Strategy, Strategy, Strategy

Why – Context and Framing

Strategy. It’s a word that gets thrown around so often that it starts to lose shape.
People say “we need a strategy,” or “we can’t act without one,” as if the absence of a 30-page document is an immovable barrier to action.

This article exists to challenge that mindset and offer clarity. Strategy isn’t just a plan. It’s not just vision statements or a Gantt chart in a slide deck. Strategy is a practice. A way of thinking. A mode of working.

Understanding the difference between strategic thinking, strategic planning, and strategic enablement helps demystify what strategy really is — and unlocks the ability to move forward with both agility and direction.

What – The Three Faces of Strategy

1. Strategic Thinking

Strategic thinking is what happens when we do the work and learn through it. It’s emergent. It’s iterative. It’s messy.

When I constructed my 90-day plan as CTO, I wasn’t just making a to-do list — I was building an engine for strategic thinking. It allowed me to develop insights, test assumptions, discover dependencies, and spot systemic opportunities. It helped inform two outputs:

• A clearer strategic plan
• More effective tactics to enact change

This is the first face of strategy: insight born through engagement.

2. Strategic Planning

Once you've done the thinking, strategic planning captures that insight. It gives it structure: goals, objectives, and timelines that help organise teams and investments.

Think of strategic planning as the scaffolding that allows others to join the build. It supports alignment, prioritisation, and shared direction.

The idea of a digital strategy at Macquarie is one such output. Through our earlier thinking and engagement — including the 90-day plan — we shape a high-level roadmap and focus areas (e.g., Digital Experience, Platform Alignment, IAM) that others can now orient to and execute against.

3. Strategic Enablement (and the Project Myth)

This is where most people get tripped up.

Too often, people assume that because we don’t yet have a published strategy document, we can’t act. Or worse, they assume a project is a strategy.

Projects are not strategic in and of themselves. They are vehicles — tactical instruments — to realise aspects of a strategy.

This is a key strategic principle:

“Projects are how we deliver on strategy, not how we define it.”

So What – Three Use Cases

1. Digital Strategy (Emergent and Intentional)

Our work on digital strategy has emerged over time. We started by engaging across the organisation, listening to needs and pain points, and clarifying our operating model. This was strategic thinking in action.

As we refine, we’re moving from emergent insight to an actual strategic planning artefact: a digital experience strategy with a vision, focus areas, and underpinning plans — ready for broader engagement and activation.

2. Unified Identity and Access Management (IAM)

We’ve launched a 12-week engagement to develop a unified identity strategy — a decision made precisely because we had multiple in-flight IAM projects with no shared strategic framework.

Here, a third party is helping accelerate our strategic thinking so that we can land a plan that shapes future decisions, rationalises architecture, and aligns delivery.

It’s a great example of building a strategy while doing — and recognising that sometimes, the window to think is mid-flight.

3. Observability and the Project Trap

In the observability space, we had a moment of strategic misalignment. I made a comment that we didn’t have an observability strategy, and someone responded by pitching a full strategic framework within a tactical project.

That’s a trap.

Instead, we pulled it back and reframed:

• Use the network monitoring initiative to build a working pattern
• Integrate that pattern into New Relic
• Use that working pattern to inform a broader, long-term full-stack observability strategy

This is what good strategic enablement looks like. The project becomes a testbed — not the strategy itself.

What Next – Guidance for Leaders and Teams

1. Don’t wait for the perfect strategy to start.
   Start doing. Learn by doing. Think while moving. Let action inform direction.
2. Know which type of strategy conversation you're having.
   Are you exploring? Planning? Delivering? Avoid conflating the three.
3. Be vigilant about project ≠ strategy.
   If a project is underway, be clear about whether it is testing assumptions, delivering outcomes, or shaping future planning.
4. Build patterns as you go.
   As with observability, even tactical work can become strategic if you extract patterns and share them with intent.
5. Use time-bounded planning (90-day windows).
   Short, clear cycles force action and reflection. They keep momentum alive while giving space for emergent thinking.

Final Word

Strategy is not a thing you wait for — it’s something you cultivate.

So next time someone says, “We don’t have a strategy,” ask back:
“What are we learning right now that could help shape one?”

That’s where real strategic leadership begins.

 

Context Matters

 Why Setting Context Matters: A Key to Alignment and Decision-Making

In any organisation, people constantly make decisions, prioritise work, and respond to requests. However, when context is missing, confusion, misalignment, and inefficiencies can take hold. Whether it’s a project driven by conflicting deadlines, a cost-cutting initiative that ignores operational realities, or day-to-day work where requests are dismissed as unreasonable, the root issue often comes down to a lack of context.

