How To Make Your Ideas Stick

Effective proposal writing techniques for engineering leaders

As an engineering leader, you’ve likely faced the challenge of writing proposals for ideas you’re passionate about, whether it’s drafting design docs, request for comments (RFCs), memos, or even slide decks. The format might change depending on context, but the fundamental challenge remains: how do we make our ideas resonate?

Throughout my career, I’ve witnessed numerous promising ideas fall by the wayside or need a lot of back and forth due to a lack of clear articulation. The culprit? Often, a missing ingredient from the six crucial elements of a persuasive proposal.

Knowing how to craft proposals that communicate and inspire action will ensure that your next proposal isn’t just read, but acted upon.

1. Establish context

At the heart of a compelling proposal lies the establishment of mutual understanding. Begin by elucidating the “why.” Resist the urge to dive straight into the solution.

For instance, if you’re proposing a shift in system architecture, listing the current system’s flaws might seem intuitive. However, the real starting point should be “Why now?” What future changes do you foresee that necessitate this shift? Relate your proposal to your organization’s KPIs, OKRs, or overarching strategy.

Drawing inspiration from Stephen Covey’s The 7 Habits of Highly Effective People, it’s paramount to prioritize understanding before seeking to be understood. By ensuring your proposal resonates with your audience’s concerns, you pave the way for consensus.

Example of establishing context in a proposal:

With the rapid growth of our user base and the increasing complexity of our application, our existing architecture is becoming a bottleneck. Recent post-mortem analyses of outages have pointed to scalability and tight coupling issues.

Our company’s OKRs aim for a 20% increase in user engagement and a 30% growth in active users over the next year. To achieve this, we need an architecture that is resilient, scalable, and can be iterated upon quickly.

2. Identify the problem

Once mutual understanding is established, it’s imperative to identify the core issue or opportunity your proposal targets.

Begin by articulating the current state, grounding your discussion with metrics and data. Subsequently, spotlight the primary areas of concern with the existing situation and, based on this, formulate your hypothesis.

Overall, you should seek to emphasize the gravity and ramifications of the problem, positioning yourself as the authority spotlighting an urgent issue.

Example of identifying the problem in a proposal:

Current state:

Our monolithic application has been the backbone of our services for the past five years. During this time, we’ve seen:

User growth: A 300% increase in active users.

Feature expansion: The introduction of 50+ new features, increasing the complexity of our codebase.

Deployment frequency: An average of one thousand deployments per month, with each deployment introducing an average of three new features or improvements.

While this growth and activity indicate a thriving product, they’ve also introduced challenges:

1. Latency concerns: Our API response times have gradually increased over the past year. During high-traffic periods, we’ve observed a 30% increase in API response times compared to the previous year, impacting user experience.

2. Tight coupling: The intertwined nature of our services has become more evident. 20% of new feature releases in the past six months have resulted in regressions in unrelated areas, indicating a lack of modularity and separation of concerns.

3. Deploy time: The complexity of our application has affected our deployment times. Each deployment now takes an average of one hour, a 25% increase from the previous year. This affects our ability to swiftly deliver value to our users and maintain a reasonable MTTR.

Hypothesis: By migrating to a microservices architecture, we can achieve faster deployment cycles, better scalability, and independent service evolutions, leading to improved uptime and stable user experience.

3. Present options

When proposing solutions, it’s vital to consider various options. As Chip Heath and Dan Heath advise in Decisive: How to Make Better Choices in Life and Work, follow the W.R.A.P process: widen your options, reality-test your assumptions, attain distance before deciding, and prepare to be wrong.

The W.R.A.P process will help you avoid common pitfalls in decision-making, such as the framing trap, confirming-evidence trap, overconfidence trap, and forecasting trap.

This also builds credibility as an honest analysis rather than a biased proposal. This stage is about demonstrating your critical thinking skills.

Example of presenting options in a proposal:

Option 1: Incremental refactoring
Pros: Lower immediate risk, can be done during regular sprints.
Cons: Longer overall transition period, potential for accumulating tech debt.

Option 2: Big bang rewrite
Pros: Clean slate, can design with best practices from the start.
Cons: High risk, requires significant resources, longer time to see benefits.

Option 3: Hybrid approach (starting with core services and expand outwards)
Pros: Balances risk and allows for learning and iteration.
Cons: Requires careful planning and coordination.

4. Create a roadmap

With a recommended solution, it’s time to detail the implementation. Envision your proposal as a meticulously planned sequence.

Create a timeline detailing the steps, assign responsibilities, and set expectations for each stage.

