Four Habits of Strategic Leaders

By Melissa Karz
Partner, Next Step Partners

We hear it all the time in 360-degree assessments: “This person is on a great trajectory, but needs to improve his/her strategic thinking.

It’s one of the most common development goals for rising stars and recently promoted senior executives. But it’s also a problem that can hamstring entire executive teams when leaders are too narrowly focused on their own team goals and challenges.

A strategic mindset is what allows people to identify threats before they become crises, to grasp new opportunities, and to create breakthrough innovations. Senior leaders are often asked to “be more strategic”, but knowing how exactly to achieve that can be confusing and challenging.

Strategic thinking gives leaders the ability to develop effective plans that both align with organizational objectives and account for the economic situation. It helps executives to chart a path forward, set goals and determine priorities.

Common obstacles for leaders

  • | “I’m not very organized with my time…”
  • | “I don’t feel like I am adding value if I am not ‘doing’…”
  • | “I don’t delegate to my team members as much as I should…”
  • | “I don’t really know how to step back…”


This article explores what it actually means to be a more strategic leader and provides insights for leaders to improve in this area.

Why is strategic thinking a challenge?

First, let’s address why strategic thinking comes up so often as a developmental goal. Here’s the deal: a large part of what likely got you promoted to this role in the first place was your ability to drive execution, deliver results and provide expertise. You’ve been recognized as smart, responsive and accountable.

But the transition from tactical leadership to strategic leadership calls on you to ask questions rather than answer them, to focus on your highest value work rather than “block and tackle,” to chart new paths rather than continue to operate within and execute the status quo.

To successfully transition to being a strategic leader, you must change your mindset and redefine your own value. This can be painful! After all, you’re pretty great at what got you here and you’ve been rewarded for it. It’s familiar and comfortable. Old habits and mindsets are hard to change.

The Strategic Mindset

Mindsets drive behavior and action. Maintaining your familiar, comfortable, tactical mindset will trap you in a box that will prove difficult to escape. It will be hard to make strategic thinking something that you bring to everything you do—the small conversations and the big decisions. While setting aside time for reflection gives you a moment to think big, a strategic mindset gives you a lens to think big in every moment.

The tactical mindset is about getting things done, putting out fires and being the expert. The strategic mindset is about aligning with organizational objectives, discovering the unknowns and being a facilitator between ideas, people and plans.

A tactical mindset allowed Han Solo to lead the rescue of Princess Leia in Star Wars. A strategic mindset allowed Billy Beane to create a winning team out of the Oakland A’s in spite of financial constraints, as portrayed in Moneyball.

Being more strategic doesn’t necessarily mean making decisions that affect the whole organization. Nurturing a relationship, such as one that could provide unique insight into a supplier, a customer or a competitor can be highly strategic.

So, can the approach you take to managing your time.

  • Are you setting a large portion of your time aside for strategic big picture activities like visioning and relationship building?
  • Are you proactively going into your quarter, month, weeks and days with the big picture in mind and structuring your activities accordingly?
  • Are you getting the most strategic activities done first?
  • How are you structuring your thinking?
  • Do you have the end in mind?


4 Habits of Strategic Leaders

Mindset aside, there are four key things that strategic leaders do regularly.

1 | Align to organizational objectives

Strategic leaders are always tapping into the vision, values and goals of the organization and finding ways to align to it. They are constantly looking at where they want to take the business, what is needed to get there and how to make the best use of the talent on hand. They look for gaps to fill as well as hidden resources.

With the larger goals of the organization top of mind, they look for connections they can make across functional teams, departments and even operations. They put as much value in building relationships with peers as they do coaching their teams and building a leadership pipeline.

Questions that can help you align with organizational objectives include:

  • Where is the business today?
  • Where does it want to be in six to twelve months?
  • What changes do I need to make to my teams to support these objectives?
  • What skills are missing?
  • What peer relationships do I need to nurture?
  • What competencies need to be developed in the leadership pipeline?
  • How are we defining success?

2 | Identify highest value activities

Every leader faces an abundance of “important activities” and urgent demands every day. When you first get promoted to a senior leadership position, one of the hardest parts of the transition is getting out of the weeds. Let’s face it: every potential use of your time is not equally important. You have to prioritize and focus on the things that need your attention.

