Accidentally in Code

Tag: strategy

Getting More Strategic
Strategy – how to be strategic, and how to be seen as strategic – is one of my ongoing obsessions. Years ago, I read Good Strategy/Bad Strategy, and it’s guided my thinking ever since.

One of the things that book helps clarify is that being strategic and being seen as strategic can work against each other – good strategy is obvious, and usually it is executed on more than it’s talked about. An ongoing frustration for other under indexed people in tech I talk to, as we build products and organizations without drama, whilst being told we’re just “not strategic” enough. The strategy required to sidestep problems that never happen or that creates optionality to quickly resolve is somehow invisible.

But I think as we rise up the org chart, strategy is the job. Strategy defines your job, and evolves it to meet the organizational need. Not just one strategy, but multiple strategies that need to fit together and be coherent.

Your product strategy. Your technical strategy. Your team strategy. Your you-as-a-leader-but-also-a-human-being strategy.

As we find our groove in the resource constrained era we are in currently as opposed to the everything strategy of ZIRP (zero interest rates), by definition we need to make more harder choices, and strategy is how we know what those choices are, and when and how to make them.

This is the first rule of strategy: strategy is contextual. A crucial insight, because often when leaders fail, it’s because they tried to apply a strategy that worked in one context, to a different one, without considering the difference.

This is true when you change companies, and I think the reason why there is such a high failure rate for executive hires*. Ones I’ve watched fail came in with a playbook, usually including the org chart they wanted, and expended all the goodwill and capital in pursuit of that goal, whilst achieving very little.

It’s also the case that when the market changes, our strategy must change. One of the core features of ZIRP-era engineering leadership was hiring for the sake of it, and number of people as a proxy for many things it maybe (probably) shouldn’t have been. One of the biggest shifts has been the layoffs and the mantra of “doing more with less”. Regardless of personal feelings on this topic and what is actually realistic, it is apparent that hard choices and discipline are a key feature of the post-ZIRP era.

We could talk about these strategies – product, technical, team, you, like some balanced stool. But realistically, I think it’s more like the image above. The product strategy is a storm (especially pre-product market fit). The technical strategy is a half built shelter (you’ll get to it properly once you have product market fit). The team strategy is an umbrella (the most flexible and controllable). And the you as a human strategy is nowhere to be found.

This is the second rule of strategy: timeframe varies with the level of uncertainty you’re navigating.

The idea of a proximate objective is the next logical step in pursuit of your overall strategy, if you achieve it, you confirm your course. If you fail, you learn and reconsider your options.

We often talk about strategy like it’s defining the end state, setting and describing the destination. But strategy is about defining the incremental steps – the proximate objectives – that can take us towards that end state. Strategy is understanding where we are at – context – and the path from there to where we need to go**. Any strategic “plan”, is best executed as a set of proximate objectives.

This mistake of how strategy is talked about is why it can be so hard for some people to be seen as strategic. When we think strategy is depicting the end state, and undervalue the proximate objective definitions and execution that it takes to get there, the person who talks more about the end state can be seen as more strategic than the person who actually reaches it.

We need four things for strategy:
- Time – energy – to think deeply about it
- Context to situate it
- Direction to identify proximate objectives
- Expertise to chart the path
All of these need to come together to create and deliver an effective strategy. It’s a balance between all of them, leaning into different ones at different times.

To illustrate, why each of these are important, I think it’s helpful to consider the extremes of each.

When someone is all time, we call them a political operator. This is the person who manages up to get credit, but the people underneath them ask what it is that they do.

When someone is all context, we say they can’t see the forest for the trees. They miss the big picture fixating on the details.

When someone is all proximate objectives, we call them a thought leader and it’s not a compliment. Execution is an exercise left to the reader.

When someone is all expertise, they present solutions in search of problems. They don’t seem to understand impact.

Devaluing these things gives us a reason not to do them. So many engineers will tell you they hate politics, and yes, there is definitely toxic workplace politics. But there’s a baseline where politics is getting things done. It’s convincing people that the idea is good, and that it can be executed. My favourite explanation of this is Nik Means talking about Eiffel’s tower.

