Inside Ai Part V: Managing without Managers

How we divided the role of manager

Robbie Allen
13 min readApr 3, 2017

This is Part V in a series on how Automated Insights revamped its organizational structure and operating model. Start at the beginning with Part I.

The perception of employees in a “managerless” organization

The traditional role of “manager” inside of most companies is fundamentally flawed. Not only do we expect managers to be the leader for their group, handle resource allocations, hire and fire, and possibly manage budgetary concerns, managers should also be a confidant for their employees and provide career development advice.

I don’t know about you, but I’ve had very few managers in my 20 year career that did a great job of both managing my performance (i.e. providing feedback on how I was doing) and helping with career development. But it wasn’t their fault. The problem is that in most organizations, managing performance and assisting with career development are conflicting responsibilities. That’s to say nothing of the differing skills needed to do both for which managers are rarely trained.

Traditional Employee/Manager Relationship

With a typical organizational structure, employees are precious resources that are not encouraged to move around. To move between groups generally requires an act of god and shouldn’t be attempted lightly. It’s not in the best interest of the manager because when an employee leaves, the manager loses the headcount or possibly needs to hire a backfill. Inefficient organizations are ever-expanding. If there is any chance that a manager might not get a backfill for an employee that’s moving on, there’s even more incentive to make it difficult for her to move.

From the employee’s perspective, your options are pretty limited to move within a company. If you are part of the “Engineering” organization within a line of business, there aren’t many places you can go unless it is to another Engineering group in a different line of business.

Most job hopping inside a big company looks like this:

Inside of smaller companies or organizations with a single Engineering group, your options are even more limited. If you are a developer and your company only has one Engineering group, there is no where to move.

When Organizational Boundaries Don’t Matter

Compare this with the kind of movement we’ve had within our customer journey-based organization in the last eight months:

Number of people changes across Squads per month

Some interesting facts about the last 8 months:

  • We average 4.75 people moving to a different Squad every month. That’s right at 10% of the company every month.
  • 76% of the company has changed squads (38 moves out of 50 people) in eight months.
  • Every Squad has had at least two people move in and out.
  • We’ve gotten rid of eleven of our initial eighteen Squads.
  • We’ve added seven Squads that weren’t present originally.

Needless to say this kind of movement isn’t possible inside of most companies. Also, it requires a different mindset by the employees that are used to rigid organizational boundaries, but after the first few months most of our employees got comfortable with it.

For those that wonder if this kind of movement causes too much disruption or is necessary in the first place, I’d argue that you only think that because you’ve become indoctrinated with the traditional organizational approach. When you no longer have to constrain where people sit in an organization based on their job title, you are able to be much more nimble and move people around to where they can be most impactful. Think of it as iterative organization design. When changing the organization isn’t a big deal, it’s easier to keep your company aligned with the customer journey. For a new product in a new industry like we have at Automated Insights, this kind of agility is critical as we figure things out.

So What About Managers?

With our new Squad approach, we had to figure out where Management fit in. Going back to Part I, this provided a prime opportunity to rethink the role of manager starting from first principles.

We created an Agile framework around Squads to focus on optimizing their metrics. Squad Leaders are accountable for their metrics and every Squad Member plays a role in improving their metrics. It made sense that the Squad Leaders held their Squad Members accountable for doing their part. Half of the management equation (performance management) would thus be handled by Squad Leaders.

That still left out career development and we heard consistent feedback that it was lacking at Ai. It didn’t make sense to me to have Squad Leaders, who were supposed to be focused on execution and performance, take on the responsibility of doing career development for their Squad Members. Not to mention that it’s not always the case that your Squad Leader is the best pick to offer career advice.

The answer was clear to me. We needed a separate function inside the company that addressed career development, so we created the Ai Guide Program. Think of it as an internal mentorship program, but I didn’t want to use the word “mentor” because it’s an overused and abused term that carries certain baggage. We thought “Guide” was just as applicable because we are helping guide employees through their career at Automated Insights.

So we split apart the role of manager into two. Squad Leaders manage performance and Guides provide help with career development. Next, I’ll go into detail about both roles and the expectations we set for each.

I want to thank Joe Procopio for writing up much of the material that I use in the remainder of this article. I pulled much of it straight from the internal docs Joe wrote, which we use to help onboard new employees.

Squad Leaders

A Squad Leader is responsible for the performance of their Squad. The top priority of each Squad Leader is to maximize the positive impact of their Squad on the overall system.

Squad Leaders are facilitators, with the authority to assign and prioritize tasks that best meet their Squad’s metrics. Squad Leaders should encourage autonomy from their Squad Members, allowing each Squad Member to complete their assigned tasks using their own experience and best practices.

