Organizational Flattening: Understanding the Trend, Career Challenges, and Opportunities (1/2)

Nerd Journey: Career Advice for the Technology Professional

What happens when layoffs lead to organizational flattening, fewer managers, and larger teams? It’s a trend we’re seeing in the tech industry at large right now impacting team dynamics and career paths. To understand what’s really happening and the overall impact, we pulled in former guests Abby Clobridge, Shailvi Wakhlu, and Leanne Elliott in a roundtable format.

In episode 347, we explore the trend and the unique challenges it presents to consulting firms, managers, and individual contributors working with and inside flatter organizations. Listen closely for the impact to job levels, what this means for top-tier individual contributors, how companies are thinking about knowledge management, employee loneliness and wellbeing, and where some unexpected opportunities lie for those willing to step up.

Original Recording Date: 09-27-2025

Topics – Framing Our Discussion and a Slightly Different Format, Defining the Trend, Impact on Career Structure and Ambiguity, The Challenge of Reaching Top Tier Positions, Internal Risk and Potential Loss of Knowledge, Strains on Execution, Impact to Team Dynamics, From Problem to Opportunity

1:01 – Framing Our Discussion and a Slightly Different Format

• For today and in next week’s episode, rather than introducing a guest to share their career story and lessons learned, we’re trying something a little different.
• Recently we sent a follow up question to a former guest whose response sparked an idea for this format.
  • The trend of organizational flattening in our industry has been top of mind for us. We’re seeing the continued layoffs in tech often times result in fewer management layers and an increase in the number of people reporting to a single manager.
  • This topic is too big and has too many angles for a single conversation. We wanted to bring together multiple expert perspectives on this issue in a single episode. We’ve reached out to a handful of former guests and sent them specific questions on this topic. Those guests were kind enough to record their answers and send them back to us.
  • Consider this a Nerd Journey roundtable or collection of hot takes from trusted voices. Our goal is to amplify their advice and provide a diverse set of strategies for navigating this landscape.
  • In the first episode (this week), we explore the trend of flatter organizations and the consequences for your career path and team culture. Next week in part 2 we will focus on actionable insights for thriving in this environment.
• Here’s the full set of episode links we will share throughout the conversation if you would like to hear more from one of the former guests who participated:
  • Abby Clobridge
    • Episode 292 – Library Science: Information Architecture and the Synthesis of Details with Abby Clobridge (1/2)
    • Episode 293 – Enterprise Knowledge Management: A Consultative Approach to Solving the Right Problems with Abby Clobridge (2/2)
  • Shailvi Wakhlu
    • Episode 210 – A Collection of Ambiguous Experiments with Shailvi Wakhlu (1/2)
    • Episode 211 – Structure the Levels of Contribution with Shailvi Wakhlu (2/2)
    • Self-Advocacy: Your Guide to Getting What You Deserve at Work by Shailvi Wakhlu
    • A special 15% off link for Nerd Journey listeners to Shailvi’s self-advocacy course can be found here.
  • Leanne Elliott
    • Episode 237 – The Psychological Transition of Layoffs with Leanne Elliott (1/2)
    • Episode 238 – Managers as Culture Keepers with Leanne Elliott (2/2)
    • Episode 340 – Task Cohesion: Managing a Larger Team in a Flatter Organization amidst a Climate of Uncertainty with Al and Leanne Elliott (1/2)
    • Episode 341 – Champion Your People: Role Clarity for the IC in the Chaotic World of Work with Al and Leanne Elliott (2/2)
    • Subscribe to the Truth, Lies and Work Podcast

2:48 – Defining the Trend

• Abby Clobridge is the founder and principal consultant at FireOak Strategies and has deep expertise in the realm of knowledge management. Abby was a guest in episodes 292 and 293. We wanted to get an outside perspective from someone who works with many different organizations on various projects.

Our question for Abby:

• Within your customer base and set of prospects, do you see companies currently doing organizational flattening of management layers with an increased number of direct reports for managers? And if you have seen it, what do you think is the reason for this? We’ve heard of 20 or more people under a single people manager.
  • Several of Abby’s clients are going through huge changes, sometimes resulting in entire teams and departments (like IT) being eliminated. In some cases, IT work is being shifted to MSPs (managed service providers), which has pros and cons.
  • According to Abby, the economic climate and the rise of AI adoption has made this year tumultuous for everyone.
  • Abby is seeing companies put more and more people under a single people manager.
  • She tells us that managers with extremely large teams have no way to build real relationships. The large team often results in employees not being able to rely on their manager for much from day to day.
  • “That kind of dynamic is a recipe for cultural toxicity really quickly too.” – Abby Clobridge

4:25 – Impact on Career Structure and Ambiguity

• Shailvi Wakhlu is a leadership speaker and data consultant with experience building and leading large organizations, including structuring of job levels for career paths. We spoke to her in episodes 210 and 211 She’s also the author of Self-Advocacy: Your Guide to Getting What You Deserve at Work.