Effective leaders and teams don’t just give direction—they set the context. They ensure that people understand the bigger picture, make informed decisions, and engage meaningfully in their work.

What: The Key Challenges of Context-Setting

There are four key challenges organisations face when it comes to setting context:

1. Providing context proactively – People perform better when they understand the purpose behind their tasks. Without context, they may follow instructions blindly or disengage. Leaders and teams must habitually explain the ‘why’ behind tasks, initiatives, and decisions.

2. Seeking context before reacting – It’s common for employees to dismiss a request as impractical or misguided without understanding the reasoning behind it. Instead of defaulting to “That’s daft,” teams should be trained to ask, “Why is this needed?” A simple clarification can change perceptions and improve collaboration.

3. Leadership and vision-setting – Leaders must continually set the context, especially during times of change. A new manager, for instance, should communicate their 90-day plan upfront—explaining the phases of learning, strategising, and execution—so their team understands the approach and aligns with it.

4. Promoting a ‘Context Mindset’ – Creating a culture where context is valued ensures it becomes a natural part of decision-making. This means embedding context-sharing in daily operations and encouraging teams to ask for context when it’s missing.

So What: How to Make Context-Setting a Habit

To address these challenges, organisations should integrate context-setting into everyday practices. Here’s how:

1. Leaders and teams must habitually explain reasoning – Setting context should be second nature. Instead of just giving a directive, explain the ‘why’ behind it. For example, rather than saying, “We need to cut software costs,” provide context: “We need to reduce costs, but we must also consider how this software supports critical operations.”

2. Standardising context-sharing in communication – Context should be a built-in part of emails, meetings, and reports.

   • Start meetings with “What’s the context?”

   • Use an “In Brief” or focus statement at the top of reports and emails.

   • Make it a habit to explain background information before diving into details.

3. Encouraging curiosity and teaching context-seeking behaviours – Employees should feel empowered to ask for context when it’s missing. This means:

   • Assuming positive intent when requests seem unclear.

   • Using “Yes, and” approaches to build on ideas rather than dismissing them.

   • Asking clarifying questions to ensure alignment before acting.

What Next: Practical Steps to Build a Context-Driven Culture

1. Start small—build habits. Leaders can model good context-setting by always providing background information in meetings, emails, and conversations.

2. Encourage teams to ask ‘Why?’ Train employees to seek clarification rather than assume the worst.

3. Embed context into documentation and processes. Establish a standard practice of including a “context” section in all major reports, requests, and decisions.

4. Reinforce the behaviour. Recognise and reward teams that demonstrate strong context-sharing and seeking behaviours.

Setting context isn’t just about improving communication—it’s about ensuring alignment, reducing wasted effort, and fostering a culture where people make informed decisions. By making it a habit, organisations can create a more engaged, efficient, and collaborative workplace.

A Pragmatic Approach (aka Zealots and Cowboys Part II)

 NOTE - 21/10/202 - resurfaced as it appears part II has been dropped from the Alinement Network, I've dropped it here for reference and will tidy up later as there are a few issues below.  and it was written a long time ago.

The most challenging aspect of the pragmatic approach is its simplicity. It appears blatantly apparent, and for some readers, there may be a sense of 'You're telling me to suck eggs.' Yet, keeping this practical perspective in mind is at the core of the pragmatic approach. 

Reflecting on the descriptions of Cowboys and Zealots provided in Part 1, you will recall two unique approaches to 'Best Practice.' The zealot tends towards a Just Do it; model. That focuses on the Framework or method as the solution. As an example, apply ITIL out of the box. It'll do it.

Compare that to the cowboys who aim to drive a pure quick win approach without considering long-term plans. That is, Do something, anything, but nothing against a plan. The fundamental principle that both methods omit is that One company's best practice can be another company's burden.

The above sentiments are, in fact, indicators of the difficulty inherent in a pragmatic approach. That is an approach that endeavors to manage the business urgency and expectations to articulate the business problem or opportunity to be addressed using the Framework of the method or best practice to assist in planning (and prioritising) the way forward.

If there is a crucial differentiator for the pragmatic approach from that of the zealot and cowboy, it is the adherence to Deming's principles of Plan, Do Check, Act. Concentrating on upfront planning. 

Many of you would have heard of the 5 P's - Poor Planning Prevents Proper Performance or a derivative of this.

The following Pragmatic approach has come about through hard-won experience in problem management, project salvation/closure, and turn-around situations, all of which in some shape or form have been dependent or impacted by 'Best Practice' thinking. 

