Gen Y Leaders, Boomer Coach

[This article was originally published in The International Journal of Coaching in Organizations, 2008, Issue #3. It is reprinted here with the kind permission of John Lazar, co-founder and editor of IJCO. The complete third issue of IJCO in 2008 can be found by clicking on the Download button below.]

Sandy Smith explores the impact of generational differences on the coaching process, offering insight into the challenges and developmental opportunities for the coach. In this paper, Smith offers insight into a new style of work environment and how a unique generation of new leaders is challenging executive coaches to re-examine their beliefs, expectations and basic coaching paradigms. Aligning with the developmental focus of this journal issue, Smith concentrates on the devel- opment of these leaders within the context of developing companies. Smith identifies the opportunities she has experienced regarding her own development that she believes may have wider applicability for coaches working in this domain.

I am a 50-something executive coach with thirty years experience working with technology companies, fifteen of those years as an executive coach. Today, I work with senior leaders in a variety of organizational contexts and industries. It has been my observation that the maturity of the organization and the experience of the leader impact virtually every aspect of the coaching engagement. Companies with longer histories are more predictable and slower to change.

The more seasoned leader can also be more resistant to change. Many times a mature leader will attribute success to certain behaviors and may be more reluctant to try new things. Marshall Goldsmith (2007) addresses this issue, encouraging the leader to determine whether a leader was successful because of, or in spite of, a given behavior. Younger leaders have fewer solidified leadership patterns because they have less experience.

Usually the top leader has the most influence on the company. The Gen Y CEOs are the founders who have been able to negotiate that role during start-up funding and are therefore able to form the company to their own ideals. These Gen Y CEOs differ greatly from their older and more established counterparts – the Boomers and even Gen X’ers. They take risks, are more optimistic innovators and are comfortable in what others might experience as chaos. They are hiring their contemporaries, trans- forming the workplace and achieving success by doing it their way.

THE TECHNICAL STARTUP – HOME OF THE GEN Y LEADER

The early stage company is distinctly different when compared with a mature company. The first task of a startup is proof of concept and later proof of viability (as a business model). This is typically an iterative process with many factors being tested in parallel and lots of false starts. It can seem quite chaotic. Through this repetitive process, successful tactics get reinforced and those that fail to produce results are abandoned.

Today’s Internet companies, termed Web 2.0 companies, use an experimental model where features are launched and user reaction determines their fate (Tapscott, 2008; Lacey, 2008). This model capitalizes on the young leaders’ comfort with change and, because it continues throughout the company’s evolution, it may extend the young leader’s viability as the company grows. Kurtzman (2005) observes, that while startups are not as complex as established companies with multiple business units, divisional structures, and hundreds or even thousands of employees, they are often more complicated to run because large companies adjust their strategy annually and structure every other year, the startup is a work in progress with every element of the company in play on a real-time basis.

He further notes that the leadership skills necessary in a startup differ quite dramatically from those needed in a mature company—given that speed, not perfection, is the hallmark of the startup. It is these characteristics which make the startup an ideal environment for Gen Y’ers.

THE GEN Y LEADERS – WHO ARE THESE NEW LEADERS?

Generation Y represents a cohort born between 1980 and 1994 with a reputation for strong positive parental attention coupled with high educational aspirations and expectations. They have experienced repeated affirmation that they can accomplish anything they set their minds to, and as a result, many are more confident and ready to test new ideas than any previous generation (Twenge, 2006; Howe & Strass, 2000).

This generation was also exposed to ethical breaches in business and politics that occurred so regularly that these breeches seemed a predictable part of our societal landscape. As a consequence, Gen Y’ers have become cynical about the way things have been done before them. In addition, this generation is the first generation to grow up accepting technology as a natural daily part of their lives (Tapscott, 1999). When we combine these factors we further understand why these young leaders are uniquely positioned to thrive in technology startups.

Common themes I’ve observed while working with these young and successful leaders include:

• They are extremely optimistic, expecting both to become wealthy and to change the world.
• They want to be respected – acknowledged for their gifts and not discounted based on their age or lack of experience. They don’t relate to their elders’ concept of paying your dues.
• They don’t value experience, traditional approaches, rules, or structure that they didn’t create.
• They want to work with people in their own image and choose where they work, based on recommendations from their peers.
• They seamlessly integrate work and social life – colleagues are their friends and the workplace is also a primary social gathering spot.
• They experience a kinship with people of their generation embracing diversity – global, racial, sexual orientation – without even thinking about it.
• They fluidly dance between competitive (better than you) and collaborative (help you whenever you ask).
• They tend to distrust authority, particularly of older generations. This is understandable because we, their elders, often think we know better.

