Organizational Flattening: Intentionally Model Behaviors to Build the Culture You Want (2/2)

As managers inherit larger teams inside flatter organizations, we might immediately point out the challenges. But what about opportunities? Despite the trend, those who seek to lead (in a management capacity or otherwise) have the chance to intentionally build a better culture.

We pulled in former guests Shailvi Wakhlu, Neil Thompson, and Abby Clobridge in a roundtable format to get actionable strategies.

In episode 348, we present actionable strategies for managers and individual contributors to thrive in this new environment. Listen closely to understand the importance of improving one’s communication skills, the unique opportunity and impact of the player coach / team lead, the critical elements of a manager’s role, and advice for job seekers in a tough market.

Original Recording Date: 09-27-2025

Topics – Framing Part 2 of Our Discussion, Opportunity for the Player Coach, Modeling the Benefits of Improved Communication Skills, Management Support of Strong Communicators, Individual Contributors and Communication, Succeeding as a Manager of a Large Team, The Culture of Large Teams, Advice for Job Seekers in a Tough Market, In Closing 1:01 – Framing Part 2 of Our Discussion

• Last week in Episode 347 – Organizational Flattening: Understanding the Trend, Career Challenges, and Opportunities (1/2), we introduced a slightly different format that we’re continuing this week based on an industry trend.
  • 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 (last week), we explored the trend of flatter organizations and the consequences for your career path and team culture. This 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:
  • 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.
  • Neil Thompson
    • Episode 193 – Communication for Specialists with Neil Thompson (1/2)
    • Episode 194 – Question Askers and Problem Solvers with Neil Thompson (2/2)
    • Teach the Geek YouTube Channel
  • 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)

1:42 – Opportunity for the Player Coach

• We’ll start by discussing the opportunity of being a player coach (another way we often reference the team lead or tech lead role).
• 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:

• As organizations flatten and there are less manager roles, does this create an opportunity for people to become a technical lead or team lead to help the manager scale? We would love to hear any perspective you have on how the team lead / tech lead (i.e. player coach type role) changes as a result of the org changes.
  • Even without the trend of flattening or decreasing the number of managers, there has consistently been an opportunity for people to demonstrate the mindset of group leadership. Someone could be a project lead, a team lead, or a technical lead.
  • The technical lead focuses more on technical standards to which a team needs to adhere.
  • “I think anything that you do that helps your manager manage the team, scale the team, grow the output, or just have better focus…has always been a good way to get your foot in the door for those type of roles in the future.” – Shailvi Wakhlu
  • Shailvi remembers working at companies where several people wanted to someday get into a management role. Even in times of heavy hiring, there is no way to accommodate everyone who wants to eventually do this.
    • People stepping into those lead roles would have a leg up on other candidates for future management roles.
    • “If I see somebody is doing a fantastic job of managing a project, I know that there is a subset of manager responsibilities that they’re able to handle. If I see them doing team events…if I see them stepping up on technical leadership, defining standards…all of these things kind of point to that same larger skillset. And I always encourage that even if there is no formal capacity in which you can do this, even if you create your own opportunity and showcase that…this is a space where I see our team could improve…even without the manager title I think you have plenty of options to contribute at that stage…and definitely in this type of a market where there are less manager roles.” – Shailvi Wakhlu
  • Shailvi believes the job market will bounce back, and when it does, there will not be enough people who have been managers and have done things like performance management, skill assessment, and hiring. People who can showcase they have some of this experience and the right mindset have a good start toward landing a management role.
    • Before Shailvi was a manager, she was the hiring lead on her team of 2 people. Shailvi defined the standards (measurements, rubrics, etc.) for the interview process. She tells us doing this made it far easier to transition into a full-time manager role.

5:25 – Modeling the Benefits of Improved Communication Skills

• We wanted a perspective on communication in this current climate and reached out to a former guest with expertise in this area.
• Neil Thompson is the founder of Teach the Geek, an organization that helps technical professionals in STEM (science, technology, engineering, and mathematics) improve their public speaking and presentation skills. He’s also the host of the Teach the Geek Podcast. We originally spoke to Neil in episodes 193 and 194.

