Most managers and leaders don’t understand how powerful coaching can be.  It is often confused with mentoring or consulting, which, valuable though they can be, pale in comparison with the dramatic gains that happen during most coaching engagements.  At a recent conference I led a panel that took this question from the audience: What can good coaching help me with? The immediate reply was: What is it that is holding you back?  Coaching is the best way to accelerate the gains you are making in your career, and also help you overcome the impediments you may encounter. And it is easy and fast.  No book or free advice will ever do that for you. 

 This case study is from a real, live client of mine, in which we (or, I should say, he) transformed his career path with about 16 hours of my coaching time over a five-month period. That was roughly three one-hour calls per month.


Nick had spent his life in agencies, starting early on as an art director, an entry-level spot in a small but growing agency.  Over the last two decades he had grown his skills and had advanced to greater responsibility.  He changed agencies twice, this last time landing at Red Sidecar, which at that time had been a smallish group of 30 people with a fun, charismatic leader, Jason, and Angela, the creative director.  Nick reported to Angela.

When Red Sidecar was small, there were only a few people in the creative department with Nick, but as the company grew, it became known in its region for high-quality creative and great execution of ad campaigns and marketing programs.  Within a bit more than a decade, the agency had grown to more than 100 people, and Nick was now one of Angela’s top creative directors.

But lately, Angela had been wanting less, not more.  She wanted less of the grind, less of being part of every pitch, every campaign. She wanted to separate from the company—not completely, but she wanted the time and space to go back to school and get an advanced degree or explore some new ideas. Inevitably, it was time for her to create a layer of leadership beneath her. She chose Nick to step into that role.

I met Angela at a conference where I was a speaker, and she told me she had someone who could benefit from our leadership coaching program.


My First Calls with Nick

It turned out that Nick and I had met before, at a training class on managing teams. Nick told me that although he thought it was a great class, it had, paradoxically, made him feel less capable.

Despite a string of promotions during his years at Red Sidecar, Nick was filled with self-doubt.  He was not sure what it meant to be a manager; he felt even less certain about what he would need to do to be a leader.  In fact, his greatest fear was that people would think he was a “shitty leader.”  To me, this was a very valid fear. Leading empowered teams requires a different, less authoritarian, style of managing.  If you’re not a good manager to start with, it can be a challenge. The agency business is filled with horrible managers—people who had been very good specialists, like Nick, but were pressed into progressively deeper leadership roles, without training and with only the mentorship of those ahead of them in that progression. And those people were also lacking in management skills and unhappy with their role.

This is the tragedy of the specialist-to-leadership transition:  In many ways, everything that the specialist had to be good at (serious, deep and intense focus on the work) ends up being a negative behavior in a manager. Often uncertain with their role, they revert to what they know best—being a specialist—and neglect performing or learning their role well.  Nick confessed to having done that and felt that at any moment he could not tell whether he was exercising good leadership or just doing what he had always done.

Research on managers and teams shows that several negative effects often occur when the most qualified specialist (the “deep specialist”) gets promoted into a managerial role: over-managing (often called micromanaging) or poor delegating; being too serious (teams do better with relaxed managers); and spending too much time interacting with the team (over-managing), reducing its effective productive time.

One of the other challenges is that many of these promotions are not “clean”; the manager is still expected to do specialist work.  In agencies this can extend well into the upper echelons of the organization.  Angela, for example, still had several clients that she was responsible for, and regularly was the lead creative person on new business pitches. Being a partial manager is often the worst of both worlds, preventing the specialist from full transition to the behaviors of a leader, and also destroying their productive hours with frequent managerial meetings and interruptions.

When I asked Nick about his target for utilization (how he spends his time) he told me he was still billing a minimum 50% of his time to clients.  He revealed that it was pretty much his top priority, and that he had been “beating that number” by a considerable amount every month. That was a behavior he knew how to do from decades of being an awesome specialist.


Changing Perspectives

During our next couple of meetings, we discussed thinking about his time allocations differently: How to reverse the formula and ensure he was at least 50% utilized as a manager.  Nick decided to set his billable goal as no more than 50% in order to create space to focus on being a manager.

Around this time, he settled on two goals for our coaching work:

  • Gain mastery of the idea of leadership and what it takes to be one; hopefully enough so that he would not be a “shitty leader,” in the words and reactions of others.
  • Rewrite his new job description to reflect what he wants the job to be, and to understand what he is responsible for, but also what he needs to not

The second goal arose from a revealing moment: When Nick shared his job description (JD) with me, I asked him if he understood what he needed to do in order to fill that role well.  Nick realized that he had no idea of what he needed to do. He then suggested the second goal, feeling that it would be a good measure of success for us. If he could write a JD that he knew how to do, and Angela approved it, he would feel far more as if he could succeed in this new role.

Often, JDs are written like a land grab, filled with statements about the territories over which the manager rules, but often devoid of definitions of what the desired behaviors, interactions, and results look like; “These are your lands, take good care of them.”  No company would ever give such an ill-defined work description to a junior specialist, but somehow it is fine to do it for the deep specialist who has few management skills!


Transitioning from Craftsman to Behaviorist

Great managers are masters of understanding and shaping behavior, and like a master craftsman, the skills needed to help others come from mastery within; no manager can manage behaviors and interactions of others until they understand their own.  One of the best ways to kick start this process is to conduct some form of 360-degree feedback capture from the new manager’s team and peers.  By our fourth call, Nick had sent out the introduction email to eight of his people and I had followed up with a simple five-question survey.