Context is important. Yes, you’re delivering something bigger, but the details need to add up. You can’t gloss over all of them, you need to learn how to distinguish which are important and which are not.

Proximate objectives chart your path. They explain the steps you expect to take between where you are and where you plan to be. Explaining them helps bring people along with you.

Expertise is ultimately how you deliver things, you need to understand how to deliver and how to validate. Execution is when the strategy becomes real.

Strategy is hard, and being seen as strategic – especially for under-indexed people – can be even harder. We need all of these four things to develop our strategy and move things forward. And we need to be recognized as doing all of them in order to be seen as strategic.

Coming back to our problems of strategy – the product, technical, team, and you.

Product strategy drives your proximate objectives. Whilst product strategy may seem like the job of product management – and to a certain extent it is, but hopefully your product team does not operate in a vacuum. Engineering needs to provide input, but engineering also needs to understand the product strategy, because everything else needs to fit in with it.

Your team exists for a purpose, and the clearest part of that purpose is delivery of the product strategy. You need direction and alignment to identify proximate objectives. Direction – where the product strategy is going, alignment on what is most important, and what will be delivered when.

Technical strategy evolves the context. Your technical strategy is often about surfacing the underlying work that allows you to deliver on the business need. It has to be well justified, because ideally it’s pro-active rather than reactive – i.e. you implement it before the emergency rather than during it.

Any technical strategy needs to start with what problem is being solved. A problem is not the absence of a technology – unless, I understand, that technology is AI – but rather the problems that technology would solve. So “we don’t have containers” is not a problem. Number of incidents or environment inconsistencies is. Good technical strategy changes the context over time – making more possible – like building roads on the territory you’ve chartered.

Your team strategy must be grounded in execution. The product and technical strategy define the organizational need. Your team strategy is about how your team is going to meet that organizational need, within the constraints of the business.

Post-ZIRP, this has been a big challenge. Doing more with less means having fewer people, less flexibility, less margin of error. You need to figure out how you retain key people when money is tighter and promotions are harder to come by. But amidst all of these challenges, you have to execute. If in a ZIRP era, you could build the team then deliver, now you must deliver as you build the team.

The you as a person strategy requires that you carve out time to be strategic. In this market, many of us are doing-doing-doing to prove that we’re worth keeping around, but at some point, your job is no longer what is being done this week, and more about what is possible next quarter (and the quarters after that). It’s never been easier to be DDOS’d by the job and think that means we’re doing a good one, but you could be missing key things if you’re too focused on the day to day, or week to week and not enough on the month to month.

To wrap up, strategy is about more than just a vision; it’s about navigating the path to get there. We need to balance time, context, direction, and expertise to ensure we’re not only seen as strategic but are genuinely creating a strategic path forward for the teams we’re responsible for – and our own evolving needs to competently lead them.

* I can’t find a great source here, although the search results suggest it’s commonly accepted #. # possibly, which links out to a site requiring login.

** I love Tanya Reilly’s description of the map in The Staff Engineer’s Path.

Image credit: Joe Groove
September 23, 2025
On Being “Strategic”
Ages ago, a work colleague / friend offered me the following piece of advice: “We need to make sure you’re seen as strategic”.

I’ve thought about it a lot ever since. It was the first time I realised I was on the edge of (perhaps in?) the trap of “she’s just not that strategic”.

Because, y’know, you can deliver huge projects, scale teams/processes/etc, fix systematic issues and still… just be “so great at execution” 🙄

This is not new – there’s an article in HBR from 2009.

“When we asked how they would interpret our data, we heard three explanations. First, several women noted that they tended to set strategy via processes that differed from those used by their male counterparts. This suggests that what may in fact be visionary leadership is not perceived that way because it takes a different path. Second, we heard that women often find it risky to stray away from concrete facts, analyses, and details. And third, many women betrayed negative attitudes toward visionary leadership. Because they thought of themselves as grounded, concrete, and no-nonsense, and had seen many so-called visionary ideas founder in execution, they tended to eye envisioning behaviors with some suspicion”

The article resonates with me. Particularly the distrust of “strategic leadership”. I have definitely seen examples of “strategic leaders” who failed to deliver, often putting the blame on team or circumstances, like the strategy was perfect, the failure was “just” in execution. This is part of why the book Good Strategy / Bad Strategy resonated so much – the concept of the proximate objective, the value of strategy as something that actually effects change.