Here’s what we asked Neil:

• How do you think team leads or technical leads (sort of that player coach role) play into the development of strong communicators? Where do they help people where managers cannot?
  • Players (or individual contributors on a team) don’t see themselves as managers and would not be modeling themselves after managers. A player coach is way closer to each member of the team’s current role than a manager.
  • Player coaches who are adept at communicating well can model these skills for other members of technical staff and educate them on the benefits (and potential opportunities) of improving their communication skills.
  • Neil points out it could very well be a player coach was moved into that role because of their communication skills. Technical staff members are far more likely to want to invest in improving their communication skills once they see and understand the benefits of doing so (thanks to the modeling of player coaches).

7:09 – Management Support of Strong Communicators Another question we had for Neil:

• "What challenges will managers face trying to develop good communicators when their team is huge, and what can they do to be more effective when this happens?
  • With a large team, one challenge will be getting buy-in from all team members on the idea of improving their speaking skills.
  • Assuming this is the case within your organization…Neil encourages leaders to let their direct reports know that improving speaking skills increases visibility within the organization, and opportunities tend to come to those with greater visibility.
  • Technical people will not want to be passed over for opportunities based on something they can control, especially if they recognize the reasons others have been given new opportunities was due to improved communication skills. And they would certainly be motivated to improve communication with decision makers who can give them opportunity.
  • As part of his work at Teach the Geek, Neil encourages companies to develop speaker training programs for developing technical staff members.
    • One challenge to this approach is getting technical staff to agree on the priorities of this kind of training program. Neil suggests sending out a survey to technical staff members to make sure this is well understood. Technical staff may want to understand how to better engage an audience, get ideas for balancing technical depth and clarity, ways to minimize the use of jargon, etc.
    • If you do take a survey of technical staff, incorporate at least the top 3 priorities as indicated by survey results into a speaker training program.

9:07 – Individual Contributors and Communication We also wanted to know from Neil:

• How can the individual contributor develop those strong communication skills to build rapport and communicate the value of their work to a busy leader?
  • If technical staff members have gone through a speaker training program like was mentioned earlier, they will want to look for opportunities to practice continued development of those skills.
  • Neil highlights the importance of organizations offering speaking practice opportunities for members of technical staff.
    • One easy way to do this is through a lunch and learn. This forum is a great way to allow people to give presentations covering their work progress / accomplishments that both managers and even non-technical staff members can listen to and learn from.
    • Neil points out the usefulness of this information for nontechnical staff members such as HR personnel responsible for screening job candidates. Sitting in on these presentations can, for example, improve the quality of those screening conversations and overall candidate selection rather than relying solely on job descriptions which may be outdated.

10:31 – Succeeding as a Manager of a Large Team Another question for Shailvi:

• What are your top suggestions for succeeding as a manager of a large team in this environment?
  • Shailvi says in today’s environment, the definition of a larger team of direct reports has changed.
  • “A few years back that large team definition was…more than 8. Nowadays I think it’s very common to see people who have 8, 10, 12, 15 direct reports…and nobody’s blinking an eye.” – Shailvi Wakhlu
  • At her previous job, Shailvi had 6 direct results that trickled down to an organization of 30 people total reporting up to her.
  • Success when you have a large number of direct reports takes a lot of intentionality.
  • “What is your role as a manager? One is to provide clarity for your team to make sure they are aligned with business goals…to make sure they know what is going to be rewarded, what is not rewarded, things like that. The other big piece is making sure you are available to help grow the careers of everybody who has taken a chance on you and is putting the fate of their careers…in your hands. So how do you make sure you do those two pieces successfully?” – Shailvi Wakhlu
  • Shailvi emphasizes the importance of streamlining communication and information sharing in both directions (from you to your employees and in the other direction). Make sure people know what they can expect from you.
    • Do people know what you will communicate and when you will communicate it? For example, will you openly communicate the necessary context so that people can effectively recalibrate?
    • Do people have the psychological safety to share their challenges and concerns with you?
    • Are team members comfortable sharing their professional goals with you (i.e. opportunities and growth areas), and are you providing critical feedback to support pursuit of these goals?
  • Shailvi also highlights the way a manager delegates as key to success.
    • Having a large team means there is opportunity for people who want to move into some type of leadership role to gain experience.
    • “It’s very important to make sure that you are public in your appreciation for people who help you in the smooth running of the team…. If it’s a non-promotable task…if it’s a housekeeping task that nobody’s ever going to get promoted because of…do not outsource that. I think you do a disservice to people’s careers if you’re asking them to do…general housekeeping and you’re basically asking them to do it above their existing job. And, you’re never going to consider that work important enough to actually think that they’re performing at a higher level. So, delegate work that is actually useful. Delegate work that is actually helping them improve their skills and their visibility in showcasing that they have leadership capabilities….” – Shailvi Wakhlu, on managers delegating responsibility which allows the right type of experience

14:48 – The Culture of Large Teams One last question for Shailvi:

• How can leaders create a culture that is impactful within their organization when the structure of the organization is designed to allow less time spent with each person underneath a leader?
  • Shailvi feels this is extremely relevant in a world where managers have too many people reporting to them. There is often not enough time to get information flowing between the manager and direct reports for the benefit of the company.
  • Some of the work Shailvi does as a consultant is with organizations who want to build strong teams optimized for performance, productivity, and profitability.
  • “I feel that…leaders tend to anchor on the limited time they have with all the people who report up to them that they just sort of spend that in getting status updates…. It’s very one-sided.” – Shailvi Wakhlu
    • Status updates can be shared in an e-mail or updated on a JIRA board.
  • “The part that I encourage leaders to think about is how do you create a situation where everybody on your team understands the link between their work and business success…where there is no ambiguity about it, where they clearly understand…this is the part of my job that is going to help the company succeed? And that is how you build that excitement with people….” – Shailvi Wakhlu
    • A sense of personal ownership usually breeds accountability. To them it won’t just be finishing a project but rather helping the company succeed with a specific goal.
  • “Creating that culture of transparency, open communication…I think that is something that takes intentionality on the part of the managers. It takes repetition where you keep showcasing how you’re rewarding work, how you are setting expectations. You can’t have unevenness….” – Shailvi Wakhlu
    • Leaders should use the limited time they have with employees to understand their motivations. Work to help your people with their careers, help them understand the opportunity in front of them, and consistently provide clarity.
  • “How you show up as a leader is something that is more important than anything else that you say. Are you accountable for your own actions? Are you taking ownership of larger pieces that are under your area of ownership? When leaders can…structure what they want to spend time on, it goes a really long way.” – Shailvi Wakhlu

17:57 – Advice for Job Seekers in a Tough Market

• To close our discussion, we wanted some actionable advice for navigating a tough job market. We’ll hear once again from Abby Clobridge. Abby 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.

Our question for Abby:

• In a tough job market, what do you think job seekers should be doing to stand out that maybe they aren’t right now?
  • Treat your job search like you would a portfolio project. Show what you are doing and what you are learning by building something tangible. It could be automating something, creating a dashboard, or writing a blog describing how you would solve a problem.
  • Abby says we can also host micro conversations made up of 3-4 peers, mentors, or formal colleagues in a roundtable format. These can be virtual or in-person. This can strengthen your network and benefit everyone involved.
  • We can also practice visible curiosity by posting about a book we read or a tool we used. Abby calls this “learning out loud” and something that can act as a signal to future employers that we are engaged, adaptable, and someone who wants to connect people.

19:12 – In Closing

• 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 Neil Thompson in episodes 193 and 194.

• What did you think of this format, and what other questions need to be answered on this topic? Send us an e-mail at nerdjourneypodcast@gmail.com to chime in.

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• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.
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