Delegation will be key to your success—and for many leaders that includes shifting your mindset about delegating. As a senior executive, you simply can’t get bogged down in the minutiae every day. But while you may recognize the need to give up some control to your direct reports, this can be hard to do. It’s something we address often in executive coaching engagements.

We often find that leaders make assumptions about the skills, capabilities and motivation levels of others by applying a one-size-fits all delegation approach. Instead, good leaders need to asses each individual’s will and skill level in order to determine who can be trusted to handle what, and how much direction vs. support each individual needs. The ultimate goal is to need to provide less hands-on direction and more support.

But you won’t be comfortable delegating until you have a clear understanding of your own highest value activities. This understanding will guide you in determining what other aspects of the business can be delegated to your direct reports. You need to know what only you can do and what can be done by others, while always keeping at the forefront the organization’s goals.

As a senior leader, highest value activities often include:

  • Coaching direct reports to build a leadership pipeline and improve retention
  • Nurturing strategic relationships with peers and brokering connections to break down silos and foster greater collaboration
  • Bringing the big picture view to your teams that are focused necessarily on their specific tasks and goals, by creating a climate that sets them up for success
  • Challenging the status quo to spark innovation
  • Creating a culture that supports the vision and values of the organization

We often gain insights for clients by conducting 360-degree interviews with probing questions that bring to the surface an individual’s strengths, organizational needs and highly specific areas for improvement.

Lack of strategic thinking can hamstring entire executive teams. Click To Tweet

3 | Seek under-the-radar information

Senior leaders are tasked with seeing the big picture and guiding the organization based on this view. What’s needed is a wide and far-reaching perspective. You need to be able to see multiple angles of the present situation to be able to discern the opportunities and threats coming ahead.

But as leaders move up, they move away from the front lines and day-to-day interactions with customers. Their sphere can become very insular, which paradoxically keeps them from grasping the information needed to see the complete picture. Strategic leaders are always looking to expand their understanding and know the unknowns.

Bringing important under-the-radar information to the surface starts with asking good questions. Some strategy questions relate to core business fundamentals (e.g. market analysis). Others relate to how we think through problems (e.g. looking at our blind spots). Either way, when you ask good questions you are improving the thought process behind business decisions.

Download our leader’s practical guide to asking strategic questions which includes a range of sample questions to incorporate into your meetings.

Expanding your perspective also involves actively seeking information outside your sphere: both within your organization and outside it. Developing stronger connections with peers, both internally and externally, as well as with customers through regular conversation will improve insight into current situations. Reading industry and business publications and attending industry conferences (or sending others on your behalf) can help you stay abreast of market developments.

Strategic leaders regularly meet with people outside their organization (customers, partners and peers in other industries) to stay close to shifting trends. Relationship building with people from across the industry helps to cross-pollinate ideas. The intention is to get outside the bubble. Bubbles don’t just keep others out. They keep you in.

Some goals that might help you expand your perspectives include:

  • Meet with two external contacts per week
  • Read industry/business publications two hours/week
  • Attend two industry conferences each year


4 | Schedule time for reflection

Leaders need to prioritize setting aside time to think. Between meetings, emails, phone calls and actual work, there’s little time for strategic reflection unless you plan for it.

Without time for reflection, decision making becomes reflexive and based on past experience rather than a clear perspective on the current situation and potential opportunities. To come up with new, innovative approaches and to be able to gauge the likelihood of success, you need to devote some serious time to thinking.

In this context, it’s critically important to schedule time for reflection on a daily, weekly and quarterly basis. Here are some suggestions for carving out “strategic thinking” time:

  • Spend 15 minutes at the start of the day determining what to delegate and to whom
  • Block out 15 minutes at the end of the day to wrap the day’s event into the “big picture”
  • Block out 30 minutes per day for brainstorming on a different key topic or decision
  • Block out 1 hour/week for strategic thinking time – no email, phone
  • Block out 1 day per quarter for a personal strategy “retreat”
  • Hold department off-sites twice/year to do strategic planning





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