Why Do Careers Get Stuck in the Middle Management?


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 to develop skills required to expand the circle of influence.

Let us unpack the hypothesis by solving the following questions:

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

What is a high-quality problem?

Expanding your impact beyond the role of an individual contributor requires the ability to establish the why (clarity) and the expertise to determine the how (playbook). If we plot these two capabilities on a graph, it is easier to see this journey 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 and 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.

High-Quality Problems

  • Based on intrinsic motivations (e.g. recognition, challenge, collaboration)
  • Drives you to embrace your vulnerabilities and areas of growth
  • Requires a self-discovery of first principles
  • Expands your worldview by bringing a shift in how you approach your challenges

Low-Quality Problems

  • Based on extrinsic motivation (e.g. promotions, pay, title)
  • Success is driven by building upon your existing strengths
  • Based on proven strategies on beaten path
  • Do not influence who you are as a person, worse, can lead to strong non-productive biases


Let’s say I am a male designer who did not attend a design school, picked up the skills for experience design for web and mobile on the job, and someone who has spent most of the life in a tier 1 city. Let us say I have been fairly successful throughout 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 high-quality and #2 is a low-quality problem.


  • For a 20% pay cut, an NGO 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 derived from male privilege and city-life for an ever-growing intrinsic motivation for community impact


  • For a 30% 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 on day 1
  • 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 the pay hike

What are the common traps in middle management?

The following traps prevent people from pursuing high-quality problems.

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 (e.g. an expected promotion), we force it by chasing labels (title, brand, etc.)

Seeks clarity (1).png

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

After the first few years in our early 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 mentorship from 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. 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, our individual “purpose” often 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 get unstuck.

How can you expand your circle of influence?

For the purpose of this article, let us assume you are at a place that you are comfortable referring to as your habitat, a workplace environment where you have found the belonging. If you are in search of one, you may find this article relevant on 10 Questions to Ask Interviewers on Work Culture.

It is hard to spell out actionable suggestions to grow your impact without context. So the following examples assume 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 and execution. In reality, most roles require you to be adept with certain elements of both capabilities. Here’s one way of showing that 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

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 expertise

2. Context-agnostic impact: Strong performance built over time across multiple contexts by repeating leading practices of the primary craft to be known as an expert in the role

4. “Polymath” performance: Performances that are outsides 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.

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 amongst 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 re-org internal operations to deliver seamless digital experiences across pre-sales, enrolment, and claims processing.
  • Description: This will require a research-first mindset to first 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 Professional 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 expertise 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 the technology solutions. Software applications are not being adopted effectively in spite of hard work and overtime even after creating them as specified by the client. 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 intrinsi­cally 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 driving overall technology effort from hiring to building at a niche start-up
  • Independently able to create high performing solutions at scale using a range of frontend and backend technologies
  • Attempting to seek a balance between “beating your own drums” 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 partner with like-minded technologists to continue to innovate in the open-source community

“Polymath” Performance

  • Status-quo: While the engineering problem the team is attempting to solve is quite a niche and they have made significant progress, without a known brand of VC backing the start-up, the team has a very little 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’s the reason this article ISN’T titled “How to unstuck your career from middle management?” There isn’t one prescription that will take you there and if there’s someone 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!

PS: The definition of a high-quality problem also has direct relevance in establishing a definition for quality of life. You can read about it in a series of short slides here – Codifying Quality of Life.

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