When we view these young leaders relative to a developmental model, we see evidence that early success of significant magnitude creates a very different profile with a complex set of challenges and opportunities. While the linear stage theories are largely outdated, we can still imagine new skills and knowledge building on prior development – a progressive process.

So, what happens when the young, bright twenty-something leaps from college (or college drop-out) to CEO, skipping the progression of supervisor to manager and up the leadership ladder? How does he build emotional intelligence with so little time for reflection and interactions colored by the fact that he is the boss? How does he develop his capacity for intimacy when so much time is focused on work? Where and how does learning take place? What is the role of the coach in this fast-paced, youth oriented culture? Finally, how will engagements with these new leaders be different from coaching with more traditional clients and companies?

 

HOW ARE THESE ENGAGEMENTS DIFFERENT?

Coaching young leaders in a startup environment is different in at least three ways: the coach’s effective presence, how the process works, and what we actually do to help the leader effect change.

The coach’s effective presence

Jung called the total personality, known and unknown, the self. He identified two aspects: the persona or public self, and the shadow, the private self. Tolbert and Hanafin (2006) state, “Presence represents the translation of personal appearance, manner, values, knowledge, reputation and other characteristics into interest and impact.”

Presence is use of the self with intent. Tolbert & Hanafin (2006) identify three principle categories of presence: be honorable, be an effective change agent, and be curious. Hanafin (2004) created a great construct called the Perceived Weirdness Index (2004): when working as a change agent within a system, the practitioner must be similar enough to those in the system to avoid being rejected but different enough to provoke change. The client must perceive our “weirdness” within an effective range.

The significant age difference between these clients and me is an immutable reality. Other aspects of myself tend to communicate similarity, such as my love of technology, how I dress, and my general comfort in a fast-paced, changeable environment. Further, I can make some intentional adjustments in things like my speech patterns and interaction style. Speech patterns are absorbed often unintentionally. I have favorite phrases from startups like “I’m down with that” or “go for it” that are not helpful with financial services clients.

Any coach working in this milieu needs to make intentional adaptations. For me, I typically get up quite early to write, meditate and exercise. Young startup clients often get to work midday and work into the night. l chose to shift my schedule in response. Perhaps my most intentional and challenging shift was to a more casual interaction style, less focused on goal achievement. I think of these adaptations as both necessary to be effective and also as a means to demonstrate respect.

Respect is the cornerstone of any successful engagement, but it is exponentially more important in working with younger clients. Why? Because they have had so many experiences where people who were older considered themselves better based on seniority. Their perspectives have been discounted based on their youth. This dynamic is the source of great tension between young innovators and the experienced staff they ultimately need to hire. The issue is often framed as a matter of respect.

How do we coaches demonstrate respect? It begins with a careful inventory of our beliefs and biases. We need to cultivate an open mind and a non-reactive presence. In addition to delivering respect, it can keep us from embarrassing ourselves. I remember a huge mural in one client’s entry, which I thought of as almost graffiti. Months later, when the client was moving to a new building, I sat in on a move meeting where the discussion was whether to sell the wall or pay to have it cut and moved. The artist was now internationally recognized and this work was quite valuable!

Presence requires a balance of belief in the client and belief in yourself as coach. Certainly there have been times when I wanted my perspective to prevail but the client’s needs nearly always must take precedence. It is critical to believe that the client knows something about what she wants to accomplish, what’s best for her, and what matters most.

These clients are seldom interested in my credentials or certifications. They don’t care that much about references unless they are from a contemporary or directly related to their work. What they care about is how a coach interacts with them. And while smarts, flexibility and a bit of lightheartedness help, it is presence that gets or loses the contract. Interestingly, in computers and networks, the term presence signals that a user is available and willing to communicate. Perhaps that is what we need to be demonstrating with our coaching presence.

Being in a state of non-anxious presence isn’t always easy. First exposure to the start-up environment can be a bit startling. Work with a mature company and leader is more planned and structured than with young leaders in startups. Like the technology they invent, the engagement unfolds, finding its path organically.

I have traveled my own journey from an initial stance of seeing so many things that “shouldn’t be that way” to a more relaxed assessment of what is, to a focus on those developmental aspects that I’m uniquely qualified to address. I am much less oriented to prevention than to effective response. A notable example concerns the issue of sexual harassment. In a mature company, leaders are expected to know the law, HR people present training. The Gen Y environment is significantly different with an open, even sexually charged, interaction style. Context and the views of the participants dictate whether there is a problem.

