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How to Overcome the Technical Strategy Spiral

This post is part of the Technical Strategy program to help engineer leaders level up on a key leverage point in their career. The program covers the Technical Strategy portfolio, calibrating with company strategy, technical strategy tradeoffs, and executing technical strategy.

About the Authors

Harsh Sinha

Harsh Sinha

Harsh is Chief Technology Officer and a board member at Wise. Previously he was Director of Product at PayPal and Director of Engineering at Ebay. Harsh also advises and invests in early stage start ups.

Bryan Dove

Bryan Dove

Bryan is the CEO at CommerceHub. Before CommerceHub he was the CEO of Skyscanner, where his role included leading and growing Skyscanner’s engineering team at an accelerated scale across ten global offices. Bryan has more than two decades of CTO and technology leadership experience, including successful tenures at Microsoft and Amazon Web Services where he led organizations at scale.

Matt Greenberg

Matt Greenberg

Matt is the CTO at Reforge. He brings a unique cross-functional perspective on product, growth, and engineering after more than a decade leading engineering teams and shipping product in both B2B and B2C companies as VP of Engineering @ Credit Karma and CoSo Cloud.

Apply here to become a Reforge member

Organizations are always seeking great engineering leaders — leaders who do more than just execute strategy. They shape it with their unique perspective on technology. And they find ways for technology to drive the strategy: educating peers on what is possible, guiding the roadmap to increase efficiency and value, generating innovation, and making strategic decisions about execution.

But technical strategy is often overlooked and underdeveloped as engineers advance in their career. In this post we are going to cover:

  1. Why better execution doesn't lead to engineering career advancement.
  2. The Strategy Stack, what technical strategy is, and the purpose it serves.
  3. How Technical Strategy builds great companies.
  4. The Technical Leader Death Spiral and how it limits career growth and company growth.

Better Execution Does Not Lead to Career Advancement In Engineering

Early in an engineering career, you ascend by getting better and better at delivering high-quality execution. Your primary responsibility is to focus on the "how" of the product, not the "what" or the "why."

But there is an inflection point that happens mid-career as engineers are promoted to leadership (i.e Engineering Manager) or more senior IC roles (i.e. Staff or Principal Engineer). At this point, you are typically development and delivery experts. Better execution isn't enough for continued growth. What made you successful early in your career does not make you successful going forward.

Rather than solving a more intense version of a problem you are used to, you need to solve new problems requiring completely new knowledge and muscles. Two key muscles that need to be developed are people leadership and technical strategy. People leadership is talked about often. But technical strategy?

The Technical Leader Spiral

As engineers approach this mid-career transition, they start to get pulled into more strategic discussions to answer questions like “what should we build” in addition to “how should we build it?” In these strategy conversations, execution expertise doesn’t help, so technical leaders often shy away from these conversations over time and focus on where they add more value. We call this the Technical Leader Death Spiral. Let's break it down a bit further:

  1. Underdeveloped Strategy SkillsThe spiral begins because of underdeveloped strategy skills. Engineers control the "how." The how is hard — you need the hard skills to execute, and everyone respects that. But it consumes so much time that you lose track of building a muscle around the "what" and the "why."
  2. Reliance On An Execution MindsetBecause of underdeveloped strategy skills, technical leaders rely on an execution mindset when solving technical problems. They lean into overdeveloped “how” skills to keep driving impact instead of the "what" and "why." This often manifests when engineering leaders in the room constantly say no (i.e. "We can't do this because..."), making it difficult to have a generative conversation.
  3. Reinforcement of a Reputation For ExecutionThis reliance reinforces their reputation internally as the person who executes, rather than participates and shapes strategic discussions and decision-making.
  4. Exclusion from Strategy DiscussionsWith an execution reputation, the technical leader is even more likely to be excluded from strategy decisions in the future, leading to strategic skills being underdeveloped even further.
Downward Strategy Spiral with highlight: Exclusion from Strategy Decisions

Great Technical Strategists Increase Their Influence, Impact, and Scope

The tech leader spiral has three particularly negative effects on an individual's career progression. It can:

  • Limit your influence
  • Limit your impact
  • Limit your scope

Strategic Fluency Matters For A Seat At The Table

Many engineering leaders want a seat at the table to help shape company direction. Strategic fluency is critical to get a seat. Leaders of the business functions already have a seat. If you want a seat you have to show that you not only understand strategy but that you can communicate it back.

