Making the Call: How to Drive High-Quality Strategic Decisions

Posted by
March 23, 2021

Topic: Strategic Leadership

Written by Karin Blair


A new strategy client reaches out for help. They are in the blessed position of having just raised a tremendous amount of capital. 

The question most on the CEO’s mind: “How do we allocate this large infusion of capital for the greatest impact?”

When I hear his question, I feel the weight and consequence of the decisions ahead. My stomach tightens. My mind begins to spin. What process can guarantee high‑quality strategic decisions? I am gripped already, and I can feel the CEO’s angst and uncertainty. Investor expectations are huge — so much promise and possibility. 

And yet he knows there are too many ideas pulling the organization in too many different directions right now. The leadership team senses it too.

“Who are we?” they ask.

“Who do we want to be?” A diabetes company? A technology platform? A direct‑to‑consumer provider? 

High‑Quality Strategic Decisions Embrace Uncertainty

No matter how many times I get this call, I always have to remind myself to take a deep breath and settle into the discomfort of enabling the team to make these high‑stakes decisions. Despite years and years of trying to find that guarantee of results, I have to relearn each time that strategy resides in the world of complexity. Where performance is relative (to competitors) and cause and effect cannot be controlled or predicted. 

Strategy resides in the realm of:

  • Many high‑value, competing ideas
  • More choices with fewer known paths to follow
  • More change and more interdependence
  • No right answers

The realm of surrendering to not knowing.

Strategic decisions, such as deciding where to allocate capital, demand a lot of us as leaders. All decisions aren’t created equal. Decisions range from what to have for breakfast, where to go to college, who to marry, where to go on vacation . . . to whether to acquire a company. We use the same term for the routine to the complex and the small to high stakes.

In an HBR article on strategic decisions, Phil Rosenzweig suggests, “You have to know what kind of decision you’re making in order to make it well.” 

With strategic decisions, we can actively influence outcomes, and performance is relative to your competition. These are decisions of high complexity and high consequence.

And they are rarer than the everyday choices we encounter. So it’s not like we get a lot of practice. Practice that would be helpful when the responsibility and accountability for the outcomes can feel overwhelming. When all eyes are on you to know the way. Heck, that is why you are paid the big bucks, right? How could you surrender to not knowing? What would that say about your capability? What would that do to your credibility?

I vividly remember an annual leadership meeting from my corporate days. The CEO took the stage and said he was navigating “uncharted waters.” 

He had leveraged his experience for great impact up to that point, running the plays of past playbooks. But the road ahead was unknown and uncertain. There was no predictable path based on experience. We were reaching the limits of the expert model of knowing, of the knowable. And he admitted it. Frankly. Poignantly. I couldn’t have been more inspired, committed, or proud when he declared this. By acknowledging the unknown terrain we’d stepped into, it was easy for me to trust that we would collectively “find our way.” 

The CEO’s leadership capability and credibility had long been established. And, by surrendering to the not knowing, he broke free of “all or nothing” thinking— we know or we don’t, we can or we can’t. In doing so, he gave us space to create our future. 

The quality of strategic decisions is a function of:

  • leaders’ capacity to lead themselves and others through natural discomfort and fear in the face of uncertainty, and
  • leaders' and their teams' capacity to think strategically.

Recognizing Discomfort Avoidance During Strategic Decisions 

How much ambiguity and complexity can you tolerate? Truly? What happens to you in the face of that complexity? Of that not‑knowing? Do you know

For example, when writing this article, I was tempted to share some tried‑and‑true processes for making robust strategic decisions. And most likely, you are reading it wanting one. We are compelled to seek answers — to seek processes that can control the desired outcome. Cause and effect. Follow the SOP (standard operating procedure) to get the needed result. 

SOPs are:

  • Routine
  • Predictable
  • Repeatable

And they are the wrong tool for managing complexity.

