How to be a strategic leader

Check out this useful guide to strategic leadership to level up your impact at work.

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Are you trapped in busy work?

If you're responsible for leading a team, project or organisation, you'll know how hard it is to keep perspective. Most people are drowning in operational overwhelm, making it hard to do the things we love.

In this guide, learn the basics of strategic leadership - what it's about, why it matters, and how to improve your skills.

Read through or jump to a section below.

1. What is strategic leadership?

First of all, WTF is leadership?

There's are lots of definitions out there, ranging from the pithy to the benign, but we define it as follows:

A leader is someone who turns virtuous intentions into visible action.

Leadership is virtuous action

You don't need to be a chief executive, run a large team, or head up a country to be a leader. You don't need to have a large following or a senior position. You don't need to be a people manager. You need to care about doing worthwhile things and do them. You need to make decisions about things you care about and take visible action on them.

You need to make decisions about things you care about and take visible action on them.

Whether you do that at home, at school, with your friends or at work is less important. What counts is taking action on your values and making it possible for others to do the same - through your example, support, or empowerment.

Sometimes, that means creating something new and different, while other times, it means supporting the work of others. In all cases, it means doing the right thing and helping others do that too - by watching you, working with you or benefiting from the conditions you've created.

The golden thread is values. Leaders know what they stand for, and they act accordingly.

Leadership is not about people or power

If you're making decisions, taking action or leading others down a path that is not congruent with your values, that is not leadership.

Here are a few other things that are not leadership:

  • Popularity - You don't have to be a charismatic extrovert to be a leader
  • Power - You don't have to hold a role, title or status to be a leader
  • Manipulation - You don't have to convince or persuade people of things to be a leader
  • People management - You don't have to manage people to be a leader
  • Task management - You don't have to manage tasks to be a leader.

Sometimes, leaders have or do those things. Occasionally, they don't. However, those are not the defining characteristics of leadership. Those characteristics are intentional values and visible action. The two go hand in hand, and you're not a leader without both.

Most people have values or things they care about but don't make them visible to others or bring them into their work. Others have great ideas and good intentions - but no follow-through.

Lots of people are taking visible action too, but it isn't necessarily values-led. Which, by the way, is totally fine.

People are great and if they're not changing the world, it isn't because they're bad people. It's more likely they haven't set the intention or thought much about it, especially at work. They do what they need to, and focus their discretionary energy elsewhere. That's cool. It's totally fine.

... It's not leadership, though.

Defining strategic leadership

The difference between operational and strategic leaders is all about perspective and intention. While many leaders are quite happy fulfilling their job descriptions on a short-term basis, focusing on one project and task after another, strategic leaders are different.

They maintain a long-game perspective to their work, and make intentional, considered choices about how they will focus their time, energy and attention to make the most meaningful progress.

A strategic leader makes intentional choices about how to achieve their goals.

While operational leaders are agents of the "what", strategic leaders are agents of how - they put their energy into working out the most effective ways to make progress, and mobilise the resources necessary to make that possible. 

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2. Why you should be a strategist

Strategic skills are the most in-demand skills of the future, according to the World Economic Forum. As the world becomes more automated and knowledge work becomes more complex, your capacity to solve problems, make judgement calls and devise creative solutions will be the most valuable tools in your toolkit.

It's not just a future-proofing exercise, though. Strategic leaders consistently report more fulfilment at work and more meaningful progress on the things they care about. You get more respect, too.

According to Forbes, strategic thinking is the leadership quality that correlated best with perceptions of “success” and “effectiveness” in the workplace — far more so even than communication skills and innovation. People respect leaders who are ready for the future. 

Not only that, being strategic has powerful impacts on your life, work, career and organisation.

Strategic skills minimise burnout

Burnout is one of the most challenging health crises facing the modern workplace, after years of pandemic uncertainty and ambiguity.

Over three quarters of leaders report that work stress negatively impacts their lives and relationships. Almost 60% of leaders report feeling worn out at the end of each day. Not only that, but burnt-out leaders are more likely to plan a job change, driving up turnover.

Strategic leaders are better able to manage their time and energy, mitigating the risk of overwhelm and burnout. 

Strategic skills maximise potential

Most organisations are inefficient and burdened by siloes. Strategic skills unlock hidden potential and productivity, seeing opportunities to work better together. This leads to more creativity, more innovation and people who can make the best use of their skills and capabilities, in service of a bigger goal.

Strategic skills increase fulfilment

Purpose is the single-most important criteria for engaged staff and interested job seekers. When we can see why our work matters and how it helps others, we're significantly more likely to stay motivated and leave work each day with a sense of satisfaction. Check out these results from a Wednesday Wonder survey.

