view from a balcony in a luxurious therater

How To ‘Be More Strategic’ – Questions To Ask From The Balcony

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“Be more strategic.”

This advice comes along in the careers of most professionals seeking a management or leadership role. They reach a point at which it is not enough to be productive or to be an expert. In order to progress in their careers and contribute at a higher level they must be–and be seen as–strategic. But what is it to be strategic? Advice about being strategic is often a little vague, accompanied by the exhortations to get out of the weeds” and “see the bigger picture.” But once you get out of the weeds, what do you do? It can be tempting to think that some people “have it” and some don’t. But I have seen clients build their own strategic capability as well as coach others on their teams to develop a more strategic mindset and approach. Strategic thinking can be learned and practiced.

Let’s start with what is not strategic. It is not strategic to pack your calendar with meetings focused on execution, spend your time reacting to crises and responding to requests, have a short-term mindset or limit your focus to your own functional area. Thinking strategically is inherently proactive and creative, even disruptive, and is not limited to mere operational efficiency. The arena of the strategic thinker encompasses the bigger picture, cross-functionally within your organization and also more broadly in your market or industry. It embraces a wide time horizon, including reflecting back on experience and projecting out into the future. It is also an area of uncertainty. The strategic thinker is always wondering, questioning, conjecturing, connecting, hypothesizing, making bets.

All of this requires devoting time to reflection, what Harvard professors Ronald Heifetz and Marty Linsky call “getting in the balcony,” from which vantage point you can see the whole dance floor. I have found that many clients instinctively grasp this metaphor (which I love in part because it is not a sports metaphor), and they quickly see the value of stepping out of the action to observe: Are the dancers moving to the same beat? Is someone trying to waltz through the conga line? Who is that guy doing the worm? But then many aspiring leaders get anxious about what to do when they are up there, and how long do they have to stay? What if they don’t have any good ideas? This fear is normal and indicates that you are in uncharted territory—which is at the heart of creative leadership. 

Principally, what you do from the balcony is observe and ask questions—questions that challenge assumptions; seek out connections, patterns and anomalies; broaden your lens; identify trade-offs. And you can pop up there any time for a few moments or linger for more extended periods. But it is important that you consistently access the perspective from the balcony and invite others up with you. 

To develop your strategic thinking skills or to help someone else build theirs, practice is key. You will need to take control of your calendar, setting aside blocks of time and creating buffers between meetings. Whether you have just five minutes or a longer stretch of time, it helps to have a tool kit of go-to questions. They are the engine of idea generation. Jennifer Garvey Berger suggests creating a strategic question “cheat sheet,” which you or your team can consult at any time. Here are some sample questions to help you build your strategic thinking habit and capacity:

Questions to ask after a meeting:

  • What are my key take-aways from the meeting? (Compare notes with someone else–did they leave with the same impression? What did they see that you missed?)
  • If a decision was made, what were the assumptions and trade-offs that went into the decision? 
  • Put yourself in the shoes of any other stakeholder in the room. How would they have viewed the meeting?
  • What was the content of the meeting? What else was going on: subtext, relationships, power dynamics, etc.? What was not being said?

Questions to ask before giving a presentation:

  • Who is my audience? What do they care about ? What do they need to hear?
  • How can I frame the material to put it into the larger context for them?
  • How might my presentation strengthen trust and relationships?
  • If I expect conflict, how can I ensure that the conflict is constructive?
  • How might I lay the groundwork for my presentation (pre-communicate, get input, etc.)?

Questions to ask about a project:

  • If this project fails, what would be the potential causes of failure? How could we prevent/mitigate those causes?
  • How does this project relate to our strategy or to other activities within the organization? How might we involve other stakeholders?
  • What does success look like and how can we set ourselves up for success (resourcing, clarity, accountability)?
  • What are our blind spots? How could we shed light on those areas?
  • What if….?

Questions for getting a wider perspective

  • What is going on in the organization, market or world and how might this affect our activities, product, etc.?
  • What is our top priority? What are we choosing not to do?
  • Once this crisis has passed, where do we see ourselves in a year?
  • What are the most important big questions we need to answer?

As you can see, none of these questions allows for an easy or clear answer, so when you are practicing these questions, you are also getting yourself and your team more comfortable with navigating volatility, uncertainty, complexity and ambiguity—the world we live in. Practice questions like these and coach others to do so as well, or brainstorm a set of questions for your team, and you will start to generate new ideas and insights.