Great Coaches Ask, Listen, and Empathize

Historically, leaders achieved their position by virtue of experience on the job and in-depth knowledge. They were expected to have answers and to readily provide them when employees were unsure about what to do or how to do it. The leader was the person who knew the most, and that was the basis of their authority.

Leaders today still have to understand their business thoroughly, but it’s unrealistic and ill-advised to expect them to have all the answers. Organizations are simply too complex for leaders to govern on that basis. One way for leaders to adjust to this shift is to adopt a new role: that of coach. By using coaching methods and techniques in the right situations, leaders can still be effective without knowing all the answers and without telling employees what to do.

Coaching is about connecting with people, inspiring them to do their best, and helping them to grow. It’s also about challenging people to come up with the answers they require on their own. Coaching is far from an exact science, and all leaders have to develop their own style, but we can break down the process into practices that any manager will need to explore and understand. Here are the three most important:

Ask

Coaching begins by creating space to be filled by the employee, and typically you start this process by asking an open-ended question. After some initial small talk with my clients and students, I usually signal the beginning of our coaching conversation by asking, “So, where would you like to start?” The key is to establish receptivity to whatever the other person needs to discuss, and to avoid presumptions that unnecessarily limit the conversation. As a manager you may well want to set some limits to the conversation (“I’m not prepared to talk about the budget today.”) or at least ensure that the agenda reflects your needs (“I’d like to discuss last week’s meeting, in addition to what’s on your list.”), but it’s important to do only as much of this as necessary and to leave room for your employee to raise concerns and issues that are important to them. It’s all too easy for leaders to inadvertantly send signals that prevent employees from raising issues, so make it clear that their agenda matters.

In his book Helping, former MIT professor Edgar Schein identifies different modes of inquiry that we employ when we’re offering help, and they map particularly well to coaching conversations. The initial process of information gathering I described above is what Schein calls “pure inquiry.” The next step is “diagnostic inquiry,” which consists of focusing the other person’s attention on specific aspects of their story, such as feelings and reactions, underlying causes or motives, or actions taken or contemplated. (“You seem frustrated with Chris. How’s that relationship going?” or “It sounds like there’s been some tension on your team. What do you think is happening?” or “That’s an ambitious goal for that project. How are you planning to get there?”)

The next step in the process is what Schein somewhat confusingly calls “confrontational inquiry”. He doesn’t mean that we literally confront the person, but, rather, that we challenge aspects of their story by introducing new ideas and hypotheses, substituting our understanding of the situation for the other person’s. (“You’ve been talking about Chris’s shortcomings. How might you be contributing to the problem?” or “I understand that your team’s been under a lot of stress. How has turnover affected their ability to collaborate?” or “That’s an exciting plan, but it has a lot of moving parts. What happens if you’re behind schedule?”)

In coaching conversations it’s crucial to spend as much time as needed in the initial stages and resist the urge to jump ahead, where the process shifts from asking open-ended questions to using your authority as a leader to spotlight certain issues. The more time you can spend in pure inquiry, the more likely the conversation will challenge your employee to come up with their own creative solutions, surfacing the unique knowledge that they’ve gained from their proximity to the problem.

Listen

It’s important to understand the difference between hearing and listening. Hearing is a cognitive process that happens internally — we absorb sound, interpret it, and understand it. But listening is a whole-body process that happens between two people that makes the other person truly feel heard.

Listening in a coaching context requires significant eye contact, not to the point of awkwardness, but more than you typically devote in a casual conversation. This ensures that you capture as much data about the other person as possible — facial expressions, gestures, tics — and conveys a strong sense of interest and engagement.

Effective listening also requires our focused attention. Coaching is fundamentally incompatible with multitasking, because while you may be able to hear what another person is saying while working on something else, it’s impossible to listen in a way that makes the other person feel heard. It’s critical to eliminate distractions. Turn off your phone, close your laptop, and find a dedicated space where you won’t be interrupted.

Coaching conversations can take place over the phone, of course, and in that medium it’s even more important to refrain from multitasking so that in the absence of visual data, you can pick up on subtle cues in someone’s speech.

In my experience taking brief, sporadic notes in a coaching conversation helps me to stay focused and lessens the burden of maintaining information in my working memory (which holds just five to seven items for most people.) But note-taking itself can become a distraction, causing you to worry more about accurately capturing the other person’s comments than about truly listening. Coaching conversations aren’t depositions, so don’t play stenographer. If you feel the need to take notes, try writing one word or phrase at a time, just enough to jog your memory later.