With an execution reputation, Product and other functional leaders decide what to build and set priorities without technical leaders in the room, limiting their ability to influence and guide decision-making.

Not Caring About Technical Strategy Limits The Impact For You and Your Team

At senior levels, you often need context from other functions to drive effective impact in your function. When decisions are made in isolation, you lack context that could have ultimately helped you drive more impact. If you are always focused on the execution, your impact will be purely execution. If you can zoom yourself up and see strategy, then your impact can be strategic.

Not thinking about technical strategy not only drags you down, but also those around you. As an engineering leader, if you don't value technical strategy, the team around you won't value it either. This leads to stunting the growth of the team, not just yourself.

For us to be successful, we need to continuously grow and learn individually and together as a team. Part of this is pushing each other to get better over time — leading by example, starting with oneself.

— Harsh Sinha, CTO at Wise

Tech Strategy Strengthens The Most Important Partnership In The Company

Every tech company at its core is built on a partnership between product and engineering. You've probably heard Product Managers wishing they were more technical. Since they aren't, they need you as a partner. Strategy is not just about conceiving an idea, but also about achieving that idea through partnership. Being the best partner is one of the best ways to position yourself within the company and increase your scope.

For example, a perception exists that an engineer's role is to explain why something isn't feasible. This happens because engineers are trained to look at how things might fail and prevent that from happening, but it creates an environment where product leaders feel like engineers always reject their ideas and shutting down the conversation.

Great technical leaders take a different approach. Instead of providing all the reasons something can't be done, they provide thought partnership about what is possible given current constraints.

Great Companies Are Built On Great Technical Strategy

Failing to execute on technical strategy not only limits an individual's career growth, but company growth as well. Great companies are built on a great technical strategy. Engineering leaders that can conceive and implement differentiated technical strategies are able to build sustainable companies. There are three reasons for this:

Great Technical Strategy Enables Speed

Speed is critical as organizations grow. At the lowest level, engineering teams are making a million tradeoffs that either create future friction or future speed. A good technical strategy enables future speed for your organization. This means your company can get farther, faster than others.

"High velocity and good quality can go hand-in-hand. When designing systems, we encourage our Engineers to think beyond the current scope, region, and implementation. Their implementations should always adjust for the capabilities to extend things in the future."

— Harsh Sinha, CTO at Wise

Tech leaders without the right understanding struggle to prioritize the right work or evaluate trade-offs effectively as they build. This leads to teams that fail to sequence and prioritize appropriately. These teams don’t find the fast lane to scaling product delivery.

Defensibility Is Rooted In Technical Strategy

Great companies are built on defensibility that prevents competitors from copying your product tactics. At the root of different types of defensibility is almost always a great technical strategy. A great example of this is Zoom.

Zoom is the largest online meeting and conferencing product. When they started, they were entering a very crowded space with a lot of new competitors entering all the time. So how did they win? Talk to some Zoom customers and ask them why they use Zoom over others, and you'll often hear that "it just works." Meaning, better video and audio quality.

That value prop was enabled by technical strategy. The company was founded by the engineers from the Webex team because they saw that Cisco didn’t want to do the work to solve endemic debt in the platform. Few customers were happy in the busy web conferencing space. Their goal was to build something that would work on mobile networks (circa 2010). So they built from the ground up, even writing assembly language to make sure Zoom performed better than the rest. It’s beaten everything else on the market because of superior reliability and quality.

