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How to Pair Up The Employee with The Right Manager

This post lists the key insights from this article, from the VP engineering of Smugmug, Nathan Broslawsky.


We are living in an enlightened age of management and leadership. In more and more companies, managers are being evaluated on their ability to coach, grow, and develop leaders within their organizations, and there is an ever-growing corpus of literature and material out there to help aid in this pursuit. This evolution of the manager role has put the spotlight on the manager-employee relationship and has elevated its importance.

Yet, despite all of these resources available to improve leadership skills, there is woefully little dedicated to evaluating whether an employee is paired up with the right manager. In fact, the only time the subject of “finding the right boss” comes up is in the context of finding a new job.

“Don’t pick a job. Pick a Boss. Your first boss is the biggest factor in your career success. A boss who doesn’t trust you won’t give you opportunities to grow.”

William Raduchel

It is increasingly important for organizations to make very conscious decisions about how they pair their employees with managers. The power, or empowerment, to structure and assign these relationships is a responsibility that should be taken incredibly seriously, and it extends beyond simply having someone with a manager title and budgeted headcount.

The decision to pair an employee with a manager should not simply be a by-product of organizational structure: it should be a deliberate representation of the management ethos across the company.

This post is for those organizational leaders; it describes a non-prescriptive framework that can continually be referenced for new hires, re-orgs, or any other types of manager transitions.

There are four main factors to consider when assigning a manager to a new or existing employee: Alignment around Objectives and GoalsSubject Matter ExpertiseCareer Progression, and Values.

1. Objectives and Goals Alignment

In many organizations, the primary factor in pairing an employee with their manager is alignment around a particular set of company objectives or goals. If the manager is given a particular area of ownership or is chartered with a particular objective, the entirety of the reporting structure under them will work in support of those goals. The main benefit of this is that it is inherently intuitive for both the manager and the employee: the manager is able to coach and develop their employees while also managing their workload. The danger of over-indexing on this particular factor when assigning a manager is that shifting company priorities may result in the frequent changing of managers or an employee not being able to explore new areas due to a loyalty or attachment to their manager.

2. Subject Matter Expertise Alignment

For many employees, it is an extremely compelling prospect to be managed by someone who is an expert in their field. This can be incredibly valuable, as this alignment is in direct support of the manager’s responsibilities to train, coach, and mentor those on their team. Assembling a team with this factor as a guiding principle enables team members to learn from not only their manager, but from each other as well. The danger of over-indexing on this factor is that the employee may eventually feel as though they have surpassed the expertise of their manager, or that the employee is not exposed to other potential areas of interest beyond the purview or expertise of their current manager.

3. Career Progression Alignment

Understanding the career aspirations and growth goals of their employees is a fundamental responsibility of a manager. Because of this, unrelated to the organization’s goals or even the subject matter of the role, an important factor in choosing a manager for an employee is that the manager can coach and mentor their reports in support of their career goals. In many cases, seniority and similar career paths are a consideration; this can help to find common ground relatable experiences. This particular factor is particularly powerful for those employees who have a clear vision for where they want their career to take them. The danger of over-indexing on this particular factor is potentially sacrificing the manager’s connection to the employee’s day-to-day work in favor of focusing on what’s next for the employee.

4. Values Alignment

Possibly more abstract than the other three factors, “Values Alignment” is about the “human connection” between an employee and their direct report. There are major benefits that come from emphasizing this factor when assigning a manager to an employee, such as the employee’s morale and trust that comes from this safe space and relationship. The danger in over-indexing on this factor, similar to Career Progression, is the potential that the manager has a lack of connection to the employee’s day-to-day work, but also that there could be employee frustrations stemming from the manager’s inability to relate to or understand that work.

Through a combination of these four factors, companies should optimize for the resilience of the ever-important employee-manager relationship through organizational change.

A Balancing Act

The goal is not to identify the perfect target ratio of these factors for your organization (because there isn’t one). The goal should be to be deliberate and intentional about the decisions you make when it comes to pairing employees and managers.

Selecting a Hiring Manager

The ideal time to talk about choosing a manager is before the hiring process even begins. A well-informed decision at this time has the potential to create a relationship that lasts for many years.

As the interview process commences, more information will come to light around these factors. The hiring manager (and the rest of the interview panel) will have their own specific biases around what they are looking for:

  • Is the person interested in working on these types of projects (Objectives & Goals Alignment)?
  • Is the person teachable and willing to learn from the hiring manager (Subject Matter Expertise Alignment)?
  • What is this person looking to accomplish professionally, and can the hiring manager help with that (Career Progression Alignment)?
  • Can the hiring manager establish a personal and trusting relationship with this person (Values Alignment)?

Additionally, the candidates in the pipeline will be similarly evaluating the company’s choice in a hiring manager, possibly unconsciously. They will want to know how they are assigned projects, who in the organization they can learn from, how the company is going to invest in their career growth, and whether they feel like they will be able to have a fulfilling relationship with the hiring manager.

It is important that these internal and external biases are continually explored and acknowledged throughout the interview process. If done diligently, this will help identify and attract the best candidates to the team and ensure the best onboarding experience once they accept.

The First 90 Days

Many organizations use these first three months as an evaluation (or even probationary) period for new hires, but frequently overlooked, it is also an opportunity to evaluate the organization’s choice in manager for the new hire.

One strategy that works well for this evaluation is periodic skip-level 1:1s. These meetings between the new employee and their manager’s manager provide a great opportunity to understand how supported the new employee is feeling, what the employee is looking for within the company, and how the manager-employee relationship is developing. These meetings should certainly happen less frequently than the regularly-scheduled 1:1s between the employee and their manager, but should happen 2–3 times over the course of that first 90 days.

Manager Transitions

A manager change is not something to be dealt with lightly. In the case of an “ill fit” or the employee or manager simply not getting something they want out of the relationship, this can be a valuable coaching opportunity for the manager before any changes are made.

Ultimately though, if the decision is made to change managers, it is important to evaluate the four factors again, but this time with all perspectives properly represented: the company’s, the new prospective manager’s, and the employee’s.

Any change in reporting structure should be done thoughtfully, infrequently, and consensually.

Once a new manager is identified, the change should be handled delicately. If possible, this should be handled personally by either the current manager or the manager’s manager, as is situationally-appropriate. The person addressing this change should handle the situation with empathy and be prepared to listen for any feedback or concerns that the employee has. A follow-up meeting can be scheduled with the employee, the previous manager, and the new manager to ease the transition by sharing any background and career development plans, and also provide room for questions. The two managers may have different styles, different areas of ownership, or different values, and these are all open for discussion.

6 min​ read

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