Pragmatism is focused on ensuring a practical, matter-of-fact approach is used to assess the situation and solve problems or drive opportunities. It is in no way absolute and continuously improves from scenario to scenario.

The Pragmatic approach (in brief) consists of the following five steps; Note these five actions can be mapped against the principles of the plan, do, check, and act:

1. Define and confirm the business problem/opportunity

2. Define your scope, approach & principles

3. Create & Communicate Direction

4. Check, correct, and communicate

5. Iterate or complete

Step 1, focusing on the problem/opportunity definition, is critical. Often your sponsor may have a loose or high-level idea of what the problem or opportunity is. It would help if you didn't simply run with this perception, taking some time to understand the scenario objectively. Often involving interviews, observations, and other formalised methods to ensure the rounding out of the problem or opportunity to be addressed.

Once you have evolved a solid understanding of the situation (i.e., do your analysis), arrange to quote back and revisit the mandate with your sponsor, ensuring that your primary stakeholder has a clear understanding and agrees with the opportunity you have defined.

Step 2 of this pragmatic approach is the establishment of some Guiding Principles for the work to be done. 

Examples of recent guiding principles used by teams I am working with include:

• Accountability through demand
• Adopt and Go!
• Org structure (functional model) does not equate to a hierarchy.

The core idea behind the principle-based approach is that they are clear and concise. With all of your stakeholders able to comprehend, associate with and adhere to during the initiative. These principles are for testing your solution and implementation in the future.

SCOPE is the nemesis of any best practice initiative. Control the scope; make sure it is agreed upon. Any changes to the scope are to be approved and accounted for appropriately. The risk for anyone involved in an improvement initiative is that discovery and business demand will always tempt away from your original goal.

Step 3: Create and Communicate Direction (CCD) 1 . We have all heard of or experienced initiatives on varying scales that have failed due to the lack of communication. The concept of CCD is the idea of answering four key questions for each of your major stakeholder groups. These are:

• Why are you communicating with them?
• What is it you want to tell them?
• How should they respond or participate?
• What next/if/else.

Naturally, messages will be more complex and complete. Being able to answer the above questions for any of your stakeholders at any time, be it in an elevator, presentation or meeting will help you improve your chance of success.

By the time you hit step 4 of the pragmatic approach, communications should almost be second nature. At this point, you work with the relevant stakeholders and team members to confirm your progress against the original problem/opportunity statement, guiding principles, scope, and proposed solution. Taking corrective action where

required as well as communicating the success and challenges of the program thus far.

Finally, upon completing all the above activities, you will either iterate through another cycle to deliver on the following priority or complete the task at hand. The rationale behind the need for iteration is that this particular approach is not meant to be a complete project management methodology and provides the opportunity for small

iterative cycles within a larger project or program of work.

As stated earlier in the document, the approach we have outlined above is in no way absolute or complete; it is provided in the hope that you will see one or two ideas in here that grab your attention. If you have any thoughts or observations, do not hesitate to add comments to this post. As stated, we are continuously trying to improve this idea of a 'Pragmatic' way of doing things.

'Zealots, Cowboys and the art of pragmatism' (Part 1 of 2)

“Zealot’s, Cowboys and the art of pragmatism” (Part 1 of 2)

Pragmatism (prăg'mə-tĭz'əm)[1] a practical, matter-of-fact way of approaching or assessing situations or of solving problems.  It is also one of the most difficult things to achieve when working to promote 'Best Practice' and emphasise the need to do things the right way.

Interestingly having a pragmatic disposition when endeavoring to promote, execute or implement a given ‘Best’ or ‘Good’[2] practice could be one of the most valuable traits you could exercise. 

Many of us involved in 'Best Practice' initiatives suffer from the 'Curse of Knowledge'. That is   when "we know something it becomes hard for us to imagine not knowing it."[3]  As a result we tend to minimize the effort it takes for others to understand the ideas, experiences and consequences of a particular initiative.   It is this particular curse that causes us to underestimate the effort required to communication.  Therefore lowering our ability to empathise with the recipients of the proposed change.  Consequently any improvement or change we attempt whilst suffering the curse can go one of two ways; the path of the zealot or that of the Cowboy

In going the path of the zealot, we have the effort being run by true believers; evangelists or theorists. .  This approach most commonly manifests itself in the form of very complex and uncompromising ideas that lose sight of and fail to take into account the original organisational problem to be addressed.  One trap Zealots fall into is the tendency to often overlook the immediate maturity of the organisation they are working to change, underestimating the effort and time required to achieve the change.

