force. So, I ask myself this question:

If I take an obvious solution to the extreme, what would happen?

For example, too much process makes everything bureaucratic. Too much importance on profits retards investments. Once accomplished, we can begin balancing the two to arrive at an optimal solution for the situation at hand.

We often don’t learn the value of listening techniques in building relationships. Consequently, people might not realize we are listening; this needs to occur to build relationships.

Closed questions encourage specific or limited responses. For answers, they usually require one word, short phrases or a response from a menu of possibilities. Often, they begin with the words, “Who,” “How,” “What,” “Where” and “When.” “Yes” and “No” are often typical responses.

Even though many discount their value, when combined with other listening techniques, closed questions become extremely valuable in building relationships. They clarify specifics for us, pinpoint the facts, verify what we heard, nail down agreements and commitments, and test whether we can move.

Some examples include:

• Are you going out to the plant? (Yes/No)
• Which color do you want? (Facts)
• You want me to call the vendor . . . right? (Verification)
• Is seems you’re saying [X], correct? (Verification)
• Would today, tomorrow or the next day be better? (Menu)
• Do you agree? (Agreement)
• Will you help me? (Commitment)
• Do you need to tell me anything before we move on? (Testing)
• Is there anything else I need to cover? (Testing)

From a relational perspective, closed questions convey the feeling that you:

• Have a purpose for your conversation
• Grasp the details
• Understand them
• Respect their time by getting to specifics

The effect of closed questions is to encourage people to:

• Conclude that you’re listening and digesting
• Focus and sort through fuzziness
• Shorten their answers
• Clarify agreements and commitments

Closed questions have downsides. They can make discussions feel every interrogative and restrictive if used alone. Nevertheless, when integrated with other listening techniques they can reduce misunderstandings, demonstrate that you’re listening and build relationships.

When learning listening techniques, we often don’t learn their value in building relationships. As a result, we might be listening, but the other person doesn’t know it. The latter must occur to build relationships effectively.

Open-ended questions encourage a wide range of responses. Pragmatically, they retrieve an accurate assessment of the person’s thoughts and feelings. Relationally, they invite longer, deeper responses. This encourages feelings of freedom thought and expression.

Often, they begin with the words, “How,” “What,” and “Why,” or can include phrases such as “Tell me about . . .” and “Fill me in on . . .” Wording and tone should encourage the expression of thoughts and feelings, not just facts.

Some examples include:

• How do you think this project will go now?
• Fill me in on what you feel you want me to do.
• Why do you think Mary would be better than Nancy?
• How do you feel about that?
• What’s your reaction to Bill’s comments?

From a relational perspective, open-ended questions convey your desire to have answerers feel:

• Free to answer as they please
• You value their thoughts and feelings
• They control the direction of the discussion

The effect of open-ended questions is to:

• Minimize negative emotions
• Establish the questioner as someone with whom it’s easy to converse
• Encourage conversation and a longer interaction period
• Direct conversation with a talkative person

The downside of open-ended questions is that they can make discussions feel scattered or lacking purpose. That’s why we need to integrate them with other relationship building techniques.

Nevertheless, open-ended questions are often the first listening technique we learn. However, they let the other person know we are listening to them because we can’t use them well if we aren’t.

In the November 2010 issue of the Harvard Business Review Jeff Weiss, Aram Donigian, Jonathan Huges discuss in their article “Extreme Negotiations” the importance of affecting process not just outcomes in negotiations. The same holds true in problem solving since negotiations are only problems of bringing two sides to agreement. Thus, you can get different solutions by changing your problem-solving process.

In one simple situation, Manager A took the initiative of drafting a plan for review. Manager B did not like it. Thus, they decided to collaborate on the next rendition. As another example, two hiring managers couldn’t agree on a candidate, so they changed the process by requiring the candidate to write a business plan for his hire.

Here are some techniques I use to alter the problem-solving process. I change the:

• Process by having another person or group create it
• Point at which people work independently and then come together
• Definition of the problem to include more lower-tier variables
• Makeup of the people or teams involved in the process
• Documentation required even to the point of using different forms and templates
• Timetable of when a solution is needed
• Any screening and filtering steps to allow more or fewer options
• Stakeholders involved in the process usually by adding new ones
• Objective of the process such as focusing on options not the solution
• Facilitator of the process
• Location of any meetings such as from office to offsite
• Forum for any meetings such as in person versus video conferences
• Initial parameters of what constitutes a viable option for processing

Of course, each problem-solving situation presents its own additional aspects that could effect change in process. So, if you’re not getting the solutions you want, change the process.