My desire to control, while acute, actually decreases my ability to see and influence things in a complex and unpredictable world — the world of strategy. A part of me will always want to believe that if I just “study hard enough,” I can wrap my arms around the complexity. I can see it all, understand it, and as a result, control it. Instead, what I experience is exhaustion and frustration at a futile exercise.

There are other avoidant behaviors: 

  • Your tendency may be to shut down divergent conversations because you are too uncomfortable with the not knowing. 
  • You might cling to “right‑ness” in the face of uncertainty. 
  • You might feel uncertain in the face of perspectives that are different than your own, that challenge your strategic thinking — your “rightness” and your “knowing.” Perhaps you even feel insecure. 

Or maybe you oversimplify. You make a choice black or white, ignoring the complexities. Or it could be you’re the type who will “go along to get along.” Let others figure it out, and support whatever they say. 

These are all shortcuts to making decisions. But will they make the best decisions? 

What if our biology hasn’t caught up to the complexity of the world we now seek to navigate? What if instead of helping us (like keeping us safe from the threat of a lion), our biology is leading us astray?

If we could recognize and manage discomfort avoidance, what might become possible?

  • What if we could hang in with the discomfort of not knowing just a little longer? 
  • What if we accepted that none of us can see the whole picture, and that everyone is holding an important piece of the puzzle? 
  • What if instead of being consumed by these habits, we could see them, feel them, name them — and then liberate ourselves? 
  • What if the biggest step we could take toward making more robust strategic decisions would be learning how to do this?

How to Orient in the Discomfort to Make Strategic Decisions

The more transformational your strategy, the more the “not knowing” will be present. Transformational strategies challenge paradigms and beliefs about the way things are. It’s like how Cirque du Soleil caused us to reimagine a circus or how Uber re‑imagined the business model for getting a ride from point A to point B. With the benefit of hindsight, we can see that these were brilliant strategies. But imagine making those calls before the world had changed!

Our job as strategic leaders is to orient. And that includes orienting ourselves in the face of not knowing, of not being able to see the whole picture. 

I am learning through my writing that I have a “creative process.” Which ironically doesn’t meet this definition of a process at all:


Process: a series of actions or steps taken to achieve a particular end.


The same actions or steps don’t produce these articles. Rather, it is an orientation — a “you are here.” And “here” is a valuable and necessary part of the experience. I settle into the discomfort and orient to receive, see, or become aware, not to control.

With enough repetition, I am learning to trust. Trust in the parts of the writing experience when I have lost my sense of direction. Trust that clarity will emerge — as long as I can stay open to it. As long as I can not‑know for a little bit longer.

Repetition — with practice — and trust. I have a client whom some refer to as “the Oracle.” He has an uncanny intuition and the ability to identify the next big technological breakthrough. He has had enough experiences to trust that only when he is deep in the muck of not knowing will the “fog clear.” It can be hard to trust without the experience that shows us we can. But you have to try it at least once to experience it.

Try to embrace that trust that you can let go of the outcome and still achieve the outcome. 

Hard to conceive. And yet . . . what if it were true? 

The Bottom Line: Surrender to Not Knowing

So here we are, the end of the article, and no answers. No processes. Are you frustrated? Agitated? How is the not‑knowing impacting you? Personally, it is driving me crazy. I want to fix, solve, resolve. My desire to control doesn’t release easily. 

Clarity, Action, Impact — that’s my brand promise. Can we have clarity, decisive action, AND not knowing? Yes. But only by surrendering to the not knowing. And to be willing to hang in with that discomfort longer and in new ways. 

How might you experiment with that possibility? I will be running my own experiments in providing this client with strategy coaching. Trying to let go of the outcome and still achieve the outcome. My stomach tightens as I type. 

For now, I invite you to stay here, in discomfort, with me just a little longer.

Note: If you are interested in learning more about how we tend to avoid the discomfort of not knowing, check out the work of researcher Jennifer Garvey Berger. She identified five mind traps that prevent us from thriving in complexity.

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