Empathize

Empathy is the ability not only to comprehend another person’s point of view, but also to vicariously experience their emotions. Without empathy other people remain alien and opaque to us. When present it establishes the interpersonal connection that makes coaching possible.

A key to the importance of empathy can be found in the work of Brené Brown, a research professor at the University of Houston whose work focuses on the topics of vulnerability, courage, worthiness and shame. Brown defines shame as “the intensely painful feeling or experience of believing that we are flawed and therefore unworthy of love and belonging.” Empathy, Brown notes, is “the antidote to shame.” When employees need your help they are likely experiencing some form of shame, even if it’s just mild embarrassment — and the more serious the problem, the deeper the shame. Feeling and expressing empathy is critical to helping the other person defuse their embarrassment and begin thinking creatively about solutions.

But note that our habitual expressions of empathy can sometimes be counterproductive. Michael Sahota, a coach in Toronto who works with groups of software developers and product managers, explains some of the traps we fall into when trying to express empathy: We compare our issues to theirs (“My problem’s bigger.”), try to be overly positive (“Look on the bright side.”), or leap to problem-solving while ignoring what they’re feeling in the moment.

Finally, be aware that expressing empathy need not prevent you from holding people to high standards. You may fear that empathizing is equivalent to excusing poor performance but this is a false dichotomy. Empathizing with the difficulties your employees face is an important step in the process of helping them build resilience and learn from setbacks. After you’ve acknowledged an employee’s struggles and feelings, they’re more likely to respond to your efforts to motivate improved performance.

When you coach as a leader you don’t need to be the expert. You don’t need to be the smartest or most experienced person in the room. And you don’t need to have all the solutions. But you do need to be able to connect with people, to inspire them to do their best, and to help them search inside and discover their own answers.

Motivate by Telling Stories

How do leaders motivate their team? First, by hiring the right people. Internal drive cannot be taught. Once a person is hired, they must feel a connection. Without that connection to a moral purpose, productivity suffers, and the job becomes less fun. Going through the motions is not rewarding!

Connection happens when you see past the details of a task to its human consequences. When you feel connected to the moral purpose of your work, you behave differently. Now “moral purpose” might sound lofty but it needn’t mean saving a puppy or curing cancer; it can involve any kind of human service. And at the end of the day, all business is about service.

That’s where leaders come in. The first responsibility of leaders — whether front line supervisors, middle managers, or executives — is to compensate for the inevitable alienation that complex organizations create, and provide employees with a visceral connection to the human purpose they serve.

Leaders can maintain a lively sense of connection through storytelling. It needn’t be an elaborate ritual involving an audience gathered for a relaxed evening. It isn’t. Most storytelling is brief. It involves using concrete examples that reframe a moment by personifying human consequences.

People’s feelings about their work are only partly about the work itself. They are equally, if not more so, about how they frame their work. Do they see what they’re doing as a mindless ritual? Do they see it as empty compliance? Or do they see it as sacred duty? If you change the frame you change the feeling. And nothing changes frames faster than a story.

For example, in one study at a large healthcare provider, we examined why some employees were somewhat casual about hand hygiene while others were zealots. Hand washing in hospitals is one of the most critical factors in avoiding hospital acquired infections. While many doctors, nurses, housekeepers, and technicians were mostly attentive to this innocuous act, a handful of employees were relentlessly vigilant. It turned out this group was far more likely than their peers to have personally been infected in the past while they were a patient in a hospital—or had a family member who was. They were motivated because they had a personal or vicarious experience with the human consequences of a seemingly simple task, and that made them feel differently.

Research shows that once a task becomes familiar, our brains devote far less cognitive resources to it. One of the downsides of this brilliant design is that we disconnect. We stop seeing past our work to the people we affect.

Any organization where there is strong sense of moral motivation, the leaders are always storytellers. They understand and act on their responsibility to overcome the inevitable alienation of routine organizational life by connecting employees with those they serve.

Making Decisions

Intuitive problem solving is not always the best decision making process.

