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A Framework for Scaling Intentional Leadership

Published in

Startup Grind

12 min readMar 26, 2017

I’ve recently been working on exercises that establish practices for intentional leadership in organizations — specifically early startups that are at the point where their leadership MUST start to scale. Many of the successful leaders you see (or know the names of) in startups are examples of leaders who had the requirements of leadership thrust upon them, and those that have been successful, reacted well to that challenge.

On the other hand, I think there’s no small set of people who have the potential to adapt well to the challenges of leadership, but just like any other skill gap, they lack the framework.

To that end, I’ve created the foundation of a process that I’d call something like, Intentional Leadership through Inquiry — which makes it sound especially savvy and kind-of philosophical, and I figured that would do.

The basics of the process follow a set of steps that can be summarized:

Practice inquiry to determine the questions (problem statements) that you need to resolve to be a responsible leader in your organization
Use patterns in the problems you need to resolve to determine the tiers of your organization that require leadership, and the focal patterns, areas of leadership that share a similar problem for which you can identify a shared theme
Identify the key problem statement that allows you to actually engage in the resolution of the many problem statements that require leadership
Establish the capabilities and themes that might represent opportunities to solve these problems, and how they each represent a thematic practice that you can use as a tool to solve organizational problems
Organize problem statements that represent a focal pattern together so that you can review which of your thematic practices can best be applied to this collection of problems (in a way that makes for a meaningful impact in that focal pattern at-large)

Now, if the basics are in fact too basic, here is an actual, working example.

1. Practice Inquiry

This is a collection of problems “I” would want to have resolution for as a leader of a ‘product’ organization or department. I came to this randomly as each question/problem statement was thought up, and realized the groupings and categories as they were discernible.

Team Member Growth

How do I empower the team to ensure that they are individually growing in capabilities and establishing strengths?
How do I use team strengths to increase organizational capability to align with department and business goals?
How do we capture and discern team strengths so they can be leveraged across teams?
How do we systemize and track progression against strengths so an expert’s progress is clear to leaders (or themselves)?
How do we intentionally support and foster strengths in educational practices (of which we currently have none)?
How do we keep pressure for team growth high but not so high as to create burnout?
How do we counteract our likelihood to ignore practices here and have excuses for no progress?
What is the human capital strategy to ensure that team members feel rewarded both by actual rewards and this growth process in a way that retains their presence here at my company as they grow?
How can I ensure that team member’s are challenged to grow by diverse interaction?
How can I increase specialization and automation of efforts to allow for team members to have more time for growth opportunities?
…

Department Growth

What are the department goals and then the back-fill from those goals necessary so that we create appropriate operational practices?
What are key department risks and then the same as above?
What are trigger points in departmental growth or lack of growth and how do they affect the above?
How do we organize this information so that it’s consistently visible and easy to digest for the larger team?
How do we clearly discern the stages of experience in a department and make it clear to team member’s the requirements of stage progression (junior, leader, etc.)?
How can I track, organize and translate key moments of progression in scale in department growth to potential business opportunity?
How can I increase automation of departmental efforts to allow for departmental growth to shift to new opportunities?
…

Business Growth

What are the business goals and then the back-fill from those goals necessary so that we create appropriate departmental direction?
What are key business risks and then the same as above?
What are trigger points in business growth or lack of growth and how do they affect the above?
How do we organize this information so that it’s consistently visible and easy to digest for the larger team?
…

Individual Projects

How do we collect and organize individual projects in a way that allows for projects to be led and parented by team members?
How do we require project leaders to document and share information to leadership related to project progress?
What is the appropriate structure for projects to contain as artifacts of being a ‘project’? (i.e. owner, stakeholders, exec. alignment steps?
How do we negotiate between the self-directed project creation and the assignment of projects with key organizational value?
How do we ensure projects have the right buy-in from stakeholders to ensure they’re crafted to organizational value?
How do we deliver upon projects in phases of MVP and phase learning to support organization-wide implementation?
How do we organize project information so that it’s consistently visible and easy to digest for the larger team?
How do we track progress on projects to reduce risk and increase the success rate of projects and the “growth” of the practice?
…