Like a conductor leading an orchestra, your proposal should coordinate a unified effort toward the intended result.

Example of outlining a roadmap in a proposal:

Phase 1: Identify and isolate core services.
Duration: 1 month
Responsible: Architecture guild

Phase 2: Develop the first set of microservices and integrate them with the existing system.
Duration: 3 months
Responsible: Teams A and B

Phase 3: Gradual rollout to a subset of users and gather feedback.
Duration: 1 month
Responsible: QA team, DevOps, and user feedback group

Phase 4: Full transition and decommissioning of old components.
Duration: 2 months
Responsible: All engineering teams

5. Highlight risks

Analyze potential risks and challenges associated with the proposal, as well as the likelihood and impact of those risks. Provide strategies or plans to mitigate these risks, showing preparedness and foresight.

Examples of highlighting risk in a proposal:

Risk: Integration challenges with existing systems
Likelihood: High
Impact: Moderate
Mitigation: Begin with a pilot project focusing on one or two core services to understand integration pain points. Use this pilot to develop best practices for subsequent integrations.

Risk: Potential downtime during transition
Likelihood: Medium
Impact: High
Mitigation: Schedule migrations during off-peak hours and ensure rollback strategies are in place. Communicate potential downtimes to stakeholders well in advance.

Risk: Team’s learning curve with new architecture
Likelihood: High
Impact: Medium
Mitigation: Invest in training sessions and workshops focused on microservices best practices. Pair experienced team members with those less familiar during the initial phases.

Risk: Increased initial costs
Likelihood: Medium
Impact: Medium
Mitigation: While there might be an upfront cost due to the transition, the long-term benefits in terms of scalability, maintainability, and faster deployment cycles are expected to offset these initial expenses. Regular cost-benefit analyses will be conducted to ensure we remain on track.

Risk: Complexity in monitoring and logging across services
Likelihood: Low
Impact: High
Mitigation: Adopt centralized logging and monitoring solutions that provide a holistic view of the entire system. This will aid in quicker issue detection and resolution.

6. Prompt action

Summarize the proposal’s main points and clearly state what you’re asking stakeholders to do next, whether it’s providing feedback, giving approval, or allocating resources.

Include any additional information, data, charts, or references that support the proposal but might be too detailed for the main body. This provides a deeper dive for those interested.

Example concluding aspect of a proposal:

In light of the challenges posed by our current monolithic architecture and the company’s ambitious growth targets, transitioning to a microservices approach emerges as a strategic imperative. The hybrid approach, which combines the strengths of incremental refactoring and a more comprehensive rewrite, offers a balanced and pragmatic path forward.

We’ve identified potential risks associated with this transition and have proposed robust mitigation strategies to address them. The success of this initiative, however, hinges on a collaborative effort, cross-functional alignment, and shared commitment.

Next Steps:

Feedback round: We invite stakeholders to review this proposal and provide feedback by [specific date].

Pilot execution: Post feedback; if there are no strong objections or concerns, we will commence the pilot project.

We’re at a pivotal juncture, and the decisions we make now will shape our product and capabilities for years to come. Let’s collaborate, innovate, and steer our organization towards a future-ready architecture.

Final thoughts

In conclusion, crafting a persuasive proposal goes beyond organizing information in a digestible pyramid structure. It’s about weaving a narrative that resonates with the organization’s core objectives, prospecting a path forward, anticipating risks, and compelling stakeholders to take action.

When writing your next proposal, see it as more than a document. It’s a powerful call to action, a catalyst for change, and a testament to your leadership acumen. The quality of your proposals can shape the trajectory of your projects, teams, and, in the grander scheme, your evolution as an engineering leader.

This article was originally published on on Nov 29th, 2023.

The Role Of A System Architect

Unraveling growth challenges: Could a system architect be the solution?

Serverless Architecture from Classic Programmer Paintings

Most startups that go through hyper-growth tend to face the inevitable Bottlenecks of Scaleups, as masterfully described by ThoughtWorks.

Having navigated the hyper-growth journey myself, I’ve witnessed firsthand how these technical bottlenecks can impede business progress, causing churn and chaos.

Bottlenecks of Scaleups

In light of these challenges, I wondered if a system architect’s role could hold the key to identifying and circumventing these bottlenecks and reducing complexity like this infamous Amazon Deathstar.

Amazon internal service dependency visualization

To that end, this article explores the benefits, operating philosophy, guiding principles, job description, career progression, success criteria, and implementation approaches for the role of a system architect.

