Scaling an engineering team comes with many challenges Scaling an engineering team comes with many challenges

Scaling an engineering team comes with many challenges. As organizations grow, it becomes difficult to maintain effective communication, onboard new engineers quickly, coordinate work across larger teams, accommodate varying expertise, ensure cultural fit, and facilitate knowledge sharing. These issues often lead companies to hire freelancers or contractors to quickly add engineering capacity. However, integrating external engineers also poses difficulties in building team cohesion and full productivity.

Sam Halcrow

April 8, 2024


Scaling an engineering team comes with many challenges. As organizations grow, it becomes difficult to maintain effective communication, onboard new engineers quickly, coordinate work across larger teams, accommodate varying expertise, ensure cultural fit, and facilitate knowledge sharing. These issues often lead companies to hire freelancers or contractors to quickly add engineering capacity. However, integrating external engineers also poses difficulties in building team cohesion and full productivity.

This guide examines the key problems with scaling engineering teams. It also looks at why hiring freelance developers and contractors can take a long time to maximize their effectiveness. Understanding these challenges is the first step toward developing better strategies for growing an engineering organization. The goal is to scale teams sustainably while minimizing disruptions to productivity and culture. With careful planning, companies can overcome common hurdles and build high-performing, collaborative engineering teams.

Communication Issues

Larger engineering teams inevitably involve more communication overhead. With more people involved, it becomes harder to keep everyone aligned on priorities, plans, and progress. Communication bottlenecks frequently arise as information must pass through more channels. This greater coordination burden can slow down product development, delay releases, and reduce overall team productivity.

Simple day-to-day communication becomes more complex with additional team members. Setting up meetings and syncing schedules grows more difficult. Conveying new information through email, Slack, or other tools requires broader distribution lists. Even informal chats require more effort to loop in relevant stakeholders.

Managers must work harder to disseminate context and strategic direction to more people. Technical leads face greater challenges sharing architecture plans, API specifications, or systems diagrams across a larger group. The added communication friction makes it tougher for teams to stay in sync and work together efficiently.

More people means more potential for misalignment, confusion, ambiguity, and duplicative or wasted efforts. Keeping a large team marching in the same direction is a constant battle. Without tight coordination, groups can diverge onto conflicting paths or lose sight of company goals. Clear communication gets harder at scale.

Onboarding Time

Onboarding new engineers takes a significant amount of time and effort. When bringing on new team members, whether employees, contractors, or freelancers, it takes time for them to ramp up and become fully productive.

Some of the key onboarding challenges include:

  • Learning the codebase - Large and complex codebases can take weeks or months to fully grasp. New engineers need to study the architecture, styles, conventions, and structures before they can comfortably contribute.

  • Understanding systems and infrastructure - Beyond just the code, new hires have to learn all the systems, tools, and infrastructure that support the software development. This includes build pipelines, testing frameworks, dependency management, hosting environments, and more.

  • Absorbing tribal knowledge - There are often undocumented processes, tribal knowledge, and "how we do things here" that new engineers must absorb. This tacit knowledge is difficult to transfer quickly.

  • Building relationships - Developing connections and rapport with teammates is crucial. Without trusted relationships, it's challenging to collaborate effectively.

  • Getting up to speed on current projects - Engineers need insight into existing initiatives, priorities, and roadmaps to quickly contribute. Lack of context slows progress.

Due to these onboarding challenges, it typically takes weeks or months for new engineers to truly ramp up and operate at full productivity. Some industry surveys suggest that average onboarding time is over 6 months before peak productivity. This long ramp up time applies equally to new employees, contractors, and freelancers.

Coordination Complexity

As engineering teams grow in size, coordination becomes more complex. There are simply more people that need to work together and align on goals, requirements, and schedules.

With a larger team, it becomes harder to schedule work in an efficient way. Ensuring that team members aren't blocked and have all the information they need is challenging. There can be delays in getting answers to questions or feedback on work.

Context switching also becomes more costly with larger teams. When an engineer has to constantly change between projects and tasks, it leads to losses in productivity. They have to re-orient themselves whenever shifting gears.

Larger teams require more formal processes and documentation around project planning, task tracking, and team communication. Without sufficient coordination, projects risk becoming disjointed and team members feeling frustrated. Careful planning and organization is essential.

Varying Expertise

Larger engineering teams inevitably have members with varying levels of expertise. Some may be experts in front-end development, others in machine learning, while still others specialize in DevOps. With a small team, it's easier to get a sense of each person's skills and strengths. But as the team grows, it becomes increasingly difficult to track who has expertise in what areas.

This makes it challenging to match the right engineer to each task or project that comes down the pipeline. Often, managers will just assign work based on who seems to have availability. But that engineer may not have the specialized skills to complete the task efficiently. This mismatch of expertise to assignments can lead to delays, friction, and subpar outcomes.

Engineers get frustrated if they keep getting assigned work that doesn't align with their capabilities. And managers get frustrated when projects take longer than expected because the wrong skillsets were applied. With a larger team, more time and care needs to be taken to thoughtfully match people and skills to each project. Otherwise, varying expertise across the team can become an impediment rather than an asset.

