Using a ‘Silicon Valley For the Rest of Us’ Approach for OKRs

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Wednesday, May 31, 2023

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5 min read
Headshot of Dan Montgomery with orange bubble callout and a star in its center

Key takeaway: Agile strategy is a five-step model applicable to organizations of all sizes, providing a solution to the unpredictability of the future. Its key principles involve emphasizing strategic thinking, envisioning desired outcomes, and regularly adjusting plans through frequent check-ins. 

How can the workplace fuel personal and organizational growth? And how can this mindset transform society?  

Dan Montgomery, the Founder and Managing Director of Agile Strategies, is driven by the idea of the workplace as a “theater” for personal, organizational, and societal growth. His diverse career led him to develop a unique approach to objectives and key results (OKRs) — “Silicon Valley for the rest of us.”  

In his book, Start Less Finish More, Building Strategic Agility with Objectives and Key Results, he covers: 

  • The five steps to creating an Agile strategy
  • OKRs in organizations 
  • How to implement OKRs 
  • What it means to be strategically agile 
  • Why agility is important 

On an episode of the Dreams With Deadlines podcast, he discusses these five steps and his approach to building strategic agility. 

Too many decision-makers are bad for OKRs

Dan says that we’re witnessing the rise of the overburdened matrix organization, where decision-making is slow. These organizations must be more agile to pivot in response to changing circumstances. How? 

They need to prioritize horizontal alignment, using shared OKRs to cut across silos and wire them together. 

OKRs and strategic agility are the antidotes to an overburdened matrix organization.  

Strategic agility: why you need to start with the end in mind

Strategic agility encourages you to be flexible about reaching outcomes, requiring you to continuously sense the environment and pivot in the right direction at the right time. 

This outcome focus fits in perfectly with the ecosystem style of business present in companies like Apple and Amazon. Apple created an ecosystem of application developers for the iPhone, with their success tied to the success of their application developers. Amazon did the same with all its suppliers. This ecosystem business creates value for the customer, supplier, stakeholders, and employees. 

“OKRs are a team sport.” 

OKRs are a well-matched tool for strategic agility — they’re flexible enough to account for environmental changes while centering teams with one goal rather than individual tasks or to-do lists. 

Creating your “minimum viable strategy”

Where Agile talks about developing a minimum viable product, Dan talks about a “minimum viable strategy.”   

The minimum viable strategy focuses on the plan’s foundations: purpose, values, and a handful of priorities. This strategy is reflected in dynamic OKRs, updated based on feedback, findings, and lessons learned. 

“Typically, the OKR cycle is a quarter and that's a good place to start. Some may need to be longer and some should be shorter.” 

As part of the OKR cycle, teams must embrace trial and error. If an initiative is successful, it can be scaled up. However, when scaled, something else may shift in that environment, requiring a change — it’s not a static approach.  

The 5-step agile strategy cycle 

To help organizations implement this approach, Dan has developed a five-step scale-independent model. These steps include: 

  1. Assess 
  2. Focus 
  3. Commit 
  4. Act 
  5. Learn 

1. Assess 

This first stage involves observing your environment and asking questions such as: 

Conversations are prevalent in this stage, where you must attack fixed mental models, giving you an accurate, updated assessment of your business. 

2. Focus 

The second stage involves decision-making, where you’d ask questions concerning what you’re going to do, like:  

  • Are we going to go all the way into direct-to-consumer marketing and delivery?  
  • Are we going to stick with bricks and mortar?  
  • Are we going to expand into China?  

These conversations are all about brainstorming, getting all the possibilities out on the table, and making a choice. 

It’s important to remember how fast-paced OKR cycles are. Saying “no” to something right now doesn't mean it’s off the table forever. So say yes to some ideas and park the rest — you can revisit these later. 

3. Commit 

This stage is where OKRs come in. Objectives are aspirational statements, while key results are specific, targeted measures.  

“I think the objective can be like poetry — it should be inspiring. It should hit you in the gut. It should get you out of bed in the morning. The key results keep you honest — they're very specific and measurable.” 

Here, these types of questions are relevant:  

  • In the near term, what kind of outcome are we committing to?  
  • What will success look like?  

Without such specific goals, you have no way to determine if you’ve achieved them.  

4. Act

This stage is where “the rubber hits the road.” You have a quarterly OKR and a weekly check-in to review your team’s actions. As Dan says, it’s like an Agile check-in. 

Questions you may ask during this stage include:  

  • How are we doing on key results?  
  • What did we get done? 
  • What obstacles did we run into?  
  • What are we doing about them? 
  • How are we feeling?  
  • Are we going to achieve our goals? 

Employees tend to set and forget OKRs if you don’t bring them into your regular agenda. 

5. Learn

This is the final step, which involves an evaluation at the end of each project.  

Dan found in his evaluations that many professional services and consulting-type organizations never made time for learning. Realizing its value, he built it into his five-step system.  

Questions to ask at this stage include:  

  • What worked?  
  • What didn't work?  
  • What would we do differently next time?  

By implementing a five-step agile strategy cycle and embracing a "minimum viable strategy," you can assess your environment, commit to specific goals, and continuously learn and improve. This approach enables you to navigate changing circumstances, innovate, and achieve success. 

This article is based on an episode of Dreams With Deadlines by Quantive — the strategy-meets-execution podcast where you'll hear of real trials and victories in business. The show is hosted by me, Jenny Herald, VP of Product Evangelism at Quantive. Subscribe via Apple, Spotify or wherever you listen to podcasts to hear my discussions with thought leaders and learn how to shrink the gap between strategy and its day-to-day implementation. 

Dreams with Deadlines is the one and only strategy meets execution community. We’re a global network of ambitious leaders who are passionate about using OKRs and agile practices to achieve audacious goals and build a better future.

Whether you’re new to OKRs or a seasoned pro, the Dreams with Deadlines community is where you’ll find the knowledge, connections, and resources you need to achieve your goals with greater confidence, efficiency, and impact.

Join for free to get access to our private Slack forum, exclusive events, and curated networking opportunities to fuel your personal and professional growth. 

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