Benefits of having a System Architect

My hypothesis is rooted in the belief that a clear and purposeful approach to technical architecture can prevent false starts and accumulating tech debt.

Picture a system architect whose sole responsibility is to observe the big picture and facilitate knowledge sharing across teams, breaking down silos for better collaboration.

This individual would need to possess exceptional skills in designing and managing the overall technical architecture of a system. Their role includes assisting teams in defining system components, services, and interactions.

The benefits of having a system architect would ultimately translate into:

  • Improved alignment and coordination — Foster a common goal and architecture across teams, leading to more efficient and effective development.
  • Enhanced technical expertise — Offer a deep understanding of system design and architecture, guiding and mentoring other engineering team members to elevate the organization’s overall technical capabilities.
  • Improved quality and performance — Co-create a well-designed system architecture to boost performance and reliability, resulting in quicker time-to-value, better user experiences, and heightened customer satisfaction.
  • Reduced technical debt — Proactively manage system architecture to prevent tech debt buildup, saving time and resources in the long run.

Harmonizing With the Agile Philosophy

You may be curious how this role fits into the agile methodology that many organizations follow. On the surface, the role of an architect may be antithetical to being agile.

However, several sources discuss the role of an architect in an agile environment. For example, Agile Architecture describes it as:

The role of the architect in an agile project is to provide guidance and direction to the team on the technical aspects of the project. The architect is not a dictator, but rather a facilitator and coach, who helps the team find the best solutions to their technical challenges.

Similarly, the Scrum Alliance discusses the role, stating that:

[the architect] is responsible for guiding the team to make technical decisions that align with the project’s goals, scope, and delivery schedule. They should be able to communicate the technical vision to the team and help the team understand how their work contributes to that vision.

Large-Scale Scrum (LeSS) Framework’s view on the architecture role is more philosophically aligned with how I see the role. The following statements on the Architecture & Design page in the chapter “Technical Excellence” shape their opinion about software architects:

  • The sum of all the source code is the true design blueprint or software architecture.
  • The real software architecture evolves (better or worse) every day of the product, as people do programming.!

  • The real living architecture needs to be grown daily through programming by master programmers.
  • A software architect who is not in touch with the evolving source code of the product is out of touch with reality.
  • Every programmer is some kind of architect–whether wanted or not. Every act of programming is some kind of architectural act–good or bad, small or large, intended or not.

LeSS promotes the idea that architects are regular team members. They should participate in hands-on engineering and especially mentoring through design workshops and pair programming. LeSS warns against architecture astronauts (a.k.a. PowerPoint architects):

These are the people I call Architecture Astronauts. It’s very hard to get them to write code or design programs, because they won’t stop thinking about the architecture… They tend to work for really big companies that can afford to have lots of unproductive people with really advanced degrees that don’t contribute to the bottom line.

#211 — The Architect by Comic Agile

Guiding Principles

Now that we have some grounding philosophy behind a system architect’s role in an agile organization, let’s discuss the guiding principles of this role.

For this, we don’t need to reinvent the wheel. Principles proposed by Agile Architecture hold strong:

  • Value people — You must recognize the value and importance of people and their expertise. No dictators or PowerPoint architects.
  • Communicate! — Communicate effectively with all stakeholders and tailor information to their needs.
  • Less is more — Minimize complexity and strive for simplicity in design and communication.
  • Embrace change — Be prepared for change and welcome it as an opportunity for competitive advantage.
  • Choose the right solution for the enterprise — Customer centricity. Make sure the solution is right by verifying it with the customer.
  • Deliver quality — Foster a culture of craftspersonship and sustainable development at a pace that can be maintained indefinitely.
  • Model and document in an Agile fashion — Leverage proven and effective modeling/mapping and documentation strategies.

Carving the Job Description

Equipped with the guiding philosophy and principles, if you were to recruit someone for this role, let’s see what the job description could look like. A system architect typically collaborates with other teams in several ways:

  • Guide system design and architecture — Provide guidance and expertise to other teams on how to design and build systems that align with the overall architecture of the organization. This can involve working closely with teams to understand their needs and requirements and recommending the best approaches.
  • Review and provide feedback for technical designs — Review and provide timely feedback for RFCs proposed by teams. This can involve evaluating the proposed designs to ensure they align with the system’s overall architecture and do not introduce any potential issues or technical debt.
  • Help resolve technical challenges — Help teams resolve technical challenges during development. This may involve providing guidance on approaching a particular problem or working with the team to develop a solution.
  • Participate in planning and estimation — Participate in planning and estimation meetings with other teams. This can involve providing input on the technical feasibility of proposed features and estimates for the time and resources required to implement them.