Strategic skills increase earnings

Strategic professionals are our most valuable employees. For budding strategists, this is great news. Your ability to set direction and solve tricky problems makes you an incredible asset to any organisation. Companies with clear, aligned strategies consistently outperform those without, and their leaders share in that success.

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3. Five skills of a strategic leader

Being strategic is not an inherent skill, however - you can learn to look at problems differently and strengthen your strategy muscle with intention and practice.

There are five critical skills that every strategic leader needs to develop:

  1. Performance
  2. Influence
  3. Flexibility
  4. Decisions
  5. Systems

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1. Performance leaders are focused

“You cannot overestimate the unimportance of practically everything.”
― Greg McKeown, Essentialism: The Disciplined Pursuit of Less

Most leaders are extremely busy. Trapped in the hamster wheel, answering email after email and barely keeping up. It’s hard enough with just a few people to manage – the idea of running an entire organisation seems impossible.

Strategic leaders aren’t busy. They know the secret to success isn’t how frantic they are – when they become frantic, performance suffers.

In Michael Porter’s groundbreaking CEO study in 2006, they followed 27 CEOs of large businesses for a full 13 weeks – and the results were surprising. They discovered that CEOs are extremely agenda driven, spending almost half of their time on activities that furthered their big goals – some up to 80%.

The most successful CEOs spent their time connecting with senior leaders, providing useful strategic direction and monitoring the wider health of their organisation and culture, rather than getting trapped in the nitty gritty. Rather than putting in double-digit hours, 7 days a week they worked, on average, 9 hours per day – being careful to make space for personal wellbeing.

This sort of space isn’t a luxury, it’s critical behaviour for sustainable success that doesn’t lead to burnout.

Twitter CEO Jack Dorsey echoes this sentiment on an episode of The Boardroom: Out of the Office podcast. “I would rather optimize for making every hour meaningful – or every minute meaningful – than I would maximizing the number of hours or minutes I’m working on a thing.” Instead, Dorsey focuses on making space for meditating, exercising and learning throughout his day.

Focus isn’t about doing more. It’s about getting rid of all the things that don’t serve the big picture. When Steve Jobs took Apple back over in the late 90s, he knew what he had to do. At the 1997 Worldwide Developers Conference, Jobs famously addressed the crowd to talk about the importance of focus.

“People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully. I’m actually as proud of the things we haven’t done as the things I have done. Innovation is saying ‘no’ to 1,000 things.”
- Steve Jobs, former CEO of Apple

Jobs was clear: focus is not about willpower and discipline, but the courage to say no to what isn’t the most valuable use of time and effort. That year, Jobs overhauled the way Apple worked, getting rid of all non-critical ideas, projects and initiatives to direct energy to just the most valuable and high-potential business lines.

2. Influential leaders prioritise connection

Your communication skills have been critical to your success so far. Crafting the right message, saying the right thing, and building the right relationships are important at all levels of the professional ladder - but to take the step toward CEO, communication isn’t enough. You need to become an influencer, with the power to shape people’s thinking and behaviour.

Successful CEOs know that it’s not what they say that counts – but how they connect with others. When we confuse influence with talking people into things, we focus on reports and slide decks. But that keeps us focused on ourselves. Real progress comes from the power of connecting with others.

In Lead the Room: Communicate a Message that Counts in Moments, leadership communication expert Shane Hatton explains this clearly: with communication, we get engagement and with connection, we get trust. With influence: we drive change.

Ineffective leaders focus on popularity and try to get everyone on board, exhausting themselves and bending in every direction to keep everyone happy. But the most effective CEOs know that quality beats quantity every time. True change doesn’t rely on everyone getting on board, but inspiring tribes of committed followers to make things happen.

Seth Godin, author of Tribes: We Need You to Lead Us spells this out plainly: “…great leaders don't try to please everyone. Great leaders don't water down their message in order to make the tribe a bit bigger. Instead, they realize that a motivated, connected tribe in the midst of a movement is far more powerful than a larger group could ever be.”

Howard Schultz, CEO of Starbucks, has known this from the beginning. When he pitched his concept of Italian-inspired cafes to the founders of Starbucks, he was met with resistance. He had over 200 no’s before finally proving his concept could work, and credits much of his success to building a powerful team, treating them with respect, and instilling faith in the big picture.

"When you’re surrounded by people who share a passionate commitment around a common purpose, anything is possible."
- HOWARD SCHULTZ, CEO of Starbucks

3. Flexible leaders are always experimenting

Today’s leaders are expected to manage increasingly complex pressures – environmental sustainability, social responsibility, economic uncertainty, technological advancement and legislative change, to name a few.

Juggling this kind of ambiguity and delicacy doesn’t call for military-style toughness and order – it asks for flexibility.