Squad Leaders are contributors, and work alongside the other Squad Members. We believe that the best leaders lead by example, not by mandate.

Assignments and Experiments

Anytime we’ve had a performance issue with an employee in the past, the most common complaint was the manager did not make it clear what was expected.

To address this, we stress our Squad Leaders give assignments that are clear, written, and contain expected deliverables and due dates. When more than one assignment is given at the same time, or if the Squad Member is working on more than one project at the same time, the Squad Leader must provide the prioritization of the tasks and the expected percentage of time allocated to each.

Squad Management

Managing the Squad will often result in a mix of “hands on” tasks vs. “management” tasks. The Squad Leader should delegate as much “hands on” work as possible. However, it’s up to the Squad Leader to find the right balance, and that balance is often a moving target from sprint to sprint.

Availability and input are essential to managing the Squad. The Squad Leader should be available at all times to advise on assignment definition, priority, and any blocking issues. They should also be available to communicate and integrate with other squads whenever necessary. That said, Squad Leaders should, whenever possible, let each Squad Member determine the best course of action for completing assignments. We do not believe in micromanaging.

Continuous asynchronous feedback is an important tool for the Squad Leader. This may be accomplished with 1 on 1s, informal conversations, or directly or indirectly in meetings and standups. A good benchmark is to check in with each Squad Member individually once a week informally and/or once per sprint formally. This is important for both deadline management and Squad Member development.

Hard conversations are also part of the job. We conduct sessions with the Squad Leaders on how to have hard conversations and how to approach performance issues. A Squad Leader can escalate ongoing problems to his Tribe Leader.

Once a month, a survey is sent to each Squad Member to evaluate the performance of Squad Leaders. We’ve found this feedback to be very useful. We continue to tweak the format and content of the surveys, but it’s an important tool to help Squad Leaders understand areas they need to improve.

Isn’t a Squad Leader a Manager?

Some may say that a Squad Leader sounds like traditional manager. To be honest, I’m not that interested in semantics and debating what is or isn’t a manager. I’m more concerned with starting from a clean slate, evaluating our leadership and management needs, and putting a system in place that solves those needs. Our Squad Leaders are a different than traditional managers. They are less worried about “headcount” because they are managing a small team (again, we try to keep Squads to 3–6 people). As I described earlier, Squad Members shouldn’t get too comfortable with who their Squad Leader is because there is a good chance it will change soon. And because of our agile approach, it is easier for us to try our promising Squad Members as Squad Leaders, and if it doesn’t work, they can go back to being a Squad Member. It’s not a binary “management or individual contributor” decision that plagues so many high potential employees.

The other point I’d argue is the duties of a Squad Leader don’t cover everything a company should be doing to make use of and develop their employees. That’s where the Ai Guide Program comes into play, which I’ll describe next.

Guide Program

The Guide Program is designed to provide employees a trusted resource to guide them through their career. Guides are intended to aid in overcoming work and workplace challenges as well as provide advice on professional growth.

While Squad and Tribe leadership focuses on the performance of their respective teams, the Guide Program focuses on each individual, one-on-one, to facilitate the success, fulfillment, and growth of every employee.

The Guide Program is OPTIONAL. Unlike the work that is done within a Squad, if an employee doesn’t care about career development, that is their decision. We strongly encourage participation and I have a strong feeling that participation is associated with being a “good” employee, but at this point we have not mandated it.

I believe strongly that the company has a duty to offer career development assistance to its employees, but that is the extent of the responsibility. The employee is entirely responsible for taking advantage of that assistance and following through. I feel the same way about traditional mentor/mentee and advisor/advisee relationships. The mentee/advisee/employee is entirely responsible for being proactive and making things happen. It is NOT the responsibility of the Guide/mentor/advisor to schedule meetings or follow-up.

Guide Objectives

The following scenarios illustrate the types of issues and questions that Guides are supposed to help with.

Advice and assistance on skill development:

  • “I want to be a better data scientist/developer/salesperson, etc.”
  • “I’m not a data scientist/developer/salesperson but I want to learn R/Ruby/How to close deals, etc.”

Mentorship on professional development:

  • “I want to be a more effective leader/communicator/negotiator, etc.”
  • “I want to learn how to build a company/create a product/public speaking, etc.”

Insight on career progression:

  • “I want to be a Squad Leader”
  • “I want to lead people/product/process/policy, etc.”