Overall, the specific ways in which a system architect collaborates with other teams will vary depending on the needs and goals of the initiative and the members working on it.

Enterprise Architecture Footprints

Now that we have a job description, one may wonder how someone would become an architect and what would their career trajectory look like.

Various avenues exist for senior engineers to advance in their careers. On the individual contributor (IC) path, adding a system architect role alongside roles like SRE, Data Engineer, and Staff Engineer is a viable option.

Illustrations below help visualize what that may look like courtesy of CodeCapsule.

Career Growth: What Paths After Senior Engineer

The Skills Map of Senior Tech Career Progression

Note the key difference between an architect and staff/principal engineers: while the latter focus on ensuring their teams’ work functions correctly, architects take a broader view, looking after how all the pieces fit together.

Before you ask, yes, staff and principal engineers also do think about how their work fits into the broader ecosystem, but most often, they don’t consider that their full-time concern.

This role sits at the intersection of ‘What’ (is it we are trying to do/solve) and ‘How’ (are we going to approach the design), and ‘Why’ (are we doing it this way) as described by Peter Cripps.

On Thinking Architecturally

Becoming an architect also has to do with having increased communication and relationship skills, on top of solid tech skills, as ‌architects have to deal with and influence larger groups of people across multiple teams and organizations.

Measuring Success

Introducing the role of a system architect into an organization is a strategic move aimed at improving the technical architecture, fostering collaboration, and overcoming growth challenges.

However, to validate the effectiveness of this role, it’s essential to measure its impact and quantify the value it brings to the organization.

Here are some potential KPIs that can help gauge the effectiveness of the role:

  1. Technical debt reduction: Measure the decrease in technical debt over time as a result of proactive architectural decisions made by the system architect. (Related: How Google Measures and Manages Tech Debt)
  2. System performance and reliability: Evaluate the performance and reliability metrics of the system after the system architect makes architectural improvements.
  3. Collaboration and team satisfaction: Conduct surveys or feedback sessions to gauge how well the system architect facilitates collaboration and team communication.
  4. Time-to-Market reduction: Determine how architectural improvements by the system architect have contributed to faster product development and time-to-market.
  5. Resource optimization: Assess how architectural decisions have led to better resource utilization, whether regarding hardware, cloud services, or personnel.
  6. Impact on productivity: Analyze the impact of architectural improvements on the productivity of engineering teams.

Measuring success should not be a one-time activity. Adopting a continuous improvement approach is crucial, wherein feedback from stakeholders, teams, and customers is regularly collected and incorporated into the system architect’s strategies.

Feedback loops enable the system architect to adjust their approach based on real-world experiences and emerging challenges. This will help protect the organization against a gatekeeper or an ivory tower architect, which would be antithetical to the role’s intention.

Considerations for Implementation

Differentiating from EMs and Senior/Staff/Principal Engineers

While engineering managers (EMs) and engineers are usually involved in making architectural decisions, their focus is typically on the domain or squad they operate in. The system architect’s distinctiveness lies in their primary focus on enabling effective cross-squad collaboration and communication, particularly regarding cross-cutting technical implications.

Reporting structure

A role like a system architect often reports directly to engineering leadership, offering broad oversight and visibility across multiple teams. As such, it may be positioned under a Director or VP, or above, depending on the organization’s hierarchy.

Determining the number of architects

Given the depth of domain knowledge required, complex domains may require experienced architects. Hiring for this role may entail identifying existing engineers with the right skills and interest in stepping into the architect role. This may affect the pace of filling the role based on the current team’s availability and skills.

In Closing

In conclusion, I hope this exploration helps gives you a better sense of how this role could be introduced and the benefits it could bring.

I’ll leave you with this timeless video by KRAZAM. Enjoy!

How To Run Effective Sprint Planning Sessions

A Step-by-Step Sprint Planning Guide for Engineering Leaders

Sprint Planning Meeting from Classic Programmer Paintings

If you’ve been an engineer for some amount of time in the tech industry, you have probably experienced the highs and lows of sprint planning meetings. Maybe it has felt a bit like this painting by Marie Bashkirtseff. I’ve personally been in the trenches, both as a participant and as a leader, and have witnessed the wide array of approaches and their varying levels of effectiveness. It became apparent to me that the success of sprint planning lies in finding a structured and efficient approach that aligns the team and maximizes productivity.

