Hiring Senior Leaders, Getting Started with Six-Week Cycles, and Other Listener Questions

Key takeaways

Prioritize cultural fit and chemistry when hiring executives, with decision-making based on 'how it feels' rather than just resumes or credentials.
Start new processes or cycles immediately, using small, non-critical projects as testing grounds, and expand once benefits are demonstrated.
Align the entire organization to a shared rhythm, like six-week cycles, to improve transparency, motivate teams, and prevent task pile-ups.
Adapt product development principles to other industries by working around milestones, setting budgets rather than strict estimates, and maintaining shorter planning cycles.
Trust your intuition and experience over extensive data analysis in decision-making, focus on speed and momentum, and be willing to experiment regardless of imperfect data.

Summary

Strategic Executive Hiring at 37signals

Jason and David discuss their approach to hiring a COO, emphasizing the importance of chemistry and cultural fit over traditional qualifications. They explain their use of a recruiter to access a broader pool of candidates and highlight the importance of intuition—‘how it feels’—when selecting a high-level executive. Elaine, their chosen COO, was picked not solely for her resume but for her ability to complement and balance the existing team, bringing calmness and healthy conflict. They also reflect on the long, thoughtful process involved, which included multiple interviews and a focus on gravitas—an overall weight of presence and trustworthiness—that Elaine possessed, making her a fit for their unique leadership style.

Implementing Six-Week Cycles for Better Workflow Management

Kimberly introduces the topic of transitioning to six-week work cycles, with Jason and David sharing insights on effective implementation. They advise starting immediately rather than waiting for a perfect moment, suggesting small initial projects that aren’t critical but serve as testing grounds. The importance of small, focused teams is stressed, as larger groups tend to slow progress due to communication complexity. They explain how the entire company can operate on the same rhythm, leading to better transparency, trust, and motivation through regular reporting and shared progress. David adds that the cycles help prevent task pile-ups and promote consistent momentum, with the benefits becoming evident when the whole organization adopts the same cadence.

Adapting Product Principles to Service-Based Industries and Professional Work

Addressing a listener’s question, Jason and David talk about applying their product development principles—originating from software— to service-based industries like accounting or legal services, which operate on hourly billing and fixed deadlines. They recommend working around key milestones, such as tax deadlines or industry events, and emphasize reducing estimates to budgets to give teams autonomy in meeting these deadlines. They also highlight the value of shorter planning cycles—like six weeks—to improve focus and accountability, contrasting it with annual goals. The discussion underscores that regular rhythms foster clarity, reduce overwhelmed end-of-cycle rushes, and enable ongoing progress even in traditional professional environments.

Product Development Philosophy: Intuition, Speed, and Decisiveness

The hosts emphasize their reliance on intuition and experience over extensive telemetry or data analysis when making product decisions. They share that internal user feedback and live testing are their primary tools, with minimal use of A/B testing or analytics on user actions. Jason and David believe that trusting gut feelings—built upon years of experience—is more effective than awaiting perfect data, which often only reflects past actions rather than future possibilities. They advocate for rapid experimentation, quick launches, and continuous iteration, arguing that speed and momentum are crucial. Slowing down to analyze too much can hinder innovation and progress, and errors along the way are acceptable as part of long-term improvement.

Show notes

In this episode of Rework we're turning the spotlight onto you, our listeners, with another episode of listener questions.

Today, Kimberly Rhodes sits down with Jason Fried and David Heinemeier Hansson, the co-founders of 37signals, to pull back the curtain on the intricacies they faced when hiring a COO for their team, and the intuition-driven decision making they used to ensure their new hire would be a good fit and complement the team.

Plus, how to help your company get started with working in six-week cycles, and adapting product development principles to professional services companies.

Listen in to explore Jason and David's unconventional yet remarkably effective strategies for business development and growth.

Show Notes:

[00:00] - Kimberly introduces the topic for today’s podcast, listener questions, with a question from Justin who asks, "I saw that you hired a COO in 2021 after not having someone in that role for a while. What’s the 37signals approach to executive hiring?"

[00:46] - Jason discusses their decision to use a recruiter for hiring their new COO and shares which qualities were more important to them than the candidate's resume.

[03:20] - David elaborates on the challenges of hiring executives, the importance of chemistry, and how Elaine complements their team.

[06:41] - Reflecting on adding a third person to a team with a long history—why it was important to find someone who could introduce a dose of healthy conflict without making everything a grind.

[08:07] - Jason shares how long the hiring process took, and what made them think that Elaine might be the right fit.

[09:13] - David shares the importance of "gravitas"—having the weight and legitimacy to inspire trust and confidence in the team and how Elaine stood out compared to others in the hiring process.

[10:44] - Kimberly shares this two-part question from Reuben: “What's your suggestion for helping a company get started with working in six-week cycles—is there a specific time to start? And are all the teams across 37signals synced on six-week cycles?”

[11:07] - Jason shares his perspective on getting started with six-week cycles, his advice on when is a good time to start a cycle, and the one time he wouldn’t.

[12:50] - David discusses the importance of individual focus in problem-solving and why he believes in starting with a small team to test Shape Up's effectiveness before implementing it company-wide.

[15:41] - The benefits of having the entire company operate on the same clock frequency.

[16:27] - Kimberly shares a question from a mystery caller asking for advice on adapting product development principles to professional services type companies, like public accounting or legal that work on hourly billing and tax deadlines or legal deadlines that they have to meet.

[17:21] - Jason and David share how to apply the core ideas of Shape Up to diverse service types and internal areas of your organization.

[19:43] - The value of setting shorter goals over six weeks, rather than annual goals to increase the chances that things will get done.

[20:11] - How shorter cycles help prevent the pile-up of tasks and overwhelming situations that often occur at the end of longer timeframes.

[20:49] - Kimberly introduces a listener question about whether the 37signals team uses telemetry or relies on intuition in their product development process.

[21:14] - Jason discusses their approach to product development, emphasizing the importance of other factors extensive telemetry, and A/B testing.

[22:12] - David shares the challenges they have encountered with telemetry and A/B testing.

[26:11] - The value of speed, forward momentum and making decisions instead of stalling to find a perfect solution.

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