When Individuals Solve Problems Intuitively the Result Is Magic

To understand what intuitive problem solving is, we need to recognize first that when working out any problem, from picking out a necktie to solving a quadratic equation, we make our way through five stages:

Rather than progressing through these stages one after another, we move back and forth between stages before landing on a solution and making a plan.

For example, pretend you’re ordering food online. You begin by quickly generating a solution — Mexican (stage 2) — but as soon as the thought enters your mind, you evaluate (stage 3) and remember that you had Mexican the day before, so you generate another solution (stage 2) — Indian. Upon evaluation (stage 3), however, you fear your hefty Chicken Tikka Masala go-to might outsize your appetite. At this point, you take a step back and define the problem (stage 1), asking yourself “What kind of meal would leave me feeling satisfied but not overly stuffed?” A better question leads to a better answer: sushi (stage 2). You do a quick gut check to make sure sushi is truly what you desire (stage 3), and you move forward with your order (stages 4 and 5).

This is called intuitive problem solving, and it comes so naturally to us that, when we solve problems in this way, we’re wholly unaware that we are doing it. All we have to do is place our attention on the problem and, much like a car’s automatic transmission, our brain shifts gears for us. As a result, intuitive problem solving is remarkably efficient. Magical, even.

When Groups Solve Problems Intuitively the Result Is Often Chaos

Intuitive problem solving is so magical for us as individuals that we assume it should fare just as well for groups. When we hold a meeting, we gather around a table, place our collective attention on the problem, and let our automatic transmissions take over. But, all too often, this turns out to be a mistake.

In order for groups to collaborate effectively and avoid talking past one another, members must simultaneously occupy the same problem-solving stage. But because intuitions are private to their owners, attendees in group meetings are unable to easily discern what problem-solving stage they each are on. Consequently, members unknowingly begin the meeting on different stages.

Imagine a software team who gathers to discuss a disgruntled VIP customer, threatening, quite publicly, to jump ship to a competitor. While one attendee thinks the path forward is obvious and focuses on crafting an implementation plan (stage 5), another is intent on generating alternative solutions (stage 2), while yet another attendee is still trying to figure out whether the exit of this pompous hellion is, in fact, even a problem (stage 1). Perhaps it’s a blessing!

As the meeting progresses, things get even more chaotic. Without realizing it, each attendee continues to switch stages without notifying others. The result is a disorganized meeting that traverses many stages, yet conquers none.

To solve problems as a group, we need to jettison the assumption that intuitive problem solving is sufficient, and instead embrace a more methodical approach — one that homes in on just one problem-solving stage. In other words, we need to stop with the automatic, and start learning to drive stick.

The Power of Methodical Meetings

In a methodical meeting, for each issue that needs to be discussed, members deliberately and explicitly choose just one problem-solving stage to complete.

To convert an intuitive meeting into a methodical one take your meeting agenda, and to the right of each agenda item, write down a problem-solving stage that will help move you closer to a solution, as well as the corresponding measurable outcome for that stage. Then, during that part of the meeting, focus only on achieving that outcome. Once you do, move on.

A Template for Conducting a Methodical Meeting

Pair each agenda item with a problem solving stage and a measurable outcome.

Agenda ItemProblem Solving StageMeasurable Outcome
Select a venue for the offsiteGenerate solutionsList of potential venues
Discuss VIP customer issueDefine the problemProblem statement
Implement new sales strategyMake a planList of actions / owners / due dates
Review new budget proposalsEvaluate solutionsList of strengths and weaknesses
Choose a new ad agencyPick a solutionWritten decision

If you don’t know which problem-solving stage to choose, consider the following:

Do you genuinely understand the problem you’re trying to solve? If you can’t clearly articulate the problem to someone else, chances are you don’t understand it as well as you might think. If that’s the case, before you start generating solutions, consider dedicating this part of the meeting to defining the problem (stage 1) and ending it with a succinctly written problem statement.

Do you have an ample list of potential solutions? If the group understands the problem, but hasn’t yet produced a set of potential solutions, that’s the next order of business. Concentrate on generating as many quality options as possible (stage 2). Even if you end your discussion with only a slightly longer list than with which you began, you’ve made important progress.

Do you know the strengths and weaknesses of the various solutions? Suppose you have already generated potential solutions. If so, this time will be best spent letting the group evaluate them (stage 3). Free attendees from the obligation of reaching a final decision—for which they may not yet be ready—and let them focus exclusively on developing a list of pros and cons for the various alternatives.