Sprint planning is the backbone of Scrum-based agile project management, providing the framework for teams to organize their work and establish clear goals for each iteration. Yet, all too often, I’ve seen these meetings devolve into chaos, resulting in misaligned priorities and a waste of valuable time. Recognizing the need for a better way, I embarked on a journey to refine and iterate upon a process that consistently delivers exceptional results.

Through countless iterations and learnings, I’ve developed a process that has significantly improved the effectiveness of sprint planning while keeping the meeting overhead low. This process has helped my teams regain focus, enhance collaboration, and achieve remarkable outcomes.

In this article, I aim to share my insights and provide you with a step-by-step guide to streamline your own sprint planning, ensuring that it becomes a powerful tool for success.


Before we go any further, I will state this is an opinionated view on sprint planning and it follows these four underlying principles:

  1. Bulk of the sprint planning happens 2 weeks leading up to the sprint start: Allotting adequate time for gathering requirements, aligning priorities, and preparing for the upcoming work is vital. This two-week timeframe allows for thorough preparation and sets the stage for a successful sprint.
  2. Sprint planning session is mainly for high-level sprint review and alignment: The sprint planning session itself should primarily focus on reviewing the high-level aspects of the upcoming sprint and ensuring alignment with the team’s goals. Detailed discussions and refinement of tasks should occur prior to the planning session.
  3. Each team member is an owner and driver of their work stream: Engineers are not “ticket takers” but leaders who take responsibility for problem definition and own end-to-end execution. Consequently, each team member is responsible for creating tickets and breaking down work into manageable chunks, ensuring a proactive and self-driven approach.
  4. Tickets in the sprint are conscious commitments to deliver: The team takes a proactive and accountable approach to managing workload. Promptly flag any potential delays, emergent work, or setbacks and involve the stakeholders to renegotiate commitments in alignment with the evolving circumstances. It’s crucial to avoid scope creep during the sprint. If new tasks or requirements emerge mid-sprint, renegotiate commitments for existing work rather than merely piling new tasks on top.


Before diving into the tactical sprint planning process, there are a few prerequisites that need to be in place:

  1. Long-term roadmap for your team: Having a clear vision of your team’s long-term goals and initiatives is essential. This roadmap will serve as a guide for prioritizing work during sprint planning, ensuring that each sprint contributes to the broader objectives. If you don’t have this, at minimum having OKRs is important so that everyone is aligned at a high level on how the day-to-day work ladders up to more overarching business (or mission) objectives.
  2. JIRA plan of Epics: Use a project management tool like JIRA to create a plan and map out Epics based on your long-term roadmap. Breaking down large-scale goals into actionable initiatives upfront facilitates better planning and execution.
  3. High-level visual roadmap: Develop a low-fidelity visual roadmap that outlines drivers & their work streams per sprint for the entire quarter. Fill out as much as you have clarity on upfront. Keep this updated as the rest of the quarter progresses with the goal of having a light of sight at least 1–2 sprints out. This holistic view of the work to be accomplished provides clarity and alignment for the rest of the team and an easy-to-consume visual for stakeholders outside the team.

Here’s an example of a high-level visual roadmap using Confluence Roadmap Planner

Tactical Steps

Now, let’s dive into the tactical steps to streamline your sprint planning process:

What a typical schedule of ceremonies looks like for my teams

Part 1: Two weeks prior to the sprint start

During the current sprint planning session, take the following steps:

  1. Create the future sprint: Create the upcoming sprint in the JIRA backlog. This will serve as a staging ground for the upcoming sprint. You could also just pre-create all six sprints for the quarter ahead of time to serve as buckets to allocate work to in advance.
  2. Prospect: Start moving any follow-up tickets or future work from your backlog into that upcoming sprint as you are reviewing the current sprint.

Part 2: One week prior to the sprint start

One week before the start of the sprint, begin populating the sprint with tickets from the backlog. Follow these guidelines:

  1. Align on upcoming priorities: Leverage rituals such as 1:1 meetings, working sessions, and stand-ups during the week to discuss and align with team members on the upcoming priorities. Determine who will be working on each task. Each team member should be responsible for populating their sprint with tickets async.
  2. Ensure sprint backlog is fully populated: 1–2 days prior to the sprint start date, ensure that the upcoming sprint is fully populated with tickets. Each ticket should have an assignee and be appropriately story-pointed. This can happen individually async but you can hold optional sprint planning office hours for any last-minute discussion and alignment.
  3. Add thematic focus to the visual roadmap: Update the high-level visual roadmap with the thematic focus of each individual’s sprint. This step provides a clear understanding of each team member’s responsibilities and aligns them with the overall goals. This can be done during office hours or asynchronously, ensuring that everyone is on the same page.