The use of a 360 survey in a coaching situation is different from the usual HR application. In the coaching model, we are really helping the manager calibrate their understanding of themselves against how they appear to others.  This perceptual challenge is illustrated in the Johari Window shown below.  The 360 and the subsequent discussion are designed to help the manager understand the gaps in mutual perception (Blind and Hidden) as well as what beliefs are common to all (Arena).

I’ve found that many specialists-turned-managers are pretty good at knowing what people see them as—especially from the less positive perspective—but they can be more misaligned in understanding how much people value them and appreciate their caring.  The “hidden” aspect of that manager is usually not so hidden.  And this is often a key to the first shift that the specialist needs to do—understanding how they appear to others when wearing their new “manager clothes.”

Since becoming a manager, Nick had come to believe his people saw him as uncaring, despite how caring he actually felt.  But his 360 results actually confirmed that people thought he was very caring and very competent.  Not surprisingly, most people felt he was trying to do too much; that his desire to do well and care became caring too much, sugar-coating feedback, and generally interrupting progress.  Nick was over-managing with friendliness, because he didn’t know what to do otherwise.


The Inner World of the New Leader

Coaching is better than mentoring or self-help management books because every leader is different.  More important, we all have inner leadership skills, and our best leadership style comes from accessing those skills and the experiences that formed them.  No book can help us do that.  Great leaders are people who have come to understand what they want their style to be, and it flows naturally from their values.

One key activity during the middle weeks of our coaching was for Nick to envision what leadership meant to him.  He asked, “What should I do as a leader?” to which I replied, “What kind of leader would you want to be?”  We did some role-playing work and Nick quickly realized that he had spent his whole life working with leaders, and he actually had strong opinions about what he liked and didn’t like in a leader.  He had once left an agency just because he did not like the leader’s perspective on the business and Nick’s role.

That visceral sense of what great leadership felt like (as a recipient) allowed him to start thinking about how he could create that same feeling within others.  We explored more deeply what he saw them doing, and also how Nick felt when he thought of those experiences.  A useful tool for a manager is their own emotional compass—developing the “somatic” sense of the moment, the ability to detect what is happening through their sense of presence.  Mastering that sense allows great managers to measure their activity and their impact upon the environment without distracting intellectual analysis; they can feel what’s going on and how they are doing.

With a few weeks of practice, Nick began to understand how to interpret discussion and behaviors on a new level.  He started asking me for alternative ways of doing things, such as how to solicit opinions, not as the only way to do it, but as a different way, so that that he could assess its impact.  He was tuning his compass.

At one point at this stage of the process, Nick asked his direct reports what they would have him do and what they would suggest he focus on. Wisely, he realized that their advice might not be correct or optimal for him, but by asking, he opened the door for discussion about how he was managing and how they felt they were being managed.


You Can’t Manage Unless You Can Measure

As we entered the final phase of our work, Nick renewed his focus on his new job description.  I’ve found that the way to avoid the land-grab statements that have no action to them (“Nick will be responsible for ensuring creativity throughout the agency”…uh, how does he do that?) is to instead define things he can influence (business results,) and how his teams need to operate (team interactions,) along with the leader’s own behaviors that will make those happen.  This changes the vague statement “responsible for ensuring creativity” to a list of actionable things, such as:

  • “Ensure that all creative work scores high enough for the desired quality before it is sent to a client.” (business result)
  • “Make sure teams know how to assess creative quality and how to do it actively.” (team interaction)
  • “Monitor the use of the creative scorecard to ensure it is applied appropriately and consistently.” (personal behavior)

We further ask that every item in the list be measurable and under the control of the assigned parties–a bar that is rarely met, and lacking that, the link between the goals and the individual and group performance can become quite muddy.

Nick went at it with impressive zeal.  He quickly realized how any one aspect of the list would influence another and decided that he wanted to co-construct the same sort of list for each of his direct reports.  Within just a couple of sessions, he had built a model and a job description that he knew he could succeed in; one that would create the kind of results that the agency needed. We scheduled a call with Angela.

Nick spent a lot of time preparing a presentation of the information in a Keynote document.  Angela joined us for a half hour and Nick walked her through how he was thinking about the job and his responsibilities.  She loved it and later gave him the go-ahead.


Wrapping up and Next Steps

Within a couple of weeks Nick had rolled out his plan to his teams and briefed the partners team, of which he was a member.  He reported that people seemed to understand the model quite clearly, asking relevant questions about things he might add or had missed.

Nick seemed to be changing, too. During what ended up being our last call, he displayed a quiet confidence in his thinking. He was relaxed, even when reviewing things he did not understand.  He became adept at helping his managers deal with complex issues, reminding them of things that he had learned during our sessions.  Nick also realized that his feedback on the creative work was not necessarily what his team needed.

In a further shedding of his old specialist role, he assigned a couple of his managers the task of defining a scorecard which everyone could use to assess the quality of the work—the more people who can see what is wrong, the more people there will be who can make it right.

On our last call, Nick proudly reported that he was doing fewer billable hours than ever, and that his teams were doing the best work they had ever done.

The speed of Nick’s transformation surprised me.  I learned a lot in watching him use his new ideas and awareness to shape himself into a leader.  He had done things I doubt that I could have done.  And in just a little over 16 hours of our time together, Nick had become a coach to his people and, in reality, a great manager.

In our final discussion, which we were fortunate to have done in person at a conference that we were both attending, he asked if there was a way that we could continue, but without the frequency and intensity—after all, he had a big department to run.  I suggested we start a “reflective practice,” a once-a-month coaching model, where we would work together to extend the gains he had made.

Postscript: Within just six months, Angela would announce an even bigger shift in her role, promoting Nick to the top creative leadership position in the agency.