Point of contact for day-to-day work/life issues:

  • “I need help with this technical issue/marketing assignment/brownbag, etc.”
  • “I’m not happy/productive/satisfied etc. because…”

Serve as a sounding board for questions and ideas:

  • “I’ve got this great idea for…”
  • “What’s the best way to go about…”

Help with expanding your professional network:

  • “How do I get involved or more involved with…”
  • “Is this event/class/group, etc. worth doing?”

Provide insight on company culture:

  • “Why does the company do…?”
  • “I need to be more trained/effective/motivated, etc. — How can the company facilitate that?”

Guide Program Structure

It is important to establish a Guide Administrator role. Currently, the Guide Administrator at Ai is our Head of HR. She’s the one that oversees all logistics related to the program. There are enough moving pieces with the program that it is critical to have a point person responsible for it or things will fall through the cracks.

To start, we have each employee select 1–3 Guide choices in order of preference. Ideally, the Guide should be able to help with ALL the objectives listed in the previous section that are pertinent to the employee. That may or may not be the case, so when choosing Guides, it’s best for the employee to prioritize the objectives she most wants to concentrate on, and choose the people that best fit the highest priority objectives.

Employees will have one Guide at a time and the Guide relationship will last for six months. At the end of the six months, employees go through the selection process again.

Why did we pick six months versus another timeframe? There are a couple factors at play. First, the timeframe needed to be long enough that we could expect meaningful results based on the Guide and employee meeting every other week. Three months seemed too quick. Twelve months seemed too much time and if the relationship wasn’t working, there would be a lot of wasted time. We picked six months as the middle ground. After having gone through our first six month period, it seemed to work.

After the six months are over, Guides are encouraged to continue the relationship indefinitely on a voluntary and informal basis. We hope the Guide and employee develop a relationship that lasts beyond the Guide Program.

Anyone in the company can be a Guide, provided they have been at the company for at least 6–9 months.

An employee’s current Squad Leader cannot be their Guide. By having a Squad Leader and Guide be the same person, we’d start to see the conflicts of interest I mentioned earlier that often plague traditional managers.

Guides should have a maximum of three employees at one time in order to be most effective, although some can have up to five when necessary. This is why employees select three people as potential Guides. Some employees are very popular Guide picks, but taking on more than 3–5 employees would be a non-trivial time commitment and likely dilute their usefulness to all of the employees they are guiding. Rarely have we had to assign an employee their third choice of Guide.


In our first six month Guide program, we strongly encouraged employees to create at least three goals related to their career. It could be something small (e.g. “Research React and Angular to determine if I’d like to become a front-end developer”) to more substantial (“I want to become a Squad Leader”). This proved to be more challenging for our employees than I anticipated. Many employees struggled with creating career-oriented goals and would start to pull away from the program as a result. We had to soften our approach to goals and not make a vital part of the program.


Employees and Guides must meet a minimum of once a month, and should meet twice a month or more, for a total of six to twelve meetings (or more) over six months. These meetings should be formal, private, and a minimum of a half-hour, but what is discussed at these meetings will be up to the employee. Guides and employees are encouraged to also meet informally throughout the six months. As with any relationship, the more communication, the more rewarding the relationship. Our hope is that after the six months is over, a tight bond has developed between the Guide and employee that will continue.

We reimburse up to three coffee or (inexpensive) lunch meetings throughout the six months.

There will be a three-month midpoint check-in (once during each six-month relationship) with both the employee and the Guide. This is to check how the guidance is going and see how far along employees are to achieving any goals they created.

At the end of the six months, there is an individual feedback process, for both the employee and the Guide. This takes the form of a survey that is shared with the Guide, employee and Guide Administrator.

Guide Training

All Guides get initial training for establishing and managing their relationship(s). The Guide Administrator is available for any questions or concerns that arise, either with the program or with any relationship.

Professional Development Resources

Guides and employees should discuss options for external resources for professional development, such as classes, conferences, and/or learning materials. The company can offer financial assistance and/or allow workday time on a case-by-case basis.

New Hires

New hires are assigned a Guide within their first week of employment for a maximum duration of 90 days. This Guide can assist in onboarding to ensure the employee is set up to hit the ground running in their new role.

After this initial period, the employee will move into the formal Guide Program where they will have the opportunity to choose their Guide and set up goals that will enhance their technical skills, personal and/or professional growth.

Managerless or Managerful?

Even though I’ve describe Automated Insights as “managerless”, we still have roles that provide some of the same functions as traditional managers. If you combined our Squad Leader and Guide into one person, that’s a decent representation of a traditional manager. But trying to conform to traditional roles is not something I’m interested in. I think too much emphasis is placed on the shoulders of traditional managers and what we’ve done at Ai is an attempt to rectify that.

Next in the final article in the series, I’ll review some of the major lessons learned from a year of change at Automated Insights.

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