Reframing What it Means to be an Executive

Stomach aches, slime mold & impossible problems

Tom Critchlow
October 11, 2023
  • We assume that executives are “in charge” and capable of exerting influence over their organization
  • However it’s important not to overstate the power of this influence
  • Instead, executives must grapple with emergent, unplanned systems
  • And, executives must grapple with impossible problems - tensions to be negotiated, not resolved
  • To succeed, you need to operate with a lighter touch and embrace the “work around the work”

“Executives are just ordinary people who were put in charge of enormous projects worth hundreds of millions of dollars. Do you have any idea what kind of responsibility that is, and the kind of stomachaches it gives me? Sometimes I felt that I just couldn’t fill this executive role anymore. I invested unbelievable efforts in denying my self-doubts and pretending to be a great manager, so I was constantly anxious. This anxiety was wearing me out.”

All by Myself? Executives’ Impostor Phenomenon and Loneliness as Catalysts for Executive Coaching With Management Consultants

I love this quote - executives are human too! Most people equate being a senior leader with power and control - the idea that you achieve the “inner circle” of an organization and finally (finally!) get access to decision making and are able to exert influence over how the organization is run.

Influence over how the organization is run? Sure. But don’t get too comfortable. With many of the companies I work with there’s a common frustration, even from senior executives that things don’t work how they want. They’re supposed to be “in charge” and yet they still can’t easily change the organization. They mistake influence for command and control.

And especially in 2023, the command and control version of executive leadership isn’t how things work.

But let’s back up. What even is an executive?

What even is an executive?

There’s no good singular definition, but I find it helpful to think about it two ways: firstly as the ownership of significant resources:

[You’re an executive] at the point where you are:

  1. Controlling a budget or P&L
  2. Making strategic decisions on how to use those funds to meet strategic/future, vs tactical/immediate, business objectives. source

And secondly as a mental state:

A manager starts with their team and their contribution to the problem/solution. “How can marketing do better at X? What’s the impact to marketing? How can I make a business proposal to get marketing more resources to do x”) The manager spends 90% of her time thinking about her team/department/role, and 10% of the time thinking how the whole company needs to move together to reach the next level.

An executive thinks like the CEO first. Their first team is the whole company. They have a deep sense of the market, how the business operates together as a machine. Their particular department (even their role) is the secondary consideration. An executive spends 80% of her time thinking about what we need to accomplish as a company, and how all the teams need to work together to achieve those things, and only 20% of her time thinking about her department/role. source

Both of these definitions implies a sense of agency - the ability to control and influence how their organization operates. Unfortunately, this hides the complexity and challenge of actually getting things done…

Why is it so hard to drive change through an organization? Why, even as an executive, is it so challenging to have an impact?

Well, there’s lots of reasons but two big ones we’ll explore here - firstly, our very notion of organizations as being planned and orderly is wrong. And secondly, as an executive you aren’t tasked with hard problems, you’re tasked with impossible problems.

Part 1: Organizations aren’t Built, They Emerge

It turns out that our default mental model of how organizations operate is just kind of… wrong. We don’t build organizations in an orderly fashion. Organizations are emergent, organic creations.

Moving off the Map: How Knowledge of Organizational Operations Empowers and Alienates is a great paper that follows a team as they create a process map of their entire organization:

A process map is a detailed physical portrait of the operations being redesigned. Often a large-scale diagram located on the walls of a conference room, the map is used to understand current work and coordination practices and to guide redesign options. To build the map, team members begin by collecting all information about the operations being redesigned: What were the work activities? Who did the work? What interactions and hand-offs occurred?What information and tools were used? How long did each work activity take? What happened when errors were found?

Mapping out not just how the organization is supposed to work, but how it actually works is a powerful experience:

“Some held out hope that one or two people at the top knew of these design and operation issues; however, they were often disabused of this optimism. For example, a manager walked the CEO through the map, presenting him with a view he had never seen before and illustrating for him the lack of design and the disconnect between strategy and operations. The CEO, after being walked through the map, sat down, put his head on the table, and said, “This is even more fucked up than I imagined.”

The CEO revealed that not only was the operation of his organization out of his control but that his grasp on it was imaginary. They learned that what they had previously attributed to the direction and control of centralized, bureaucratic forces was actually the aggregation of the work and decisions of people distributed throughout the organization. Everyone was working on the part of the organization that they were familiar with, assuming that another set of people were attending to the larger picture, coordinating the larger system to achieve goals and keeping the organization operating. They found out that this was not the case.”

This process of seeing the whole organization at once is akin to the overview effect that astronauts get when they see the whole world as a blue marble suspended in space. It brings about a deep emotional reaction. In the paper they describe how this “overview effect” of seeing the whole picture was both empowering:

“Observing the organization as continuously in the making gave employees an overwhelming sense of possibility, sparking ambition”

and alienating:

You really start understanding all of the waste and all of the redundancy and all of the people who are employed as what I call intervention resources. The process doesn’t work, so you have to bone it up by putting people in to intervene in the process to hold it together. So it is like glue. So I would look around [the company] and I would see all these walking glue sticks, and it was just absolutely depressing and frustrating at the same time.

Successful executives are the ones that have realized that the organization is emergent and unplanned, have recognized how empowering this is AND have learned that you can’t go around showing people the whole map - because it drives some people insane.

