Posted: 25 Aug. 2021 10 min. read

Why do careers get stuck in middle management?

Breaking through biases and blind spots

Hypothesis: Most high-performing careers hit a wall in middle management because practitioners shy away from taking risks to address high-quality problems. The conditioned responses to seek career progression act as traps that make it harder for practitioners to develop the skills required to expand the circle of influence.

Let’s unpack the hypothesis by addressing the following questions:

  1. What is a high-quality problem?
  2. What are the common traps in middle management?
  3. How can you expand your circle of influence?


What is a high-quality problem?

A high-quality problem is one that requires self-discovery of a first principle which in turn, brings a shift in how you view your challenges.

To expand your impact beyond the role of an individual contributor requires the ability to establish the ‘why’ (clarity) and the specialisation to determine the ‘how’ (playbook). If we plot these two capabilities on a graph, it is easier to see the career progression in the form of milestones.

This progression is best achieved as a by-product of working on high-quality problems. 

A high-quality problem requires self-discovery of a first principle that brings a shift in how you view your challenges. It is based on intrinsic motivation (recognition, challenge, collaboration) and needs you to embrace your weaknesses. If done right, such an experience can help you expand your worldview.

A good number of careers get stuck in middle management because of the comfort of solving low-quality problems efficiently.

Low-quality problems use your strengths, but they do not influence who you are as a person. They are mostly triggered by extrinsic motivation (promotion, pay, title) and often lead to strong non-productive biases.



Let’s say I am a male designer who did not attend a design school, picked up experience design skills for web and mobile on the job, and spent most of their life in a tier 1 city. Let’s say I have been fairly successful through my 5-year long career and I earn in surplus of my core lifestyle needs working at a mid-stage start-up solving a first-world problem in India. 

Throughout my career, I have observed a growing urge to create an impact in the community that goes beyond the form factor of a digital screen.

If I have the following two offers in hand as part of my next post-Covid career move, I would think #1 is a high-quality problem and #2 is a low-quality one.

Offer 1:

  • For a 20 percent pay cut, a non-governmental organization wants me to spend the next 12 months visiting the hinterlands of the state—to understand the trend for the low representation of girl children in secondary schools—to define outreach programs and influence policy decisions to restore balance.
  • An opportunity to build upon a weak skill in service design, eliminate any personal biases stemming from male privilege and city-life, for an ever-growing intrinsic motivation to make an impact in the community.

Offer 2:

  • For a 30 percent hike, an early-stage start-up wants to leverage my prior experience to strengthen their design team for a web app in the same industry as my current role where I can deliver high impact right out of the door from day one.
  • An opportunity to operate in the comfort zone leveraging known strengths, inadvertently bring over biases from prior experience in the same domain, primarily driven by the extrinsic motivation of increase in pay.


What are the common traps in middle management?

Expecting a predictable linear progression, inability to recognize the role of community at work in your growth, and a self-centred purpose are common traps in the middle years of a career that prevent people from pursuing high-quality problems. Here are the three common traps:


Trap 1: Expecting (and enforcing) a linear career progression

The academic experience conditions us for a linear annual progression. Real-world problems and solutions are hardly linear. The number of high-quality problems we need to crack increases for every incremental career progression we seek. When this doesn’t happen organically (such as, an expected promotion), we force it by chasing labels (title, brand, etc.)


Trap 2: Switching careers for a job instead of for a tribe

After the initial years early in our career, our long-term progression has a weaker correlation to individual brilliance and depends on the collective impact of the tribe we work with—whom we seek as mentors and whom we collaborate with. Finding that tribe is often more rewarding than hunting for a specific role.


Trap 3: Seeking purpose as a fact-finding mission

Think of a leader who inspires you. It can be anybody. No matter what they defined as their life’s purpose, I bet they arrived at a point in their journey where they absolved their own identity—they removed the “me, myself, and I” from their search for a purpose—to give undivided attention to their calling.

Thus, often, our individual “purpose” is not a fact-finding mission.

It is simply a by-product of the experience— the experience of truly bonding with our habitat, be it family, work or community, the experience of being ourselves without being judged, and the experience of contributing passionately without any fear of failure.

Once we find our habitat, we begin to become unstuck.



How can you expand your circle of influence?

You will organically grow as a leader by progressively challenging status-quo to solve intersectional problems by developing an original thought to drive clarity and pursue implementation.

For the purposes of this article, let us assume you are at a place where you are comfortable being—let’s refer to this as your ‘habitat’, a workplace environment where you feel belonged.

It is hard to spell out actionable suggestions to grow your impact without context. So, the following examples assume the context of the crafts involved in building digital products.

At the risk of generalization, you may say that most careers fall into two buckets: strategy or execution. In reality, most roles require you to be adept with certain elements of both capabilities. Here’s one way of showing progression based on your ability to define the “why” and execute the “how”.