Deloitte’s 2017 CEO research, which tracked the behaviour of 24 global Fortune 250 CEOs, saw researchers ask the question: “What does it take to be un-disruptable today, and what will be demanded of CEOs and their organizations to avoid disruption tomorrow?”

They found that today’s CEOs stressed the importance of embedding constant exploration, experimentation and improvement at every stage of their decision-making process and value chain.” Their success wasn’t about their ability to toughen up, but to build the confidence in changing tack, taking risk and innovating while cultivating confidence with possible failure.

Salesforce CEO Marc Benioff underscores the importance of this agility, actively building the same attitude in his teams.

“I respect the spirit of innovation,” Benioff says. “Sometimes that spirit is going through me and sometimes it’s going to come through someone else … I try to cultivate a beginner’s mind; I try to let go of all the other things that have ever happened so far in our industry (which is a lot of stuff) and go, ‘Okay, what’s going to happen right now?”

The old myth of the heroic, visionary leader is dying, as we recognise that success is more about perspective and willingness to change than the magic powers of a single individual.

When Mary Barra assumed the helm at General Motors, she scrapped many of the stuffy old policies at the century-old company – famously shortening their old 10-page dress code down to just two words: “Dress Appropriately” – to work on building an organisation that was comfortable with taking new directions. 

“In this era of rapid transformation, you have to have a culture that’s agile”
- Mary Barra, CEO of General Motors

Rather than doubling down on their traditional business model, Barra has made huge shifts, investing in areas as diverse as insurance, electrical vehicles, self-driving cars and ride-share services. With Barra at the helm, GM has ushered in a new approach to old problems, as she empowers the team to innovate, operate independently and embrace the challenges of climate change and a changing social context with both arms. 

4. Decisive leaders take action

 The pressure to get things right is immense. In an operational role, accuracy counts for everything, and many misguided leaders take this approach into more senior roles, panicking about their capacity to predict the future and make the right calls.

This pressure is unsustainable. When you’re responsible for the big picture, your planning horizon makes it extremely risky to try and predict all of the variables.

“There's no harm in hoping for the best as long as you're prepared for the worst.”
- Stephen King

Never fear: strategic leaders know that detailed and operational business planning is generally a waste of time. As soon as you plan how long something will take, and the precise steps to take to achieve a goal, that will change.

Rather than spending weeks and months planning detailed steps, strategic leaders nail their long-game, set up the right conditions for success and get ready to tackle unexpected issues.

Rather than waiting for perfect information, the most successful leaders focus on decisiveness and direction instead.  

Jerry Bower, CEO of the private-label manufacturer Vi-John uses a 65% rule of thumb: “Once I have 65% certainty around the answer, I have to make a call.”

Instead of focusing on accuracy, Bowe hones in on impact. “I ask myself two questions: First, what’s the impact if I get it wrong. And second, how much will it hold other things up if I don’t move on from this?”

Using this approach, Bowe frees up his time to focus on the big picture as far as possible.

The data backs this up. In the longitudinal CEO Genome Study, published in 2017 with ten years of data, the authors were clear:

 “Our analysis suggests that while every CEO makes mistakes, most of them are not lethal. We found that among CEOs who were fired over issues related to decision making, only one-third lost their jobs because they’d made bad calls; the rest were ousted for being indecisive.”

5. Systems leaders focus on how things fit together

The old path to leadership depended on your expertise. Years spent accumulating knowledge at university, compounded by more years of doing your job well.

With the explosion of knowledge work and the increasing complexity of modern business, it’s not quite this easy anymore. Most senior leaders are managing teams of incredible experts  who know more about their job than they do – and rightly so. The more senior you are, the more you’d have to know for this model to make sense.  No-one expects the CEO to be a marketing whiz, IT guru, legal boff and technical expert all in one.

As an expert, your job was to have the answers, but as a strategist, your job is to ask the right questions, create the right environment, and empower your team to work together.

Don Yager, chief operating officer of cloud tech company Mural Corporation, famously asks his frontline team: “What are our policies that suck?”

The power of a question asked with humility and openness shifts the inherent power dynamic between leader and follower, making it possible for people to contribute their knowledge and be honest about what needs to shift.

In “Questions Are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life,“ MIT Leadership Center executive director Hal Gregersen outlines his findings, providing that the world’s most successful companies are led by people who ask ‘catalytic’ questions to drive progress.

These questions not only challenge false assumptions in the system, but they give people the energy to do something about it,” Gregersen said.

When you think of Rose Marcario, Marc Benioff, Jeff Bezos, Elon Musk, any of those folks, they systematically, habitually create conditions where they themselves are likely to be wrong, uncomfortable, and reflectively quiet, such that a question would emerge that they otherwise wouldn’t ask. 