So if the organization is unplanned and emergent - how does that change your leadership style? How does that change how things get done? Enter the slime mold…

Enter the Slime Mold

In the wonderful presentation Organizations and coordination headwinds, Alex Komoroske uses the analogy of slime mold to look at organizations as emergent and unplanned systems. Alex walks through why things get harder as organizations grow in size, and why alignment is so important. The key, according to Alex is to recognize the power in adaptability and resiliency that emergent systems have:

  1. You should prioritize a stable, well-communicated north star for the whole team
  2. Alignment is incredibly important but you should aim for eventual convergence and good enough over perfection, leaving slack in the system
  3. Focus on smaller, more iterative projects that converge on the north star, instead of trying to get there in large ambitious multi-year projects.

In short, you want to aim for loosely coupled and tightly aligned teams.

This style of leadership is essentially recognizing that rigid systems fail harder. The balancing act is of course getting the tension right between ensuring everyone is working towards a common goal, while leaving room for teams to have autonomy and self-control.

It turns out, this isn’t the only paradox that executives need to wrestle with - there’s 6 more!

Part 2: Impossible Problems & Executive Paradoxes

Being an executive requires grappling with nuance and complexity - you can’t just stay in your lane anymore.

From a wonderful paper If I Say It’s Complex, It Bloody Well Will Be: CEO Strategies for Managing Paradox they interview 20 CEOs and explore the tensions inherent in their role. The driving thrust of the paper is that executives deal in complexity and paradoxical choice all the damn time. It’s an eye opening paper with lots of juicy quotes. From one of the CEO’s:

“It’s very easy to lose your way in complexities. When talking about organizational structures, people will always perceive them as very complex. And then I say, “I don’t see why it has to be so complex at all. In which way is it complex?” It’s not because I don’t realize that it is complex, but because if I start declaring that it is complex, it bloody well will be.”

This quote strikes at the heart of being an executive - just like we saw above in part 1 you need to recognize the organization is emergent, while not shouting that from the rooftops because it freaks people out. You recognize the complexity, but you can’t go around telling people it’s complex!

The full 7 paradoxes from the paper are here:

Complexity factor Manager’s problem Paradoxical tension Example of resolution
Paradox of location How to combine the need to be present with empowering the leaders in my organization? You need to be omnipresent, but at the same time stay away. You need to be present to talk about the big issues and to listen in on current concerns in the organization, but you need to stay out of operational issues.
Paradox of change The more initiatives I try to drive, the less seems to happen. To create change, you need to stay the same. Success in changing an organization comes from persistently staying with only a few messages and tasks, no matter how boring that may be for the leader personally.
Paradox of creativity I was hired to bring fresh ideas, but the more I try, the less people listen. The more ideas you launch, the less ideas will succeed. Although a leader may have many ideas, a large organization is only receptive to a few ideas at a time. A leader needs to pace initiatives to refrain from overloading the organization.
Paradox of diversity Diversity improves problem solving and creative work, but culture clashes rip the organization apart. You need to become more heterogeneous and homogenous at the same time. The organization’s purpose is used to unite people. New relationships are built through co creation. Celebrate the diversity in multiple ways, and do not accept it as an explanation for conflict.
Paradox of direction I want to empower people, but at the same time I need to be sure that they follow our direction. Direction and independent action needs to be combined. Strategic priorities are clear, and managers are given high degrees of freedom in executing the strategy, including acting across units. This is enabled by a broadly involving strategy process that allows also harsh feedback on the strategy to reach top management.
Paradox of innovation I need to both deliver short term results, and invest in innovation and entrepreneurial initiatives. Operational excellence needs to exist simultaneously with innovation and entrepreneurial initiative taking. Only in a high trust culture with a clear direction do people feel that they have the possibility to drive initiatives outside a predefined agenda, and only then can the leader be sure that operational excellence and new initiatives are not at odds.
Paradox of globalization I need to create both local market adoption, but make use of the potential synergies in the global organization. Success builds on becoming more global and local at the same time. Global integration and local adaptation works best if they are combined with a dense social network where people across markets know and trust each other

Just like in part 1, the most successful executives (those without stomach issues?!) are those that recognize the nature of the role as dealing with impossible problems rather than treating their inability to resolve these tensions as a personal failure:

“The executives reported learning to grasp recurring difficulties as inherent to senior positions and not as a sign of managerial inadequacy. With the encouragement of their management consultants, the executives had also realized that managerial knowledge and skills, important as they may be, cannot substitute for their cultivation of an emotional capacity to contend with role distress, which is nowadays part and parcel of executive roles.”

(Ok I’m biased as a consultant, because that quote comes from All by Myself? Executives’ Impostor Phenomenon and Loneliness as Catalysts for Executive Coaching With Management Consultants)

So what?

Aside from realizing that a lot of executives are permanently grumpy from stomach issues, what can we learn? Well, I think there’s a few interesting more practical takeaways:

  1. When dealing with execs, we know being clear and concise is important, and this just emphasizes the degree to which executives are juggling a lot - they’re dealing with impossible projects and slime mold! You want to try and reduce their stress and mental load with every interaction. We’ll look at ways to do this in future emails.
  2. As an executive, just because you earned a seat at the table doesn’t mean that you automatically get to command the organization. Alignment around a shared vision, consensus building, political capital, etc still matter.

And maybe the most surprising takeaway that I’ve seen from my own consulting work is that you don’t need to be an executive to start operating with agency and influence. Inside most orgs it’s possible to build “social capital” and learn how to work with impact even before you get to the “managing a P&L” stage.

This is the through-line we’re going to explore in the “seeing like an executive” series here on the NEW MBA - it’s about learning how to see organizations in new ways, learning how to situate your work correctly and learning the power of communication.

In short - the work is important, but the work that gets you to the leadership level is the work around the work.

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