Has the group already spent time debating various solutions? If the answer is yes, use this part of the meeting to do the often difficult work of choosing (stage 4). Make sure, of course, that the final choice is in writing.

Has a solution already been selected? Then focus on developing an implementation plan (stage 5). If you’re able to leave the conversation with a comprehensive list of actions, assigned owners, and due dates, you can celebrate a remarkably profitable outcome.

Most bad meetings are not caused by lazy, power-tripped leaders, or entitled, self-centered attendees. Instead, they are caused by a simple mistake made by everyone involved. We assume our go-to way for solving problems alone, intuitively, can be effectively deployed to solve problems together. But more often than not, it can’t. Instead, we should hold methodical meetings, discussions that deliberately and explicitly aim to conquer just one stage at a time.

Granted, conquering just one problem-solving stage, I’ve come to learn, sounds a bit underwhelming to some — like taking a small bite out of large woolly mammoth. But those who try methodical meetings are met with an often profound revelation: thoroughly conquering any individual problem-solving stage, even an earlier one, frequently allows you to leap frog ahead, sometimes to the very end of the problem-solving life cycle. As the famously methodical Steve Jobs once noted: “If you define the problem correctly, you almost have the solution.”

IT in Local Government

In the past decade, the environment in local government has experienced a significant shift, transforming IT from a back-office tech support function with limited visibility to a strategic, fully integrated function focused on exceptional service delivery and innovating both core and customer facing business processes and services. In government, this has happened in the context of an explosion of “innovation” related roles, such as Chief Innovation Officer, etc. that have helped raise the profile of technology teams, staff, and departments.

From a collaboration standpoint, Microsoft continues to impress me. Office 365 and the tools being added are frequently becoming part of core business processes. It’s common now for staff to create, share, and edit documents entirely online – bypassing local file servers altogether. That sounds simplistic, but that’s in fact a big change in how people create and manage data and opens the door to technologies like AI/ML as they become more integrated in Cloud services. It also integrates data across workloads while tying it into a secure fabric. It gives us a lot of flexibility in how we deliver IT services across the enterprise.

Satya Nadella, CEO of Microsoft, was quoted saying “we’ve seen two years’ worth of digital transformation in two months.” For government, in some cases, it’s been more like ten years’ worth. It is not hyperbole to say this is perhaps the biggest opportunity for digital transformation that government has ever seen.

Examples: organizational-wide adoption of digital signatures and routing; full deployment of teleworking services; digital community engagement (e.g., Zoom Town Halls, etc.); complete transition online of permitting and payments; a heightened focus on digital services for the community and efforts (and funding) to address the digital divide.

7 Attributes of a Deputy CIO

1. Management savvy

A CIO’s lieutenant must be ready to lead team members to high levels of performance, which in today’s IT, means more than simply getting the best out of individual contributors. “The best candidate for the second-in-command position should also come prepared to juggle competing priorities, use an analytical mind to measure success based on KPIs, remain flexible to change, be open to constant learning and have confidence in their own ability to lead,” advises Joe McKenna, global CIO for Syntax, a managed cloud services company.

An even temperament is another desirable attribute. “Your No. 2 can’t be hot-headed or a doormat; they need to be able to read the situation and apply the appropriate mix of ‘pushing the agenda’ while still being able to compromise when needed,” explains Mike Michalik, CTO of Evoque Data Center Solutions.

2. Forward thinking

A second-in-command should be able to help the boss look down the road to spot trends and potential opportunities. This capability requires a unique combination of skills and personality, says Dave Messinger, CTO of on-demand digital talent platform provider Topcoder. A deputy “needs to drive multiple visions — technology, cultural, financial — forward with enthusiasm,” he states.

3. Technology fluency

A No. 2 doesn’t have to be an expert in absolutely every IT area but should possess a deep understanding of current and promising enterprise technologies, as well as the key vendors in each area.

Cybersecurity insight and expertise is essential, however. Given the endless number of threats IT departments must defend their organizations against, a No. 2 should have a solid grasp on the latest cybersecurity tools and practices, advises Thomas P. Keenan, an adjunct professor in computer science at the University of Calgary. “I’ve been involved in a CIO panel … and that keeps coming up as a key competence that any CIO would need,” he explains.