Part 3: On the day of the sprint start

During the sprint kickoff/review meeting, follow these steps:

  1. Complete the current sprint: Close the current sprint and ensure that any remaining tickets are completed or appropriately moved to the following sprint.

  2. Review the completed sprint: Review the sprint report briefly at a high level to get a sense of where you landed. This is a good opportunity to celebrate achievements and identify any challenges or carryover work. If possible, review the results of shipped work from the previous sprint and track progress against your OKRs. This is also an opportunity to reiterate the team’s thematic goals and their connection to longer-term objectives.

  3. Conduct a sprint review per person: Share the high-level visual roadmap and dive into a sprint review for each team member. Use the following checklist:

    1. Ensure thematic alignment: Confirm that the main thematic focus of the tickets aligns with the roadmap at a high level.
    2. Story point verification: Verify that all tickets are appropriately story-pointed, reflecting their complexity and effort. Bonus: See my previous post on how to estimate effort.
    3. Epic alignment: Ensure that the majority of tickets belong to an epic aligned with a roadmap initiative. This ensures that the work being done is driving the team towards its long-term goals.
    4. Anticipate bandwidth constraints: Prospect forward and consider any time off, on-call duties, or other events that could impact a team member’s bandwidth. Update the visual roadmap accordingly to avoid overallocation and underestimation.
    5. Load balancing: If an individual’s sprint load appears excessive, either move some tickets to the future sprint or load balance the workload with another team member.
  4. Repeat for all team members: Go through the checklist above for each team member, ensuring that no unassigned tickets remain in the sprint.

  5. Start the sprint: With all preparations in place, kick off the sprint.

That’s a Wrap

If you made it this far, congratulations on equipping yourself with the knowledge to run effective sprint planning sessions! Remember, implementing these practices is just the beginning of your journey toward optimized sprint planning and team success.

As you put these principles and tactical steps into action, you may wonder, “How do I know if this is working?”. One key indicator of progress is the improvement in sprint planning accuracy. Keep a close eye on the alignment between planned and actual outcomes i.e. planning accuracy or variance, and assess whether the commitments made during sprint planning are being met consistently.

Source: Head First Agile

Furthermore, don’t underestimate the power of feedback. Retrospective meetings at the end of each sprint cycle provide an excellent opportunity to discuss what went well and what can be improved. By actively soliciting and incorporating feedback, you can fine-tune your approach over time and drive continuous improvement.

Happy sprint planning!

Power Of Prospection

From Childhood Daydreamer to Future-Minded Leader

The Daydreamer by Morgan Weistling

As a young boy, I always had a tendency to daydream and play out things that could happen in my head.

I remember a particular incident from my childhood when an uncle of mine started a tutoring practice in the early 90s teaching students how to write code. This was back when computers were a new thing and the internet was just in its infancy.

He invited my family to tour the facility on inauguration day. He later asked me what I thought about it. In my head, I analyzed the part of town where the facility was located, what they were teaching, and the perceived demand for those kinds of courses at the time. Without thinking much, I blurted out a rather honest and brutal assessment. I told him that it wasn’t going to be successful. Keep in mind, I was just a 12-year-old boy at the time, so luckily, everyone took it rather lightly and had a good chuckle. Fast forward a couple of years, and he ended up shuttering the business.

It was a setting very much like this one (source)

Over the years, I developed a habit of playing out things in my head this way. My family, especially my dad, was well aware of my, shall we say, future-mindedness. He would often tell his friends about it, and they would have a chuckle or two at my expense.

Here’s where things get interesting. I distinctly remember one time when my dad’s friend had a messy personal problem he was dealing with. He knew about my reputation for engaging in forethought or having premonitions, according to him, and asked to chat with me and get my take on his situation. This was a bit odd to me given that I was only 13 or 14 at the time, and he was a 45-year-old man. But the whole thing had me intrigued, so I went with it.

A Father Encourages His Son At The Playground by Emily Flake

He took me through the predicament he was in detail. In the end, I told him I see it all working out in his favor eventually. Maybe it was framing bias. By then, I had gotten into a habit of never explaining my train of thought but just giving them the “answer.” That’s what they were interested in anyway, and I didn’t have the interest or energy to debate the logic of my reasoning.

Fast forward a few years, and the situation played out just like how I had predicted, much to the excitement and relief of our family friend. This experience made an impression on him. So much so that offered to introduce my family to a journalist he happened to know in a prominent global magazine publication (rhymes with the word dime) at the time.