The four phases of progression are defined as follows:

  1. Context-specific wins: Early career characterized by strong wins within the confines of a specific context, bound by skill, scope, industry, and a narrow window of time.
  2. Context-agnostic impact: Strong performance built over time across multiple contexts by repeating leading practices of the primary craft to come to be known as an specialist in the role.
  3. Cross-disciplinary delivery: Roles that challenge status-quo, by attempting to solve problems with a known history of failures, requiring integration of two or more disciplines beyond the primary area of specialisation.
  4. “Polymath” performance: Performances that are outside the bounds of traditional roles for problems rarely attempted by discovering and applying novel first principles that have wider applications beyond the focus of inquiry.


Let’s apply this to three specific career points on the graph—points A, B and C.

Example A: Digital Strategist at a Health Insurance Company


  • Able to study market drivers in the insurance sector and understand the role of digital capabilities across industries.
  • Able to define investments needed in digital infrastructure and competencies to effectively win a higher share of the market.
  • Able to effectively drive consensus among the leadership team on strategic priorities.
  • Intrinsic Motivation: Acutely concerned about the impact on members’ lives since most of the work is limited to fancy decks outlining “art of possible” that the organization is not able to execute upon.

“Polymath” Performance

  • Status-quo: Most of the company operations and digital storefronts perform as siloed stove-pipe experiences.
  • High-quality problem: Define a member-first culture and strategy to reorganize internal operations to deliver seamless digital experiences across pre-sales, enrolment, and claims processing.
  • Description: This will require a research-first mindset to understand the unmet needs of the members, followed by the ability to create the political will to uproot what is working from the company’s standpoint, in favor of re-engineering processes, systems, data, and architecture for a seamless member experience.


Example B: Project Manager at a Technology Services Firm


  • Able to drive technology implementation projects for clients with a team of designers and engineers.
  • Experienced in managing estimations, staffing, and delivery methodologies.
  • Proven specialisation in managing risks and issues in scope, software quality, and timelines.
  • Limited say in driving the direction, identifying the outcomes, and determining the pace of execution.
  • Intrinsic Motivation: Dissatisfied with lack of impact of technology solutions. Software applications are not being adopted effectively despite hard work and overtime, even after creating them per the client’s specifications. The adopted solutions undergo significant change control to suit what users need after the fact.

“Polymath” Performance

  • Status-quo: Client investments in technology solutions provide limited returns because of a lack of effort to empathize with end-users despite tracking ‘green’ on metrics for defects, schedule, and spending.
  • High-quality problem: Drive an inside-out change to create a product-first culture that rewards a creative, entrepreneurial, and intrinsi¬cally motivated way of thinking, to iteratively explore and create useful experiences without the fear of failure.
  • Description: Nurture talent with strong product instincts, redefine technology delivery framework and create a product mindset across teams to focus on the “why” behind the efforts in addition to the “how”, including influencing client stakeholders to adopt and support outcome versus output approach.


Example C: Full Stack Architect at an Early-Stage Start-up


  • Self-taught engineering lead at a niche start-up driving overall technology efforts from hiring to building.
  • Independently able to create high-performing solutions at scale using a range of frontend and backend technologies.
  • Attempting to seek a balance between “tooting your own horn” versus drawing attention to some of the niche engineering problems attempted by the team.
  • Intrinsic motivation: Be able to drive organic recognition of the team’s work in the industry and collaborate with like-minded technologists to continue to innovate in the open-source community.

“Polymath” Performance

  • Status-quo: While the team is attempting to solve the engineering problem which is quite niche and they have made significant progress, without a known brand of venture capital firm backing the start-up, the team has limited identity in the community.
  • High-quality problem: Author and distribute quality content on culture and practices of the engineering team as a contribution to the community and in turn build an audience over time to help seek differentiated talent.
  • Description: Create jargon-free actionable content written by engineers for engineers to share wins and challenges, embrace vulnerabilities of an early-stage start-up to authentically story tell the journey to win over supporters, well-wishers, and potentially, future employees.


The wrap-up

As you can see, the specific high-quality problem to solve, based on intrinsic motivations, is highly contextual to your situation and aspirations. That is the reason this article is not about “How to unstick your career from middle management?”

There is no single prescription that will lead you there and if someone is selling it, I would be very cautious.

You owe it to yourself to define that pathway based on your understanding of the situation, often driven by an underlying desperation, followed by a personal journey to investigate the nature of impact you want to deliver.

I trust this article offers one possible framework to approach that journey. Good luck!


About the author

Rohit is a product manager, Deloitte Digital, at Deloitte Consulting India Private Limited, with 16 years of experience in collaborating with clients in retail, insurance, and healthcare industries for building analytics, web, and mobile solutions. He works closely with designers, engineers, and product managers to create the lego blocks for the culture, craft, and community to build a differentiated workplace while helping clients reimagine their future in the digital ecosystem. In his current role, he is focused on scaling the adoption of product thinking principles in creating and delivering digital solutions that elevate the human experience.

The views expressed here are of the author and do not necessarily reflect the views of his current, former, or future employers or any organization with which he is associated.