The coaching process

In my experience, the change process unfolds in very different ways with the Gen Y Leader. Perhaps an easy way to understand this is in comparison with a more traditional coaching approach. Below are two pictorial views illustrating a typical coaching process as I conceive of it for a traditional engagement (Figure 1) and for a Gen Y start-up (Figure 2).

Traditional engagements can be much more linear, sequential and structured. Perhaps this is due to a slower pace and also the leader’s comfort with structure and predictability. These leaders often ask how the engagement will proceed and what we’ll do when. Authors who write about coaching best practices often advocate working on a constrained set of changes (Goldsmith, 2007). This facilitates the measurement of results, which is important for the leader and for the justification of expenses.

Working as a coach in this environment may seem easier because there are fewer fire drills and the predictability of a structured model is somehow comforting.

In the startup engagement with young leaders, two differences are striking: the number of things in flux and the speed of change. Connor’s Managing at the Speed of Change (1993), is a useful resource. Connor advocates adjusting the change volume to a level that people can absorb. This makes such good sense. However, in a startup, change volume is exponentially higher, with little focus on trying to reduce it. Working long and hard is a badge of honor. They pride themselves in their ability to be fast, responsive, and agile. In fact, one of the programming methodologies is actually named Agile. It isn’t always pretty but it can generate amazing results. I work in mature technology companies that try to maintain, or mimic, that fast pace of the startup. The younger leaders accept it with much less challenge than their older colleagues.

While holding coaching principles sacred, these engagements also have elements of mentorship, advising and consulting driven by the start-up mantra: do what has to be done. The coaching approach requires maintaining one’s balance amid all of the activity and adherence to guiding principles. The guiding principles I believe critical for the coach include: managing one’s anxiety, maintaining respect, remembering that these are the client’s decisions, teaching fishing rather than offering fish (unless immediate starvation is imminent), and adhering to one’s ethical principles.

The contracts I have made with young CEOs tend to be much less specific relative to measurable results. This reflects the reality that this is usually the first time they have engaged a coach and often their first significant leadership assignment. They may even be trying to do something that no one has done before. We set a general direction, taking action and choosing our next step based on results of the last action.

Interaction is the key and therefore these engagements can involve more onsite time. For one client, I committed to two days a week for a year. The “workday” started around 11AM and executive team meetings often started at 10PM and went into the night. While this may seem irrational, it mirrored the development engineers’ hours and left the day for interacting with business people on the traditional schedule. I received invitations to “hang out” instead of meeting requests and the conversations weren’t bounded by a rigid schedule but rather started and ended guided by the dialog.

The intake process is different because little historical information exists. Often they have no prior boss or performance review. Typically they don’t know what they want to work on. They don’t have much understanding of the expectations that others will have of them. The result is that they need more guidance from the coach. This is a challenge in that they distrust people who tell them how to behave or what they have to do. Therefore, it takes more time and care along the way. Even when initial goals have been identified, the engagement tends to unfold in a more organic way with experimentation being the norm.

At the heart of the engagement is a focus on skill building, strategy development, and other issues—but often in a different way. They want to start from a clean slate choosing what they will and won’t do without much regard for traditional wisdom, best practices or proven techniques. These interactions often challenge a coach’s belief structure.

The following example is illustrative. A young CEO posed this question: “Why do I have to have company meetings? I can just tell someone if I want them to do something different.” Answers bounced in my head: setting the vision, functional alignment to achieve common goals, reporting results, motivating people, and so on. Then rethinking; if there is regular interaction and people ask when they want to know something, maybe company meetings aren’t really required – yet. As coach, I was often trying to balance timing needs for structure in a very young and growing company. The coach in this setting needs to continually call into question whether or not an established ‘best practice’ is appropriate for this client/company at this time.

 

INTERVENTIONS TO HELP LEADERS GROW

Several factors govern what we do: the client and company goals, what the client has the ability/willingness to address, and the most urgent issues. Almost every engagement in this sector involves some work on leadership and management skills, top leadership team development, vision and strategy alignment, decision making skills, role clarity, interpersonal interactions, problem-solving and execution. Some of the most frequent issues that arise are around policy and rules, improving relationships between young innovators and experienced leaders, and dealing with issues of wealth and making a difference.

The diagram of this new engagement style (Figure 2) depicts the coach/client dialog at the center of the engagement. It is in this dialog that the majority of the work is done. I use the term dialog quite intentionally meaning an exchange of ideas and opinions. Good coaching skills of listening, mirroring, registering impact, invitational challenges are all useful here. These dialog sessions can be either a planned time or a short conversation following an event.