Alternatively, the path of the Cowboy tends to take a myopic view of the problem focusing on ‘Quick’ wins that are not necessarily sustainable in the long run..  This particular path also has a tendency loose focus on the business problem at hand due to the conviction that doing what is right at any cost will cause others to realise the folly of their ways.  The Cowboy in pursuit of their own solution will often compromise the practices and behavior’s that are considered so crucial to the solution or change to be implemented.

Each path has it’s challenges, the Zealots path will most probably struggle to get started due to the difficulty sponsors and potential adherents will have in understanding the what and why of a given ‘Good Practice’.  Counter to this is the way of the ‘Cowboy’; who’s ideas will succeed in the short term due to the energy, drive and charisma of the lead.  Unfortunately success and sustainability of such initiatives tend to fade when the ‘Cowboy’ moves on. 

Who are they?  How do you recognise a Zealot or a Cowboy?  Even better how do you recognise it in yourself?  These are the challenging questions.  Zealots I have encountered in the past have traditionally come from the ranks.  Most probably having attended a foundations course and moved onto mastery of their given practice.  So much so that they often see the methods, frameworks and techniques they have learnt as the actual solution to all business problems.

A derivative of the Zealot form the rank is one that has transcended industries, and has a strong practical experience of ‘Best’ practice at work in their previous jobs.  As they’ve seen it work correctly they become evangelical about how things should be done, and become uncompromising in what their new organisation should do.

The Cowboy on the other hand can be an entirely different beast to the Zealot.  Possibly a Line Manager, or Project Manager with the job thrust upon them.  Or someone who sees the immediate application of the Best Practice as their next career achievement.  In reality they may not even understand the true value proposition of what they are endeavoring to do.

How do I know this (You may ask)?  I have worn the robes of a zealot and the ten gallon hat of a cowboy over the last couple of years, and have generally found that using these approaches to embed change are fraught with danger to both your career and personal wellbeing without the benefit of really achieving the change you have in mind.

On the occasions I have worn the Cowboy hat, I have had a lot of fun.  I’ve definitely achieved the change locally and it has been sustainable to a limited extent within the small group that was affected .  Unfortunately from an organisational perspective; it didn’t even get noticed.

When wearing the robes of a Zealot I’ve not really been the lead evangelist, but have had the benefit of observing others strive for sponsorship and success.  On all occasions I can vouch that this has been a resounding failure with the organisation unable to understand the vision of the Zealot and subsequently moving to remove the lead evangelist from the organisation or simply getting frustrated with the low volume (if any) of change.

It is with these experiences in mind that I have become (?) an advocate of the pragmatic approach.  That is an approach guided by practical experience and observation rather than just theory.[4]  You can in-fact view the pragmatist as someone who can effectively balance and utilize the skills of both the zealot and the cowboy. 

What if any insights do you have on Zealots and Cowboy?  We would love to hear your thoughts and experiences.  It is our intention in part 2 of this article that we provide you with some insights on a ‘Pragmatic’ approach, and some tips on how to dressing in white robes and ten gallon hats.

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[1] http://www.answers.com/topic/pragmatism

[2] Good Practice – Ref ITIL BOOKS

[3] Chip Heath, Dan Heath “Made to stick: why some ideas Survive and Others Die”, 2007, Random House Inc. New York

http://www.amazon.com/Made-Stick-Ideas-Survive-Others/dp/1400064287/ref=pd_bbs_sr_1?ie=UTF8&s=books&qid=1231668295&sr=8-1

[4] LucidIT @ ITSMF 2006 http://www.lucidit.com.au/

Thinking - Hanging it all together

I am in the throes of a number of projects and conversations amongst other things, and realised that I am continuously hanging things together, to come up with interesting idea's, solutions or philosophies.  I've been doing it for years.

With this in mind I thought I would put 5 Why's to some good use and capture my thoughts for later reference. (Especially as I've posted nothing here for years)

Here is an example of what I am talking about. Having read the book 'Making the impossible possible' the story of cleaning up America's most dangerous Nuclear weapons power plant sometime ago. Observing the continuing trend towards outsourcing. The advent of the marketing term 'Cloud' and what it really means.  

As well as talking to peers in the industry and challenging the idea that Cloud and Mobile are technologies in themselves but representative of changes in business operating models and philosophies.  I've come to the conclusion that wholesale divestiture of IT Groups will occur during my career.

What do I mean by 'Wholesale Divestiture of IT', much like the clean up of the nuclear weapons factory mentioned above, there will be a company or government, that at one time decides IT is too hard, too costly and too prohibitive, and not a core skill of the organisation.  Therefore lets clean the mess up and move to a wholesale service provision model.