The idea was that he could write a little story about me and my “psychic abilities.” Whoa, I thought. I’m no psychic. Luckily, my parents were on the same page and felt like that would be a terrible idea to put a spotlight on me at such a young age. It would likely attract all the wrong kinds of attention. Now looking back it was almost like a Minority Report precog origin story. I’m glad we walked off that ledge.

Precogs from Minority Report

Fast forward 25 years, and now I finally realize that what I was engaging in is known as prospection in psychology. I was tapping into an innate human ability to anticipate and evaluate future possibilities.

During my time at BetterUp, I had the privilege of learning more about this topic. According to Tomorrowmind, a book authored by Gabriella Rosen Kellerman and Martin E. P. Seligman, two esteemed members of the company’s science board, daydreaming is not merely a form of idleness, but instead an important catalyst for prospection, creativity, and innovation. This insight has helped me better understand the value of letting my mind wander and appreciate the benefits it can bring.

This process is facilitated by a group of brain areas known as the default mode network (DMN), which becomes active when we’re not focused on a particular task. The DMN is particularly skilled at helping us imagine and plan things, and when we start daydreaming, it turns on and we start making new connections and ideas. While many of these initial ideas may seem like gibberish, a few will offer enough value to pique the interest of other networks in the brain, which will sense, refine, and further develop these ideas (source).

The Default Mode Network

So while I’m still not a psychic, I’ve leaned into that ability to engage in creativity and prospection by intentionally engaging what I now know is my DMN, which has paid dividends in my engineering career, where anticipating problems and coming up with creative solutions is a big part of the job.

Although the key to this is to be very intentional about daydreaming and prime your DMN. Here are some tips on how to do that:

  • Carve out time for daydreaming: Set aside some time each day to let your mind wander and engage in free thinking. This can be as simple as taking a walk or sitting in a quiet space and letting your mind roam.
  • Focus on positive possibilities: When daydreaming, focus on positive possibilities and outcomes. This can help activate your brain’s reward system and boost your motivation and creativity.
  • Use visual and sensory cues: Engage your DMN by using visual and sensory cues to help trigger your imagination. For example, you could use a vision board, a journal, or a specific scent to help you tap into your creative flow.
  • Practice mindfulness: Mindfulness can help quiet the chatter in your mind and create space for deeper thinking. Consider incorporating mindfulness practices like meditation or deep breathing into your daily routine.
  • Seek out novel experiences: Novel experiences can help activate your brain’s reward system and encourage prospection. Try new activities, travel to new places, or read about unfamiliar topics to keep your brain engaged and curious.

So go ahead, let your mind wander, and see where it takes you. You never know, it might lead you to your next big thing!

How to hire engineering talent without the BS

Building a culture of inclusive technical interviews

“Team leads review candidate’s whiteboard, binary-tree inversion solution” from Classic Programmer Paintings

As a candidate in my early career, I experienced all sorts of technical interviews, ranging from being asked to write an algorithm on a piece of paper with an ink pen (not kidding) to doing leet coding in an IDE. Looking back, the best experiences were when the interviewer wanted me to succeed, was empathetic, and presented me with a problem that reflected how I would solve problems in the real world without gotchas.

Since then, I’ve been on both sides of the table hundreds of times and reflected a lot about the problem that plagues technical hiring: how to assess whether a candidate is both technically proficient and has the right mindsets and behaviors to succeed in your organization.

Most organizations have a technical interview process that attempts to evaluate both qualities to varying degrees of success. They may also use platforms like HackerRank or Karat to assess technical strength. But all too often, these approaches can lead to suboptimal outcomes, filtering out great talent or, worse, providing a poor candidate experience that hurts the company’s reputation.

We all know the head-scratching brain teaser, “Why are manhole covers round?” that was part of the Microsoft interview loop, which has become somewhat of an industry joke.

Also, we’ve seen some famous examples, such as the creator of Homebrew getting rejected by Google because he couldn’t solve a leet code problem. In fact, this is such a prevalent problem that engineers have started maintaining a list of companies that don’t have a broken hiring process.

Most hiring managers, including myself, will admit it’s hard to nail technical interviewing if we are not super intentional about it. In my experience, I’ve observed several pitfalls we should all keep in mind if we want to build an inclusive hiring culture — or, dare I say, “fix” technical hiring.

With this post, I’m hoping to highlight some of those anti-patterns, or what a good technical interview is not, and then dive into some things that make for an exceptional interview.


