Preparing to be bold in the moment

Vienna Opera Backstage, Austria

Avoiding risks can be a sneaky head game. I started McGee’s Musings as part of a class I had designed at the Kellogg School. The class routine created a rhythm for the blog that gradually led to maybe 1500 subscribers and a smidgen of internet visibility. But then I let it languish. I was in a new environment with different rhythms, there were fixes and improvements that I ought to make before I wrote the next post. Habit killers. Risk avoidance masquerading as good intentions.
The argument is that you must summon your courage, be bold, and face your fears and your risks.


But it might be easier to cheat; to arrange your circumstances and your environment so that boldness becomes the path of least resistance.

In my second year in college I was the stage manager for a large musical play, written and performed by fellow students. The group had hired a professional director from Off-Broadway. Tony was probably in his late thirties or early forties. I was twenty.

It was 7:30, the curtain was going up in 30 minutes for an invited audience to the final dress rehearsal before opening night. Behind the curtain, was what looked like chaos. Carpenters were putting the finishing touches on one set piece and repairing another that had broken. Electricians were on ladders tweaking the focus of one of the lights. Costume designers were fixing a hem. Tony was standing center stage with hammer in one hand, nails in the other, screaming that we weren’t going to be ready. I was trying to do my job which was to make sure that the curtain did go up on time. Without conscious thought I walked up to Tony; “Tony. You’re not helping. If the curtain doesn’t go up at 8, then you can fire me. Until then, get off of my stage.” Tony dropped the hammer, tossed the nails aside, and stormed off.

I was bold and the curtain went up on time, right?

The curtain did go up on time, but it’s a mistake to think that I was bold or brave. You can choose to describe it that way afterwards, but that misses something more important. I did what I did because it was my job. Said so right on the business card I didn’t have—stage manager. Ages of theater tradition backed me up. It was MY stage and it took no boldness to lay claim to it.

If bold action is called for, then strategy must design for it in advance. To know what behavior will be called for and to build that into the environment and the structures where the action will transpire. It is not enough to simply paint a picture of the desired future; the strategist must understand the journey well enough to prepare and equip the team for the obstacles that will arise. You can’t simply prepare for any and every contingency. Nor can you rely on an inventory of particular skills and knowledge, “just in case”.

The management challenge is to delve into this middle space of the journey. Pointing at the peak looming in the distance translates into breaking the journey down into daily treks, rest and replenishment stops, forays into the next leg of the terrain. Imagining the journey in that next level of detail is where you anticipate decisions that might have to be made and options to be weighed. Understanding the likely terrain and the possible options is where you prepare now to do what will look like bold then.

Reflections on reflection

When I was in high school, the most revelatory book I read was whatever I had just finished. Its insights were my insights and I shared them with whoever was in my vicinity. This annoyed my father for certain and likely most of my classmates, friends, and family.

As I acquired a bit more life experience to go with the words on the pages passing before my eyes, my assessments became more cautious. Any book can produce a moment of insight. What I’ve come to value is a book whose influence is more lasting and pervasive. This influence reveals itself as I find myself adopting new frames and pushing a title on my friends and colleagues. When a book gives me a new lens on the world and I find myself looking through it more routinely, I know that I’m on to something.

On that score “The Reflective Practitioner: How Professionals Think In Action” by the late Donald Schon ranks among my top ten. I stumbled on it in the late 1980s during the early days of my Ph.D. studies. The title caught my eye in Wordsworth, a bookstore that occupied a prominent spot in Harvard Square and in my household budget. It offered a label for what I was becoming and provided a bridge for a gulf I was trying to cross.

The essence of Schon’s argument is that professionals operate by building theories of practice of how their corner of the world works. Like good scientists they test their theories against the real world they operate in and on.
The best professionals do this explicitly and mindfully. They make the time to both do their work and to reflect on their work. Reflective practitioners acquire experience and actively engage in making sense of that experience.

This process allows two things. It offers a way to introduce new knowledge and ideas into practice. New ideas and theory become important when we aren’t satisfied with accepted practice. Second, it makes clear that what happens in practice determines whether new knowledge and ideas stick. Reflective practice is a way to achieve both/and possibilities instead of treating theory and practice as an either/or question.