There’s an interesting post on strategy here, and I can’t claim to mastery in all these things, but some things I keep in mind to try to manage perception of how “strategic” I am:
- When possible, expose the underlying strategy. E.g. when someone is focused on an individual piece, step back and explain how it fits into the bigger picture.
- Ask good questions. Use what you learn to reframe discussions to get to a better outcome, more quickly.
- Document document document. Something I love about distributed work is that it relies more heavily on written communication – so I always have my recipts. In particular, any regular reporting should empasize progress against overall strategy.
- Be willing to play a long game. It’s easier to sell people on progress than an idea. Make sure to build a narrative as the pieces build on each other.
- Make time to think (and write).
August 9, 2021
Book: Good Strategy/Bad Strategy

I loved Good Strategy/Bad Strategy (Amazon) and learned so much from it. What really stood out to me was the depth required in defining strategy, and the way of thinking that takes that depth, and constructs a long term trajectory built on proximate objectives – the next steps that seem totally possible from where we are now. This was the kind of book I was recommending even before I finished it, I definitely think it’s worth the time. I’ve included many quotes below, all emphasis is mine.

Early in the book he gives the example of Napoleon, who split his ships into two columns, destroying 2/3 of the other fleet with no loss to his own.

Good strategy almost always looks this simple and obvious and does not take a thick deck of PowerPoint slides to explain. It does not pop out of some “strategic management” tool, matrix, chart, triangle, or fill-in-the-blanks scheme. Instead, a talented leader identifies the one or two critical issues in the situation—the pivot points that can multiply the effectiveness of effort—and then focuses and concentrates action and resources on them.

He is damning on the sub prime crisis, and specifically about Lehman brothers taking on more risk without mitigating it.

Being ambitious is not a strategy.

These two examples in the opening nailed – for me – the idea that strategy is unrelated to ambition, and charisma – it’s not how motivating the presentation it is, or how grandiose the claims… it’s about what it actually is, the reality it exists in, and the effects that unfold.

A good strategy does more than urge us forward towards a goal or a vision. A good strategy honestly acknowledges the challenges being faced and provides an approach to overcoming them. And the greater the challenge, the more a good strategy focuses and coordinates efforts to achieve a powerful competitive punch or problem solving effect.

Damn!

Unfortunately, good strategy is the exception, not the rule. And the problem is growing. More and more organizational leaders say they have a strategy, but they do not. Instead they espouse what I call bad strategy. Bad strategy tends to skip over pesky details such as problems. It ignores the power of choice and focus, trying instead to accommodate a multitude of conflicting demands and interests. Like a quarterback whose only advice to teammates is “Let’s win,” bad strategy covers up its failure to guide by embracing the language of broad goals, ambition, vision and values. Each of these elements is, of course, an important part of human life. But, by themselves, they are not substitutes for the hard work of strategy.

The section on bad strategy was gripping and recognisable – such a clear articulation, so pointed, so damning. I was taking pictures and sending it to friends, as it so clearly articulated things we have complained about.

The definition of bad strategy is on point.

Bad strategy is long on goals and short on policy or action. It assumes that goals are all you need. It puts forward strategic objectives that are incoherent and, sometimes, totally impracticable. It uses high-sounding words and phrases to hide these failings.

As is the failure mode. This is such a good articulation of something I have been calling “failing managers blame”.

When a leader characterizes the challenge as underperformance, it sets the stage for bad strategy. Underperformance is a result. The true challenges are the reason for the underperformance.