In this series’ previous post, I wrote about using Wordle to help identify word usage and phrasing trends by people as a prelude to identifying personalities in a real-time sense. In this series’ first post, I wrote about using everyday conversation to identify personalities. In this post, I will combine the two concepts to validate our findings, which I call extrapolation. Essentially, we try to predict responses to our questions by changing topics.

For example, after listening to someone, we notice he talks extremely pragmatically about things. Extrapolating, we can ask him a couple decision-related questions such as, “Why do you like your house?” In our minds, we predict a pragmatic response. If he does respond with answers such as, “It’s close to work,” “In the school district we want,” and “We were able to get a good price,” then they support our findings. However, if he responses with, “The setting is beautiful,” “We liked the ambiance when we walked in,” or others, we know we need to work further.

Again, the challenge is being able to spot trends in word usage. The series’ previous post lists five other word pairs in addition to the one here: pragmatic versus emotional. Another challenge is avoiding iron-clad perceptions of people; our observations and conclusions should be ongoing and fluid as new discussions arise. It is quite possible for people to assume different personalities in similar situations depending upon their moods.

For instance, people will often behave one way when they’re happy and another when they’re angry. That’s why results from classical self-reporting personality assessments can vary. The book Was That Really Me? by Naomi Quenk does an excellent job highlighting this phenomenon.

However, this only reinforces the persistent point that personality assessment requires ongoing practice and modification.

Other posts in this series:

• Assessing Personalities thru Everyday Discussions (1.0)
• Real-time Personality Assessment (Pt 2): Important Qualities
• Real-time Personality Assessment (Pt 3): Word Themes

The inverted problem-solving technique (IPT) involves looking at the opposing aspects of a problem. To see IPT’s value it helps to write down the problem. In simple terms, if the problem involves “doing something,” IPT suggests exploring “not doing it” as a potential solution (or “to do it” if “not doing it”).

For instance, I first ran across it as a child when I wanted to learn to play. The book, Complete Chess Course, by Fred Reinfeld had a section called “The Nine Bad Moves.” Rather than immediately teach you good moves, Reinfeld had you learn what not to do. Later, I applied the concept when I developed my training methods: I first identified what I didn’t like about training that I took.

We often spend extensive time evaluating and determining the best solution. In reality, there are often many solutions. Thus, IPT suggests that we look at avoiding a bad decision as a potential solution rather than trying to determine the best. For example, in change initiatives and technology rollouts not only ask, “What can we do to make this successful?” but also ask, “What shouldn’t we do?” Too often people only focus on what needs doing to solve the problem.

Additionally, IPT helps us explore problems deeper by qualifying its various parts. Often, we only ask, “Is this part causing the problem?” Such an evaluative approach limits us to “yes/no answers.” Rather than ask “Is this department hindering the rollout?” ask, “How is this department hindering it?” and “How isn’t it?”

We can even apply these questions to the problem itself (Why is it a problem? Why isn’t it?). After all, it’s not unusual to find people working on the wrong problem. Moreover, the answers themselves will help us find solutions.

In “Before You Make That Big Decision,” which appeared in the June 2011 Harvard Business Review, Daniel Kahneman, Dan Lovallo and Olivier Sibony* suggest that one way to overcome unconscious biases in decision making is that we ask the question: Is the base case [for the decision] overly optimistic? They make the point that:

• “Most recommendations contain forecasts, which are notoriously prone to excessive optimism.”
• “Groups with a successful track record are more prone to this bias than others . . . [especially if the] . . . team has been on a winning streak.”

However, in daily business life we often view those who try to rein in or express contrarian views as downers. As a result, in the desire to show who is less negative, a race to the top of optimism’s ladder begins and at some point becomes Pollyannaism.

Moreover, as we saw in the benefits of viewing a glass half-empty rather than half-full, the fear of being in an adverse situation can be a powerful motivator for taking action. Thus, a Pollyanna state could reduce a group to complacency. That means a team in the midst of success is less likely to change than one in the midst of crisis.

While clearly defining the demarcation zone between optimism and Pollyannaism is difficult, it once again highlights the failure of success and casts doubts on “nothing breeds success like success.” In fact, as the writers suggest, the best indicator that Pollyannaism might have infected a business culture is the degree of success it has been having.

After all, it’s kind of hard to reach a Pollyanna State if you’re not even in the State of Optimism.

*Olivier Sibony is a director in McKinsey’s Brussels office.