Our question for Shailvi:

• In our previous conversation we talked a lot about job levels. Do you think flatter organizations make it more difficult to clearly define those job levels, or are big companies that are cutting head count to flatten even thinking about this? What do you wish these companies would consider?
  • “The stated reason that companies move towards flatter organizations, I think, is because they want to get rid of hierarchy. They want to say…we don’t want the lack of a higher title to restrict you from having a greater impact on the company. And I think that’s a fair goal…. However, I think in reality how it actually ends up playing out is, one, when you have a very flat organization…people don’t know what will be rewarded. And two, there is a lot of ambiguity about what everyone’s job is…. If everyone is responsible for something, typically no one is responsible for something.” – Shailvi Wakhlu
  • It makes sense that a company would want people at all levels to feel empowered to contribute.
  • Accountability comes through making distinctions in roles. Shailvi gives the example of senior engineers being expected to be more on top of certain things, and the same expectation would then not apply to junior engineers.
  • People are thinking about the kind of contributions that would be rewarded within an organization as well as how to grow their career. Typically, titles are used to acknowledge the level of contributions an employee has made. Moving from one well-defined job level to another gives a person a sense of progress and something to aim for.
    • “So, if there is not that definition of what is expected at each level, some people…may not have the tools to figure out what they should aim for…. Instead, I think the reason people started defining job levels was so that you could anchor on outcomes and impact.” – Shailvi Wakhlu
  • Years ago, companies would anchor on years of experience and hand out titles based on that metric, but the flaw in this approach was that it did not reward impact.
    • A specific job level shares the expectation of an employee’s impact on technical progress for the company, business results, communication skills, etc.
    • “If you want people to anchor on that, if you want people to strive for that higher skill set, you have to actually define them. If you keep them super ambiguous, if you keep it super hidden, then…I think that’s also a reason why companies end up with things that look like favoritism.” – Shailvi Wakhlu, on job levels
    • Without clearly defined job levels, a person doesn’t know what they need to do to showcase the kind of impact a company would like them to have.

8:41 – The Challenge of Reaching Top Tier Positions

Another question for Shailvi:

• We’ve spoken a lot on the show about the individual contributor’s career path or what we call the technical career path and getting up to the role of principal engineer inside an organization. Would the flatter organization mean it becomes infinitely harder to rise to the level of principal engineer, that highest tier of individual contributors?
  • Flatter organizations are not necessarily handing out titles that can help you when applying for a different job.
  • “Even if within your own company people know you contribute at a very high level, that external signaling may not be very obvious to another employer. When you have…principal engineer, staff engineer, those type of titles…it is easier for a new company to understand just in context that you were in the highest tier of individual contributors.” – Shailvi Wakhlu
  • Shailvi might split this into 2 pieces – rising up inside your existing organization and transitioning to a new job or different organization which may have a harder time measuring your impact.
    • Shailvi does not think a flatter organization stops you from reaching top-tier individual contributor. It may, in fact, open up new opportunities to work on highly impactful projects. Access to these projects is usually based on past performance on projects, how you advocate for your work, etc.
    • “If you keep showcasing that you are capable of handling more and more complexity, eventually you will get the highest value projects that have that very high C-suite level visibility…. Just the fact that it’s a flatter org should not stop you from having impact at the highest levels of what affects the business, what has the most visibility, and what is most critical to the company’s stated goals.” – Shailvi Wakhlu
    • The problem will come when you are trying to join an organization where job levels are very clearly defined. A company may want a principal engineer, and even if you have the impact of one but don’t have the title on your resume, applicant tracking systems may disqualify you automatically. If you are relying on people reading your resume, add as many indicators as possible that the projects you worked on were at the highest level of impact. Shailvi suggests possibly stating that the principal engineer title did not exist because of the flat organization (if that was the case).
    • Professional networking is very important to help showcase the level of your impact if you’re looking to land a principal title somewhere but don’t have that at your current company. Shailvi mentions talking with others in our industry, talking with recruiters, and talking with hiring managers.
    • “There are many ways that you can show up as an industry leader that are outside of your company. You can talk at industry conferences. You can have a lot of content that you put out there which makes it very clear to people….” – Shailvi Wakhlu