Cultural Fit

Cultural fit is an important consideration when scaling engineering teams. As the team grows larger, it becomes more challenging to maintain a cohesive culture. With more diverse personalities and work styles, conflicts can more easily arise if the team does not mesh well together.

Engineers often have certain cultural values and norms around how they operate. For example, there may be shared attitudes toward working long hours or expectations around code quality. When new engineers join the team, their own cultural values may not align. This can create friction as the existing team feels the need to defend their norms.

Personality clashes are also more likely to occur as team size increases. With more people, there are more opportunities for interpersonal conflicts and less camaraderie. Engineers may form cliques based on shared interests or values, undermining the sense of team cohesion.

Cultural fit issues present obstacles to the team working smoothly together. Tensions can arise that hinder collaboration, knowledge sharing, and overall productivity. As a result, it becomes vitally important when scaling up to evaluate cultural alignment and have strategies for integrating new members into the team culture.

Knowledge Sharing

Knowledge sharing is critical for effective collaboration and productivity across engineering teams. However, it does not happen naturally, especially as teams scale in size.

In small teams, communication tends to be more informal and team members interact frequently through meetings, messaging, and water cooler chats. This facilitates tacit knowledge sharing, where insights, experiences, and know-how are exchanged.

As teams grow larger and more distributed, there are fewer opportunities for organic knowledge sharing. Often team members specialize in certain domains and have less visibility into each other's work. Silos emerge that inhibit cross-functional learning.

Without proactive knowledge management, expertise gets concentrated in pockets of the organization. Valuable tribal knowledge remains untapped. This makes it challenging to leverage the team's full capabilities.

Scaling teams need to implement knowledge sharing processes and platforms. Some ideas include documentation, forums, tech talks, mentorship programs, and internal conferences. The goal is to make know-how transfer more deliberate and accessible.

Fostering a knowledge sharing culture should be a priority. Leaders need to incentivize documenting work, collaborating across silos, and participating in initiatives that connect team members. This unlocks the full potential of large-scale engineering teams.

Freelancer/Contractor Challenges

Scaling an engineering team with freelancers and contractors can present some unique challenges compared to full-time employees. Here are some of the most common issues:

  • No existing rapport/relationships - When bringing on new full-time engineers, they often join an existing team where rapport and relationships have already been built. However, freelancers and contractors are typically new to the team and need to build connections from scratch. This can slow down communication and collaboration.

  • Learning curve on systems/code - Freelancers and contractors need time to come up to speed on the existing codebase, architecture, systems and processes. This ramp up time can reduce initial productivity. Full-time engineers already have this domain knowledge.

  • Little incentive to share knowledge - Unlike full-time employees who want to see the product and team succeed in the long run, freelancers and contractors may prioritize short-term productivity over sharing insights and expertise. Their limited time on the project also provides less opportunity to pass on knowledge.

Mitigation Strategies

As engineering teams scale, it's important to implement strategies to facilitate effective collaboration and knowledge sharing. Here are some approaches companies can take:

Improving Documentation

  • Create knowledge repositories like internal wikis to document processes, guidelines, architecture etc. Make documentation easily discoverable.

  • Standardize formatting for docs like design specs, API references etc.

  • Encourage engineers to document complex features or fixes. Capture tribal knowledge.

  • Assign documentation tasks and set expectations for engineers to write and maintain docs.

Mentorship Programs

  • Pair junior engineers with senior mentors. Facilitate knowledge transfer.

  • Schedule regular 1-on-1s for mentees to ask questions in a safe space.

  • Create forums for junior engineers to connect with senior engineers.

  • Incentivize mentors to invest time in developing mentees.

Communication Tools

  • Adopt real-time chat apps for quick conversations and collaboration.

  • Use video conferencing for daily standups, design reviews etc.

  • Send out weekly status updates and newsletters to improve transparency.

  • Create channels or groups based on projects, technologies etc.

Modular Architecture

  • Break systems into independent components with clear responsibilities.

  • Enforce separation of concerns and loose coupling between modules.

  • Standardize coding conventions and dependencies between modules.

  • Make it easy for engineers to understand and work on isolated parts of the codebase.


Scaling engineering teams comes with inherent challenges that can significantly impact productivity if not addressed proactively. As we've discussed, communication breakdowns, long onboarding times, coordination complexity, gaps in expertise, and cultural mismatches often arise as engineering teams grow. Additionally, reliance on freelancers and contractors brings its own hurdles in terms of integrating external team members.

However, these issues should not be accepted as inevitable. With deliberate effort and planning, engineering leaders can implement strategies to facilitate seamless team scaling. This includes optimizing communication channels, streamlining onboarding, coordinating workstreams, facilitating knowledge sharing, and focusing on cultural cohesion. Proactive relationship building with freelancers and contractors is also key.

The time invested upfront in scaling engineering teams effectively pays significant dividends in the long run through improved productivity, innovation, and delivery. As engineering leaders look to the future, they must make team scaling and cohesion a priority. With care and intention, large, high-performing engineering teams can be built to drive organizational success.