Network effects are a common type of defensibility in tech companies. They are often enabled by technical strategy. Products like Spotify or Pinterest have won their categories largely because of Data Network Effects enabled by technical strategy. Facebook won their category due to a Direct Network Effect, enabled and accelerated by technical strategy, that made the famous "people you may know" features possible.

No matter what type of defensibility a company has, they need to keep innovating to maintain that moat and defend against competition. As mentioned above, the best, hardest-to-cross moats are technology-driven. When tech leaders cannot participate effectively in creating these moats, companies lose defensibility.

Bad Tech Strategy Leads To Degrading Product Market Fit

In the Reforge Product Strategy program, Casey Winters (CPO at Eventbrite) talks about how Product Market Fit is not static:

"The expectations of the customer continue to increase and change over time, and in fact, total satisfaction is likely an asymptote impossible to achieve. So what is product/market fit then? Product/market fit is not when customers stop complaining and are fully satisfied. They’ll never stop complaining. They’ll never be fully satisfied. Product/market fit is when they stop leaving. Represented visually, customer expectations are an asymptote a product experience can rarely hope to achieve, but product/market fit is a line a product can jump over and try to maintain a higher slope than over time."

— Casey Winters, Reforge Partner and CPO at Eventbrite

In other words, product-market fit requires more work just to maintain over time. If a company does not have engineering leaders good at technical strategy, they rack up the wrong kinds of technical debt and, as a result, can't focus on making a high-performing product with the resources available to them. This leads to a poor user experience, friction to shipping new features, degrading product-market fit and ultimately churning users. Classic examples of this were early Twitter and the failwhale, Microsoft in the early 2000's, or Friendster.

What is Technical Strategy?

The word "strategy" has been stretched to a point where it is almost devoid of meaning. Too often, the terms "vision," "mission," "strategy," "goals," and "roadmap" get conflated into a jumbled mess—leaving leaders without the context they need to focus their work on the difficult task of moving the company forward. To understand technical strategy, we need to know:

  1. What technical strategy is not.
  2. The broader strategic context - The Strategy Stack.
  3. The role and purpose Technical Strategy plays within The Strategy Stack

What Technical Strategy Isn't

Engineers often confuse technical strategy with three things.

  1. Technical Strategy ≠ Product StrategyTechnical strategy and product strategy serve two different purposes. Your goal is not just to be a product manager and replicate the work of your peers. Your goal is to bring a unique perspective to the table that helps shape and influence the product strategy.
  2. Technical Strategy ≠ Building With The Latest TechnologyTechnical strategy is also not about building with the newest technology. Facebook was written in PHP, Github in Ruby. These weren't and aren't the sexiest new programming languages.Engineers commonly think the solution is to be using the latest and greatest inventions and push for innovator tech when they can. Innovator tech often has a lot of adoption issues; you often have to find and fix bugs yourself. You reach scaling challenges with it before anyone else. If you are trying to innovate on technology for areas of your product or tech stack that aren’t generating innovative value, you are paying innovation cost for a bad ROI.
  3. Technical Strategy ≠ Coming Up With The Best IdeaOftentimes strategy can be confused with just being generative and coming up with the best idea. Tech strategy in and of itself doesn’t win for companies. It’s in how it supports the partnership and business goals with product and other functions. The best technical strategies are often the ones that enable faster work and reduce friction instead of adding another product idea to the platform. In a company that is scaling, speed of execution is critical, and leading the market through execution speed comes from a savvy tech strategy.

The Strategy Stack

The Strategy Stack was originally defined by Ravi Mehta (EIR @ Reforge, ex-CPO at Tinder, Product Director at Facebook, and VP Product at TripAdvisor) to help untangle the mess of what "strategy" means and the purpose it serves. The Strategy Stack has five layers:

The Strategy Stack focused on Company Objectives and Function Delivery
  1. MissionThe world your company sees and the change it wants to bring to that world.
  2. Company StrategyThe logical plan you have to bring your company’s mission into being.
  3. Functional StrategyThe logical plan for how a specific function (Product, Engineering, Marketing, etc.) will drive its part of the company strategy.
  4. Functional RoadmapThe sequence of initiatives that implement the Functional Strategy.
  5. Functional GoalsThe quarterly and day-to-day outcomes of the Functional Roadmap that measure progress against the Functional Strategy.