12:43 – Internal Risk and Potential Loss of Knowledge

Another question for Abby:

• "Is organizational flattening causing significant skill gaps at companies and creating opportunities for companies like yours or actually making it more difficult? In other words, are companies wanting to cut employee head count also cutting down the number of consulting firms they will partner with, or are they leaning into working with consulting firms more than they were previously?
  • “Layoffs and organizational flattening and, weirdly enough, AI…that’s all creating a heightened awareness of the importance of organizational knowledge management.” – Abby Clobridge
  • Abby says executive teams are starting to understand the importance of having organizational knowledge captured in a way that is documented well and easy to access, reuse, and build upon.
    • It is important to allow people to shift roles without losing more organizational knowledge than necessary.
    • “While we’ve made huge strides with AI adoption in the workplace, there still isn’t a magic vacuum that can pull knowledge out of someone’s head. When critical staff members leave, institutional memory leaves with them. Good knowledge management can’t stop that entirely, but it can soften the blow and help organizations keep moving forward.” – Abby Clobridge
  • Flattening is a chance to re-think how knowledge flows across your organization. Fewer management layers could mean fewer bottlenecks. If done correctly, flattening can lead to greater transparency within teams and the mindset that knowledge is a shared asset. There is a balance between keeping the right level of security and making knowledge accessible, and it can look different for different organizations.
  • For companies partnering with consulting firms, Abby says it’s a “mixed bag.”
    • Some companies are cutting consulting budgets, while others are shifting to more fractional and outsourced roles. It depends on the company.
    • “To be honest, it feels a lot like the summer of 2020 where organizations were suddenly trying to pivot or figure out what they were going to do and how to handle COVID.” – Abby Clobridge

14:54 – Strains on Execution

• We wanted to know how this climate impacts company execution.

Another question for Abby:

• Does the current climate make it more difficult to help your customers “solve the right problems” when the team is leaner / smaller and is under a heavier workload? How have you adjusted your strategy to help customers solve the right problem as a result of these situations? For example, does a flatter organization make it more difficult for customers to commit to spending time in the diagnosis / discovery phase because executive leaders want faster results from smaller teams?
  • Abby says she has seen it go both ways.
    • Some teams want to get through discovery and diagnosis quickly because they are stretched too thin, but experience has revealed moving past discovery too quickly or without talking to all the right people is a mistake.
    • Most of the time Abby and her team have been able to build an approach with clients to balance speed with getting things right.
    • Several new projects are focused on preparing organizations for knowledge management in the age of AI.
    • “These are really long term investments that the organization wants to get right, so even though everyone is anxious to get started, execs realize that it’s worth a few extra weeks or a few extra interviews to make sure we’re able to get a good sense of what’s going on and what the organization is really trying to accomplish so we can give the best possible advice.” – Abby Clobridge
    • Some companies end up making big platform or system decisions far too quickly and often times without the right voices in the room. This only leads to costly mistakes.
    • “Technology decisions aren’t made in a vacuum anymore. Very few platforms live as silos. There are almost always downstream effects. So, if you move too quickly without requirements, impact analysis, and honest conversation about tradeoffs…you end up with ripple effects that can be very costly and disruptive. It doesn’t mean decisions have to drag on for months. The key is balance – moving at a healthy pace but giving people enough time to digest, weigh impacts, and make better informed decisions.” – Abby Clobridge

16:57 – Impact to Team Dynamics

• We wanted a perspective on team dynamics, so we brought in Leanne Elliott. Leanne is a business psychologist and with her husband Al, hosts the Truth, Lies, and Work podcast. We spoke to Leanne in episodes 237 and 238, and she also appeared along with Al in episode 340 and 341. The questions we’re asking her are follow ups from the conversation we had with them on organizational flattening.