Interestingly this is a great topic to consider, just what and how can one organisation position themselves to take advantage of this.  What does this mean for the traditional IT organisations when it occurs etc.  Note this is not intended to be the point of this post.

The point I am trying to get to here is that it was a series, no a breadth of reading, research and experiences that drove me to this conclusion. Something that I and many others do on a continuous basis.  Managers and Team leaders in particular do this.  There individual challenge though is to translate this thinking to action.

That is over the span of any given day a manager or executive can attend a multitude of meetings.  In fact so many meetings that the moment they are free their nose is immediately pointed at a PDA to see where the next meeting is, to scan emails etc. (Really where do they get the time to think - something else to write about)

Through-out this day they have to be able to pick up grains of ideas and insights intuitively and integrate/sythensize these elements into a holistic view.  They then need to take this perspective, package it into a picture that makes sense and inspires those they lead.

All, in truth, quite a challenge, and in someways an absolute mandatory activity that is more often than not seen as a luxury in this time-poor environment. This is in fact a strategic necessity that many people and organisations miss.

This of course then causes a downward spiral for organisations.  If space is not created for the synthesis, communication and inspiration of ideas or strategies we all become a little short sighted, at an individual, team and organisation level.  As an example, I recently had a client respond to one of my suggestions 'That's 9 months away, that's strategic it is out of our scope'.

Really, since when did the strategic Horizon shorten to 9 months? 

All sorts of things are causing and exacerbating this, everything from the current economoic climate through to the amount of information coming at us every day. Add to this our own personal practices and styles, how are we to ever adapt and change? Or are we all going to become mice on the proverbial wheel.

Think about it! If you've got the time, If you don't have the time i'd encourage you to make the time.  Make some space to stop and think, get it out of your head and start communicating it to others.

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Here's what came to gether to make the above post - Global winds churn waters of executive pool, Creative and strategic thinking - the coming competencies   8 tips for time poor executives   and of course a number of things from Endurance IT/5Why's that are definitely helpfull for this situation 

Good Gramma

Here is something I came across on my bookshelf the other day. I thought that you may find it helpfull.

"How to write good"

by William Safire

Avoid run-on sentences they are hard to read.

No sentence fragments.

it behoves us to avoid archaisms.

Also, avoid awkward or affected alliteration.

Don't use no double negatives.

If I've told you once, I've told you a thousand times: resist hyperbole.

Avoid commas, they are not necessary.

Verbs has to agree with their subjects.

Avoid trendy locution that sound flaky.

Writing carefully, dangling participles should not be used.

Kill all exclamation marks!!

Never use a long word when a diminutive one will do.

Proofread carefully to see if you any words out.

Take the bull by the hand, and don't mix metaphors.

Don't verb nouns.

Never, ever use repetitive redundancies.

Last but not least, avoid cliches like the plague.

Why? Why? Why? Why? Why? so silent....

Everyone,

I've not really been that silent, if any of you managed to read p66 of last weeks Australian Financial Review silent is not how I would be described.  (feel free to drop me a line if you are curious as I do have a scanned copy)

I've now created Endurance IT - the Site is up and running at http://www.enduranceit.com.au I will keep posting there into the future.  Although I do have a little work to do to get it working effectively so please be patient.  Also there is the issue of adding a logo sometime in the future as well.

Will I post to 5why's into the future - I am unsure, maybe some things that I feel need saying but don't match up with Endurance IT may appear here.  In the meantime though keep an eye on the Endurance IT site - I will be putting out more content sometime soon.

For those of you who have been watching this site - Thank you very much.

Cheers

Andrew

Short & Sweet - Slidument's

I am madly writing a white paper in preparation for the 2010 PacRim IT Service Management Forum and will subsequently be putting the presentation together.  During this riveting process of moving from a 'Blurt' to a paper of some quality and credibility I found myself not only referencing the concept of a 'Slidument' but actively avoiding this dire sin of presenting.  I do not want to be guilty of causing  Death-by-powerpoint.

Why am I telling you this?  Because the more people who start to understand and appreciate the burden that a mis-used tool such as powerpoint can create on society the better, and yes I do mean literally a burden.  The hours I see people spending working in powerpoint, printing them out to find that there is yet another change to the format, the image, the colour and so forth is phenomenal.  This all costs time, money and trees.

Anyway my short rant aside Garr Reynolds makes the point of slidument's in a much more eloquent way than myself so Please go have a read of this post.

Interestingly I have a second conference to attend later this month and Garr's post is very pertinent and has some sage advice I will be taking.

Cheers

Andrew