To move up into senior leadership, overcome u image of playing it too safe.

Your ability to see nuance, uncover patterns, and synthesize data makes you especially suited for strategy. So why doesn’t your boss see it?

9 min readDec 19, 2020

Photo by You X Ventures on Unsplash

“You need to be more strategic.”

Many of my executive coaching clients have been told this in a performance review. They’re told that if they want to move up into senior leadership, garner more respect and influence, and manage larger teams, then they have to become more skilled at strategic thinking.

As thoughtful Sensitive Strivers, many also find themselves puzzled by this feedback, wondering how they could be a deep thinker but not necessarily a strategic one.

Sensitive Strivers and Strategic Thinking

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On the flip side, their brains are often racing, which can lead to worry, indecision, and doubt. It’s not uncommon for them to over-analyze day-to-day experiences and be so mired in details that they fail to see the bigger picture.

Their tendency to “pause-and-check” — which is usually a gift — can cause trouble because they sometimes play it too safe, avoid risks, and point out what could go wrong in a situation versus lean into possibilities.

…None of which is compatible with strategic thinking in today’s fast-paced workplace.

What is Strategic Thinking?

In simplistic terms, strategic thinking involves long-term planning for the future. Strategic thinkers:

Hold a holistic view of their organization’s ecosystem and stakeholders.
Anticipate major shifts in the marketplace and identify emerging opportunities.
Know how to work within resource limitations and make tough calls to reach the team’s goals.
Create and inspire people to work towards a vision of what’s possible.
Don’t stand still. They are constantly moving their team towards ambitious targets, experimenting, and making informed bets.

The Harvard Business Review describes strategic thinking this way: “Strategic people create connections between ideas, plans, and people that others fail to see.”

The good news is that this type of critical thinking is exactly what your Sensitive Striver brain is built for. Your ability to see nuance, uncover patterns, and synthesize data makes you especially original, creative, and suited for strategy.

The key to becoming a more strategic thinker is to learn how to channel your thoughtfulness to work for you, instead of against you.

How to Become a More Strategic Thinker

Free yourself from execution

It’s impossible to find time to think big-picture when you’re constantly task-switching or if your day is packed with meetings.

Many managers find themselves in this trap — they are still so attached to the day-to-day execution of tasks that they have no brain space to do the strategic work necessary to advance themselves and their teams.

If this is you, you’re certainly not alone. Up to 96% of leaders say time is the biggest roadblock to strategic thinking.

You can cure this by delegating more. Empower your team to take on tasks that would offer them a learning opportunity. Audit your schedule and look for meetings that you can eliminate or outsource. Take back control of your calendar, blocking off time, and creating better boundaries.

Ruthlessly prioritize

The “urgent” is the enemy of the “important.” And if you spend your career reacting to fire-drills, you’ll inevitably find yourself in a reactive cycle of being behind the eight-ball — never proactively in front of it.

There will always be new problems and opportunities vying for your attention. So if you want to be a true strategic leader, you need to select and focus on only those projects that advance the business’ core objectives, i.e. ways to save time, make more money, or otherwise grow the organization. Otherwise, you’re simply keeping busy for the sake of being busy.

To ruthlessly prioritize, you must be able to answer the question, “What’s the most important thing I need to accomplish in this role?” Keep your goals front and center and get comfortable saying no and pushing back on competing demands, which can be tough for conflict-averse Strivers.

Look for solutions, not problems

Strategic thinkers don’t simply highlight problems; they always go a step further to offer a potential solution. They come to the table with proposals and plans for how to take action. They talk in terms of what’s going well, what could be better, and what’s possible — not what’s wrong or deficient.

Assuming a solution-oriented approach requires you to get comfortable with uncertainty and ambiguity. It means lowering the defenses of your inner perfectionist who desperately wants to avoid mistakes and failure.

Ask yourself bigger, better questions

Strategic thinkers challenge their own assumptions and look at challenges from a number of different perspectives before deciding on the best path forward. One great way to do this is with the classic six thinking hats methods:

White Hat: With this thinking hat, you focus on what you can learn from the available data, current and past trends.
Red Hat: You look at problems through the lens of feelings (yours and others), using your intuition and emotion.
Black Hat: Is the hat of caution. Look for weak points and think about how to create contingency plans to counter them.
Yellow Hat: Helps you look at the bright side. What is the most optimistic viewpoint?
Green Hat: Uses creativity and leans into freewheeling, out-of-the-box ideas
Blue Hat: This hat represents processes and prompts you to bring order and structure to your thoughts

Listen to and recruit others’ perspectives

One major mistake I see Sensitive Strivers make is assuming that the onus of strategic thinking lies entirely on them. This isn’t true. The best thing you can do is recruit a diversity of thought by bringing your team and colleagues into the process.

For example, ask your team to come to a brainstorming meeting with three suggestions already formulated. If they bring a problem to you, coach them by asking questions like:

What possibilities have you considered?
If you were me, how would you approach this problem?
Based on your experience, what do you propose as a next step?

Likewise, make an effort to discuss your ideas with different people. Many Sensitive Strivers are verbal processors and need to talk things out, either with a coach or a colleague who can offer a different perspective.

Be willing to take risks

One of my clients came to work with me after receiving feedback that his penchant to play it safe was holding back his team — and holding the company back as a result.

This client hesitated to put projects on the company’s long-term product roadmap, which led his team to set less aggressive goals and get less aggressive results than if he was able to be more strategic.

We worked together to help him find a balance between driving higher performance from his team without burning them or himself out in the process. He started small, by rolling out low-stakes pilots that he gradually expanded as he got results and feedback

To move up into senior leadership, overcome u image of playing it too safe.

Your ability to see nuance, uncover patterns, and synthesize data makes you especially suited for strategy. So why doesn’t your boss see it?

Sensitive Strivers and Strategic Thinking

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What is Strategic Thinking?

How to Become a More Strategic Thinker

Free yourself from execution

Ruthlessly prioritize

Look for solutions, not problems

Ask yourself bigger, better questions

Listen to and recruit others’ perspectives

Be willing to take risks

Written by Elizau