Our question for Leanne:

• We have seen companies with 1 or more pods under each manager where there is some kind of pod lead / team lead within each pod who helps the manager do things like track work, give team members feedback, etc. Have you seen this structure work well in flatter organizations?
  • Leanne has seen the pod structure work quite well, but more often than not, she has seen it go badly.
  • This has a tendency to create an “us and them” culture, especially when people do similar work but are part of different teams. If there is not advertisement or reinforcement of the core mission bringing everyone together, this can breed workplace incivility (cliques, gossip, division, etc.) and create microcultures.
  • With a complex structure like this, it requires more care, close monitoring, intentional management, and a willingness to make adjustments when needed.
    • “My worry is that if it’s not handled well, it’s not done with the best of intentions…then it can mean that people feel more disconnected, there’s more infighting, and ultimately more isolated.” -Leanne Elliott
  • The latest State of the Workplace Report from Gallup found that 1 in 5 employees have stated they feel lonely at work. This is an organizational issue and not just a personal issue.
    • “People often think that loneliness is about maybe being shy or introverted, but it really isn’t. There’s no link between personality and how lonely somebody feels. What does matter, according to the research, is the environment. It’s a complicated thing as well to look at your organization as a supervisor, as a colleague, as a senior manager and try and identify the people that are lonely and try to fix that. People don’t act lonely at work.” – Leanne Elliott
    • People are skilled at masking how they really feel and may seem chatty, gregarious, or outgoing.
    • “…because that loneliness is so stigmatized that people will pretend it’s fine rather than the fear of repercussions because that psychological safety doesn’t exist if they did speak up and say something about it.” – Leanne Elliott
    • Having leads in each pod who are closer to the group may foster an environment of psychological safety. But, this is not necessarily going to be the same behavior senior leaders who have the power to do something to change the environment will exhibit. A lead / supervisor may recognize there is a problem with how someone is feeling but be unable to do anything to really change the overall environment.
    • If people do open up inside the pod structure, there is a chance they will remain disconnected over time, which chips away at wellbeing.
    • “As with anything in the workplace, these types of things to…have the most positive impact require attention, require support, and require the agility to change these experimental structures when they’re not working.” – Leanne Elliott

21:13 – From Problem to Opportunity

• Maybe we could look at this trend as an opportunity?

Another question for Leanne:

• In a world where manager to individual contributor ratios are changing, does this create an opportunity for individual contributors to take more of a player / coach or team leader kind of role?

  • Leanne does think this will create an opportunity for individual contributors to take on a coach, team leader, or supervisor kind of role. People will step up into these roles when needed, and it’s usually the more conscientious members of the team who do.
    • Some may seek this role out of ego, but the small nature of the team will make this highly visible. It’s not usually out of ego that someone takes the role, but it can happen.
    • If this role is an official role, it can be a great way to develop people.
    • “It’s that chance to try out people management in a more hands-on, practical way…so less theory, on the job training. You’re close to the work as well so you understand what it really takes to deliver that rather than being a removed senior manager…. And for the group as well, people do look for someone to follow.” – Leanne Elliott
    • For groups of this size (larger than 12 or 13), it is hard to connect with everyone individually. We would often look for a shared goal, mission, or values. People look for someone to show them what that is and how to make sense of it all. The leader in larger groups gives us clarity, sets a tone, and demonstrates what is expected. This helps employees feel safe, more confident, and like they belong (all of which are great for wellbeing and lead to team cohesion).
    • “The issue with these types of supervisor roles is typically they aren’t formal. So, someone will step up, or maybe they’ll get nudged into it by a senior manager. But there’s no support, there’s no extra pay, and there’s no real recognition. Now, that’s fine initially. That’s what we call ‘hope work,’ work where someone can see the benefit of stepping into an informal role without any kind of extra pay or recognition on the understanding and the view that this will be for a finite period of time. And then the pay and the support and the recognition will come. If it doesn’t (and it typically doesn’t in informal supervisor roles), then that can build resentment over time, and it can lead to this person disengaging and burning out…which is a danger because typically it’s the high performers that will step into these types of roles. But when it is done properly…right structure, right support…then yeah, it can be a great steppingstone for anyone who is looking to move into a management role who doesn’t have any experience or training at that point.” – Leanne Elliott

• We want to say a huge thank you to all of the guests who contributed to this episode! If you want to hear more from them, you can find the full conversations…

  • Abby Clobridge was a guest in episodes 292 and 293.
  • We spoke to Shailvi Wakhlu in episodes 210 and 211 She’s also the author of Self-Advocacy: Your Guide to Getting What You Deserve at Work.
    • Here’s a special 15% off link for Nerd Journey listeners to Shailvi’s self-advocacy course.
  • We spoke to Leanne Elliott in episodes 237 and 238, and she also appeared along with Al in episode 340 and 341.

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• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.
• If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.