Eric Schmidt, former CEO of Google, echoes this sentiment. Schmidt is the first person to admit that he wasn’t the best software engineer, but that wasn’t what he was hired for. It was constant curiosity and willingness to question assumptions – and be wrong – that impressed the people he worked with.

As Jonathan Rosenberg, who worked with Schmidt describes: “He's very smart and constantly thinking about how the world is changing, how industries are being disrupted, and how to change the way he manages every day."

“We run this company on questions, not answers.”
- Eric Schmidt, former CEO of Google


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4. How to be more strategic

This list might look overwhelming, but the truth is: strategy is an everyday job. Being a strategic leader is not something you can 'tick off' but rather a practice, which is helped by a set of key behaviours.

Here are three simple things you can do to channel a more strategic outlook in your leadership:

Cultivate flexibility

Flexibility is a skill worth having – and this has never been more obvious than the events of the last 18 months, where the COVID pandemic has shattered our ideas and assumptions about how to lead, work and live.

Ultimately, leadership flexibility is about staying attuned to our environment, taking responsibility for our behaviour and learning from our experiences to keep adapting – because we’ll need to. When we stay aware of ourselves and our surroundings, take agency over our future, and build resilience in ambiguity and disaster, there’s little that can hold us back.

Signs you need to be more flexible:

  • You’re facing change or transition
  • You’re feeling out of your depth
  • What usually works to keep you sane isn't working so well anymore.

How to be more flexible

Every interaction, disruption or problem is an opportunity to build awareness, agency and resilience. Legend has it that Benjamin Franklin made a point of focusing on one virtue each week and practising it daily. Cultivating flexibility can be handled in the same way.

Here are some ideas:

  • Read widely and ask questions – what’s happening out there? What are other people doing?
  • Dismantle a problem you’re facing by starting from scratch – what if this wasn’t a problem at all? How could you eliminate the entire process?
  • Schedule time with people you trust to get a new perspective on your environment and behaviour – what is it about your leadership or your business that isn’t working well anymore? How can you shift that?
  • Next time something negative happens, think of three interpretations that might be more useful – what if this was a gift, or an opportunity for growth?

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Ask tricky questions

Whenever you find yourself wondering what you should do, try to resist the urge to seek a solution. Instead, think about the questions you can ask to understand things better and give you

We should all be asking tricky questions more often.

Rather than accepting things at face value, we need to dig deeper into why the same things keep happening, and tackle the underlying forces instead of the symptoms in our workplace. These are the kind of intangible skills we're being hired for now: critical thinking, problem-solving and creativity.

But it can be hard to do, especially when other people are involved. It's even harder when those people have power over our jobs and destinies.

How to ask good questions:

  • Use compassionate curiosity, to separate people from problems
  • Zoom out to the 'how'
  • Consider the other person's needs and fears before you ask
  • Ask questions well - consider your tone, type and timing.

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Challenge constraints

Strategic leaders don't ask if they can achieve their vision, they ask how.

This attitude requires a strategist mindset, where we focus on breaking down barriers to progress - and many of our constraints and obstacles aren't what they appear to be on the surface. Take funding, for example. Funding and resource constraints are the most commonly cited reasons for slow progress on important projects - however, money is often a false constraint.

If money were the silver bullet, the companies and agencies with the most revenue would be the best places to work, they'd have the best results, and they'd be having the most impact. But they're not.

We often do better under pressure. Our brains prefer to be lazy, so if we can buy our way out of a problem, we probably will. The data even suggests that adding constraints can help us to be more generative! For example, it's easier to think of five white things inside a fridge than it is to think of five white things.

Ingredients for challenging constraints:

Confidence in your idea - The first sale is to yourself. If you don't believe it will work and you aren't willing to risk for it, nobody else should fund it. Either you believe in it, or you don't. Make the choice.

Humility in your intention. It's not the thing that you want. It's the outcome the thing will give you. Don't get so attached to the shape of your solution that you blind yourself to better options and ideas. Be willing to kill your darlings.

Relationships with others. If natural disasters, pandemics and acts of terrorism have shown New Zealand anything over the last few years, it's that we need each other more than anything. When you're connected with like-minded people, they point you in the right direction, offer helpful advice and share with you (as long as you do the same.) You don't always need cash when you have community.

An eagle eye for process hacks. If you can't afford to do it the way everyone else does, you'll have to find a smarter way - which means you've got a golden opportunity to innovate. Automate. Cut steps out. Take a different approach. Leadership means doing something first, not following the rules.

An appetite for failure. If you're not failing at least 20% of the time, you're too far in your comfort zone. Whether you have the money or not, you've got to be willing to push the boat out if you want to get anywhere - so get experimenting!

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