Personalities

How does leadership handle directional/personality differences that might prevent or slow growth, versus contribute to it (this can’t be accidental)?
How do I resolve scenarios with no clear democratic resolution?
…

Client Projects (Appropriate to an agency or service business)

What does leadership need to know (and what categories of things to know are there) related to client projects so they can feel comfortable with their progression?
At what specific points in project progression does leadership need to participate, and what does their participation entail?
What are triggers in client projects that require the participation and integration of leadership?
How do we share and identify client project status and progression across teams and departments so we all share a sense of client success?
How do we collect from client projects the work product that is most project-like and has organizational value?
How can I ensure I’m asking the right questions to dig deeper into a client project than only a cursory glance, and seeing the patterns and trends, or opportunities, that my employees are possibly not yet senior enough to see?
How do I need to participate in categorizing the work necessary for a given client project with its lead to determine key moments in progress that might require leadership intervention?
How do I establish a system for mitigating client project risk with my project leaders so we can resolve proactively?
…

Working with Engineering (and other departments)

How can one ensure that the engineering department and team members are appropriately met with, learned from and catered to as stakeholders so that the individual, team, project and department growth support the engineering (or other department’s) organizational needs for growth on this team?
How do I ensure that this department integrates with marketing so that progress on client projects, team growth, departmental growth, individual growth or projects are captured and serve the greatest possible value as marketing tools?
…

Actual Team Growth

How can I ensure that incoming team member’s have a consistent and valuable onboarding experience?
How can I reduce the time to positive team value of incoming team members?
How can I ensure that team growth can scale on-demand to the need for organizational growth?
How can I identify (in advance) risks in team growth and track, and dedicate solutions for and resolve them proactively?
What work processes out of client work and projects need a distillation and collection (in location or explanation) so that they support new team growth?
…

Leadership

How do I collect and determine my own growth path as a leader to determine and share my own progression with my team?
How do I establish a set of advisors or peers that drive or assist in my progression as a leader?
How can I be held accountable to a support structure that clearly identifies when I’m unable to lead my team?
…

2. Determine Patterns

While collecting these problem statements, I was able to identify the tiers of leadership my business represented:

Business > Department > Team (Project) > Individual > Self

The tiered structure is intended to demonstrate that business needs drive departmental needs which drive team and project needs and so on. It can also be honest to look at the structure in the reverse, saying that the capabilities of the individuals collected form the capabilities of the team and the team capabilities organized by department inform the departmental capabilities and so on. I don’t think this is a shocking revelation or anything, but it’s good to be considerate of.

Seeing the Focal Patterns

While the above problems are not complete and likely will never be, they allow me to start to identify patterns in the direction of the various efforts. Some of these patterns can start to be rolled together into themes (which may share individual topics in more than one location/tier), such as:

Risk Assessment — Moments in which leadership is required to proactively identify risks in various business tiers based on the available information.

Path Identification/Creation — Moments in which leadership assists in identifying the appropriate path for growth based on the most complete summary knowledge.

Information Process Creation — Moments in which leadership sets the requirements for what constitutes the complete set of items necessary to allow for an individual item’s success.

Summary Knowledge Collection — Moments in which leadership collects knowledge to support the direction of the business-at-large from various tiers.

Collaborative Value Creation — Moments in which leadership sees and sets the opportunity for shared value and collaboration between departments/teams and enforces them.

Opportunity Innovation — Moments in which leadership, with the right knowledge and process, is the only individual capable of seeing an opportunity or growth path.

Direction Resolution — Moments in which leadership must enforce a direction for progression to counteract stagnation/no growth.

… (And many more)

3. Identify the KEY problem preventing scale

How to move forward from here?

Now that there is a summary of where you need effort, identify the problem statement that allows for you to make an impact. The below is honestly probably something most organizations can just re-use. So, you know, just run with it.