A typical client/coach dialog can be about clarifying the vision, asking who needs to understand it, what are the key tasks and activities, how can results be measured, and finally, who will do what to make it happen. Within the dialog, the coach needs to register impact about what makes sense and what needs to be worked further. So much of my own development has been to optimize my ability to be a good dialog partner. To be useful, I have to be able to assess my biases, understand the basis of my ideas and opinions, and have best possible understanding of this specific context.

Ethical considerations often arise in these client/coach dialogs and again represent some of the differences between past generations and Gen Y thinking. I remember having a casual conversation with a client about a tech company attorney who was disbarred for out-of-compliance activities. My client said that it might be fine for him since he had made more money than he would make in his entire career as an attorney. I realized that I had no idea how this multi-millionaire ex-attorney felt about his choices. I realized that his ethical framework was being structured through exposure to the rarified atmosphere of Silicon Valley. I’ve come to realize that these young people have yet to refine their own ethical framework. I’m often designing methodologies to surface beliefs and values or to improve understanding of impact of considered actions.

Facilitation can be used to surface and address issues that impede success. In one company I facilitated an executive team offsite with a goal of clarifying roles and optimizing working well together. The first theme to emerge was the chasm between the young founders and the recently hired executive members with more business experience. It was a clash of values pitting innovation against tradition; intelligence against experience.

Facilitated activities can be used to help polarized groups find common ground. One process that works well takes the client through the following steps: (1) Note their own beliefs about colleague(s); (2) Recall the specific experiences that generated the beliefs; (3) Note what they think colleagues believe about them; (4) Engage in dialog with each other to validate or revise their perspectives.

Sometimes members of competing viewpoints will use nearly the same words to describe their complaints, for example, “You don’t listen to me.” Becoming aware of common ground allows the team to bridge those gaps and begin working better together.

One other common challenge for young founders is managing multiple competing pressures around control, wealth and making a difference. The Founder’s Dilemma phenomenon is nicely explained in Wasserman’s (2008) Harvard Business Review article. He points out that founders often want to maintain control, generate wealth and pursue their world-changing vision. It’s tough to get all three.

How do people get money out of this company without giving up control either to funders, the SEC, or a seasoned CEO? The tension between experienced leaders and young innovators can be intense around this issue. The young are optimistic. I remember a heated debate in response to an offer to purchase the company. An experienced leader (mid-30s) said, “You don’t know how hard it is to make just one crummy million”. The founder’s response was, “I don’t care.”

Some discussions are at the boundary of consulting and coaching. An example that comes to mind is a conversation about how to structure the product management function. My client had no experience with the role of product management but knew something had to change from the current approach. We talked about what he wanted and what he wanted to avoid. I subsequently explained the principles and various structures other companies used. The client ultimately built a structure that differed considerably from that used by others who were managing this function—yet he infused his own structure with some of the best practices from other companies.

The coach needs to be a person whom the client can trust to hold his best interest at heart – someone who will honor the client’s perspective before giving advice. We need to manage our own impulse to share wisdom until invited by the client. We need to be willing to stand with the client when they have chosen their way and it doesn’t work out that well. As for the successes, they belong to the client.

THE CROSS-GENERATIONAL OPPORTUNITY FOR A COACH

I’ve learned plenty about myself through working in these environments. I had a good toolbox. I felt comfortable with my coaching theories, models, practices, and process; yet, I found myself continually focused on adding new competencies. Now I realize I was working way too hard. While theories and tools are important, they do not make a great coach. It’s a powerful intervention to work with a client for a year and almost never dip into the tool bag that once seemed my greatest asset.

So, if our value isn’t in our tools and what we know, where is it? Ironically, maybe it’s not in the “doing” but rather in the “being”. When I was first making my transition from consulting to coaching, it felt like I didn’t “do” anything in the coaching model. Just asking questions seemed a pretty weak intervention set. Now I reflect on Virginia Satir who said she didn’t really know how she helped people, or Carl Rogers who thought people changed in the presence of unconditional positive regard.

I’ve learned some things about business along the way. I’m more comfortable with ambiguity and understand the value of disruptive change. I’m less confident in my perspective and happy about it. When I need to let go of long-held beliefs it seems freeing rather than de-stabilizing. I read to expand my perspective, and am less driven to affirm what I believe. I under- stand why young people get frustrated with us. Sometimes we don’t get it. Sometimes we don’t try, maybe because we’re so invested in holding onto what we know. I’ve rekindled my interest in wide ranging conversation and experimentation. I’m just a little less careful.