A key part of The Strategy Stack is that each function has its own respective strategies that contribute to achieving the Company Strategy.

The Strategy Stack, focused on Mission and Company Strategy

Technical Strategy

Within The Strategy Stack, Product Strategy answers the question - "What should we build, and why?" Technical Strategy answers the questions - "What technology should we invest in to build it, and what else is possible?" Together, they connect to help achieve the Company Strategy with product development and delivery.

A difference in product strategy vs technical strategy is the audience that consumes it. Technical strategy is answered for the technical teams within the company to help guide their decisions on the technical side.

The "what else is possible" is a key component. A core part of technical strategy is a proactive investment to enable future capabilities. Good technology strategists are trying to constantly determine how to execute the product strategy faster or create new products that we couldn't before. They enable things for the business that product strategy alone can’t build.

An Example Of Spotify Circa 2014

Let's look at a very high-level hypothetical example of Spotify in 2014-2015 making an investment in mobile. The company saw itself as having a significant market share that was starting to be challenged by Apple and Google while still competing with Amazon Music and Pandora.

Their audience was primarily active on mobile devices. The product team created a mobile-first product strategy and marketing deployed a marketing strategy to acquire new mobile customers and transition desktop consumers to be active on both platforms.

The technical strategy prioritized investment in re-thinking their encoding to better support streaming on the go. It solved how to handle buffering and caching so that it was more resilient to spotty cell coverage. Over time, this significant technical investment has paid off for Spotify where users experience great streaming even when walking or jogging. On other platforms like Apple or Amazon the user has disconnected and needs to download songs in order to use them. That friction led to a number of users moving to Spotify for its superior mobile value prop enabled by the technical strategy.

The Strategy Stack focused on Mission and Company Strategy for Spotify

Company Level

  • Company MissionGive a million creative artists the opportunity to live off their art and billions of fans the opportunity to enjoy and be inspired by it.
  • Company StrategyDiscover and listen to millions of songs, for free, across all devices.

Product Strategy

  • Product StrategyEnable the highest quality mobile experience in the market.
  • Product RoadmapSpotify's product roadmap might have included features specific to the "on the go" use case like activity-based playlists for working out or cell data saving mode.
  • Product GoalsThe product goals might be outcomes around the number of active mobile users.

Technical Strategy

  • Technical StrategyInvest in encoding, buffering, caching to enable the highest quality mobile streaming experience.
  • Technical RoadmapThe sequence of implementations and technical pieces that enable the strategy.
  • Technical GoalsTechnical goals might be around the size of the stream vs bitrate of quality, performance metrics on 3G bandwidth, etc to help measure whether the strategy is being achieved.

Getting Better At Technical Strategy

The best leaders learn technical strategy early in their careers. This allows you to apply technical strategy on a micro scale first, getting reps and building the muscle progressively. The worst case is that you find yourself in an engineering leadership position without this knowledge and set of tools and need to dig out of your own personal technical debt.

This is why we spent hundreds of hours building the Technical Strategy program with Reforge. The program provides technical leaders with a toolkit to ascend the strategy spiral. We go deep on understanding the strategy stack in which you work today, as well as a set of frameworks that leverage your technical knowledge to better generate and synthesize ideas with business and product peers. The end result is that you will be able to make more efficient execution decisions, contribute to driving product roadmaps, and re-envision the way that company strategy can work with technical innovation.

Get more information here. Apply to Reforge to join our next cohort of Technical Strategy.

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Harsh SinhaBryan DoveMatt Greenberg