Problem Statement

How can a leader solve the many problems in the various tiers of their business and be attentive to the different focuses that are specifically the requirements of leadership, with obviously limited time and capacity?

Capabilities

I need people to solve my problems for me
I need to solve problems that solve other problems
I need to create other leaders so that my problems are divided
I need to group effort into areas that share focal patterns that can be reused to solve problems
(There are so many more — this is just the baby steps)…

These capabilities may have multiple actual solutions, but there are also thematic practices in these capabilities that can be identified.

I need people to solve my problems for me (Delegation)
I need to solve problems that solve other problems (Prioritization (of impact), AKA Domino Effect)
I need to create other leaders so that my problems are divided and can be solved faster (Replication)
I need to group my effort into areas that share focal patterns that can be reused to solve problems (Affiliation)

4. Pair themes and focuses with solutions

Solution Organization

With the above (starting) set of tiers, focal patterns and thematic practices, one can begin to identify the groupings of original problem statements necessary for responsible leadership to capabilities/thematic practices that are most likely to allow for resolution. An example:

Risk Assessment (Collected from various tiers above)

What are key department risks and then the back-fill from those goals necessary so that we create appropriate operational practices?
What are key business risks and then the back-fill from those goals necessary so that we create appropriate operational practices?
What are trigger points in departmental growth or lack of growth and how do they affect the above?
What are trigger points in business growth or lack of growth and how do they affect the above?
How do we track progress on projects to reduce risk and increase the success rate of projects and the “growth” of the practice?
What does leadership need to know (and what categories of things to know are there) related to client projects so they can feel comfortable with their progression?
How can I ensure I’m asking the right questions to dig deeper into a client project than only a cursory glance, and seeing the patterns and trends, or opportunities, that my employees are possibly not yet senior enough to see?
How do I need to participate in categorizing the work necessary for a given client project with its lead to determine key moments in progress that might require leadership intervention?
How do I establish a system for mitigating client project risk with my project leaders so we can resolve proactively?

Seeing the problems facing leadership grouped by a focal pattern can provide the opportunity to more easily assign the thematic practices most aligned with this focus.

Grouping Risk Assessment problems together is already an act of Affiliation and a good first step. Then, one can evaluate the potential pattern in which delegation, replication or other solution practices are best suited for this focus.

5. Keep supple

A Note on Rigidity and Suppleness, Forging and Polishing
(This point was inspired by Seth Godin’s recent explanation of the similar.)

I think it easy to assume that reviewing this document with this many words and this much structure represents an artifact of an organization that is RIGID. The organization’s leadership implements process, structure and RULES of operation in high volume.

These practices, when operating independently, create a rigidity like that of a FORGE. We bring people in, use the rules and structure to hammer and wear down sharp edges until they fit the mold of how the organization needs to operate and subsequently are refined to a known size and shape. The organization is successful because we know the output of known sizes and shapes and ultimately we can operate and scale predictably.

This is a successful path, but it also a LIMITED one. Rigid organizations have visible ceilings. I think it is important to discern how this work is not RIGID.

Because these structures, processes and operations defined by this process are created via an act of inquiry (we care for and identify the problems as questions for which we know we seek resolutions as a team (and as leaders)), and our philosophical approach to problems, problem statements and the resolution of problems is unyielding in its quantity and depth, the practices and structures we are creating are built on a SUPPLE backbone, that allows us to not wildly implement rigidity simply because of its predictability. Instead, our flexibility in identifying and solving problems allows us to operate not as a forge, hammering our team into a predictable homogeneity, but instead to use the structures and practices above to POLISH, not forge, the organization and team to their most valuable state.

Remember, to avoid rigidity — you can’t just nab the outline here and say, ‘there we go — this is the set of problems I need to resolve to be a healthy leader and have my team kick-ass’. The entire drive to find that set, or the belief that it exists, is rooted in the assumption that you can get to the finish line with a map, and the problem is that most of the people that get there? They do it by accident.

Don’t be an accidental leader. Lead your startup intentionally.