Bassam Chaptini, CIO of Unqork, an enterprise application platform provider, recommends shying away from candidates who appear to be too focused on IT core technologies rather than on how technologies can be used to improve the business. “We work with machines, but ultimately technology is there to engage with people at some point, so you need someone who always keeps that in mind,” he observes. Client-facing skills are also important in a No. 2. “You will want someone you can depend on to represent you — and the company — in front of customers,” Chaptini says.

4. Strong leadership

Leadership qualities, such as organization, initiative and drive, are essential attributes to look for in a potential deputy. “Finding them all in one person can be difficult, but are worth searching for,” Michalik says.

Successful No. 2s tend to be amicable yet strong individuals, observes Brad Willman, CIO of Entrust Solutions, an IT managed services and staff augmentation firm. “Deputy leaders need to strike a delicate balance between being someone employees want to collaborate with, while also being an authority that staff members respect and obey,” he explains. “While many second-in-commands are charismatic, there’s not an inherent correlation between charm and leadership.”

Conventional wisdom dictates that it’s never a good idea to appoint a second-in-command who itches be the top dog, but it’s also not a good idea to turn to someone who needs the chief’s approval for every decision. “Avoid extremes,” advises Sam Maley, IT operations manager at Bailey & Associates, a UK IT auditing, consulting and management firm. “Avoid those who can’t follow rules, or those who can’t apply them outside of one specific context,” he adds.

Blind devotion to the IT chief is another negative trait. “A ‘yes person’ never makes for a good No. 2 because they won’t challenge authority and are reluctant to ask the tough questions that drive innovation,” Messinger says. “Also watch out for the overly controlling, attention-seeking second-in-command who doesn’t make big picture investor, corporate, workforce, customer and market goals top priorities,” he warns.

5. Communication skills

Great deputies are also great communicators. “They go above-and-beyond to communicate and coordinate,” Touhill notes. “They understand that communications up-down-and-across the organization makes for a better team and leads to mission success.”

The second-in-command must be able to handle multiple conversations and staff requests. “He or she must grasp and define the scope of the tasks, distill any complexities relating to the environment and integrations and, finally, drive the overall strategy through planned phases of execution,” McKenna says.

The best deputies shun the spotlight and don’t allow ambition to dilute their contribution to IT planning and operations. It’s also important for the IT leader and deputy to form a close working relationship. “The best pairings between a leader and deputy are when the leader is committed to grooming the deputy to assume greater leadership roles while the deputy is committed to supporting and learning as much as they can from the leader,” Touhill notes.

6. Business savvy

A CIO should look for a No. 2 who is business-oriented, understands finances and has an executive presence. “Most important, he or she needs to demonstrate personal excellence, a high level of self-awareness, a focus on self-development, integrity and be approachable and authentic,” says Caren Shiozaki, CIO and executive vice president for Thornburg Mortgage and a governance advisor to ISACA, an IT professional association. Ideally, the candidate should have deep experience in both business and technology. “He or she would have a successful track record in people leadership and have shown that they are self-motivated and unafraid of ambiguity,” she adds.

A second-in-command doesn’t have to be a strategic visionary, yet should be someone who fully understands the business logic of the platform the IT leader has laid out and can apply approved tactics to current and emerging problems. “With IT leaders focusing on higher-order strategic elements, deputies need to be problem-solvers and leaders in their own right,” Maley explains. Deputies should also be able to instruct team members on how to address specific technical problems, he notes.

7. Management support

Although the IT chief generally has the final call on their No. 2, it’s highly advisable to seek top management support before finalizing the hire.

Someday, when the CIO or CTO suddenly becomes unavailable, the second-in-command will need to jump in and take full control over IT planning and operations. If there’s dissention within the enterprise’s top echelon about a candidate’s ability to eventually become the IT chief, the new leader might find it difficult to exert full and unquestioned authority when it’s needed most.

“There are many talented IT professionals in most organizations, but only a few could be considered for an executive CIO role,” says Matt Mead, CTO at digital technology consulting firm SPR. “Before someone is groomed to be a second-in-command, make sure the key stakeholders are on board.”

Final point

All IT leaders must have a succession plan. “Presumably, the CEO and/or a board committee will be ensuring that is the case,” Shiozaki says. “An excellent No. 2 working for a CIO would be an ideal person to include in that succession plan.”