This notion has become a unifying thread in my own work and practice since then. We generally get better at whatever we do through the accumulation of experience. Rather than simply accumulate experience, however, we are more effective if we develop parallel skill at actively making sense out of our experience.

From systems building to systems thinking

I once believed in systems. I believe in systems now. It’s what happened in between that I want to look at.

I started my career building information systems; after summer jobs as a programmers, I knew that I wanted to be a consultant. I didn’t understand what that meant, ignored wise advice about what I ought to do, and talked my way into a job with the consulting arm of Arthur Andersen & Co.—long before it morphed into Andersen Consulting and later Accenture.

I designed and built information systems that massaged accounting data and produced reports meant to lead to better management decisions. I became pretty adept at annoying my supervisors with questions about how my programs connected to the broader business. It’s possible that some of the information my programs produced may have contributed to marginally better analysis and decisions by some middle managers. I was absorbed with the intricacies of making computers do what I told them to do.

That led to an MBA on the theory that what I needed was to understand the big picture; how did all of the pieces fit together? If I wanted to build more effective information systems, I needed to understand business as a system. How did strategy and finance and operations interact? I jumped from the weeds to strategy and the CEO’s perspective. From there it was back out to the consulting world.

I now had the systems tools I needed to design solutions that would have real impact. The flaw in my brilliant plan was that the people I was designing and building systems for seemed to have little interest in actually changing how they worked or thought. I’m fundamentally a nerd so my solution was to go back to school again; clearly I had missed something in my previous studies. If the intended users of my systems insisted on being too dumb to recognize how clever my designs were then I needed to learn how to do better designs.

I started a Ph.D. program in management information systems. Fortunately, Ph.D. programs give you access to very clever people with lots of perspective. They began to gradually eliminate the stupid and replace it with some deeper insight. The first order analysis, of course, was that thinking of users as stupid wasn’t a winning strategy. I was young—younger anyway. The second order answer was to build a knowledge base in organizational theory. The quest since then has been to develop a better synthesis; exactly of what is an evolving target.

This isn’t a new quest. It’s often framed as an either/or choice between people and technology. A more intriguing path is one of both/and. That isn’t a new thought either. But it is worth a revisit.

Exploring the messy middle

Why is the middle ground between strategy and tactics so difficult to travel? Over the next month I will be writing about and around that question.

Trying to understand my successes and mistakes in this middle ground is the through line for much of my life. While I’ve chipped away at it, I haven’t done a sustained push to make sense of the journey or its trajectory. That kind of push needs some help, hence this exploratory visible effort.

What is this middle ground? In college I was part of a theater group that wrote a Broadway scale musical from scratch and staged it in the Spring. I was the production stage manager, which meant that I coordinated all rehearsals for the director and worked with the set designers, lighting designers, technical director, and musical director to make sure all of the pieces came together for opening night. I was also a student studying mathematics and taking a course about the math underneath managing complex projects.

Perfect opportunity.

I could take what I was learning in class, apply it directly to my extracurricular life, do less work, and get myself an easy A. You can guess where this ends. I squeaked out a C by admitting that I couldn’t figure out how to apply the technology to the creative chaos of producing an original show. And the curtain went up on opening night with the collective efforts of all of the cast and crew.

That was an early step on an exploration of how you mix people, processes, and technology to go from a germ of an idea to opening night. Opening night might involve actual curtains; it might also involve launching a new information system or an entirely new organization. What holds my attention is that middle space between the idea and its realization.

What I’ve learned is that there is a middle in this middle.

We know a lot about big ideas; we call it strategy in business and organizational settings.

We know a lot about the details of user interfaces, and writing code, and designing procedures, and arranging finances, and all of the tactics that go into a working organization.

In the middle, it gets fuzzy. As we move along that path from grand idea to final result, there is always an area of mysterious transition where we turn from grand thoughts to dirty work. We all know this. Some of us learn how to get across that transition; others seem trapped on one side or the other. Is there a way to eliminate or reduce the mystery and magic in the middle? This promises to be a messy but fruitful exploration. Stay tuned.