So let’s first start with attributes that may seem like logical things to assess on the surface but aren’t representative of real-world experience and are likely to filter out great candidates


Simply recalling syntax, algorithms, concepts, or talking points doesn’t necessarily signal that someone will be a great engineer — it just shows they can think on their feet and recall facts and figures. Maybe they have spent a lot of time memorizing concepts without a deep understanding.

It’s always best to let the candidate look up information if it involves remembering specific details or, even better, having links to relevant references handy to share with them to save time.


Measuring the speed at which a candidate solves a problem doesn’t always correlate with how effective or efficient they’ll be in their day-to-day work. They may have just practiced a lot for coding challenges or interview questions. In fact, you may be doing a disservice to yourself by filtering out slow thinkers or neurodivergent candidates that are likely to not shine thinking on their feet.

Best Practices

Alright, so what makes for a good interview? In my experience, it’s essential to recognize that a successful interview is not just up to the candidate; the interviewer also plays an equally important role. Here are some attributes to get right in order to conduct an effective technical interview.


There is no advantage to creating a surprise factor. Give candidates a heads-up about the attributes or topics the interview will cover and any other information you can reasonably share upfront.

Consider using a candidate experience platform such as Guide, which makes it easy to set up an engaging candidate hub with all the information they need in one central place. This will go a long way in reducing anticipation anxiety and allow the candidate to show up confidently.


The interview should aim to assess the candidate’s deep understanding of concepts and skills that reflect what they will be doing in their day-to-day job. Rather than focusing on shallow technical concepts like a quick sort algorithm, ask questions that require a deep understanding of what the candidate will actually be working on, like building an API or a small service for example.

Some ways to make it even more realistic beyond the standard interview format:

Paid Trial — Offer the candidate a small paid project with you and your team. Of course, this is a very time-consuming process, so it’s more realistic when you don’t need to hire at a fast clip.

Take Home — Provide a take-home assessment option for candidates with a live component to discuss the solution they came up with to get signals on a deep understanding of what they’ve put together. The industry is split on take-homes, and there are several tradeoffs to the live whiteboard vs. the take-home, as laid out here by Andrew Rondeau but offering candidates a choice can help strike a balance.

Pair Programming — Another option would be to have one of the senior engineers on the team pair with the candidate on a problem where they would build on an existing project by adding a feature or two. This would give them a sense of what it would be like to collaborate with them while also closely mirroring how engineers solve problems in the real world.


A mountain of research-backed evidence shows that unscripted conversations are ineffective and lead to biases, interviewer idiosyncracies, and reduced hiring accuracy.

Ensure you have a set of attributes you look for and are aligned internally across the interview team to ensure a consistent candidate experience. For example, you could aim to get signals on dealing with ambiguity, code structure, testing, and user experience. You then want to ensure all interviewers know what great looks like for each. Ideally, you have a point-scoring system to determine how a candidate performed.

When you add new interviewers to the pool, ensure they are well-calibrated with the rest of the group by having them shadow and reverse-shadow interviews. After each interview, they should debrief with their counterparts to ensure they are aligned on the score. This will ensure interviewers’ subjectivity and personal biases are not creeping in.


Setting some expectations and guiding the candidate through the interview is important. Don’t expect them to read your mind in terms of what you are looking for. For example, I always tell the candidate upfront how I would like to spend our time by setting the agenda and expectations for each interview portion.

You know the attributes you need to get signals on. If the discussion is not going in a direction that will yield valuable signals, steer the candidate back on course.

Don’t hesitate to interrupt and ask if the candidate missed something. I promise you are not “giving away” the answer to the test. This is not an academic setting. In fact, this is an excellent opportunity to have a rich conversation and assess their self-awareness and communication skills.


Remember that even the most experienced candidates can feel nervous or unsure during an interview. Show some empathy and try to put the candidate at ease. Acknowledge the pressure they might feel and let them know there are no “gotchas” in the interview. Imagine how you would have felt in their shoes, and think about what would have improved the experience.

Don’t forget to get back to the candidate after the interview in a reasonable amount of time, ideally no more than 72 hours, to inform them about the decision. If you are not handling the comms with the candidate, ensure your internal team receives your post-interview feedback ASAP so they can keep the process moving.


Ultimately, it’s important to remember that technical hiring isn’t just about finding the most technically proficient candidate — it’s about finding the right fit for your team. Creating a realistic technical assessment can help you identify top talent and build a strong, diverse team ready to tackle any challenge.

And remember, it’s not just about what the candidates can offer you — they’re also evaluating your company and the hiring process. So, it’s crucial to create a positive candidate experience that shows them you value their time and contributions. By being empathetic and understanding during the interview process, you can make your company stand out as a great place to work.