Why we fail to create strategy:

The essential difficultly in creating strategy is not logical; it is choice itself. Strategy does not eliminate scarcity and its consequence—the necessity of choice. Strategy is scarcity’s child and to have a strategy, rather than vague aspirations, is to choose one path and eschew others. There is difficult psychological, political, and organizational work in saying “no” to whole worlds of hopes, dreams, and aspirations.

I was particularly fascinated by the distinction between leadership and strategy, and charisma as a driver of bad strategy – I’m sure we all have examples of bad (but charismatic) leaders, however some of the most strategic leaders had no charisma. Whilst leaders have to get people through the change than strategy entails (charisma is helpful here), the strategy itself is figuring out what purposes are worthwhile and possible to accomplish. This has to be grounded in reality, not wishful thinking.

I do not know whether meditation and other onward journeys perfect the human soul. But I do know that believing that rays come out of your head and change the physical world, and that by thinking only of success you can become a success, are forms of psychosis and cannot be recommended as approaches to management or strategy. All analysis starts with the consideration of what may happen, including unwelcome events.

Good strategy is about reducing ambiguity such that people can actually deliver.

Phyllis’s insight that “the engineers can’t work without a specification” applies to most organized human effort. Like the Surveyor design teams, every organization faces a situation where the full complexity and ambiguity of the situation is daunting. An important duty of any leader is to absorb a large part of that complexity and ambiguity, passing on to the organization a simpler problem — one that is solvable. Many leaders fail badly at this responsibility, announcing ambitious goals without resolving a good chunk of ambiguity about the specific obstacles to be overcome. To take responsibility is more than a willingness to accept the blame. It is setting proximate objectives and handing the organization a problem it can actually solve.

I found this piece on timeframes helpful. I am now somewhat obsessed with proximate objectives – such a helpful description of a way of thinking.

Many writers on strategy seem to suggest that the more dynamic the situation, the further ahead a leader must look. This is illogical. The more dynamic the situation, the poorer your foresight will be. Therefore, the more uncertain and dynamic the situation, the more proximate a strategic objective must be. The proximate objective is guided by forecasts of the future, but the more uncertain the future, the more it’s essential logic is that of “taking a strong position and creating options,” not of looking far ahead.

Gilbreth’s building techniques as an example, “business process transformation” or “re-engineering”. I love this articulation – it really ties into my thoughts on the judicious application of process, and the need for empathy.

Whatever it is called, the underlying principle is that improvements come from re-examining the details of how work is done, not just from cost controls or incentives.

The same issues that arise in improving work processes also arise in the improvement of products, except that observing buyers is more difficult that examinings one’s own systems. Companies that excel at product development and improvement carefully study the attitudes, decisions, and feelings of buyers. They develop a special empathy for customers and anticipate problems before they occur.

This definition of “culture” is not an interpretation I have thought of or heard before, but was immediately helpful in the way I consider and approach things.

We use the word “culture” to mark the elements of social behavior and meaning that are stable and strongly resist change.

The importance of context – this is so critical, and explains why so many leaders who move to a new context fail – because they don’t acknowledge the context, and just try and do the same again.

A good strategy is a hypothesis of what will work based on functional knowledge and your knowledge of your own business – this is a crucial insight. Many people find success in one area, and then fail in the next because they apply the same strategy in a different context. Good strategy is only good in context.

Treating strategy like a problem is deduction assumes that anything worth knowing is already known—that only computation is required.

There was a whole section on why we have to question our ideas and consider more than one, which I think is really important – the first idea often seems like the one that will work, but I think the first idea is often the one that is just the easiest to contemplate.

Thus, when we do come up with an idea, we tend to spend most of our effort justifying it rather than questioning it. That seems to be human nature, even in experienced executives. To put it simply, our minds dodge the painful work of questioning and letting go of our first early judgements, and we are not conscious of the dodge.

Finally, the section on keeping your head and heard mentality was really helpful – the example of re-enforcement in financial markets where optimism begets optimism and problems beget panic is a good but extreme example – human emotions are contagious, and this happens in less measurable ways elsewhere, too.

I really recommend it – I learned a lot. It gave me tools, and also confidence to call the strategy I already do what it is.

January 30, 2019